This article is about what comes after those conversations.

Most consultants go straight from discovery conversation to proposal. They trust their memory, trust their read of the room, and start writing scope.

That’s where proposals get built on the wrong foundation.

The gap between what a client says in a live conversation and what they actually mean — or what they actually prioritize — is real. They’re thinking out loud. They’re listing problems in the order they come to mind, not in order of importance. They may not have fully connected the dots themselves yet. And you’re filling in the blanks with your own assumptions, which may or may not be right.

I’ve written scopes based on what I thought I heard, only to get back a response that was polite but deflating: you’ve addressed things we care about, but not the thing we care about most. You end up rewriting the scope before the engagement has started. It’s avoidable.

The Email Playback

After each significant discovery conversation, send a structured email that plays back what you heard and asks the client to correct anything you got wrong.

It does four things:

• Forces you to synthesize before you invest time scoping — which surfaces gaps in your own understanding

• Confirms alignment on the problem before you propose a solution

• Gives the client space to think more carefully than they could in a live conversation

• Creates a written record that matters later if scope is disputed

How to write it: Use the question framework as your structure. Pre-populate each answer based on what you heard. Do not send a blank form and ask the client to fill it in.

A client who won’t spend 20 minutes drafting answers will spend 20 minutes correcting yours.

Pre-populating the answers is what makes this useful. It shows you were listening. It gives the client something to react to rather than something to construct from scratch. And corrections are far more likely to surface the real priority than open-ended prompts are.

Template:

Subject: [Client name] — notes from our conversation

Hi [Name],

Great conversation [yesterday / last week]. I wanted to capture what I heard while it’s fresh and make sure I have it right before we go further.

Below are my notes by topic. I’ve filled in what I understood from our conversation. Please reply inline with any corrections, additions, or things you’ve been thinking about since we spoke.

What are the issues you need help resolving?

Based on our conversation, the main issues seem to be:

— [Issue 1, as you understood it]

— [Issue 2]

Is this a fair summary? Anything missing or out of priority order?

[Continue through the remaining question clusters]

Let me know if I’ve missed anything or if your thinking has evolved since we spoke.

Writing the Business Case

Once the email playback comes back confirmed, synthesize the answers into a written business case. This is not a proposal — it’s a four-part summary you can read back to the client to confirm alignment before you name a number.

The four parts map directly to the discovery clusters:

1. Project context — what the situation is and why it matters now

2. Opportunity or challenge — what specifically needs to change

3. Impact — what will be different if you succeed, and how it will be measured

4. Investment rationale — why the value justifies the cost

Here’s what this looks like assembled from a real engagement. The client was the CEO of a B2B SaaS company. The engagement that resulted was approximately $500,000. The raw material was a set of inline email replies:

You’re running a B2B SaaS platform that has grown through acquisition, and the result is a fragmented user experience that no longer reflects the value the product actually delivers. Users have no compelling reason to log in daily, and the platform isn’t getting credit for what it does on their behalf.

The core challenge is a platform overhaul that unifies the experience and makes the value visible. You have a customer event in March that creates a real external deadline, and internal pressure that’s been building for over a year.

If we get this right, you’re projecting a 10% improvement in renewal rates, faster sales cycles, and higher close rates. That’s the lever for the bigger things: growth, valuation, and the pressure you’re feeling from the board.

Based on what you’ve described, I’d expect this effort to be approximately four months with a team of four. That puts us in the range of [X]. Does that feel workable given where your planning sits?

The ballpark range comes at the end, after the value case is fully established. You’re naming a number in the context of a problem the client has already confirmed is real, urgent, and measurable — not floating it in a vacuum and hoping it lands.

The Most Common Mistake at This Stage

A client has a long list of high-priority problems. The budget and timeline they have can realistically address one or two of them. You can see the mismatch. But the engagement sounds interesting, and so you tell yourself: if we make decisions quickly and everything goes according to plan, this should work.

It doesn’t work. The scope gets renegotiated before you’ve started, or worse, mid-engagement. The discovery process exists specifically to surface this mismatch before you write anything. If the answers don’t add up — long problem list, thin investment reality — that’s a signal to keep asking, not to start scoping.

Knowing When You’re Done

You have enough to move forward when two conditions are both met:

1. You can write the business case clearly

2. The client responds positively to the ballpark range

A clear business case with no response to the number isn’t enough. A positive response to a number without a clear value case is a liability — you’ve agreed on cost without agreeing on what it’s for. If the ballpark lands badly, you find out now instead of after investing hours building out options. If it lands well, you’re ready for the next step.

Next: how to structure the options, price them with confidence, and what to do when the client’s budget doesn’t match what you’ve sent.

–Greg

What’s been most useful in your discovery conversations? Any questions you’ve found particularly effective? Reply and let me know.

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This is the seventh and final article in the What Comes Next series, which maps eight paths available to senior professionals navigating a career transition. The previous pieces went deep on each path one at a time: independent consulting, fractional leadership, expert networks and board roles, entrepreneurship, and teaching and traditional employment. This one is about what happens when you stop treating them as alternatives.

The framework piece made the point early: most of these paths aren’t mutually exclusive. A portfolio career is what you get when you take that seriously and design for it.

What a Portfolio Actually Is

The investing idea is useful in one narrow way. A portfolio isn’t a pile of similar holdings. It’s a mix of positions chosen to do different jobs: some for growth, some for steady income, some for a low-probability shot at a big return. You weight them against your goals and your stage of life. More aggressive early, when you can absorb a bad year. More balanced in the middle. Income-oriented near the end.

Work streams sort the same way. Some are speculative, with real upside and a real chance of producing nothing. Some are safer, unlikely to make you rich but dependable. A portfolio career is the deliberate decision to hold more than one, matched to what you need now and what you’re building toward.

The diversification can be wide or narrow. A portfolio doesn’t have to span four different kinds of work. It can be all independent consulting, diversified across clients, industries, and offerings so that no single relationship carries the whole load. The principle holds at any width: don’t let one stream become a single point of failure.

One honest thing up front: a portfolio rarely starts as a portfolio. The clean, deliberate arrangement is the end state. The beginning is usually messier, several things running at once with no clear read on which will matter. You take a project, try a workshop, start writing, say yes to a fractional conversation, and watch for signal. The considered shape emerges later, once the market has shown you what’s working. Treating the early mess as a sign of failure is itself the mistake. The mess is how you find the arrangement.

The Tension That Makes This Hard

Diversification has a natural opponent worth naming: focus. Specialization is what gives an independent leverage. A specialist is harder to compare, harder to price-shop, and can charge accordingly. I’ve made the case that specialists win, and at my firm a narrow focus was the single biggest source of pricing power we ever had.

So diversification cuts against the very thing that creates leverage. Spread too wide and you commoditize yourself into a generalist competing on price. Over-specialize and you carry the opposite risk: too few buyers for your one thing, or a market that shifts and leaves your niche behind. Both failures are real, and the balance between them is the hard part of portfolio design.

The way through is to be precise about what you’re actually diversifying. Keep the expertise focused. Let the diversification live in how you package and deliver it: the same deep knowledge expressed as consulting, as a fractional role, as a workshop, as a product. Think of it in layers. Your core expertise is the slow layer that stays specialized for years. The formats, buyers, and pathways are the faster layer that varies and hedges. That’s a portfolio that spreads risk without dissolving into generalism.

The Real Argument: The Flywheel

Diversification is the defensive case. The better case is that a good portfolio’s components feed each other.

In practice, it tends to run in a loop. A knowledge-sharing habit (writing, talks, teaching) raises your visibility and widens your network, which surfaces consulting and fractional opportunities. Fractional work puts you in the room where business leaders are wrestling with problems at altitude. Consulting puts you at the delivery level, where you see what teams actually struggle to execute. Both vantage points show you what the market is genuinely confused about, which tells you what to write and speak about next, which feeds the visibility again.

Each stream produces something the others use. The knowledge-sharing layer isn’t a separate marketing chore bolted onto the real work. It’s the flywheel’s first push, and the paid work is both the payoff and the fuel for the next turn.

A design educator and recruiter I talked with recently is a working example of this. He runs low-cost workshops in part to stay visible. He capped one pitch-deck workshop at ten people; twenty-five showed up, and a startup founder in the room approached him afterward. That conversation turned into a two-and-a-half-year fractional head-of-design engagement. The workshop wasn’t the product. It was the push that set the rest of the wheel turning.

This is also why a portfolio improves your odds in a way a single path can’t. Closing any piece of business comes down to three things: a compelling offer, access to the right people, and timing. You control the offer, you influence the access, and timing is mostly luck, the luck of reaching someone who happens to be in-market right now. I’ve written before about how that luck is something you can shape. Running several visible streams at once is one of the ways you shape it: more streams, more chances to be in front of the right person at the right moment.

Diversifying Through Other People’s Machines

One form of diversification I underplayed in the consulting article deserves its own mention here. You can hold direct client relationships and relationships with larger agencies or consulting firms who bring work to you. Those firms have a business development and marketing engine no individual can match. Plugging into one means a share of work you didn’t have to source, sitting alongside the independent contracts you maintain yourself. That’s diversification of a different kind: not just varied work, but varied origination.

This is how we work with trusted independents at DesignMap. One person we’ve brought onto projects for years also runs his own practice and picks up work through other firms, so when one stream is slow, the others usually aren’t.

The mix also shifts over time, and that shift can be designed. One version I’ve heard more than once describes a career as a set of wedges that change size: the consulting wedge narrowing as the teaching-and-writing wedge widens. For many senior independents this is deliberate, a planned move from the lead role toward a mentor’s role with age, and partly a response to an industry uncomfortable with grey hair. Hands-on consulting gets harder to win the older you are; teaching and advisory work hold up better. A portfolio lets that rebalancing happen gradually instead of as a cliff.

When a Portfolio Makes the Most Sense

Three moments stand out.

While you’re still employed. This is the ideal moment, and the one almost nobody uses. Building a second or third stream while the salary is still landing is the truest hedge there is: planting before you’re hungry, digging the well before you’re thirsty. You get to experiment from a position of security, with no pressure to monetize fast and no fear clouding your choices. The catch is that it’s also the hardest version to actually pull off, for a reason that rhymes with the innovator’s dilemma. When the job is going fine, there’s no forcing function. You’re busy, you don’t feel at risk, and the slow work of building optionality loses every time to the urgent thing in front of you. The window that costs the least is the one you’re least likely to use.

Right after you leave a full-time role. The next best time, and the more common one. A portfolio approach here can include looking for another full-time job while you test one or two independent paths in parallel. You’re not committing to independence or to employment. You’re keeping both live until the signal tells you which to weight. Eggs, baskets.

As you approach the slow-down. This is the case I find most compelling, and it’s underdiscussed. The standard retirement model says: accumulate one large number, then stop. Hit five million, retire at 65, draw it down at roughly four percent a year. The portfolio model offers a different shape. If you can keep earning some income on your own terms for longer, you can downshift earlier. Working half-time from 55 to 70 at a decent rate changes the math enough that the single large number stops being the only gate.

There’s a non-financial reason this matters too. One of the consistent hazards of full retirement is the sudden arrival of unstructured time, which turns out to be harder on people than they expect. Intellectually engaging, flexible, well-paid part-time work is a hedge against that as much as against the financial gap. If the work is good, “why stop entirely” is a fair question.

A healthcare executive I interviewed, who came up through management consulting, described his own setup in almost these terms: a full-time role, rental income, and a couple of other streams, built deliberately as a hedge. He could give notice tomorrow and be fine for months, and was quick to add that none of it happened by accident. He also pointed to consultants he works with in their seventies who still take part-time engagements, not for the money but for the mental engagement. That’s the slow-down a portfolio makes possible.

A Shape Worth Considering

There’s no single correct portfolio. But for experienced independents, one shape recurs often enough to name. Four components, each doing a different job:

• Independent consulting. The core earner, with the highest return per hour, especially when the work comes through your network or a partnership. Income is lumpy but lands fast, in weeks to months.

• Fractional or interim leadership. Senior, episodic engagements at strong rates, capped by your capacity and tied to a contract term. Ramp is measured in months.

• Entrepreneurship. A one-to-many bet: a product, tool, or knowledge business. High effort and low return while you build, then income that starts small and compounds over a year or more.

• Knowledge transfer. The supporting layer: writing, talks, teaching, workshops. It rarely pays directly, and that’s fine, because it feeds everything above it. It’s also a full pathway in its own right (the teaching and knowledge transfer piece); here it mostly plays the supporting role.

The entrepreneurial component most changes the long game. Every other piece sells your time; this one doesn’t have to. Breaking the link between hours and income, now within reach of non-technical experts thanks to AI, is the holy grail for anyone who has spent a career trading one for the other. The more weight this component carries, the more durable the portfolio becomes. I went deep on it in the entrepreneurship piece.

Who This Fits, and Who It Doesn’t

More likely to work: people who can hold several things in motion without dropping them, who have or can build visibility across more than one channel, and who value optionality enough to accept that no single stream will ever feel fully solid. The portfolio rewards range.

More likely to struggle: people who do their best work with deep focus on one thing, who find context-switching genuinely costly, or whose current situation demands one reliable income now. The sequencing point from the framework applies with force here. A portfolio is something you build toward, not something you start with. If you need income in 90 days, get one stream stable first.

The Thread Through the Whole Series

The series has worked through eight paths, but the goal was never to crown one of them. It was to replace a forced binary, stay employed or go independent, with a real map. The portfolio view is the natural endpoint of that map. The paths were never really rivals. They’re components. The work is choosing which ones fit your situation, in what mix, in what order, and staying willing to rebalance as the situation changes.

Resources and a Personal Note

A theme running under this whole series is how alone people feel working this out, as if the only honest way through is instinct and first principles. It isn’t. Structured resources, communities, and frameworks exist for exactly this kind of career. If you want a hand thinking through your own mix, what to lead with and what to build toward, reach out. I’m glad to help.

Take the Assessment

The CompoundCraft assessment scores your profile against the pathways in this series and returns a bottom-line recommendation, the trade-offs, and a 90-day plan for testing your direction. About twelve minutes, no account required. It’s the newer version I’ve been building, and a curated catalog of those resources, mapped to each pathway, is part of what’s coming as it expands.

–Greg

If you’re already running more than one stream, what does your mix look like, and which one feeds the others? Reply and let me know.

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Neither is bad. A traditional role taken on your own terms can be exactly right, and a teaching practice built deliberately can be rewarding. What makes the default wrong is not the destination. It is arriving there without asking the question the rest of this series keeps asking: does this fit my situation, or is it just the move that asks the least of me?

I am not an employment expert. I have spent a long career in this field and watched a lot happen to the people in it, clients and peers and friends. The patterns here are the ones I have seen, not laws. But I have seen them often enough to trust them, and you may recognize them too.

Traditional Employment

For a lot of senior people, going back to a full-time role is the right call, and not as a failure of nerve. If you can find a good role and it makes sense to give it the majority of your time, that is a real answer. It is something you already know how to do, which spares you the unfamiliar work of leveraging your expertise on your own. Many senior people also enjoy managing others and growing careers, which is hard to do alone. Many value being part of something larger: the structure, the mission, the scale. And a full-time job usually comes with health insurance, equity, and other benefits that are expensive or impossible to replace.

Traditional employment is not wrong for many people. For many people it is the most sensible thing on the list.

It goes wrong when it is a reflex rather than a fit. When you no longer want to give all your time to someone else’s mission and someone else’s problems. When you are done with the politics, or worn down by enough rounds of layoffs that another one is hard to face. There is a version of that fatigue people rarely name: at this level, you are often the one who has to deliver the cuts. Surviving a layoff and executing one are both their own kind of erosion.

