I assumed one thing would at least become simpler once I came back to the job market after a stretch of building a company.

I thought I would know more clearly what I was capable of.

That part was true. What I did not expect was the gap between knowing what I could do and getting the market to read it the same way.

During that year and a half, the work was messy, but not in the usual “too many projects, too little time” sense. It was messy because I had to touch nearly everything. Incorporation, equity, the option pool, pitching, fundraising, business development, product, technology, compliance, hiring, and eventually the slow work of winding things down without fully killing the idea. Once you have operated in that kind of environment, the way you look at work changes. It becomes hard to see a product problem as just a matter of features, specs, and timelines. You start seeing the pressure around it as well: the market, the people, the money, the adoption friction, the parts nobody quite owns, and the parts everyone pretends are moving.

So I went back into the market with a fairly naive assumption. I thought this experience would speak for itself.

It did not.

When companies look at a founder applying for a role, they often have a different set of questions running quietly in the background.

Are you too unstable.

Did you just fail at start-up life and now need somewhere to land.

Will you disappear and start another company the moment something more interesting comes along.

When you say you have done everything, does that actually mean you were never deep in anything.

Those doubts are not entirely unreasonable. I can see why they come up. Still, once you have spent a serious stretch of time carrying a company on your back, being put back into a highly standard candidate box creates a strange kind of dislocation.

The hardest part for me was realising that many PM roles were looking for something quite different from the kind of work I felt I had actually been doing.

That is not a dig at PMs, and it is not a way of saying feature work is easy. It is not. The point is that I kept running into a mismatch. Many companies were looking for someone who could structure requirements well, move projects along steadily, and work smoothly across design and engineering. I had done that kind of work too, but what I had really spent the past stretch doing was operating at a different density. I was not optimising inside one function. I was dealing with the whole field.

You look at the market. You look at the product. You look at people, cash flow, technical constraints, adoption patterns, and whether the organisation is actually moving or merely looking busy. You do not need to be the best at every part, but you do need to understand how those parts jam each other up.

That experience has value. It is just not the sort of value that translates neatly through a title.

What I felt most strongly in the early stage of job hunting was not frustration, at least not at first. It was a translation problem.

I had done harder work, but that did not mean it would be understood correctly.

Over time I also realised that this mismatch was not only in my head. Some recruiters could see the density behind founder experience. They could tell it was not an ordinary CV. But once you enter a formal hiring process, a lot of things are still sorted first by title, years of experience, keywords, and a fairly standard product-career ladder. If your CV says founder, cofounder, or CEO rather than PM or Director of Product, that experience is not always translated naturally into product-track seniority in the first round.

The issue is not necessarily that the capability is absent. It is that the capability is not being placed into the right box early enough.

I spent a long time thinking about that. It is not as simple as blaming ATS software or recruiters. Companies need a degree of standardisation or the process becomes unmanageable. The real difficulty, at least for me, is that the sort of experience I had accumulated is precisely the sort that does not fit a standard template very gracefully.

The judgement you build in a start-up does not automatically turn into elegant CV language. If you write it too honestly, it can look scattered. If you compress it too much, you lose the density that made it valuable in the first place. That balance is awkward.

Eventually I realised the problem was not only that I needed a job. I needed to translate myself into a language organisations could actually hear.

I was not trying to prove that I had suffered. I was not trying to make “founder” the whole point either.

What mattered was being able to explain which parts of that experience would still be useful inside a company.

For example, I now understand very clearly that a product does not move because a feature gets built. It moves when the model around it makes sense, when coordination holds, when adoption friction is accounted for, when risk is understood properly, and when the organisation’s pace matches what the product actually needs.

I also understand that many problems are not feature problems at all. They sit in unclear ownership, decisions that are never really absorbed by the people meant to carry them, or trade-offs that nobody is willing to own.

Those things do not disappear inside companies. If anything, they are often still there, just wrapped in more polished language.

So if I had to explain what that stretch of building a company actually gave me, I would not begin with “I can do lots of things”.

I would say I understand why something gets built, and why it does not.

I understand how products make it into the world, and how they die before they get there.

I understand the difference between a team that looks active and a team that is genuinely moving.

You do not get that from reading a few books. You do not even get it automatically from spending years inside a single function. You get it by putting yourself in the middle of it, getting things wrong, changing your mind, and learning to see the system more honestly.

Looking back now, the hardest part of moving from founder back to candidate was not swallowing my pride.

It was accepting that the market would not necessarily understand me in the same terms I understood myself.

I still had to prove myself.

Only this time, what I had to prove was not simply whether I could run a project well. I had to show whether I could turn a very non-standard body of experience into something other people could trust as a useful capability.

I am still learning how to do that.

But I am clearer now than I was at the beginning about one thing.

I did not come back to the market because I failed and retreated.

What I am really doing is bringing a dense, uncomfortable, very real body of experience back into an organisation, and seeing whether it can create better value from a different position.

Whether I start something again one day is not a question I need to answer publicly in absolute terms.

But one thing is clear to me.

Once you have been a founder, certain ways of seeing do not simply disappear.

You can stop building for a while.

What you do not really go back to is working as if your responsibility begins and ends neatly at the edge of your job description.