When I first started writing about “The Founder’s Journey,” I framed it as a set of transitions. That framing came from observation more than theory: founders move from idea to product, from product to business, and that transition eventually becomes a much longer process, something harder to name but very real — owning and running a company that exists independently of them.
I still think that framing holds. What has changed, after several more years of working closely with founders, is how I understand success along that path.
The short version is this: most of the founders I’ve worked with have been successful. Far more of them than people would tend to assume. But almost none of that success looks like what the founders imagined when they started.
That’s not a failure of ambition. It’s a misunderstanding the meaning of success.
There is a persistent belief in startup culture that success should feel like momentum — steady, visible, accelerating. And sometimes founders get to ride that wave. But, in reality, progress is only rarely that monotonic. Mostly forward movement is uneven, uncertain, interrupted, and often, frankly, discouraging.
And yet, when you look back over a longer horizon, progress is being made. Even when it does not fell like it.
This is something I see every January. It is a time of year when I will often ask founders to look back twelve, eighteen, twenty-four months and describe the problems they were dealing with then. Not the headlines — the real problems. Cash flow uncertainty. Customer credibility. Technical risk. Personal doubt.
Almost without exception, those problems will be gone.
And… they will have been replaced by new ones. Bigger ones. More complex ones. Problems that only exist because the earlier ones were solved.
That is not stagnation. I’m sorry to say that it but this really just success quietly doing its work. If that is reality you cannot take pleasure in, you are unlikely to enjoy running your own business.
Which brings us back to the Stockdale Paradox. Which again is something I have written about before.
The Stockdale paradox is often summarized as the need to balance realism and optimism: never losing faith in eventual success while confronting brutal facts along the way. And it is that, but in practice, it is more subtle than that.
Living with Stockdale mean reconciling yourself to the fact that success does not come from constant or accelerating progress. It comes from negotiating situations as they arise and finding a way to keep moving forward.
Not heroically. Not dramatically. Persistently. And without giving in or giving up.
Founders who succeed are not the ones who avoid brutal realities. They are the ones who learn to face them without assuming that each one is an indictment of their competence or their idea.
Early on, those realities are small and sharp. Later, they become larger and more systemic. The fact that you are dealing with bigger problems is usually not a sign that something has gone wrong. It is a sign that you’ve earned the right to face them.
Which is great and all, but not always a source of immediate comfort – to be fair. Which is why I have so much respect for the founders I work with. Without exception they have managed and continue to manage this feat.
This is one of the most important realizations I have had – when I take the time to look back on my own “journey” as a coach and mentor. When I began coaching founders, most of my work was focused on the first transition: idea to product. Helping teams turn insight into something tangible. Something testable. Something that was designed to address a customer’s real needs.
That transition is hard, but it has a particular character. There is a clear sense of movement. You are building toward something concrete, and when you really start to understand the difference between a good idea and a great product — you know you’ve crossed a threshold.
What I didn’t fully appreciate in the early days is how little of the founder’s life is actually spent there.
The second transition — from product to business — is where most founders spend the majority of their time. Years, not months. This is the long middle of the journey, and it is far less tidy.
This is where founders learn that having a product is not the same thing as having a company. Where sales cycles, cash flow, supply chains, hiring, operations, management, leadership and customer expectations begin to interact in ways that cannot be solved with a single clever insight.
It’s also where many founders begin to feel uneasy — not because they are failing, but because the rules have changed. Because they start out doing things at which they are hugely competent. And end up having to be good at things they have no experience with and no idea how to become competent.
So, one of the most ultimately reassuring things I can tell early-stage founders is this: it takes a long time to feel at home in the role of owning and running a company.
Years.
Actually, check that. This statement is hardly ever reassuring to early-stage founders, it’s an essential reflection to the ones that survive the very early stage though. The plain fact is there is no shortcut to this. No accelerator, no funding round, no milestone that suddenly makes it feel natural. No silver bullet that slays the boss demon and clears the way out of the dungeon.
Instead, you just have to get more comfortable being in that place. It is not something that has to be passed through, it’s a reality that has to be lived in. And what creates that sense of footing is exposure — to decisions, to consequences, to uncertainty — repeated, and repeated, and repeated over time.
To live with Stockdale, is to learn that success is not comfort, it is the ability to learn and apply the hard lessons that are necessary to stay on the path. Early in the journey, founders are often uncomfortable not because they are unprepared, but because everything is new. Later, they are uncomfortable because the stakes are higher. The discomfort changes shape, but it never fully disappears.
What does change is confidence in one’s ability to deal with what comes next.
That confidence is earned, not granted.
Looking across the founders I’ve worked with, a pattern emerges that is obvious to me. Again, its all about the Stockdale paradox. Every successful founder does the same thing when they encounter a contingency, a failure, a change of plan, an obstacle.
They keep moving forward.
Sometimes that movement is visible. Sometimes it is internal — a clearer understanding of the market, a better sense of priorities, a more grounded leadership style. Sometimes it is simply the discipline to not overreact.
None of this happens quickly. Almost none of it happens smoothly.
But it does happen.
And when founders pause long enough to look back, they are often surprised by how much ground they’ve covered — not in a straight line, but in a series of small, necessary confrontations with reality that they survived and ultimately resolved.
Perhaps the most important thing I’ve learned is that success is not a place you arrive at. It is a state you maintain.
Markets evolve. Companies grow. Roles change. The founder you need to be this year is not the founder you needed to be two years ago — and will not be the one you need to be two years from now.
Seen this way, the founder’s journey is less about reaching an endpoint and more about developing the capacity to adapt without losing direction.
That capacity compounds. Quietly. Over time.
For founders early in the cycle, this can be hard to believe. Everything feels urgent. Every obstacle feels consequential. But the longer view tells a different story.
If you stay focused on moving forward — not quickly, not perfectly, but deliberately — you will find your footing.
It takes time. It takes patience. And for most founders, it takes longer than expected.
But for those who persist, it does happen.