Even when going back is the goal, the reflex skips some hard facts. Senior expertise is harder to place, not because of you but because there are fewer roles at the top. Even in a good market a comparable role can take six months to a year to land, and longer in this one. Once you land it, your security is not yours. You are one reorg away from being right back here, regardless of your performance or your talent. And some people reach a point where they cannot afford to fully retire but no longer want full-time work, and “half the time for half the pay” is very hard to negotiate with most employers.

So the comparison is not job versus no job. Finding a comparable role can cost you a year, and at the end you have a job whose security still is not yours. Set that against a year spent building something you own and control, and the second option stops looking like a detour. And it is not even a choice. You can keep looking for the full-time job while you lay the foundation for an independent practice. One does not cost you the other.

The comparison is not job versus no job. It is a year chasing a role you do not control against a year building something you do. And it is not even a choice.

Two patterns recur when senior people are displaced from a large enterprise. Some move laterally, leaving the top seat at one big company for the top seat at another. It works, but it is the exception, and it gets harder the more senior you are. More common is moving down market, where there are more roles but smaller problems, more hands-on work, and less prestige, which can be hard on an identity built at the top. Watch for the founder who hires a senior leader to look more mature and then cannot actually cede control. That role rarely survives the year.

You Are Probably Already Doing Independent Work

Watch what senior people do while they search. They work with recruiters, but they also write, post, and reconnect. Some convene their peers to talk through what matters at their level. Some mentor publicly and say so. There are even exclusive paid groups, costing serious money a year, that senior people join mostly to stay visible and improve their odds of the next role. That people pay so much to stay visible between jobs says something about how secure those jobs felt.

Almost all of it is independent work in everything but name. Writing, convening, mentoring, distilling what you know and putting it in front of people. Framed one way, it is marketing yourself for the next role. Pointed slightly differently, the same effort becomes something you own that outlasts any employer. Convening a group of peers crystallizes your point of view and puts you in front of the people most likely to hire or refer you. With a small turn of the wheel, it is the start of a practice rather than a job-search tactic.

The move is not to choose between a job and everything else. It is to take the job if it fits and plant a few seeds you control while you do, so the next reorg finds you with options instead of a blank page.

Teaching

The teaching fantasy is seductive and specific. You have decades of expertise, you step back from the grind, you share what you know with people earlier in the journey, and you trade politics for purpose. It feels like a graceful next chapter.

Some of the best designers I know teach, and none of them backed into it. They teach because they care about the craft and the people coming up behind them, and they have spent years publishing and advancing the field in public. That is a chosen path, and a serious one. The default that misleads is the other version: teaching imagined as a soft landing, picked because it sounds gentle rather than because it fits. From the inside, the two could not be more different.

Start with entry. It is gated by your network, not your resume. The first role usually comes through someone who introduces you to a program head. The curriculum may be handed to you fully formed, which is less freedom and far less work, or you may build it yourself, which is the reverse, and people tend to imagine one and get the other. The subject matters as much as the format. Teaching something adjacent to your real expertise, or teaching undergraduates when what appealed to you was engaged adult learners, is a common way to end up bored in a role you thought you wanted.

The economics are the hardest part, and they are getting worse, especially in design. California College of the Arts, the last nonprofit art and design school in Northern California, will wind down by the end of the 2026–27 academic year and hand its campus to Vanderbilt. It follows the San Francisco Art Institute, closed in 2022, and Mills College, whose arts programs were gutted after a larger university absorbed it. The trend is national. Small tuition-dependent colleges have been closing at an accelerating pace since 2025, driven by a shrinking population of college-age students. The institutions people picture teaching at are the ones under the most pressure.

The benefits angle is real but narrow. Teaching can be a route to health insurance, which matters enormously when you leave employer coverage. But that generally requires permanent or tenured faculty status, which means teaching enough hours for enough years to qualify. An adjunct does not; a department head does. So keeping one class to hold your benefits works only once you are already established, and it ties your coverage to exactly the kind of school now closing.

The Realistic Ways In

Teaching gets treated as a binary whose only real form is the front of a university classroom. It is not. There is a range, running from informal mentorship up through paid coaching, live workshops, self-paced online courses, and university teaching at the far end. The low-effort end is cheaper, faster, and more realistic for most people, but the range is not a clean ladder.

The first decision is not which rung to climb but which fork to take: teaching inside an accredited program, or teaching on your own. The program path runs through people and program heads. The independent path has no gatekeepers. You just do the work.

The version that sounds most efficient is the most work. A self-paced online course seems like the scalable, easy move, but the production lift is enormous and you build the whole thing before learning whether it lands. A live workshop or Zoom course is far lower effort and gives immediate feedback, which makes it the better way to test whether you even like transferring your knowledge. The productized course is something you graduate to once the material works, not where you start. And the path can be sequential: many people who teach at a university did conference workshops for years first, maybe built a course of their own, and arrived already knowing they could do it.

Coaching is the most realistic version of this path for most people. It is a consulting version of teaching: bespoke, one client met where they are, still requiring you to crystallize what you know, but lower-stakes than a course and with clients easier to find than students. Below it is mentorship, which many experienced people already do informally. ADPList (adplist.org) is the mentorship platform I see most often in my network. Mentorship, coaching, and a single live workshop are all easier than becoming a teacher directly, and each one crystallizes your expertise even if you go no further.

That crystallization is the underrated payoff. One of my partners built a design thinking course from scratch and came back with two things: she knew far more than she could initially articulate, and teaching forced her to clarify it. You think you understand something until you try to hand it to someone else. The curriculum she built is also reusable, slow and costly to make once and cheaper to run every time after. A course you develop is closer to a product than a job. The first delivery is the cost. Every one after is leverage.

One decision shapes the whole path, and most people never make it on purpose: who are you serving? Peers in your own role, or the managers and leaders who buy what your discipline produces? They are different audiences with different needs and economics. If the people you teach are the same people who hire you, the two efforts feed each other. If not, you are running two unrelated tracks at once.

The Move Is Multi-Track

Whichever default pulls at you, the strongest version is not a single track. It is a search and a hedge at once, and they do not compete. The things you would do to support a job search or a move into teaching are the same things that grow into independent income.

A serious search already means raising your visibility, writing, reconnecting, and distilling what you know into something you can say clearly. All of that makes you a stronger candidate. All of it is also the raw material of a coaching practice, a consulting offer, or a body of work that earns on its own. Mentor while you search and it sharpens how you describe your expertise, and sometimes pays. Convene your peers and it puts you in front of the people most likely to hire you. None of it competes with going back to a job or stepping toward teaching. It leaves you with something the job alone never gives you: a source of value that does not vanish in the next reorg.

That is what the start of a portfolio career looks like. You rarely design one in a single decision. You back into a few income streams that reinforce each other, then make them intentional. That is where this series goes next, and where it ends, with Portfolio Career Design: how to turn the seeds you plant while chasing a default into a deliberate structure, so that no single employer, institution, or client holds all of your security at once.

If the two defaults are what people reach for when they want one thing to count on, the portfolio is what you build when you would rather have several.

A Note, and the Assessment

If you are weighing one of these paths and trying to figure out what to build alongside it, or which rung of the teaching range is the honest place to start, reply or reach out. I am glad to think it through with you.

If you would rather start with your own profile, the What Comes Next assessment scores you across the dimensions that matter most here: runway, how much structure you want, income variability tolerance, and how much of your time you are still willing to trade for income. About fifteen minutes.

–Greg

Have you defaulted into one of these paths, or chosen one deliberately? If you went back to a full-time role, what, if anything, did you keep building on the side? Reply and let me know.

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The One Path That’s Different

Every other path in this series is a progressively more leveraged way to sell your time. Consulting, fractional leadership, expert networks, teaching, board advisory — in all of them, you’re still present in each transaction. You trade expertise for income, directly or through a platform that facilitates the exchange. The leverage varies. The fundamental structure doesn’t.

Entrepreneurship is the path where the goal is to stop being in every transaction. You build something that delivers value whether you’re working that day or not. A product, a platform, a community. Something that generates income while you sleep.

It’s worth naming the flavors. Service-based entrepreneurship — running a consultancy, a small firm, an agency — is real entrepreneurship. It requires everything entrepreneurship requires: tolerance for risk, business development, decisions with no one above you to approve them. But in service businesses, revenue depends on people actually delivering work. DesignMap is a service business. After 20 years and significant revenue, if the partners stepped away entirely, the firm would not survive. The clients go away when the people do.

What this series calls entrepreneurship is the other kind: building an asset that delivers value without you in each transaction. That’s the specific shift this article is about. And for this audience, the thing you build will usually draw on your existing expertise — though it doesn’t have to.

What Trying Looks Like From the Inside

DesignMap spent years approaching this without fully crossing it.

The closest we got on the service side was what we call the Visiontype offering: a bespoke engagement, different for every client, but following a defined process, phases, and outputs we had developed and refined over many engagements. There was real leverage there. We weren’t figuring it out as we went. But it was still consulting. Time-for-money, just with better margins and clearer scope.

Further along the spectrum: training materials we developed for design teams, and a method for assessing designers’ career development that we’ve used and refined over many years. Both of these were, in principle, assets we could have sold independently — packaged offerings that could have been licensed outside the context of a larger engagement. We never made that move. They stayed bundled into client work, which meant they never accumulated standalone value.

The closest actual attempt at something truly asset-based was a product we called FutureCast: an automated scenario planning tool that took structured input from a user, ran it through AI transformations, and produced a formatted document mapping out four possible futures. It ran almost entirely without our involvement. I treated it as a real test.

It didn’t work. Not because of the technology — that part functioned. What was missing was something harder to see at first: the human process of alignment that our work had always been about. Looking back, the artifacts DesignMap creates have often functioned as what screenwriters call a MacGuffin — the plot device that drives the story forward while the real value is in the journey itself. In our client engagements, the Visiontype prototype matters, but what the work actually produces is something more important: people who have thought through a hard problem together, made decisions, and found the confidence to pursue a bold direction. The artifact captures that. It doesn’t create it.

FutureCast could produce the artifact without the process. Without DesignMap in the room, all responsibility fell on the user to provide good input and know what to do with the output. I spent more time on it than I should have, and I've now taken it offline. Building it was genuinely useful anyway, and the diagnosis above is most of what I got out of it.

The honest diagnosis for why DesignMap never fully crossed over is what Clayton Christensen described in The Innovator’s Dilemma: the dynamic where successful companies get stuck precisely because they’re good at what they do. We knew how to make money consulting. Any hour spent building something speculative was an hour not spent selling to clients. And the harder problem: in client work, we’re brought in to help teams identify the right problem within a defined opportunity space and move from ambiguity to a shared direction. Defining the problem space itself, for a market we hadn’t validated, felt genuinely risky in a way that client work never does.

That failure was useful. Understanding why it didn’t work has shaped how I’m thinking about things differently now.

Why This Is Finally Different

The historical barrier to asset-based entrepreneurship for experienced professionals was infrastructure. Building a product required a technical co-founder, a funded team, or years of self-teaching. Most senior professionals weren’t going to do that, so they stayed in services even when the ambition pointed somewhere else.

AI has changed this in three ways, not one.

The obvious way: build timeline. What used to require 12-18 months of engineering work can now be assembled in weeks. The less-discussed way: the number of roles required. A solo practitioner can now do what used to require a product manager, an engineer, a designer, and an ops person. But there’s a third shift that gets less attention: the minimum viable problem size.

Before, building a product made economic sense only if the problem was large enough to justify the time and cost. You needed significant potential revenue to justify a significant investment. That logic no longer holds. With build costs collapsing, it’s now perfectly rational to solve a narrower problem for a smaller audience. This is the logic behind what’s sometimes called micro-SaaS: small, specialized products that solve specific problems well, run by one or two people, generating modest but sustainable recurring revenue. The addressable market doesn’t need to be enormous if the cost to build and operate is low enough.

This is what solopreneur actually means now — not just someone working alone, but someone building a real product with real infrastructure without a team. A non-developer with genuine domain expertise and a clear problem can build functioning software in 2026 in a way that wasn’t true in 2022.

I’m living this. I’m a designer, not a developer, and I’m building a real SaaS product. The AI assistance is not eliminating the work. It’s making the work possible for someone without a technical co-founder.

One honest nuance: AI doesn’t solve the problem of picking what to build. Choosing the right problem — specific enough to be solvable, real enough that someone would pay for it, narrow enough to actually finish — still requires the same judgment and domain knowledge that good product work has always required. The barrier that collapsed was the build. The barrier that remains is the thinking.

The Planning vs. Building Tension

One of the more common failure modes for experienced professionals on this path is analysis paralysis. People who are careful, thorough, and good at anticipating problems often spend months mapping the territory before putting anything in front of anyone. I’ll include myself in this. At some point, the loop of thinking-and-planning becomes its own form of avoidance.

The opposite failure also exists: starting to build before having any real sense of direction.

The goal is somewhere in the middle. Have enough direction to start, then start making something real earlier than feels comfortable. The sooner you put something actual in front of actual people, the sooner you get feedback worth anything. Everything before that is theory.

The Work Around the Work

Every path in this series carries a version of what I’d call the work around the work — the operational, administrative, and business development tasks that surround the expertise work itself. In consulting, this is manageable: legal setup, invoicing, contracts, scope management. Real, but learnable.

In asset-based entrepreneurship, there’s an additional category that dwarfs the rest: distribution. In consulting, you have warm referrals and existing client relationships as your business development foundation. In product entrepreneurship, especially at the start, you’re selling to strangers. You need people to find you, trust you, and pay for something before they’ve met you.

That requires marketing, content, and audience-building — capabilities that most senior professionals with corporate and consulting backgrounds have never had to develop at the individual level. This is one reason why expertise-adjacent products have a structural advantage over building for a completely new market: you likely already have credibility and some distribution in the domain you know best.

A Word About the Noise

There is a loud, highly visible version of this path on social media and in some corners of Substack. Solopreneur gurus, “I made $10K in my first month” frameworks, courses on how to build a course. It’s everywhere, and it can feel exhausting or off-putting.

Much of that content is performance. The persona is the product. The expertise being monetized is often the audience itself, not a domain built over 20 years of real work.

That’s not what this article is describing. What’s different about this path for experienced professionals is the starting point: real expertise, developed over a real career, in a domain you understand deeply. You’re not manufacturing authority. You have it. The product is an expression of what you actually know, packaged in a way that delivers it at scale.

Don’t let the noisy version turn you off the genuine one. They’re not the same thing.

What This Path Actually Requires

Four conditions determine whether this path is realistic:

Deep domain expertise with a specific audience in mind. The product should solve a problem for people you understand well. Generic products built on general expertise are the hardest to sell because there’s no natural distribution channel.

AI fluency. Not necessarily coding ability, but the willingness to work with AI tools at the level required to actually build with them. Learnable, but not zero effort.

Enough runway to give it real attention. Not 10% of your time for 12 months — that’s a hobby. More like a serious majority of your working time for at least 60-90 days of genuine validation.

An identified audience, even a small one. Building without demand signal is the most common and most expensive mistake on this path.

On the financial dimension: this is the path that most changes the long-term math on later-career flexibility. A consulting practice stops generating income when you stop working. A product doesn’t have to. Even modest recurring revenue from something you’ve built, alongside retirement savings and other income sources, creates the kind of security that’s hard to achieve from any single source. Many people, even those who have saved responsibly, carry anxiety about whether it’s enough. A revenue stream that doesn’t require your presence is a meaningful hedge against that.

Who This Path Is Right For

More likely to work: deep vertical expertise, genuine AI fluency, an identified audience, enough runway to give the build real attention, and comfort with ambiguity — the ability to commit before you have certainty and treat early failure as information rather than verdict.

