More than one year ago, I left a comfortable corporate job as CTO and started working for myself. I have written here about the early lessons, the tax surprises and the emotional roller coaster of the first months. This is the post I was most curious to write: the twelve-month verdict. What did a year of going solo actually look like, now that the numbers are in and the dust has settled?
The Verdict, Up Front
Six weeks in, I wrote that I had clients, projects and revenue, but that it was not yet enough to sustain me long-term. I promised myself I would come back to that. So here is the honest one-year answer: it worked, and it worked better than I had dared to plan.
I reached break-even in month three, a month ahead of my business plan, helped by two larger engagements that landed early. By the end of the year I have four anchor clients (with significant revenue each) plus a handful of smaller work such as expert interviews, so the income came from a spread of work rather than one lucky whale.
Here is the part that still surprises me. When I wrote my business plan, I had sketched a cautious case and an optimistic one, and I had also projected the years that followed. By the end of year one I had not only beaten my optimistic first-year plan by more than double, I had already cleared the revenue target I had set for myself for year three. And I had reached it while spending only about half the costs I had budgeted to get there.
Before anyone gets the wrong idea: as I explained in my piece on the German tax trap, revenue is very much not what lands in my pocket. The tax authorities take their share, and a business has operating expenses to cover on top of that, also social security needs to be paid. But what remains is enough. Enough to sustain my family of four, which is the number that actually lets me sleep at night.
Stay in Your Lane
If I had to name the single biggest reason the year worked, it would be this: I stayed in my lane. Almost every major engagement sat squarely in the world of commercial fleets, the space I have spent most of my career in. I was brought into three M&A due-diligence processes, advising on the technology of fleet management companies that were under consideration. I did organizational consulting for a company that builds technology for commercial fleets. I created a green-field software project from scratch for a customer in this space. And I took on a fractional, interim CTO engagement with real transformational character, again in the fleet area.
The pattern is no coincidence. When I work in my own space, nobody has to explain the market to me, who the customers are, what they need, or how the industry actually operates. I am useful from day one. That domain knowledge is worth more than any of my general skills, and it is what clients are really paying for.
I am fairly sure that if I tried my luck as a generic fractional CTO, a general software freelancer or an all-purpose organizational advisor, I would be a lot less valuable. The lesson for anyone thinking about going solo: find the lane where your experience means people come to you already convinced, and resist the temptation to be everything to everyone.
The Salesperson I Had to Become
The biggest internal change has nothing to do with money. As an employee, you can afford to be a specialist. You go deep in one area and let colleagues handle the rest. As the owner of a one-person company, that is not an option. I am responsible for sales, customer support, engineering, DevOps, QA, UX, accounting and everything in between. At first that felt overwhelming.
Two things helped me make my peace with it. The first was simply accepting that selling is part of the job. There is no way around it, and the sooner you stop resenting it, the better. The second was AI. With an army of agents at my side, the one-person generalist setup is genuinely workable in a way it never was before. I even caught myself rediscovering a joy in building software that I had not felt in years (more on that in a separate post, because it deserves one). For the day-to-day, I have written about how I use AI coding agents to ship software faster, and it is no exaggeration: I now do work that used to require a whole team, faster and a lot cheaper. I quietly envy the solopreneurs who tried this before the tooling got this good.
The Lag and the Ghosts
Not everything works, and almost nothing works quickly. Some of the things I planted in the first months only started bearing fruit around month nine or ten. Other things never worked out at all, and you have to learn to live with both.
One example I will not forget: over the Easter break I prepared a detailed offer for a company I had met at a trade fair. My wife was, let us say, not thrilled about how I spent the holiday. I sent the offer and then heard nothing. No reply, no callback, just silence even after multiple calls and emails from my side. That happens, and you cannot take it personally.
It is not the only kind of disappearance. I once had an engagement die simply because my main contact left the company. Not my fault, nothing I could have done, but the business was gone all the same. And there is a quieter version that stings a little more: people who were perfectly warm when I wore a big-corporate CTO title, and who went cold the moment I no longer did.
Being on the receiving end of all this taught me one firm rule. I have started to say no, though rarely out loud, but always clear. Simply not chasing an opportunity that is not the right fit starts to make sense in my position. But I do it professionally, and I never ghost anyone or break a promise I made. I know exactly how that feels.
It is also worth being honest about where the work actually came from. Of my four biggest clients, two were related to companies I already knew from before I left Webfleet, and the other two I met through LinkedIn after I had gone solo. The lesson I take from that: your network is not only the people you know today, it is the people you stay visible to. Half my best work came from relationships I had already built, and half from simply showing up in public after I left.
And that visibility cost me almost nothing. Except for a single failed 50€ LinkedIn ad experiment, I have not spent one euro on advertising. No Google Ads, no sponsored posts, nothing. I am not claiming ads do not work, only that I have not needed them. What I have used is this blog and the posts announcing each new article. The traffic is modest, a few hundred visitors a month, and I am honestly not sure how many of those are bots. Audiences take years to build, not weeks, and I am counting in years.
The Open Door
So, would I do it again? The more interesting answer is what the year actually changed. A year ago, none of the following were realistically on the table. Today, all of them are. I could build and sell my own SaaS products. I could lean fully into consulting, or into organizational development, or into fractional CTO work. Even CEO roles are within reach now.
I am not about to chase all of these at once, of course. After writing a whole section on staying in your lane, that would be a poor look. But a year of going solo turned a single career path into a wide-open set of doors, and I get to choose which one to walk through. That, more than any single number, is the real return on the bet.
To anyone standing where I stood a year ago, wondering whether to jump: it has been worth it for me, in more ways than I expected. Thanks to everyone who helped me along the way.
