The decision that ended one chapter of my life happened on a Friday night in Amsterdam during a curfew. It was 2021. A friend had come into the city for a conference and stopped by my place for drinks. We lost track of time, drank too much, and broke the 9 PM curfew without noticing. At some point I started telling him, again, about being unhappy in the agency I had co-founded twelve years earlier. About wanting to move to Mexico. About not knowing what to do.
He looked at me and said: either you go, or you stop talking about it to me.
He sounded annoyed. He had heard the same speech before. More than once.
Something landed that night. The conversation I had been rehearsing in my own head for years stopped being abstract. On the Sunday we told my parents. On the Monday I told my business partners. A few months later, my wife and our two children and I were in Mérida, México.
That is the story I usually tell, and it is true. But it is also the easy version. It ends on the decision. The actual story is what came after, and that part is much longer and much less neat than I used to be willing to admit.
The posture stays after the role ends
The first thing nobody warns you about, when you leave the thing that has been your professional identity for over a decade, is how strange your relationship to yourself becomes.
For twelve and a half years I had been a co-founder of a creative digital agency. That was the answer to the question "what do you do". That was the shape of my week. That was the lens through which I read industry news, evaluated other businesses, talked to other founders, made friends. It was not a job. It was a posture I had developed to fit a role, and I had been holding the posture so long that I had stopped noticing it.
When you stop, the posture stays. Your body keeps trying to be the thing it was. You open your laptop in the morning and there is no team to lead, no client to call, no problem queue waiting. You catch yourself thinking about pipeline for a business that is not yours. You read a project brief in your head out of habit, on a Tuesday, with nobody to send it to.
That part lasted longer than I expected. Months, easily. Maybe a year.
Mistaking activity for direction
The second thing nobody warns you about is how easily you mistake activity for direction.
In the first couple of years after I left, I did a lot of things. I learned Spanish. I helped friends with their businesses. I tinkered with side projects. I had conversations about what I might do next. I tried a few small ventures. Most of them did not really work, and the ones that did were not the ones I was excited about. I told myself, and other people, that I was exploring. Some of it was. A lot of it was something else - the comfort of being busy enough to avoid the harder question.
The harder question was: what do you actually want to build now, given that the version of you who would have answered that question confidently no longer exists?
I did not have an answer to that question for a long time. I did not even have the right vocabulary for it. The agency had given me an identity, a calendar, a problem set, a peer group, and a sense of progress. Leaving had taken all of those away at once. Some came back quickly. Some did not. Some came back in a different form that took me a while to recognise.
The loneliness of an unstructured year
The third thing nobody warns you about is the loneliness of an unstructured year.
Running an agency is a forcing function. People depend on you. Decisions need to be made. The week organizes itself around responsibilities you cannot put down. When all of that is gone, the days become extraordinarily flexible, and it turns out that extraordinarily flexible days are not what most people thrive in. You can spend a Tuesday very productively or very poorly and nobody will notice either way. The internal pressure that the agency had been providing - the sense that things are happening because you are making them happen - has to come from somewhere new, and it does not arrive automatically.
I underestimated how much of my motivation had been external. The deadlines. The clients. The team. The weekly rhythm of a business that needed me. When all of that disappeared, what was left was not a clearly-motivated entrepreneur with new energy. What was left was a man in his forties in a new country, trying to figure out which of his old habits were actually his and which had belonged to the role.
It took me a long time to separate those.
Rebuilding the operating system
What I now understand about that period, with the benefit of distance, is that the recovery was not just emotional. It was structural. I had to rebuild the operating system I had outsourced to the agency for over a decade. I had to reprogram myself.
The agency had been my external scaffolding. It told me what to care about, what to read, what to think about, who to spend time with, what counted as a good week. Without it, I had to construct an internal version of all of that - what I cared about now, what I wanted to read now, who I wanted to be in conversation with now, what counted as a good week for the version of me that I was becoming rather than the version I had been.
That kind of rebuilding is invisible. It does not look like progress from the outside. It often does not look like progress from the inside either. You can spend months on it and not be able to point to anything you have produced. The work is happening underneath, in the form of preferences clarifying, in the form of false starts being abandoned, in the form of slowly being able to tell what is genuinely interesting from what just looks like a good opportunity.
I tried several things during this period. I built a few brand websites. I started platforms that did not go anywhere. I had ideas that lasted a week and ideas that lasted a month. I worked with a few people. I worked alone a lot. None of it added up to a clear next thing.
Some of those efforts were not wasted in the way they looked. They were the slow filtering process by which I figured out what kind of work I wanted to do next. The kind of business I wanted to build next. But to call them stepping stones in retrospect would be giving the period more coherence than it had. It was not a journey. It was a long, patient, sometimes discouraging process of figuring out what I had become, by trying things and noticing whether they fit.
What eventually switched back on
What eventually started to work, for me, was AI. Not as a tool, although it is that. As an unlock.
For most of my agency years, I had stopped being a developer in any active sense. I had started as one. I had spent the early years building things directly. As the agency grew, I had drifted further from the work and further into running the business. I told myself for years that I did not miss it. I think I did, more than I let myself admit.
When generative AI tools became genuinely capable, something switched back on. I could build again. Not as a developer in the traditional sense - I was rusty, and the languages and frameworks had moved on without me - but as someone who could specify, design, and ship things with the model as the production partner. The act of creating, which had been quietly drained out of my professional life for years, was suddenly accessible again.
That was the first time, in nearly four years, that I had felt the specific kind of engagement I used to get from the early agency days. The flow. The willingness to lose track of an afternoon. The pleasure of solving a small interesting problem because solving it is its own reward.
I started building more deliberately. Small tools. Platforms. Experiments. A workshop of free GPTs. Eventually the work I am doing now with Peter on ClockWork League, which has been the most engaged I have felt in a long time. ClockWork League is the first thing since leaving the agency that uses everything - the operator experience, the technical instinct, the design sensibility, the partnership instinct, the agency knowledge that I thought I had walked away from but apparently had not.
It turns out you do not really walk away from twelve and a half years of anything. You take it with you. The question is just whether you find a new shape that uses it, and how long that takes.
In my case, it took four years.
The honest version, for anyone mid-transition
I am writing this partly for any founder who is in the middle of a similar transition right now, or considering one. There is a version of this story that gets told in clean three-act structures - left the thing, struggled briefly, found the new thing, energy back. That version is reassuring and largely false.
The honest version is that the gap between leaving and arriving is much longer than people admit afterwards. You spend more time confused than you expect. The version of you who knows what to do next does not show up on a schedule. There are months that feel wasted but are not, and months that feel productive but are. Telling which is which in real time is almost impossible.
What helps, in retrospect, is not pretending the gap is shorter than it is. It is being patient with the process of becoming whoever you are becoming, while accepting that you will not know who that is for a while. It is also having people around you who let you be uncertain out loud without trying to fix it - a partner, a family, the occasional friend who tells you the truth, including the truth that you have been talking about a decision for too long without making it.
The decision in Amsterdam felt like the hard part. It was not. It was the visible part.
The hard part was the four years after.
I am grateful for both. I would not be doing the work I am doing now without the leaving, and I would not be doing it well without the long uncertain period in between. The friend who told me to go or stop talking did me a real favor that night. But the bigger favor was done by the years that followed, which slowly taught me that becoming someone new is not a decision. It is a process you submit to. You make a few large decisions along the way. The rest is patience, and noticing what fits.
I still miss the agency sometimes. I miss the team. I miss the rhythm. I miss a few of the projects. I do not miss being the person I had become in order to keep running it, and that is the difference.
The leaving was one night.
The arriving took until now.