More likely to struggle: people who need predictable income within 90 days, people who find the problem-selection work (not the problem-solving) too uncomfortable, and people who underestimate the distribution challenge.

This is the path with the highest potential upside and the most honest failure rate. Most product attempts don’t reach sustainable revenue. The ones that do are usually built by people who stayed in the game long enough to find out what was actually working.

Resources and a Personal Note

There are programs, communities, and tools built specifically for people navigating exactly this transition. I’m developing a curated catalog of resources mapped to each pathway in this series, with enough context to evaluate what’s actually worth your time. More on that soon.

In the meantime: this is a path I’m actively working through alongside everything else I’m doing. If you’re trying to figure out whether the conditions are right for you — what to build, how to sequence it, whether the prerequisites are actually in place — reply or reach out. I’m happy to think through it with you.

Take the Assessment

The What Comes Next assessment scores your profile across the dimensions most relevant to this path: expertise scarcity, runway, AI fluency, and income variability tolerance. Takes about fifteen minutes.

Next in the series: Teaching and Traditional Employment — the two paths people default to without much analysis, and why the default is often wrong.

–Greg

Are you thinking about building something of your own, or have you tried and hit a wall? What’s the hardest part of the shift from selling expertise to building an asset? Reply and let me know.

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They differ in nearly everything else. Expert networks are the fastest income path in this series. Board roles are the slowest. Understanding both, and why they are often best pursued in parallel, is the point of pairing them.

What Expert Networks Actually Are — And What They’re Buying

The basic model is simple. Platforms connect organizations with paid experts for one-hour consultations. Free to join as an expert. At director and VP level, typical pay runs $250–500 per hour with no ramp-up time required. By the metrics of “getting started,” it looks like the easiest path on the list.

But the framing of “they’re buying your expertise” is only partly right, and the incomplete version leads people to misjudge whether they actually qualify.

At DesignMap, we have used a leading expert network regularly for client research — a normal billable expense for a consulting firm doing strategic work. The most useful sessions had a specific quality: the expert was direct, had genuine opinions, and was willing to say things that contradicted what we went in expecting to hear. That’s what you’re actually paying for. Not credentials. Not a polished summary of someone’s career. The willingness to think out loud and push back.

The disappointing calls were with people who had no strong views and weren’t talkative. Being an expert isn’t enough. Being a direct, opinionated one is what makes the call worth the credit.

This is the same dynamic that makes user research useful or not. Some people think out loud naturally. Others summarize carefully and say nothing. Expert network calls are essentially user research for hard-to-reach senior populations — you can’t run standard recruiting when your target is a CIO at a regional bank or a VP of operations at a logistics firm. The network solves the access problem. What you bring to that call is the rest of it.

What You’re Actually Being Paid For

The most important question before joining an expert network is not “do I have enough experience?” It’s: what’s my vertical?

Functional expertise alone — deep knowledge of product strategy, or design, or HR — rarely drives consistent call volume on these platforms. What drives calls is deep familiarity with a specific industry context, buying behavior, or operating environment. The organizations paying for expert calls are usually trying to understand a market, evaluate a competitive landscape, or do due diligence on an investment. They need someone who has lived inside the specific world they’re trying to understand.

When DesignMap used an expert network for banking research, we weren’t looking for design experts. We were looking for executives who make purchasing decisions about digital products at regional banks — CMOs, CIOs, CTOs who could tell us how they find and evaluate vendors, what criteria they use, and what actually happens inside those decisions. Their value was domain context and genuine opinions. The function was almost incidental.

The implication for readers: a design leader with 20 years of broad experience across industries is probably a less compelling candidate than a design leader who spent a decade embedded in healthcare IT. Not because the first person knows less, but because the second can answer very specific questions about how healthcare organizations buy and evaluate software — which is exactly what a consulting firm or investor needs.

The vertical matters more than the title. If you have deep experience in a specific industry, that experience likely has a market on these platforms. If your career has been broad and cross-industry, be realistic about the call volume you’ll see.

Before registering, ask yourself: what are two or three specific questions someone doing research in my industry would pay to ask me? If you can name them, you’re a viable candidate. If you can only describe general functional expertise, temper your expectations accordingly.

How to Get Started and What to Expect

The major platforms for senior professionals are GLG, AlphaSights, Dialectica, and Third Bridge. Each has somewhat different industry focus and call volume; GLG is the largest, Dialectica is growing and currently has less competition for expert slots. Registration is free on all of them.

Your profile matters more than most people realize. Platforms pre-screen experts against client briefs using qualifying questions. How specifically you describe your industry context and the types of decisions you’ve been involved in directly affects how often you get matched. Generic profiles get fewer calls.

One thing worth understanding about the model before you sign up: expert networks are push, not pull. Once your profile is live, the platform does the work of matching you to briefs — you don’t go looking for calls. That’s the appeal. But it also means you have no control over volume or timing. Depending on how well your vertical maps to active client demand, you might get a steady cadence of calls, a cluster of them around a particular market moment, or very little. It’s not a path you can manage or accelerate through effort. You make yourself available and let the market find you.

Income from expert networks is transactional and immediate but not predictable. The right mental model is supplementary income, not a primary revenue stream. It generates meaningful dollars while you’re building something else — a consulting practice, a fractional portfolio, or in some cases the board relationships covered in the next section. It also functions as market validation: consistent calls on a particular domain are a signal that your expertise has genuine scarcity value in that vertical.

One compliance point most content ignores: many employers restrict outside consulting, and expert network calls almost always qualify. Check your employment agreement before registering, particularly if you’re still employed. The constraint stack from earlier in this series applies here.

Board and Advisory Roles — A Different Game

Formal board seats and advisory roles share the “monetize expertise” premise but operate on a completely different timeline, with a different value dynamic and different risks.

The distinction most people miss: a formal board seat involves governance accountability, fiduciary responsibility, and real organizational influence. An advisory role involves periodic input, no real authority, and sometimes no compensation. Both get called “board work.” They’re not equivalent, and conflating them leads to fuzzy thinking about what you’re actually pursuing.

What advisory work can pay at the top end is higher than most people assume. A colleague who works with advisors professionally shared a framework he observes in practice. Three tiers emerge. The baseline tier delivers execution and results. The mid-tier brings strong client presence and interaction skills. The top tier operates from a kind of deeply ingrained self-belief, where body language and framing naturally communicate executive-level expectations without effort. The highest-paid advisors don’t just deliver more. They show up differently.

Compensation at the top tier can reach roughly $20,000 per month for approximately four days of work. Equity is part of some arrangements; for advisors who have already accumulated significant wealth, equity often becomes the more meaningful component than cash.

These aren’t aspirational outliers. They’re the upper end of a real and functional market. Getting there requires being honest about which tier you’re actually operating at, and why.

The Career Ladder Most People Skip

The typical framing of “getting a board seat” presents it as a destination requiring years of cultivation and the right connections. That framing isn’t wrong, but it obscures a more navigable path: unpaid advisor, paid advisor, formal board member.

Most people who want board seats skip the middle step. Advisory roles are more accessible than formal governance positions, they build the relationships and track record that eventually lead to board seats, and the better ones pay meaningfully while doing so. Starting as an unpaid advisor to a company in your domain — offering genuine value, showing up with the habits my colleague described — is a more reliable path to a formal governance role than purely networking toward one.

Nonprofit board service is worth naming specifically here. It’s often overlooked by people who have their eye on corporate governance, but it’s one of the most accessible first rungs on the ladder. Nonprofits actively recruit senior professionals with operational, financial, and strategic experience. The governance responsibilities are real, the commitment is genuine, and the experience is directly transferable when you’re being considered for paid advisory or corporate board roles. If you’ve never served on a board and want to, a nonprofit board is often the right place to start.

The honest timeline for a formal board seat at a for-profit organization worth joining is 18–24 months of deliberate cultivation: becoming visible in the right professional communities, building relationships with board members and executives at target organizations, and developing a clear answer to the question every board asks implicitly — what specific governance value do you bring that we don’t already have?

The income tension is real. Board cultivation doesn’t pay while you’re cultivating. For someone with runway concerns, that creates an obvious sequencing problem.

This is where expert networks and board ambitions complement each other more directly than most people realize. The calls get you in front of investors and executives doing due diligence — precisely the people who sit on or advise boards. Getting paid for one-hour calls while building visibility with that audience is a more efficient use of time than purely attending industry events and hoping connections develop.

Who Each Path Is Right For

Expert networks work best for people with deep vertical experience in domains where organizations regularly do research and due diligence — fintech, healthcare, enterprise software, regulated industries — combined with genuine opinions and the willingness to share them directly. Particularly valuable as near-term income for people in transition who have strong industry context but aren’t yet ready to launch a full consulting practice.

Board and advisory roles work best for senior executives with clear functional ownership in areas boards care about (financial, operational, governance, and increasingly AI and digital product), strong existing peer networks at the right organizational levels, and patience for a multi-year process. The advisory ladder — including nonprofit service as a starting point — makes this more accessible than it appears from the outside. But it requires a specific governance value proposition you can articulate clearly — “I’ve been a successful executive” is not one.

Both paths favor people who have already built reputational capital and are looking to convert it. Neither works well as a path for building a reputation from scratch.

Resources and a Personal Note

Both paths have more platform infrastructure and community support than most people discover before they start looking. I’m developing a curated catalog of resources mapped to each pathway in this series, with enough context to evaluate what’s actually worth your time. More on that soon.

In the meantime, if you’re thinking through whether either of these paths fits your situation, reply or reach out. I’m happy to think through it with you.

Take the Assessment

The What Comes Next assessment scores your profile across the dimensions most relevant to both of these paths — expertise scarcity, income variability tolerance, and time investment horizon — and surfaces the tensions specific to your situation. Takes about fifteen minutes.

Next in the series: Entrepreneurship — what it actually requires, and why the sequencing question matters more than most people acknowledge before they start.

–Greg

Have you explored expert networks or advisory roles? What’s been your experience — or your hesitation? Reply and let me know.

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What Fractional Leadership Actually Is — And What It Isn’t

The term gets applied loosely. A three-month engagement leading a team through a strategic initiative. A part-time advisory relationship with an executive title attached. A retained expert who shows up at leadership meetings. All of these get called fractional. Most of them aren’t.

The clearest way to define it is altitude.

A fractional leader operates above the project level — not brought in to execute or direct a specific deliverable, but to orchestrate: deciding what should be worked on, what shouldn’t, and how. It implies a genuine peer relationship with other executives in the organization. You’re not the vendor in the room. You’re at the table.

The time dimension matters too. Engagements shorter than six months are functionally consulting projects with a different billing model. Real fractional work requires enough time to build trust, understand the organization, and accumulate impact. Six months is a floor. A year is more realistic for the kind of change that actually counts.

How It Differs From Consulting — And Where They Overlap

The two paths look similar from the outside. Both involve working across multiple organizations as a capable outsider who gains trust quickly and has to have impact without the full resources of a full-time role.

That last part is the overlap most content skips. When a CDO-level peer described his early experience in a fractional role — walking into a new organization, seeing what could be improved, confronting the question of how to gain trust and bring people along — my response was immediate.

“Welcome to consulting.”

Those challenges aren’t unique to fractional. They are the permanent condition of working from outside an organization, regardless of title or engagement structure.

At DesignMap, our longest client relationship evolved into something that looked more fractional than consulting. One of my partners worked directly with the client’s COO as a strategic sparring partner — fleshing out ideas before they became projects, adding rigor at a level above specific deliverables. Separately, I worked at the capability and resourcing level, figuring out how to staff programs across both organizations. Neither of us was executing projects. We were orchestrating above them. It didn’t start that way — it happened through years of accumulated trust — but looking back, that’s what it was.

Where fractional genuinely diverges: organizational identity (a fractional leader sits inside the leadership team, attends leadership meetings, appears in the org chart), accountability structure (outcomes over time rather than deliverables per project), and BD model (platforms and recruiters handle more of the matching than in independent consulting).

One honest framing worth naming directly: fractional is, at root, a packaging of consulting. Scope, duration, and altitude are the variables. You are sharing expertise from outside the organization, accountable for impact, without the security of full-time employment. The packaging matters — it shapes the relationship, the timeline, and the income structure. But the fundamental condition is the same.

What It Looks Like From the Client Side

Most writing about fractional leadership is from the practitioner’s perspective. The client side is more revealing.

At DesignMap, we’ve had both a dedicated full-time CFO and, more recently, a fractional CFO firm. The full-time CFO was someone whose interests were genuinely aligned with the firm’s. When the business hit a rough patch, he looked at the cost structure, included himself in the analysis, and told me directly that it didn’t make financial sense to have a dedicated CFO. He recommended we transition to a fractional arrangement.

That recommendation cost him his job. It came from real alignment — the kind where someone is thinking about your interests outside of scheduled meetings, without being asked.

The fractional CFO firm is excellent. Structured, capable, well-suited to an agency our size. The weekly check-ins are focused. Things get handled. What’s different is the proactive dimension — the spontaneous “hey, have you thought about this?” that comes from someone genuinely invested in the outcome beyond their defined scope. The relationship is structured differently: a cadence, a scope, a set of responsibilities. What sits outside that scope, I’m still holding.

That residual vigilance is worth naming honestly. From the client side, there’s often a gap between what you’re hoping for — a trusted advisor who proactively thinks about your business — and what the structure tends to produce, which is excellent, reliable, scoped support. Both have value. They’re not the same thing.

The Incentive Alignment Problem

This may be the most underexamined variable in fractional leadership.

A retainer that pays for availability and advice is not the same as an arrangement where the fractional leader has a stake in the outcome. The best full-time hires are effective partly because their incentives are tied to results. A contractor sending a monthly invoice has a structurally different relationship to the work — not because they don’t care, but because the structure doesn’t engineer alignment the way employment does.

If you’re considering a fractional role, it’s worth asking whether any performance-based elements can be built into the engagement. Whether that’s achievable depends on the client’s sophistication. But the absence of it is one reason fractional relationships often feel more like vendor relationships than leadership partnerships, regardless of the title.

The Authority Problem

You hold leadership accountability without the organizational authority that normally comes with it. You influence rather than direct. You’re accountable for outcomes you often can’t control directly.

For some people, this is genuinely fine — even preferable. The organizational politics, headcount responsibility, and budget management that come with full-time senior roles are things many experienced leaders are ready to be done with. Fractional preserves the strategy and leadership work without the overhead.

For others, it creates an untenable situation — and the client conditions have to be right for the arrangement to work at all.

A colleague took a fractional head of design role at a large organization with low design maturity. She received conflicting mandates: preserve team stability on one side, pressure from product partners to cut designers who weren’t moving fast enough on the other. She had accountability for both directives and no actual authority to act decisively on either.

She got stuck with the worst of both worlds: accountable for outcomes, unable to control the conditions producing them.

The organization wanted a transformation. Fractional wasn’t set up to deliver it — not because she wasn’t capable, but because the starting conditions made it structurally impossible.

Before accepting a fractional role, it’s worth asking explicitly: what decisions will I be empowered to make? Who will I have a genuine peer relationship with? What does success look like in twelve months — and is that realistic given where the organization is starting? If the answers are vague, that’s a signal worth taking seriously.

Who It’s Actually Right For

Profile more likely to succeed: VP or C-suite background with clear functional ownership (CFO, CMO, CPO, CHRO, CTO — roles where the model is established and clients understand what they’re buying), strong existing network in the relevant domain, comfort operating through influence rather than authority, and realistic expectations about what’s achievable within the structure.

Profile more likely to struggle: people whose professional identity is tied to building and leading teams over time. The authority gap is persistent, not just an adjustment period. Also: people whose network doesn’t map to growth-stage and mid-market companies (the primary fractional client base), and people expecting short engagements to produce impact that requires months of organizational trust to earn.

The consulting vs. fractional decision comes down to what you’re optimizing for. If it’s independence and you have BD comfort, consulting is probably the better fit. If it’s staying in leadership work with more flexibility, and you’re willing to operate through influence rather than authority, fractional may be right. Many practitioners run both — fractional retainers for income stability, consulting projects alongside. That portfolio approach is common and often sensible, and it’s what the next article in this series covers directly.

To answer the working title honestly: it’s real independence in terms of schedule, client choice, and income structure. It’s not the same as building your own practice. And whether the trade is right depends on your answers to the authority question and the incentive alignment question — both worth resolving before you accept the first engagement, not after.

Resources and a Personal Note

There are structured resources — marketplaces, communities, coaching programs — built specifically for executives making this transition. I’m developing a curated catalog mapped to each pathway that will give you enough context to evaluate what’s worth your time. More on that soon.

In the meantime: this is a path I’ve observed closely from the client side and through people in my network, including some difficult experiences. If you’re working through whether fractional is the right fit for your situation, reply or reach out. I’m happy to think through it with you.

Take the Assessment

The What Comes Next assessment scores your profile across the dimensions most relevant to fractional leadership — independence preference, BD comfort, income variability tolerance, and leadership identity — and surfaces the tensions specific to your situation. Takes about fifteen minutes.

Next in the series: Expert Networks and Board/Advisory — two ways to monetize what you know, on different timelines and with different levels of commitment.

–Greg

Have you considered fractional leadership — or tried it? What has the reality looked like compared to your expectations? Reply and let me know.

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The logic is intuitive. You’ve spent years solving hard problems inside organizations. You know things that took a long time to learn. Why not get paid directly for that expertise, on your own terms?

The problem is a conflation most people don’t catch until they’re already in it: being able to do the work is not the same as being able to run a practice that consistently generates the work. These are different skills, and the second one is where most people underestimate the gap.

I’ve spent 20 years building and running DesignMap, a design consultancy that grew to 50 people at its peak. The work itself was always the part I loved. The practice-building – positioning, BD, pricing, pipeline – that’s what took years to figure out, and where I made the most expensive mistakes. (The Freedom Trade-Off)

This is the second article in the What Comes Next series, which maps eight distinct paths available to senior professionals in transition and the framework for figuring out which ones actually fit your situation.

This article is about what actually determines whether a consulting practice works.

Three Prerequisites Before Anything Else

Before getting into positioning or BD or pricing, there are three conditions worth being honest about. These aren’t soft factors – they’re gates.

Expertise you can package, not just expertise you have. Deep knowledge is necessary but not sufficient. Can you write down your approach? Could you teach it? Could you describe what someone gets at the end of an engagement in concrete terms? If the expertise only lives in your head as instinct and judgment, it’s hard to sell. If you can turn it into something transferable and repeatable, you have the foundation for an offering. (Why Your Next Job Might Not Be a Job)

A network that knows you as a resource, not just as a colleague. Most first clients come from people you already know. The question isn’t whether you know people – it’s whether those people think of you as someone they’d pay for or refer to others when the right problem comes up. Colleagues know what you do. Potential referral sources know what problem you solve and who you solve it for. Most people significantly overestimate how ready their network is on day one.

Runway to survive the ramp. Consulting practices take time to reach steady, predictable revenue. If you need income in 60-90 days, consulting is likely not the right lead path – though it may be exactly the right thing to build toward while something faster-to-income covers the near term. And be honest about what your runway actually is: health insurance alone can add $15,000-20,000 or more per year for anyone leaving employer-sponsored coverage, which changes what “comfortable runway” means in practice. (The Constraint Stack)

Positioning – The Decision That Shapes Everything Else

Most new consultants try to be available for too many types of work. This feels safe. It produces the opposite result: longer sales cycles, more price competition, and unclear referral paths. If people can’t explain what you do in a sentence, they won’t refer you.

The specialist wins, even though specializing is scary. (Why Specialists Win)

Think about it from the buyer’s perspective. If you need help with a specific, high-stakes problem, do you want someone who does many things for many different types of companies? Or someone who has solved exactly this problem, for organizations like yours, multiple times before? The specialist commands a premium because the expertise is less comparable and the risk of hiring them feels lower.

In our own practice, our focus for many years was very specific: enterprise B2B technology companies transitioning from a collection of individual products to an integrated platform. Within that, complex technical domains like networking and security, where the depth required made generalist designers ineffective. That’s narrow. It served us well for a long time. People knew what to hire us for. We weren’t easy to compare against other firms. We could price accordingly.

The mental trick that made it easier to commit: your specialization directs your marketing and business development energy. It’s not a legal contract that forbids other work. You can take work outside your specialization for any number of good reasons. The specialization just tells you which door to walk through first.

The BD Reality

This is the section most consulting advice softens or skips entirely.

Business development in consulting is not relationship management. It’s not thought leadership. It’s not posting on LinkedIn. Those things support it. The core is something more direct: identifying people with the right problem, having a conversation that surfaces it, and closing an engagement. Repeatedly, over time, as a continuous practice.

Closing business requires three things: a compelling offering, access to the right people, and timing. You control the first. You can influence the second. The third is where luck comes in – but luck is something you can shape. (The Role of Luck in Landing New Business)

During the Great Recession, our firm was struggling. We got invited to participate in an RFP for a company in Indianapolis we’d never heard of – ExactTarget. We weren’t sure the odds were in our favor. We competed anyway. We won. That project turned into five years of steady work and the largest growth period in our firm’s history. Luck was clearly involved. But the luck was made possible by a maintained relationship – a former colleague who knew what we did and thought of us when she heard about the opportunity.

Three things consistently distinguish people who build practices from those who don’t:

Active pipeline management. BD has to be treated as a continuous, scheduled activity – not something that happens between projects. Consistency matters more than timing. You can’t predict which conversation leads to work, so you have to keep showing up. Most people stop showing up when they have work, which is exactly when the gap gets built.

Asking for referrals explicitly. Most first-time consultants wait for referrals to happen organically. They rarely do. After a project ends well, ask: “Who else should I be talking to?” This sounds obvious. It took me years to do it naturally.

But the highest-leverage version of this motion happens during an engagement, not after it. When you’re inside an organization and doing good work, there are almost always people in adjacent teams with adjacent problems. The trust is already there – and it’s transferable. Your contact can say “we’re working with Greg and it’s going well” to a peer across the organization, and that introduction carries a credibility that cold outreach never could. Asking mid-engagement – “Is there anyone else here you think I should meet?” – is one of the most productive BD moves available to a consultant, and one of the last ones most people think to make.

The related motion – proactively mapping an organization and systematically reaching out to people you’ve worked with across different parts of the same account – is sometimes called account-based marketing. It deserves its own treatment and I’ll come back to it in a future piece.

Tolerating direct conversations about scope, budget, and fit. Not manipulative sales tactics – but the willingness to have a straightforward conversation about whether there’s a real engagement here and whether you’re the right person for it. Many former corporate professionals find this genuinely uncomfortable. That discomfort is worth working through, because avoiding it is what keeps pipelines empty.

The tension worth naming: high independence preference paired with low BD comfort is one of the most common consulting profile mismatches. The path can still be right – but the BD gap needs a plan. Either build the skill deliberately, find a partner who has it, or start with a path that requires less BD while you build toward consulting.

Pricing – Two Failure Modes

Most new consultants underprice by anchoring to an employee compensation model – take expected salary, divide into an hourly rate, use that as the starting point. It feels rational. It’s wrong. Selling time makes you a commodity, invites comparison shopping, and caps your upside as you get more efficient.

The better question isn’t “what should I charge?” – it’s “what is this work worth to this specific client?” The same engagement can be worth very different amounts depending on who’s buying. Price the client, not the work. (How to Price Your Work, How to Present Your Approach and Get to Yes)

The second failure mode is subtler: underpositioning drives underpricing. If you’re positioned as a generalist, clients comparison shop you against alternatives, and value-based pricing becomes nearly impossible. The positioning decision and the pricing decision are the same decision, made at different stages.

What the First 18 Months Actually Look Like

Months 1-3: activation. You let your network know you’re available, have conversations, and likely land one or two projects through warm referrals. Revenue is inconsistent. This phase often feels like it’s working – but the pipeline usually isn’t actually built yet. It’s being fed by relationships that already existed.

Months 4-9: the gap. The easy warm referrals have been exhausted. The next wave of clients hasn’t materialized. The BD habits needed to sustain the practice are still being built, or haven’t been built yet. This is where most people seriously doubt the model. Many quit here – not because consulting was wrong for them, but because they didn’t expect this phase and didn’t have the runway or the BD discipline to get through it.

Months 10-18: stabilization. If you’ve been disciplined about BD and positioned clearly enough that referrals can flow, velocity starts to compound. Pricing typically increases as you accumulate evidence of outcomes.

The people who get through the gap almost always treated BD as a system rather than a hope, and had enough runway to survive the timeline. You rarely see the direct line from action to result. That doesn’t mean the line isn’t there.

Who Tends to Succeed – And Who Tends to Struggle

This isn’t about credentials or industry. It’s about operating style and situation.

More likely to build a functioning practice: developing or established specialization, a network that maps reasonably to their target client profile, some prior client-facing experience, 12 or more months of runway, and a willingness to treat BD as a learnable skill rather than a fixed personality trait. (The Freedom Trade-Off)

More likely to struggle: a generalist profile without a forcing function to narrow, a network that doesn’t include people with budget and buying authority in the relevant domain, runway under six months, and an expectation that good work generates referrals automatically. Quality is necessary but not sufficient – referrals require that people who’ve seen your work know you’re available, know what to refer you for, and are asked.

The honest note: the people who struggle are often not less capable. Having done many things well across a long career makes it harder – not easier – to position around one thing compellingly. That’s the paradox worth sitting with.

Resources and a Personal Note

One thing that consistently comes up in the research behind this series is how isolated people feel when figuring this out. The assumption seems to be that you have to work through it entirely on your own, from instinct and first principles.

That’s not true. There are structured resources – coaching programs, communities, frameworks – built specifically for experienced professionals building consulting practices. Most people don’t know these exist, or don’t know how to evaluate them relative to their situation. Part of what I’m developing alongside this series is a curated catalog of resources mapped to each pathway. More on that soon.

In the meantime: consulting is the path I know best. If you’re trying to figure out whether it makes sense for your situation – the right sequencing, how to think about your specific constraints, whether the prerequisites are in place – reply to this post or reach out directly. I’m genuinely happy to think through it with you.

Take the Assessment

The What Comes Next assessment scores your profile across the dimensions most relevant to consulting viability – expertise scarcity, BD comfort, financial runway, and independence preference – and surfaces the tensions specific to your situation. Takes about fifteen minutes.

Next in the series: Fractional Leadership – the path that offers many of the same autonomy benefits as consulting, with a structurally different BD model and a more defined entry point for people who want to stay in leadership roles without the constraints of a single employer.

–Greg

Are you exploring consulting as a next step, or have you already tried it? What’s been the hardest part to figure out? Reply and let me know – I read every response.

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“Network more.” “Update your LinkedIn.” “Have you considered consulting?”

Last year I spent several months interviewing five experienced professionals – employed, senior, mostly stable – about how they were thinking through their career futures. They weren’t in crisis. They were planning ahead, trying to understand their options before they needed them. (What Five People Told Me About Going Independent)

What I found wasn’t a motivation problem or a skills problem. It was a design problem. These were sophisticated people who understood risk, who were thinking years ahead – and they still couldn’t get useful guidance. Because most career advice doesn’t account for the actual situation of an experienced professional. It treats everyone the same way.

The result: most people default to one of two moves. They update the resume and start applying – which at least feels like action. Or they pick one alternative path, usually consulting, and commit to it without really understanding whether it fits their constraints or the full range of what was available to them.

Both approaches skip the most important step: figuring out what’s actually viable for your specific situation, right now.

Eight Paths – But That’s Not the Hard Part

There are eight meaningfully distinct paths available to senior professionals navigating transition:

1. Independent Consulting – building a solo practice around specific expertise

2. Fractional/Interim Leadership – part-time executive roles across multiple companies simultaneously

3. Portfolio Career Design – combining income streams (consulting + advisory + teaching, etc.)

4. Entrepreneurship – building a product or service business

5. Board/Advisory – governance roles, formal board seats, advisory positions

6. Expert Networks – paid consultations through on-demand expertise platforms

7. Teaching/Knowledge Transfer – courses, coaching, adjunct roles, content-based income

8. Strategic Traditional Employment – returning to full-time roles, but selectively and on your own terms

The real work isn’t knowing the list – it’s figuring out which paths are viable for your specific situation, and that requires mapping dimensions most people haven’t explicitly thought through.

The Dimensions That Determine Fit

Financial runway
This is the constraint that shapes everything else. Three months of runway and eighteen months of runway don’t just affect how quickly you need income – they change which paths are even on the table.

Runway is also more complicated than it appears. In my research, health insurance came up in nearly every conversation as a non-negotiable requirement. (The Constraint Stack: Why Smart People Stay Stuck) For anyone leaving employer-sponsored coverage, that’s an immediate cost – often $15,000–20,000 or more per year – that has to be covered before you make a single dollar for yourself. That’s not a rounding error. It changes what “comfortable runway” actually means in practice.

BD comfort and appetite
Several paths – independent consulting most prominently – require sustained business development work that is structurally different from anything most corporate roles involved. You’re not managing a client relationship someone else initiated. You’re generating new ones, from scratch, repeatedly.

This isn’t a soft preference. It’s a hard requirement for several of the eight paths. Many people assume they’ll figure it out when the time comes. The research suggests this is one of the most common and costly misjudgments.

Expertise scarcity
Is your knowledge genuinely scarce in the market, or do you have strong experience in a well-populated category? This affects pricing power, the length of your sales cycle, and which platforms are worth pursuing. Expert networks pay $200–500 or more per hour precisely because they’re betting on expertise that isn’t widely available. If your category is crowded, those same platforms become significantly less useful.

Independence versus structure preference
Not just “do you want to be your own boss,” but: can you actually self-direct work without external accountability structures? The research found that even highly motivated, capable professionals underestimate this requirement. Having deep skills doesn’t automatically mean you have the operating system for independent work. As one participant put it:

“I can do so much, but I don’t know where to start. And I don’t have time to waste figuring it out.”

That’s not indecision. That’s the generalist trap – where capability without a structured way to narrow options creates paralysis rather than progress.

Income variability tolerance
Paths differ not just in income level but in income predictability. Some people can absorb a lumpy year, financially and psychologically. Others functionally cannot. This is worth being honest about before committing to a path that produces feast-or-famine revenue patterns.

Time investment horizon
Some paths generate meaningful income within 60–90 days. Others require 18–24 months of consistent effort before the returns become real. Misaligning this dimension with your actual runway is one of the most common – and most expensive – mistakes. Expert network consulting can generate income almost immediately with minimal ramp-up. Building an independent consulting practice to the point of steady revenue is a fundamentally different timeline.

Where the Real Complexity Lives

The dimensions above matter. But they matter most for how they interact with each other.

Most transition frameworks stop at listing variables. This one cross-references them, because the tensions between dimensions are where actual decisions get hard – and where most people stall.

Four of the most common profile tensions:

High independence preference + low BD comfort.
Consulting sounds like the obvious answer for someone who wants autonomy and has strong expertise. It might be right – eventually. But consulting requires a sustained BD capability that most people significantly underestimate. If you want independence but have limited appetite for selling yourself, the path is real but harder than it looks. The question becomes: what’s the plan for the BD gap? Is that a skill you’re willing to build, or does it suggest a different path should come first?

Entrepreneurship as a priority + 90-day income need.
There’s nothing wrong with wanting to build something. But if you need income in 90 days, the timeline question changes everything about sequencing. Expert networks can produce meaningful income quickly with no ramp-up – which might be the smarter near-term move while something larger develops over a longer horizon. These aren’t mutually exclusive goals. They require sequencing, not choosing.

Strong expertise + thin network in your target market.
A consulting practice depends on warm referrals more than most people recognize. If your network doesn’t yet know you as available – or as an independent operator rather than an employee – the sales cycle is long and unpredictable. Expert networks can serve as a faster validation path: you generate income, learn what questions people are actually paying to answer, and build the network that eventually feeds direct consulting work.

Senior identity attached to leadership + reluctance to start from scratch.
Fractional executive work solves a real problem for people who want to stay in leadership without the constraints of a single full-time employer. But it’s worth being clear-eyed about what fractional actually involves: you’re still accountable to someone else’s organization, just on different terms. That’s not the same as independence. For some people, that’s fine – even preferable. For others, it’s a meaningful limitation worth naming before committing.

The What Comes Next assessment does this analysis across ten dimensions and maps your profile to all eight pathways. Takes about fifteen minutes.

Sequencing, Not Just Choosing

One of the consistent patterns from my research was that people framed this as a binary: stay employed or go independent. (What People Actually Need – And What I’m Exploring Next) But the best transitions rarely work that way.

Most of the eight paths aren’t mutually exclusive. Expert network consulting can run alongside building a fractional practice. Teaching can complement independent consulting. Portfolio careers explicitly combine multiple income streams. The question isn’t only which path to choose – it’s which path to start with, given your current constraints, and which ones you build toward over time.

At the start, resource constraints – time, energy, capital – require sequencing. You can’t test everything simultaneously. And for experienced professionals with limited time and high opportunity costs, trying to evaluate all eight paths at once produces analysis paralysis, not clarity.

The most useful near-term tool is a structured 90-day experiment: identify one or two realistic paths based on your profile, design a low-risk test for each, and generate actual signal before committing. Real-world actions that produce feedback are worth more than months of internal deliberation.

What that looks like depends on your profile. Someone with 18 months of runway and strong BD comfort runs a different 90-day experiment than someone with 3 months of runway who needs income now. The dimensions above determine both which paths are worth testing and what a viable test actually looks like.

What This Series Covers

Over the coming months, I’ll go deep on each path: what makes it viable, what the realistic trade-offs are, what the ramp-up looks like, and what kinds of profiles tend to succeed or struggle. The upcoming pieces:

• Independent Consulting

• Fractional/Interim Leadership

• Portfolio Career Design

• Entrepreneurship

• Expert Networks and Board/Advisory – paired, because both monetize expertise through different mechanisms on different timelines

• Teaching/Knowledge Transfer and Strategic Traditional Employment – paired, because these are the two paths people default to, and the default is often wrong

Each piece will be useful as a standalone. All of them connect back to the framework outlined here.

This framework didn’t come from theory. It came from interviewing real professionals navigating this exact transition, building assessments with real profiles, and watching where people consistently got stuck. The central finding from that research: the gap isn’t between employed and independent. It’s between feeling trapped and feeling like you have real options.

If you want to understand which options fit your situation before working through the full series, the What Comes Next assessment does the structured analysis: ten dimensions, eight pathways, personalized trade-off mapping, and a 90-day experiment framework built around your specific profile.

If you’d rather work through it in writing first, start here. Either way – the goal isn’t to convince you that any particular path is right. It’s to help you figure out which ones are actually viable, and which ones aren’t worth your time.

That’s what most career advice skips.

–Greg

What’s the biggest obstacle you’re running into when thinking through what comes next? Reply and let me know – the patterns showing up in responses are shaping what I write next.

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They face real constraints that make exploration feel impossible. Health insurance. Time poverty. Employer discovery risk. Immigration dependencies.

They have too many skills, which creates decision paralysis rather than clarity.

And they’re deeply averse to the performative self-promotion that most advice demands.

But here’s what struck me most: Despite all these barriers, every single person wanted optionality. They wanted to know that if something changed, they’d have choices.

Some were thinking about phased retirement - a way to scale back gradually while generating income. Others worried about forced retirement and needed a plan for staying engaged and earning. All of them understood that traditional retirement might mean 20-30 years without employment income, and that creating alternative revenue streams now could transform what those years look like.

The gap isn’t between employed and independent. It’s between feeling trapped and feeling like you have options.

So what would actually help?

What’s Built for Execution, Not Exploration

Most of what’s available falls into a few categories. These tools work well if you already know what you want to build and just need to execute. But they’re not designed for the exploration phase - the messy work of figuring out what to focus on in the first place.

Career coaching focuses on mindset, confidence, and finding your passion. Useful when you need clarity on personal values, but it doesn’t provide a method for testing whether your ideas are viable or help you navigate structural constraints.

Courses and masterclasses teach specific skills - how to run webinars, how to price consulting services, how to build a course. Great for execution once you know your direction. Not helpful when you’re still trying to figure out what direction makes sense.

Maven and cohort-based courses create peer learning around launching something specific - your course, your newsletter, your coaching practice. They assume you’ve already decided what you’re building and are ready to go. They’re not structured for people who need to explore multiple possibilities before committing.

Recruiters and outplacement services help you find your next traditional role. They’re optimized for placing you in existing jobs, not for helping you test non-traditional paths while still employed.

“Build in public” and personal branding advice assumes everyone can and should be visible. For people facing employer discovery risk or who reject influencer culture, this path is a non-starter.

And then there’s the AI-powered offering and one-to-many advice flooding LinkedIn and YouTube. “Just create a course!” “Build an AI-powered service!” “Launch a group program!” These might be viable paths, but they’re presented as if everyone should do them, without helping you figure out whether your expertise actually makes sense to deliver this way. It’s another source of paralysis, not clarity.

None of these address what I heard in my research:

“I can do so much, but I don’t know where to start. And I don’t have time to waste figuring it out.”

What people need isn’t more motivation, more skills, or a predetermined path. They need structure for exploration. A way to narrow their options, test ideas safely, and make informed decisions about what’s actually viable - all while respecting the constraints they can’t change.

What I Think Is Missing

Based on what I learned, I think there’s a real gap between where experienced professionals are stuck and what’s currently available to help them.

What I keep hearing is a need for structured exploration. Not a program with a predetermined outcome. Not a course that teaches you to do something specific. A process for understanding what you actually have to offer, which directions might be realistic, and what small experiments might be worth trying.

Not quitting your job, building a personal brand, or forcing yourself down a path that doesn’t fit. Something more like creating optionality while staying employed. Building clarity about what’s possible before you need it.

What I Think Would Actually Help

From 20 years of running a design consultancy focused on discovery work, I’ve seen what helps people move from ambiguity to clarity. It’s not motivation. It’s structure. Here’s what I think is needed:

Addressing constraints directly. Whatever this looks like, it has to work for people who can’t be publicly visible, who have limited time, and who need to maintain their current role. Stealth exploration has to be built in.

Peer-based, not guru-to-student. The real value comes from peers working through similar challenges together. No one person has all the answers for every expertise area. Structure and good questions matter more than a single advisor’s experience.

Discovery before commitment. Most programs assume you already know you want to consult or create courses. The harder problem is upstream: figuring out what you could offer that people would actually pay for, which options fit your constraints, and how to test assumptions without betting everything.

No predetermined outcome. Some people might realize their current path is right. Others might identify adjacent moves within their organization. Some might discover a direction worth testing. The point is discernment, not momentum for its own sake.

Respecting the trilemma. People face structural barriers to leaving employment, reject hustle culture, yet want optionality. Most advice ignores this tension. Anything built for this audience has to sit inside that bind, not pretend it doesn’t exist.

Getting out of your head and into the world. The transition from thinking to actually testing an idea with real people is a hard barrier. Small, real-world actions that generate actual feedback are worth more than months of internal deliberation.

What I’m Still Figuring Out

I don’t have all the answers here. I’m thinking through what the right format and structure would be, based on what I learned from these five conversations. Maybe a small peer group working through these questions together over a few weeks. Maybe something else entirely.

What I do know is that the focus would need to be on things like: clarifying what you actually know that others need, understanding your specific constraints, narrowing from “too many options” to testable directions, and designing low-risk experiments that work within those constraints. All compatible with full-time work.

I’m sharing this because I’d genuinely like to hear from people navigating this.

If this resonates, reply and tell me what sounds right, what sounds wrong, and what I’m missing.

If you know someone who might find this valuable, please forward this to them. The people who most need this kind of support are often the least visible because they can’t be public about exploring alternatives.

What Success Would Look Like

If this works, participants would leave with:

Clarity about what they actually have to offer and to whom. A realistic understanding of which paths are viable given their specific constraints. Confidence that they’ve tested their ideas with real people rather than just theorized about them. Connection with peers who understand the challenge. Real-world momentum instead of more internal deliberation.

And most importantly: optionality. The feeling that if something changed, they’d know what to do next.

Not everyone will go independent. Not everyone should. But everyone deserves the choice to explore it thoughtfully, without risking what they’ve built.

That’s what I’m interested in solving.

Does this resonate? What would make it better? Reply and let me know.

–Greg

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The more capable you are, the harder it can be to get started.

This isn’t intuitive. We assume that breadth is an advantage. More skills means more opportunities, right?

But in my research, I found the opposite. The professionals with the deepest, broadest expertise were often the most stuck.

The Capability Paradox

One participant had three graduate degrees and over 15 professional certifications. He’d worked in strategy roles across multiple industries. He could credibly offer services in organizational design, process optimization, technical strategy, or executive coaching.

When I asked what he wanted to focus on, he struggled. Everything seemed viable. Everything seemed interesting. But without a clear focus, nothing felt like the right move.

This is the generalist trap: capability without clarity creates paralysis, not progress.

The Science of Too Many Choices

This isn’t just anecdotal. Research backs it up.

In a famous 2000 study, psychologists Sheena Iyengar and Mark Lepper set up jam-tasting displays at a grocery store. When shoppers were presented with 24 varieties, they were less likely to make a purchase than those presented with just 6 varieties. More options decreased sales by nearly 90%.

Psychologist Barry Schwartz built on this research in his influential book and TED talk on “The Paradox of Choice.” He found that when people face too many options, they experience greater difficulty making decisions, less satisfaction with their final choice, and higher likelihood of decision avoidance entirely.

The same dynamic plays out in career decisions. When you can do many things, choosing one thing feels like closing doors. And for experienced professionals with limited time and high opportunity costs, every choice carries weight.

The Fear of Picking Wrong

Multiple participants expressed versions of the same fear: What if I invest time in the wrong direction?

“The overall process and risk is intimidating. Finding clients, balancing work and life, being compensated enough are all unknowns that make me hesitant to pursue outside opportunities.”

This fear isn’t irrational. These are people with demanding jobs and families. They might have 5 hours a week to explore. Maybe less.

If you pick the wrong direction and invest three months before realizing it won’t work, you’ve just burned your most scarce resource: time.

The result: endless analysis, no action.

When Constraints Amplify the Problem

Remember the constraint stack from the last post? Health insurance. Time poverty. Employer discovery risk.

Those constraints make the generalist trap even worse.

If you had unlimited time and no financial pressure, you could experiment freely. Try consulting in one area. If it doesn’t work, pivot to something else.

But when you’re constrained, you can’t afford to experiment broadly. You need to narrow quickly and test smartly. The problem is that narrowing requires making a choice. And making a choice feels like a big commitment when you don’t have the luxury of being wrong.

One participant with deep, broad expertise across multiple domains struggled specifically with this: the primary friction wasn't capability, it was focus. Without a way to narrow and test quickly, everything remained theoretical.

Capability plus constraints equals paralysis.

What’s Different for Experienced Professionals

Early-career people have time to experiment. They can try five different things, fail at three, and still build a career around the two that work.

Experienced professionals don’t have that luxury. If you’re 50 and thinking about the next 10-12 years of work, you can’t spend 5 years experimenting.

You need to narrow faster. You need to test smarter. You need methods that give you signal without requiring massive time investment.

But most advice is designed for people with more time and less expertise. It doesn’t account for the generalist trap.

These aren’t people looking to reinvent themselves. They’re not trying to become something they’re not. They just want to take what they already know and make it available to people who need it.

But the path from “I’m good at this” to “here’s how you can hire me” isn’t obvious when you’re good at many things.

What’s Next

In the next post, I’ll talk about what people actually need to break through this paralysis. What helps. What doesn’t. And why most “just start” advice misses the point entirely.

But first, I want to hear from you.

Do you struggle with having too many options? How do you decide what to focus on when you could do many things? Reply and let me know.

–Greg

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Constraints drive behavior more than ambition.

Every person I spoke with had capability. Every person had some level of motivation. But most felt stuck anyway.

Not because they lacked drive or skills. But because they faced structural barriers that made exploration feel impossible, regardless of how much they wanted it.

This matters because most career advice ignores constraints entirely. It assumes everyone operates with the same degrees of freedom. “Just start a side hustle.” “Build your personal brand.” “Test your idea this weekend.”

But that’s not reality for most people.

The Health Insurance Problem (And It Just Got Worse)

The most common constraint I heard was health insurance.

“Health insurance is a significant barrier,” one participant told me bluntly. It wasn’t a nice-to-have. It was a non-negotiable requirement that made leaving a traditional W2 role nearly impossible.

And the situation just became significantly more acute.

On December 31, 2025, enhanced ACA subsidies expired. According to KFF (Kaiser Family Foundation), the 22 million Americans who receive marketplace subsidies will see their average annual premiums more than double - from $888 in 2025 to $1,904 in 2026. That’s an increase of $1,016 per year, or about 114%.

For some people, it’s far worse. A 60-year-old earning $64,000 - just above the 400% federal poverty threshold - would pay $14,900 per year in premiums. Someone earning $62,000 would pay only $6,200 because they still qualify for subsidies.

This hits early retirees and small business owners especially hard. Nearly half (48%) of all ACA marketplace enrollees under age 65 are self-employed, small business owners, or work for small businesses with fewer than 25 workers, according to KFF.

One participant explained his thinking: “We’re not really looking to fully retire anytime soon, but we’re also looking to scale back. The challenge there is finding those things to fill those gaps” while maintaining benefits.

For someone supporting a family, the math is stark: going independent now means finding an extra $15,000-20,000+ per year just to maintain coverage you had before. That’s revenue you need to generate before you make a single dollar for yourself.

The conversation always comes back to health insurance. It’s the reason people stay in jobs they’re ready to leave. It’s the reason “just try consulting” isn’t viable advice for most people. And with the subsidy expiration, it just became an even bigger gate.

Immigration Status: The Absolute Gate

For one participant, the constraint was even more fundamental: immigration status.

His visa depended on employer sponsorship. Any exploration of independent work wasn’t just risky. It was legally impossible. His employer wasn’t just his source of income. It was his right to stay in the country.

“My immigration process has been a significant constraint for over a decade, shaping my career and life decisions.”

According to U.S. Citizenship and Immigration Services, many employment-based visa categories require continuous sponsorship from a specific employer. Leaving that employer can restart the entire process, potentially adding years to already decade-long waits.

This creates an absolute dependency. Not “I’d prefer to stay employed.” But “I must stay employed by this specific employer or lose everything I’ve built here.”

For this segment, optionality isn’t just limited. It’s zero.

The Employer Discovery Risk

Even for those who could legally explore, many faced a different constraint: the risk of being discovered.

One participant worked in finance, where he anticipated a likely layoff within the year. But he couldn’t openly explore alternatives.

“I’m extremely concerned about my current employer discovering my explorations, which could jeopardize my severance package.”

This is the catch-22 of employed exploration: The best time to explore alternatives is before you need them. But any visible exploration while employed can be interpreted as disloyalty, potentially triggering the very outcome you’re trying to prepare for.

The result: people who want to explore can only do so in “stealth mode.” No public LinkedIn posts. No visible thought leadership. No attending industry events as a potential consultant.

The irony is that the people who most need to build optionality are the ones least able to be visible about it.

Time and Energy Poverty

Even when other constraints don’t apply, time becomes the limiting factor.

Multiple participants described demanding full-time jobs combined with family commitments that left almost nothing for exploration.

“I’m a little burnt out,” one participant said candidly. He’d been through two acquisitions in three years, had a young family, and felt “significant time poverty due to a demanding full-time job.”

Research from the Pew Research Center shows that parents today spend significantly more time on childcare than previous generations, even as work demands have increased. For dual-income families with children, discretionary time is nearly nonexistent.

This creates a paradox: The people with the most valuable expertise are often the ones with the least available time to package and share it. By the time they get home from work, handle family responsibilities, and manage basic life admin, there’s no energy left for building something new.

“Just spend a few hours on the weekend” sounds reasonable until you’re actually living it.

The Impossible Trilemma

Here’s what makes this particularly challenging:

People face significant structural barriers that prevent them from leaving traditional employment. At the same time, they have a strong aversion to “hustle culture” and performative self-promotion. Yet they desperately want optionality.

It’s a trilemma with no easy solution.

One participant captured this perfectly:

“I don’t want to be the influencer. I’m not doing it for clicks. I’m not trying to be an influencer. I want to add value somewhere.”

But the most common advice for building optionality requires exactly what they reject: constant LinkedIn posting, personal branding, building an audience, creating content for visibility.

They can’t leave their jobs because of insurance, immigration, or family obligations. They can’t explore visibly because of employer risk. They won’t do the performative self-promotion that typical advice demands. Yet they know they need options.

This is why so many smart, capable people stay stuck. It’s not a motivation problem. It’s not a capability problem. It’s a design problem.

The paths that currently exist don’t account for the reality most people live in.

Why This Matters

I’m sharing these constraints not to be discouraging. I’m sharing them because they’re real, and most advice ignores them.

The typical “how to start consulting” content assumes you:

• Can afford private health insurance or don’t need it

• Have no visa or immigration dependencies

• Can be publicly visible without employer risk

• Have 10-20 hours per week of free time

• Can afford to invest months with no income

• Are comfortable with constant self-promotion

For most experienced professionals, at least one of these assumptions is false. Often, several are.

Understanding constraints isn’t about accepting defeat. It’s about designing realistic paths forward.

If you can’t be publicly visible, you need stealth validation methods. If you have limited time, you need high-signal activities that work in 2-5 hours per week. If health insurance is non-negotiable, you need a transition plan that preserves benefits. If you reject hustle culture, you need peer-based accountability instead of audience-building.

The constraints are real. But they’re also not all equal. Some are temporary. Some can be worked around. Some require creative solutions.

The key is acknowledging them instead of pretending they don’t exist.

What’s Next

In the next post, I’ll talk about another pattern I saw: the “generalist trap.” The paradox where having many skills actually makes it harder to get started, not easier.

For now, I want to hear from you.

What constraint feels most significant for you? Health insurance? Time? Employer risk? The influencer problem? Something else entirely? Reply and let me know.

–Greg

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These weren’t people who had been laid off or were actively job hunting. They were employed, mid-to-senior level, mostly stable. But all of them were thinking about what comes next. About optionality. About whether there might be a different way to work.

I wanted to understand: What stops people from exploring independent work? What would actually help? What do they need that they’re not getting?

What I learned surprised me. And it’s shaped everything I’m building next.

Who I Talked To

The five participants represented different industries and roles:

• A product manager at a financial services company

• A portfolio manager at a large bank

• A delivery manager who’d survived two acquisitions in three years

• A strategic leader in a tech company’s CTO office

• A VP at a healthcare startup with a background in management consulting

They ranged in age from late-30s to early 60s. Some had families. Some didn’t. Some were actively exploring alternatives. Others were just starting to think about it.

But they all shared one thing: they were thinking more deliberately about career risk than they had in the past.

What They Told Me

The conversations revealed patterns I wasn’t expecting.

Job insecurity feels systemic, not personal.

Every single person understood that their current role could disappear. Not because they were underperforming, but because priorities shift, budgets get cut, or organizations restructure.

As one participant put it: “It’s not like they need to save money. It’s just that we don’t really need to spend money on this anymore. So let’s get rid of the role.”

This aligns with broader research. A 2023 Gallup poll found that 22% of U.S. workers are concerned about losing their job to technology or offshoring. But what struck me wasn't just the awareness of risk. It was how sophisticated these professionals were about it.

They weren’t panicking. They were planning.

Retirement is evolving.

Most weren’t looking to fully retire. They wanted to scale back. To work less intensely. To stay mentally engaged without the 50-hour weeks.

“We’re not really looking to fully retire anytime soon, but we’re also looking to scale back,” one participant said. “The challenge there is finding those things to fill those gaps.”

This matches what research is showing about phased retirement. Stanford Center on Longevity research shows that more than 7 in 10 American workers think they will continue to work part or full time in retirement, yet only 14% of companies offer formal or informal phased retirement programs. Few employers offer this option even though there's clear demand.

Everyone feels stuck on the first step.

Even when motivated, people didn’t know where to begin. The combination of time constraints, unclear starting points, and fear of wasting effort on the wrong idea created powerful inertia.

“The overall process and risk is intimidating,” one participant told me. “Finding clients, balancing work and life, being compensated enough are all unknowns that make me hesitant to pursue outside opportunities.”

The “influencer” aversion is real.

Multiple participants expressed a strong desire to be seen as credible experts adding real value, coupled with a deep aversion to performative self-promotion.

“I don’t want to be the influencer,” one said. “I’m not doing it for clicks. I’m not trying to be an influencer. I want to add value somewhere.”

This tension between wanting to share expertise and feeling uncomfortable with personal branding came up repeatedly. It’s a significant barrier that most “build your personal brand” advice completely ignores.

Constraints matter more than ambition.

Health insurance. Immigration status. Employer discovery risk. Time poverty with young families. These weren’t edge cases. They were the primary factors shaping what felt possible.

One participant couldn’t seriously explore anything because his immigration status depended on employer sponsorship. Another said health insurance was a non-negotiable requirement. A third worried that any visible exploration could jeopardize his severance package if discovered.

These structural constraints weren’t problems to be solved with better time management or more motivation. They were real gates that made certain paths impossible, regardless of desire or capability.

What Surprised Me Most

I expected to hear about people wanting to escape corporate life or chase entrepreneurial dreams.

That’s not what I found.

Instead, I found pragmatic, thoughtful people who wanted options. Who understood risk. Who were planning years in advance, not reacting in crisis.

They didn’t want to quit their jobs tomorrow. They wanted to know: If something happened, what would I do? Could I build something on the side that gives me flexibility later? Is there a way to test this without risking everything?

The gap wasn’t between employed and independent. It was between feeling trapped and feeling like you had choices.

What This Means

Over the next few posts, I’ll share what I learned in more detail:

• The specific constraints that keep people stuck and why they matter more than motivation

• Why having too many skills can actually be a problem

• What people actually need to make progress (and what doesn’t work)

• Where I think there’s real opportunity to help

These conversations changed how I think about helping experienced professionals explore independent work. Not everyone should go independent. Not everyone wants to. But everyone should have the option to explore it thoughtfully, without risking their current stability.

That’s what I’m working on next.

Have you thought about going independent but felt stuck? What’s holding you back? Reply and let me know.

–Greg

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I’ve been thinking about whether a pattern I know well from design consulting might apply to professionals navigating career transitions right now. I don’t coach career transitioners—that’s not my expertise. But I’ve spent twenty years helping designers level up, and I’ve lived through my own evolution from craftsperson to strategist. I want to share what I’ve seen and explore whether it translates.

Working smarter, not harder

At DesignMap, we try to help our designers maintain work-life balance. Some agencies are known for expecting 60-70 hour weeks, all-nighters, and working weekends. We’ve always tried to instill a different mandate: work smarter, not harder.

What does that mean in practice? If a designer finds themselves cranking out screens without having answers to key questions, they should stop. Step back. Create a model or higher-level artifact that helps the client face the unknown and develop an answer before needlessly executing a solution.

The screens might be part of the eventual solution—or they might be premature. You don’t know until you’ve done the thinking.

This connects to something I mentioned in Part 1: the difference between being stuck in the second diamond (execution) versus doing the first-diamond work (figuring out the right problem to solve). When I coach designers, I’m often pulling them back into the first diamond—not because execution isn’t valuable, but because execution without strategy is just activity.

My own evolution

I think this shift is common for craftspeople. You begin by becoming expert at making something. For me, that progression was: graphic design, then user interfaces, then user experiences, then product strategy, and now edging into business strategy.

At each stage, I reached a point where growth required leveling up—not just getting better at execution, but being more strategic about the impact I could provide. Shifting left in the process. Moving from “how do I make this thing well?” to “what’s the right thing to make, and why does it matter?”

This newsletter is another version of that same evolution. I’m attempting to broaden my impact beyond my firm by sharing what I’ve learned with people outside DesignMap. It’s leverage through teaching rather than leverage through doing.

The pattern I’m noticing

Here’s where I start applying what I know to a context I’m less certain about.

When designers get stuck, they often describe their value in terms of outputs: screens, wireframes, prototypes. The coaching conversation is about shifting to outcomes: what decision are we helping the client make? What problem are we actually solving?

I wonder if professionals struggling to transition to independent work face something similar. They describe their value in terms of functions—”I manage the CRM,” “I produce financial reports,” “I run paid advertising campaigns”—rather than problems they solve.

If that’s true, a useful reframe might come from asking four questions:

What function do you execute? Start with the job-description version. “I manage paid advertising campaigns.”

What business problem does that function address? Go up a level. “The company needs to acquire customers profitably.”

What judgment do you apply that tools and junior people can’t? This is where real value lives. “I determine which audiences are worth pursuing, how to allocate budget across channels, and when to kill underperforming campaigns before they waste money.”

What happens if that judgment is wrong or absent? This reveals the stakes. “Customer acquisition costs rise, profitable segments get neglected, and budget disappears into channels that look good in dashboards but don’t drive revenue.”

If you can answer those questions, you might describe your work differently: not as “paid advertising manager” but as someone who helps companies acquire customers profitably by making the judgment calls that determine whether marketing spend drives growth or disappears.

Where this might break down

My experience is in consulting, where we’ve always had to articulate value to win work. Employees often don’t face that pressure—the “problem” is defined by someone else, and “judgment” is constrained by organizational politics. The reframe might be harder for people who haven’t had to sell their own work before.

It’s also possible that some functions genuinely are execution without much strategic judgment. That’s worth knowing, because it tells you something about what needs to be developed before making a leap to independent work.

What I’d like to learn

If you’re navigating a transition to independent work, I’m curious whether this resonates.

Does the “function vs. problem” distinction map to how you think about your value? Have you tried repositioning your work in terms of problems solved rather than tasks performed? What happened when you did?

And if you’ve made the transition successfully: what shifted in how you described your work? Was it something like this, or something else entirely?

The patterns I’ve seen in design consulting feel applicable here, but I’d rather learn from your experience than assume.

- Greg

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When I first encountered this framing, my reaction was: this is just consulting. Or at least, it’s what consulting is supposed to be when it’s done well.

I’ve been running a consultancy for twenty years. And watching the conversation around “fractional executives” and “orchestrators” and “portfolio careers,” I keep noticing echoes of lessons we learned the hard way about what makes an independent practice sustainable.

At DesignMap, we've long worked with super senior design consultants who augment our team with specialized experience. We call them wandering knights, or ronin—masterless samurai who bring hard-won expertise from engagement to engagement. It turns out this isn't just our quirky hiring practice. The Frak Conference's State of Fractional Industry Report found 120,000 fractional leaders in 2024, up from 60,000 in 2022—a doubling in two years. What struck me most: 72.8% of respondents have 15+ years of experience. The report describes fractional work as "a veteran's game." That maps to what we've seen. This path rewards experience and judgment, not just energy and availability.

What I’ve observed about consultants who thrive

They sell outcomes, not hours. Early in building our practice, we made the mistake of pricing everything by the hour or day. It capped our upside and trained clients to think of us as a cost to minimize.

The shift happened when we started offering a specific named engagement we called a “Visiontype”—a process for aligning teams around a new product vision. It had a clearly defined business problem, outcome, process, and deliverable. We weren’t selling “design help.” We were selling clarity on product direction. That’s when we could price based on value rather than time.

Blair Enns, who wrote Pricing Creativity and has spent decades training consultants on this, puts it well: “Pricing is a creative act. Yours is a customized services firm. Every engagement is a creative act. Every proposal should be a creative act. Every price should be a creative act.” That framing changed how I think about what we sell.

They work across contexts. One genuine advantage of consulting is seeing the same problem in different organizations. A big part of what we do is aligning leadership teams around a new product vision. We’ve done this enough times that we’ve developed a process—stakeholder interviews, co-creation workshops, landscape research—and we know what makes visions stick: real scenarios that feel valuable, realistic rendering that isn’t smoke and mirrors, customer validation, executive sponsorship.

When we walk into a new engagement, we’re not starting from zero. We’re pattern-matching to dozens of similar situations. That cross-context experience is something no internal employee can replicate, no matter how talented. It might also be the thing that’s hardest to automate.

The consultant stereotypes that might actually be features

Here’s where I want to think out loud, because I’ve spent years pushing back against negative perceptions of consultants. But I’m starting to wonder if some critiques describe exactly what an Orchestrator should aspire to.

“Consultants don’t do the real work.”

I’ve never heard this from actual clients. But I’ve heard it from prospective clients—particularly leaders who are also chartered with building internal teams. One went out of their way to proclaim on LinkedIn that dollar for dollar, they would always invest in their full-time team rather than spend money on outside consultants.

I found this both misguided and unnecessarily othering. In any organization tasked with not just executing but innovating, there’s a place for both internal and external expertise. Both have strengths and weaknesses. An experienced leader knows when to leverage each.

The sentiment also felt short-sighted. That leader might one day be a consultant themselves. Many of us end up there, whether by choice or circumstance. Consultants have families to feed, experience to leverage, and value to provide—just like employees. There are good and bad consultants, just like there are good and bad employees.

But setting aside my defensiveness: what if “not doing the work” is actually the point? In a world where execution can be increasingly automated or distributed, maybe the value has shifted to diagnosis, design, and judgment. Maybe the goal is to figure out what should be done and ensure it gets done well, rather than doing it yourself.

I’m not fully comfortable with this. There’s something in me that still wants to make things. But I notice the most successful consultants I know aren’t the ones grinding out deliverables.

“Consultants charge too much.”

This one I’ll defend directly. If you’re solving a problem worth $500K to the client and you charge $50K, you’re not “too expensive.” You’re a bargain. The professionals stuck in hourly billing can never make this case because they’re selling inputs, not outcomes.

Is this the same logic that applies to Orchestrators? I think so, but I’m curious whether the market for independent expertise actually supports this pricing, or whether it only works at the top.

The connection I’m hypothesizing

What if the path forward for displaced professionals isn’t to learn some new model, but to adopt one that’s worked for decades? What if the “Orchestrator” playbook is just consulting, made accessible by technology to people who previously needed a firm’s infrastructure?

I find this encouraging if it’s true. It means there’s a proven path, not just speculation. But it also means doing the work of building positioning, relationships, and a point of view—which is slower and less certain than the shortcuts being sold.

For those of you who’ve worked with consultants (or as consultants): does this connection ring true? What am I overweighting from my own experience?

–Greg

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One crowd tells you to embrace AI and “10x your productivity.” Become a content machine. Use the tools to produce more than you ever could before. The other crowd points you toward gig work and freelance platforms. Monetize your skills by the hour. Stay busy. Keep the income flowing.

I’ve been running a consultancy for twenty years, and something about both paths makes me uneasy. Not because I have data proving they don’t work—I don’t. But because they pattern-match to things I’ve seen fail before.

The volume trap

I keep seeing advice about using AI to produce more content, more deliverables, more volume. And I find myself asking: when has competing on volume ever been a sustainable strategy for an individual?

In design consulting, we use a framework called the double diamond. The first diamond is about figuring out the right problems to solve—why they matter, for whom, and what the payoff is for solving them. The second diamond is execution: actually building the solution. The volume trap, as I see it, is being stuck in the second diamond, possibly executing the wrong thing entirely.

When someone uses AI to produce ten blog posts instead of two, they’re optimizing for execution speed. But if those posts aren’t addressing a genuine need or demonstrating real expertise, what’s the point? You’ve just produced more of something that didn’t matter.

A recent Harvard Business Review article coined a term for this: “workslop.” Research from BetterUp Labs and Stanford found that 41% of workers have encountered AI-generated output that created downstream problems, costing nearly two hours of rework per instance. That’s the hidden cost of volume—someone has to clean it up.

The Wharton School published research on what they call the “AI efficiency trap.” Three-quarters of surveyed workers were using AI in the workplace in 2024, but instead of experiencing liberation, many found themselves caught in a cycle where time savings immediately converted to increased expectations. Workers reported feeling simultaneously more productive and more overwhelmed. That doesn’t sound like a path to sustainable work.

I don’t know where this leads. But I notice the people selling AI productivity aren’t asking what happens when everyone can produce at that volume, or what happens when the AI doesn’t need your prompts anymore.

The hustle ceiling

The advice to “monetize your skills” on freelance platforms feels practical. It’s action. It’s income. But it reminds me of something we’ve lived through at my own firm.

During slow periods at DesignMap, we’ve occasionally offered our designers at close to cost and called it “Staff Augmentation.” It’s the consulting equivalent of hustling—selling hours rather than solving problems. It keeps the lights on. But it’s hard to escape because you’re competing on price, and when you’re competing on price, you have no leverage. The value is defined by the buyer, not by you.

That’s the ceiling I worry about for professionals taking the gig path. You can stay busy. You can generate income. But each project starts from zero. You’re not building anything that compounds. And the moment a cheaper option appears—whether that’s someone overseas, someone more desperate, or an AI tool—you’re exposed.

The scramble

What concerns me most is professionals who end up in these paths not by choice but by circumstance. When you’re scrambling, you can’t be strategic.

We've experienced this directly. A few years ago, we were the UX agency of record for an internal incubator at Google—one of their experimental groups exploring new product directions. We had ten design consultants allocated to that work. Then the initiative was shut down entirely. Overnight, we had a large team without a project, after having let other leads pass because we thought we were covered.

Another time, we had a deal in verbal—contracts being drafted—when our client contact got laid off a week before the engagement was to begin. Gone.

When these things happen, you’re not competing from a position of strength. You’re taking whatever you can get, often at rates that don’t reflect your value, just to keep the team employed. I’ve been there. It’s not a strategy; it’s survival.

This is what worries me about displaced professionals being pushed toward hustle culture or AI volume plays. If you’re building those muscles after you’ve been laid off, you’re doing it from a position of weakness. You’re in the second diamond, cranking out execution, without having done the first-diamond work of figuring out what’s actually valuable.

The question I’m sitting with

Is there a third path? One that isn’t about producing more or hustling harder, but about operating at a different altitude?

I have some hypotheses, rooted in what I’ve seen work in consulting for two decades. But I’m genuinely curious whether the patterns that worked for building a sustainable practice translate to this new landscape of displaced professionals and AI tools.

That’s what I want to explore in the next post.

What’s your read on the paths being sold to professionals in transition? I’m skeptical, but I’m also aware I’m viewing this through a particular lens. What am I missing?

–Greg

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You control the first. You can influence the second. The third is where luck comes in.

But luck, it turns out, is something you can shape.

The Timing Problem

Making a sale requires two parties and serendipitous timing. There’s the customer, who has a problem. There’s you, with a solution. Problem plus solution should equal a match.

Where it gets tricky is timing. The customer has to be aware of their problem and actively looking for a solution at the moment you cross paths. The odds that you’ll just happen to bump into a good-fit customer when they’re ready to buy are low.

But it happens. And when it does, it feels like the universe taking care of you. This is wonderful when it happens, but you can’t run a business on it.

When times are slow and you don’t have enough work, it can be demoralizing. You start to feel powerless against forces outside your control.

The truth is somewhere in the middle. Yes, you need luck. But there’s also a lot you can do to make your own luck. Things that don’t guarantee new business, but increase the odds you’ll be in the right place at the right time.

Think Like an Investor

Smart investors know a few things that apply directly to business development.

I’ve been investing my own retirement savings for years, and the parallels are striking. Consistency matters more than timing. I bought shares of companies I knew and used - Netflix, Apple, Amazon - when they were trading at less than $10 a share. At the time, I had no idea these would become what they are. I just kept investing regularly, diversified with index funds, and held through the ups and downs.

The same is true for business development. You can’t predict which coffee meeting will lead to a project, so you keep showing up. You can’t predict when that person you helped three years ago will refer you to their new company. You just have to be in the market, consistently.

Diversification beats concentration. Your business development should be a portfolio: relationship building, content, referral asks, industry visibility. Any single effort might not pay off. The aggregate usually does.

Most of your effort should be steady and consistent. Tend to your network. Stay visible. Ask for referrals. But occasionally, take a swing at something with longer odds. A competitive RFP. A cold outreach to a dream client. A talk at a major conference. You don’t expect these to hit every time, but when they do, they can change your trajectory.

Working Your Network

Some tactics are about improving the odds on relationships you already have:

Ask for referrals. This sounds obvious, but it took me years to learn that asking for introductions to other parts of a business you’re already working with is one of the highest-yield moves you can make.

Stay top of mind. Don’t pester, but maintain a cadence. Quarterly if you don’t know any better. More strategically timed if you do: end of year when budgets are being set, or when you see buying signals like new funding rounds, leadership changes, or acquisitions.

Track departures. When someone leaves a client for a new company, congratulate them and stay connected. They now know two organizations that might need your help.

Ask explicitly. After projects end well, ask: “Who else should I be talking to?”

Be generous. Give advice and introductions. Reciprocity is powerful, even when it’s not immediate.

Expanding Your Surface Area

Other tactics are about increasing the number of potential opportunities:

Maintain a CRM. It doesn’t have to be sophisticated. A simple database of customers, prospects, and contacts you want to stay in touch with. Your memory isn’t good enough for this.

Meet new people. Attend conferences. Go to meetups. Join industry groups. Teach workshops. Accept speaking invitations.

Write and share your expertise publicly. When someone has a problem and looks you up, there should be something there that demonstrates you understand their world.

Be findable. A clear LinkedIn profile. A website that explains what you do. Show up in the places your potential clients are looking.

Two Stories From My Business

During the Great Recession, my firm was struggling. Small team, little work. We got invited to participate in an RFP for a company in Indianapolis we’d never heard of: ExactTarget. We were referred in by an old boss of one of my business partners.

We’d already learned that RFPs were often a waste of time, especially when the odds weren’t in your favor. We weren’t even in agreement about whether to participate. In the end, we did. We competed against larger, more established firms.

Somehow, we won.

That project turned into five years of steady work and powered the largest growth period in our firm’s history. We went from small project work to annual retainers supporting a dozen designers.

Luck was clearly involved. But we did things to make that luck possible. My partner had maintained a good relationship with her former boss. He knew what we did. He thought of us when he heard about the RFP. And we were open to luck. We competed, even when the odds seemed against us.

Another time, one of our early employees resigned. It’s normal for people to leave for new opportunities, but it wasn’t yet normal for us. We tried not to take it personally. We were supportive. We offered to help however we could with his career going forward.

He ended up at eBay, working on future product concepts. He introduced us to his boss. He invited us to participate in RFPs. Some we won, some we didn’t. Often they brought projects directly to us. We ended up doing years of steady work with eBay. When our main contact left for Google, we followed. They brought us in for projects there too.

The departing employee turned out to be one of our best business development channels. Not because we planned it that way, but because we handled the departure well and stayed connected.

I could tell dozens more stories like these. Each one involves some element of luck. Each one also involves something we did, often years earlier, that put us in position for that luck to find us.

The Long Game

Don’t do one thing and feel like it failed because you didn’t get a deal out of it. This is a long game.

Someone you meet at a conference might reach out two years later when they finally have a problem they know you can help with. Or they might introduce you to someone else who does. You rarely see the direct line from action to result. That doesn’t mean the line isn’t there.

You can control your offering, your outreach, your follow-through, and how you treat people.

You can influence your visibility, your network size, and how often you’re in the right rooms.

You can’t control timing, budget cycles, reorgs, or whether the person you’re talking to has the authority to hire you.

The goal isn’t to eliminate luck from the equation. It’s to put yourself in luck’s path more often. To be ready when the right opportunity comes along.

Stay visible. Tend relationships. Trust that the work compounds, even when you can’t see immediate results.

And when luck finds you, be ready to say yes.

How do you think about luck in your business development? What’s worked for you? Reply and let me know.

–Greg

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I don’t want to write a complicated dissertation about all the elements that go into a business marketing plan: value proposition, positioning statements, mission, vision, all that stuff. Those things matter, but they can wait.

Instead, I want to focus on a simpler, more fundamental choice: Are you positioning yourself as a generalist or a specialist?

This decision affects everything else. Who hires you. What you can charge. How you compete. Whether you win.

The Generalist Appeal

At a high level, these concepts are simple. A generalist can do anything for anyone. A specialist can only do certain things for certain buyers.

There’s real value in being able to do many things. When someone is described as a “renaissance person,” it’s usually a compliment. MacGyver was a badass specifically because he could make anything on the spot to get out of whatever insane life-or-death situation he found himself in.

The breadth feels like an advantage. More skills means more opportunities, right?

The Generalist Problem

Here’s the downside: generalists aren’t experts at anything.

And most buyers aren’t looking for someone who can do many things for many different types of people. They’re looking for someone who is an expert at solving their exact problem, for people exactly like them.

Think about it from the buyer’s perspective. If you need heart surgery, do you want a general surgeon who also does knees and gall bladders? Or do you want a cardiac surgeon who does nothing but hearts, 200 times a year, and has seen every complication that could possibly arise?

The specialist wins every time.

Or think about a tax situation. Would you rather hire a general business attorney, or a tax attorney who specializes in international M&A and has handled dozens of deals just like yours?

The specialist commands a premium because the expertise is worth more.

The Comparison Problem

Here’s another issue with being a generalist: you’re easily comparable to alternatives.

It’s easy to get quotes from a dozen handymen to repair a fence. (No shade on handymen. I aspire to be as skilled as they are. I’ve hired my share. I know there are great ones out there.) The work is straightforward enough that quotes are apples-to-apples. At that point, you’re competing on price.

But try getting comparable quotes for something more specialized. Migrating a complex legacy enterprise system to the cloud. Restoring a historic home to period-accurate specifications. Designing a medical device interface that has to pass FDA approval.

Suddenly, the quotes aren’t comparable anymore. The specialist who’s done this exact thing before has an advantage that’s hard to price-shop.

The Fear of Specializing

I’ve learned in my practice that specializing is scary.

You can’t help but worry: What opportunities am I closing myself off to if I don’t describe all the many things I know how to do, for all the different types of people I can help, in all the different situations?

This fear is real. The danger of specializing is that you over-specialize and there aren’t enough customers to sustain you.

David C. Baker (no relation) helped crystallize this for me. His book The Business of Expertise is essential reading if you’re struggling with this. He makes a compelling case that positioning yourself narrowly is the path to premium pricing and sustainable business.

But knowing it intellectually and actually doing it are two different things.

The Mental Trick That Helps

Here’s what got me over the hump:

Your specialization is what you focus your marketing and sales energy on. It’s who you choose to speak to. It’s not a legal contract that forbids you from taking other work.

You can still decide to take work that comes to you outside your specialization if you need the revenue, want to help a long-time client, or have any other good reason. The specialization just directs where you invest your time in business development.

This mental trick made it easier to commit. I wasn’t closing doors. I was just choosing which door to walk through first.

What Specialization Looks Like

In my design consulting practice, our focus for many years was very specific:

Enterprise B2B technology companies transitioning from a collection of individual products to an integrated platform. Companies that needed help aligning disparate internal stakeholders around a shared vision before actually designing and building the whole thing.

We got even more specialized within that. We focused on complex domains like networking and security, where the technical depth made generalist designers ineffective.

That’s pretty narrow. And it served us well for a long time.

People knew what to hire us for. They knew we’d done it before. We could command premium pricing because we weren’t comparable to general design firms.

Positioning Evolves

Here’s the thing: your positioning can evolve over time.

Our positioning is evolving now. Our clients need something different than they did five years ago. The market has changed. We’re adapting.

But it shouldn’t change as quickly as fashion. Positioning takes time to establish. You need to stay focused long enough for the market to understand what you do and who you do it for.

Think of it like pace layers in a system. Your core expertise might stay stable for years. Your positioning might shift every few years as the market evolves. Your specific service offerings might adapt more frequently based on what clients need.

The key is not changing so fast that no one knows what you do.

How to Figure Out Your Specialization

You can’t just guess at this and get it right. You have to experiment.

Test different value propositions with different target customers. See what resonates. See where you win. See what people are willing to pay for.

This experimentation is critical, and I’ll write more about it in future posts. For now, just know: you’re not looking for perfection. You’re looking for something specific enough to be valuable, but broad enough to be sustainable.

Where to Go From Here

There’s a lot more to say about positioning. How it connects to your value proposition. How to test whether your positioning is working. How to communicate it clearly in your marketing and sales. How to know when it’s time to evolve.

I’ll cover those in future posts.

For now, ask yourself: Are you positioning as a generalist or a specialist? And if you’re a generalist, what’s it costing you?

What’s your positioning? Are you struggling with the choice between generalist and specialist? Reply and let me know.

–Greg

This post is about reaching agreement on a high-level scope, budget, and approach. A detailed statement of work comes later, documenting and adding specifics to what you’ve already agreed to. But first, you need to get alignment on the basics.

Here’s how I approach it.

Make the Business Case First

When I send a proposal via email, I start with context. This is where you make the case that what you’re proposing is worth what you’re quoting.

Thank them for their time in the last meeting. Then play back the situation as you understand it:

• What the problem is and why it matters

• What the opportunity looks like

• What makes this moment urgent

• What the pain points are if they don’t address this

• What gains they’ll capture if they succeed

• What the value of a solution would be

This isn’t just politeness. You’re connecting the dots. You’re laying out why this investment makes sense. You’re reminding them of everything you uncovered in discovery, framed in a way that justifies action.

If you’ve done your discovery well, this section writes itself. You’re simply playing back what they told you, organized in a way that makes the case for moving forward.

This does two things. It shows you were listening. And it confirms alignment before you get into the details. If you’ve misunderstood something, they’ll correct you before you’ve invested hours in a detailed scope of work.

Offer Three Options

After the context, I provide a high-level description of the proposed process. Then I offer three versions of the plan: small, medium, and large. Sometimes I’ll name them something more descriptive, like Rapid, Balanced, and Deep, or whatever captures the trade-off each represents.

The largest option should be what you’d propose in an ideal world where money and time were no object. The full solution. Every deliverable. Maximum depth.

The smallest option should meet their main objectives, but with clear trade-offs: fewer stakeholders involved, less detail, lighter documentation, faster timeline.

The middle option balances value and investment. It’s usually where most clients land.

Why Three Options Works

Offering options does a few things:

It gives the client agency. They’re not just saying yes or no. They’re choosing what’s right for their situation.

It makes the conversation about scope and value, not just cost. “Which of these best fits your needs?” is a different conversation than “Can you do it cheaper?”

It anchors high. When you put a larger number on the table, the middle option looks more reasonable by comparison. This is a well-documented psychological effect.

I learned this technique from Blair Enns, a sales consultant and author of The Win Without Pitching Manifesto. Blair has written extensively about anchoring as a pricing technique. His work is a great resource if you want to go deeper on selling expertise.

Don’t be afraid to propose what the ideal engagement would look like, even if you suspect they won’t choose it. Sometimes they surprise you.

Make the Options Comparable

Here’s something important: I design the three options to be comparable, not wildly different.

Divergent ideas can and should be explored, but at an earlier stage in the conversation. By the time you’re proposing, you should have alignment on the general approach. The three options are variations on that theme, not completely different strategies.

I make the options comparable by using the same phases across all three. In my work selling product strategy and design, I use the double diamond design process. It’s a flexible framework that can contain just about any project type: Discover, Define, Develop, Deliver.

Each option includes all four phases. What varies is the depth, detail, number of stakeholders, deliverables, and timeline. This makes it easy to compare. The client can see exactly what they’re getting or giving up with each option.

Whatever framework you use in your work, apply it consistently across all three options. This clarity helps clients make informed decisions.

Leave Room to Customize

In my emails, I always say these options are starting points. We can customize, create composite plans, or adjust based on their feedback. I ask for questions and offer to meet to discuss.

This keeps the conversation going. It also signals that you’re flexible and collaborative, not rigid.

Once you get a signal on which direction makes sense, you can move to a detailed statement of work with specific deliverables, timelines, and terms.

What Comes Next

Once you have agreement on approach and budget, there’s still work to do:

Writing the detailed proposal. The statement of work (SOW) that documents everything: specific deliverables, timelines, milestones, payment terms, and legal language. This is where you formalize what you’ve agreed to. I’ll cover this in a future post.

Presenting to stakeholder groups. Sometimes you need to pitch your approach to a room full of people. How you present, what materials you bring, and how you handle questions can make or break the deal.

Demonstrating your expertise. Sharing relevant case studies and similar projects you’ve completed is critical. Clients need to see proof you’ve solved problems like theirs before.

Dealing with competitive situations. What do you do when you’re one of several firms being considered? How do you position yourself without giving everything away?

Navigating procurement. At larger companies, you might reach agreement with your champion, only to be sent to procurement for another round of negotiation. This requires a different skillset entirely.

These are all topics for future posts. For now, focus on getting agreement on your approach.

Quick Recap

• Start with context that makes the business case

• Offer three options: small, medium, large

• Make them comparable using a consistent framework

• Anchor high with the largest option

• Leave room to customize

How do you present approaches? Have you tried the three-option approach? Reply and let me know.

–Greg

It’s the wrong question. The better question is: “What is my work worth to this specific client?”

Don’t Compete on Price

When thinking about pricing, your goal is to avoid easy comparison to other options. If clients can line you up against five other consultants and compare hourly rates, you’ve already lost. Someone will always be cheaper. If you’re based in the US and not running an AI-powered operation, you will not win a price war.

Instead, compete on quality. On accuracy. On client experience. On customization. On fit. On the specific value you deliver.

Don’t Sell Your Time

The most common pricing model is time and materials. You estimate hours, multiply by your rate, and send a quote. It’s simple. It’s also the lowest common denominator.

Selling time makes you a commodity. It invites clients to comparison shop. It focuses the conversation on cost rather than value. And it caps your upside: if you get faster and more efficient, you earn less.

This doesn’t mean you shouldn’t know how much time something takes. You need that to understand your margins. But it shouldn’t be how you sell.

Sell the Value Instead

Value-based pricing focuses on what your work is worth to the client, not what it costs you to deliver. Money saved. Money gained. Risk avoided. Opportunities captured.

If your engagement helps a client avoid $500K in support costs, or accelerates a product launch that generates $2M in new revenue, the value of your work isn’t measured in hours. It’s measured in outcomes.

This is easier said than done. To price based on value, you need to actually understand the value. That requires a real discovery process.

Price the Client, Not the Work

Here’s something that took me years to fully understand: the same work can be worth very different amounts to different clients.

An enterprise company and a Series A startup might both need help with the same type of problem. The deliverables might look similar. The process might be identical. But the value is completely different.

Enterprise clients have more on the line. The upside of getting it right is larger. The downside of getting it wrong is more severe. A product launch at a Fortune 500 company might represent $50M in revenue. The same type of launch at a startup might represent $500K. Your work isn’t worth the same in both cases.

Enterprise clients face more complexity. More stakeholders. More regulatory requirements. More technical integration. More organizational politics to navigate. Your work has to account for all of this.

Enterprise clients have more budget. This isn’t about gouging. It’s about alignment. A $200K engagement that delivers $5M in value is a bargain for an enterprise client. That same $200K might be impossible for a startup, even if the work would be valuable to them.

This doesn’t mean you can’t work with smaller clients. It means you should think carefully about how you price different types of engagements. You might offer a lighter version of your service to smaller companies at a lower price point. Or you might focus exclusively on enterprise clients who can afford your full offering.

The point is: don’t set a single price for your work as if it exists in a vacuum. The value depends on who’s buying.

Discovery is the Foundation

Consulting engagements are often “complex sales.” You can’t just send a quote. You need to understand the prospect’s situation, goals, constraints, and context. Often over multiple conversations. With multiple stakeholders.

This takes time, but it’s not wasted effort. Discovery is where you learn what the work is actually worth to them. It’s where value-based pricing becomes possible.

If you can, consider offering a paid diagnostic engagement. This is a short, scoped project where you’re paid to deeply understand a client’s problem and recommend a solution. Examples include:

• A design audit that assesses their current product experience

• A process review that identifies bottlenecks and inefficiencies

• A strategy sprint that defines priorities and a roadmap

• A technical assessment that evaluates their infrastructure

Diagnostics let you get paid to do discovery. They also establish your expertise and often lead to larger engagements.

The Questions That Uncover Value

I’m not a professional salesperson, but I’ve sold a lot of consulting engagements over 20 years.

The approach that resonates most with me comes from a book called Let’s Get Real or Let’s Not Play by Mahan Khalsa. It’s a weird title, but the methodology is logical and works well for value-based pricing.

Here are the questions I use, most adapted from that book:

Understanding the problem

What are all the issues you need help resolving? Get everything on the table. Ask “why” multiple times to get to root causes. Confirm you’ve captured all the issues. Ask them to prioritize.

How do you know these are problems worth addressing? Begin to understand the impact. Connect their problem to larger business measures.

What is the impact on the business of not addressing these issues? Try to get specific. Would support costs increase? Would customer satisfaction drop? Would churn go up? Put dollars to it if you can. These numbers will later justify your fee.

What would the payoff be if success is achieved? Sometimes this is the inverse of the pain. Sometimes it’s new opportunities: increased market share, fewer heads needed, annual savings of $X. This is the value you’re pricing against.

Understanding the context

Who else is affected by this? Who else benefits from the solution or is harmed by the status quo? These people may help make the case for funding. Also identify hidden stakeholders who need to accept any solution you propose.

How does this fit into the big picture? Are there company goals or OKRs this aligns with? Executive initiatives? A conference or press event this needs to support? Connecting to larger priorities helps justify investment.

What has stopped you from addressing this in the past? This uncovers gaps in expertise (which you might fill), timing issues, lack of alignment, political challenges, or simply that the pain wasn’t acute until now.

Understanding the buying process

What investment feels appropriate? It’s uncomfortable to talk about money, but you have to. Sometimes clients have a fixed budget. Sometimes they need to make the case for it. Remind them of the cost of inaction and the payoff of success.

What kind of internal resources can you bring to bear? You’ll likely work with client stakeholders. Identify who their core team will be. The work shouldn’t just be thrown over the wall when you’re done.

What is your time frame for starting? How quickly does the sales process need to move? Are there external deadlines driving urgency?

Along with yourself, who really cares about this decision? Uncover other stakeholders who need to approve any proposal. This might be a VP or executive you haven’t met yet.

Where are you at with evaluating options? A fair question. You’re investing time to develop a proposal. You should know if they already have a preferred partner, if you’re competing against six firms, or if they’re just starting to explore.

What criteria will you use to make your decision? If they tell you, you can address it directly. Is it domain expertise? Cost? Speed? References?

What other options are you considering? Besides other consultants, they may be considering software solutions, an internal effort, or just not tackling it right now.

Where will the money come from? Another uncomfortable question, but important. If budget is pooled from multiple groups, you’ll need to speak to the value for each.

You mentioned a start date. What needs to happen before that? Helps you understand the process. Maybe they need to talk to two more firms. Maybe they need internal alignment first.

What are our next steps? More meetings may be needed. More materials to review. Figure this out before ending your conversation.

What Comes Next

At some point, you’ll have enough information to propose a solution. In the next post, I’ll cover how to structure a proposal, why I always offer three options, and the most important thing most consultants forget: making your buyer successful.

What’s your current approach to pricing? Are you selling time or value? Reply and let me know.

–Greg

Round after round of layoffs. The reasons vary: overhiring during the pandemic, mandates to adopt AI and increase efficiency, pressure to boost stock prices through cost cuts, shifting budgets toward AI infrastructure. Whatever the explanation, the result is the same. Experienced professionals are being displaced.

If you’re one of them, your instinct might be to find another full-time role at another company. That’s a reasonable path. But it’s not the only one.

Here’s another option worth considering: What if you packaged your expertise and sold it directly to companies that need it?

The Opportunity

While large enterprises are cutting costs, smaller companies are hungry for expertise. Series A and B startups. Mid-sized companies trying to professionalize. Growing teams that need to level up but can’t afford to hire a full bench of senior leaders.

These companies have real problems. They’re feeling pressure to adopt AI. They need better systems and processes. They want to move faster but don’t have the internal experience to figure out how.

They need people like you. Not as a full-time employee, but as an expert who can come in, solve a specific problem, and help them move forward.

Do You Have Something to Offer?

Not everyone is cut out for consulting. But if you’ve spent years inside a large organization, you may have developed something valuable without realizing it.

Ask yourself:

Have you figured out a better way to do something? Maybe you’ve developed an approach that’s easier, more efficient, produces better results, or provides more transparency than what most teams do. Something you take for granted that others would find valuable.

Can you systematize it? Could you write it down, create a framework, build a template? If your expertise only lives in your head, it’s hard to sell. If you can turn it into a repeatable process, you have something transferable.

Could you teach it? Could you train others to implement your approach? Could you help a team get started, then hand it off? If so, you’re not just an expert. You’re someone who can create lasting value for an organization.

Can you package it into clear deliverables? Being great at something isn’t the same as having something you can sell. A sellable offering has defined scope and outcomes a buyer can understand. If you can’t describe what someone is paying for, it’s hard to put a price on it.

Would someone actually pay for it? This is different from “is this valuable?” Some expertise is genuinely useful but companies expect to get it for free, or handle it internally. The question isn’t just “can I do this?” but “is there a market for paying someone to do this?”

If you answered yes to these questions, you might have the foundation for an offering.

Can You Actually Do This Right Now?

Having expertise isn’t enough. You also need the conditions to make consulting viable.

Do you have financial runway? How long can you afford to experiment before you need income? Some people have savings or a partner with stable income. Others need money immediately. This dramatically affects whether consulting makes sense right now or whether you need to find something else first.

Do you have a network? Most first clients come from people you already know. Do you have relationships from your career that could become clients or refer you? If you spent 15 years at one company and don’t know anyone outside it, that’s a different starting point than someone with broad industry connections.

Do you have access to buyers? Having expertise and having access to people who would buy it are two different things. Can you reach decision-makers at companies that need what you offer? If not, how would you find them?

Be honest with yourself about where you’re starting from. These aren’t reasons to give up, but they’ll shape how you approach the next steps.

One more thing: You don’t have to choose one path or the other. You can explore consulting while also looking for a full-time role. In fact, the exercise of distilling your expertise, thinking through how to communicate its value, and articulating the problems you solve might actually make you a stronger candidate in your job search. The clarity you gain from asking “what would I offer as a consultant?” often translates directly into better positioning for full-time roles.

What Might This Look Like?

Here are some examples of experienced professionals and the kinds of offerings they might build:

People Operations / HR

• A compensation specialist could help startups design salary bands and equity structures

• A talent acquisition leader could help companies build recruiting processes and interviewing frameworks

• An L&D professional could help teams develop onboarding and training programs

Finance

• An FP&A leader could help growing companies build financial models and forecasting processes

• A controller could help startups prepare for their first audit or set up accounting systems

Product

• A product manager could help early-stage companies define product strategy and roadmapping practices

• A product ops leader could help teams implement better prioritization and planning processes

Design

• A UX leader could help companies establish design systems or user research programs

• A design ops professional could help scale-ups build their first design team

Engineering

• A platform engineer could help companies design scalable infrastructure

• A security leader could help startups implement security practices before their first enterprise sales

Marketing

• A demand gen leader could help companies build lead generation systems

• A product marketing professional could help with positioning and launch playbooks

Operations

• A rev ops leader could help companies connect their sales and marketing systems

• A business ops professional could help scale operations during rapid growth

These are just examples. Your offering will depend on your specific experience and what problems you’ve learned to solve.

Test Before You Build

Before you invest heavily in an offering, you need to find out if it resonates. And you need honest feedback.

Here’s the hard truth: friends and family will tell you what they think you want to hear. They’ll be encouraging because they care about you, not because your offering is strong. You need reactions from people who don’t know you and have no reason to be polite.

The good news is you can test before you have everything figured out. You don’t need a website, a logo, or a polished pitch deck. You need conversations with potential buyers who can tell you whether the problem you solve is real and worth paying to fix.

I’m not an expert on product discovery. I know just enough to be dangerous. But I know how important it is.

If you want to go deeper, I recommend The Mom Test by Rob Fitzpatrick. The title refers to the idea that even your mom will lie to you about your business idea because she loves you. The book teaches you how to ask questions that get honest, useful answers. It’s short, practical, and will save you from building something nobody wants.

I’d also recommend looking at Jim Morris at Product Discovery Group. Jim is a product discovery coach I’ve worked with. His focus is on products rather than services, but the principles of validating ideas with real customers apply just as much to consulting offerings.

The core lesson: validation from strangers is what matters. Don’t skip this step.

What’s Next

In future posts, I’ll go deeper on developing your offering, experimenting with positioning and packaging, and getting feedback from the market before you commit.

For now, start with the basics. What do you know how to do that others would find valuable? Can you systematize it? Could you teach it? Do you have the runway and network to make this work?

If the answers are yes, you might have the foundation for something real.

What expertise have you developed that might translate into an offering? Reply and tell me what you’re thinking.

–Greg