The first serious conversation about someone buying the agency I ran happened many years before I actually left it.
(We actually received an approach after just six months of starting, but it turned out not to be that serious).
Approaches come in when you run a good agency. Most are tyre-kickers or people building a list and you learn to spot those quickly. But every so often one is real. Real enough that you sit down and have proper conversations about it.
I remember the feeling clearly, because it was two feelings at once.
The first was excitement. Someone wanted to buy the thing we’d built. That’s quite a moment. You spend years privately wondering whether the business is actually any good and then somebody turns up willing to put money on the answer being yes. They tell you about something you’ve done that caught their eye and has impressed them – you can’t help but feel proud.
The second feeling was guilt. And that’s the one I didn’t talk about for a long time.
The thought you don’t share with anyone
Here’s what the guilt actually was, now I can look at it honestly.
I was worried about what a deal would say about me. That I’d be “getting rich” off the back of other people’s work. That I’d be cashing out whilst the team who helped build the thing carried on earning a salary. I ran the scenarios in my head. How would we announce it? What would people think of me? Would they feel like they’d been sold?
Part of me imagined being excited and proud to announce a deal. Part of me was terrified because of how people may react.
Over ten years of running the agency we had plenty of approaches and a couple of genuinely serious conversations. The pattern in my head was the same every time. Excitement first, then guilt about the excitement. Then excitement again. Then guilt again.
I’ve since learned I wasn’t unusual.
If the thought has arrived for you, you’ll recognise it. You catch yourself looking at what agencies like yours sell for. You notice a flicker of envy for friends with jobs they can simply resign from. And underneath it sits the same worry I had – that wanting out means you’ve stopped caring and that the people around you would see a sale as some kind of abandonment.
Nobody posts about this bit. The exit content you see is all celebration, strategy or even difficulties during an earnout. The shame that comes before any of those gets carried alone.
Wanting out isn’t failure
Wanting to sell your agency, or leave it, or hand it over, isn’t a betrayal of the business or the people in it.
Think about what an approach actually means. Someone looked at the thing you built and decided it was valuable enough to want to own. That is not evidence you’ve failed the business. It’s close to the strongest evidence available that you’ve built it well. A business that someone else would pay for is, almost by definition, a business that works without depending entirely on you, with clients that stay and with a team that delivers.
That’s not a business you’ve betrayed. That’s the job, done.
The guilt tells you the opposite story. That the honourable founder stays forever, keeps carrying it and treats the exit as something slightly grubby that happens to other people. But run that logic forward and it ends somewhere bleak – the only acceptable way to finish is burnout or the grave. (Soz, that’s a bit grim!) Nobody would sign up to that in any other career or job.
You’re allowed to want the exit. You’re allowed to be excited when someone asks.
What my team actually thought
And the fear about how the team would take it? Here’s what I found.
Most of them either didn’t care anywhere near as much as I’d imagined, or were genuinely happy for me.
The truth is, most cared but not that much.
That’s it. That’s the anticlimax. The story in my head, in which a deal would be received as evidence I’d been in it for the money all along, was mine. It wasn’t theirs. Good people are mostly getting on with their own lives and careers. They can see that founders carry a different risk and should get a different reward and the ones who valued working there cared far more about what a deal would mean for their day-to-day than about my bank balance.
I spent years quietly braced for a judgement that, as far as I can tell, almost nobody was waiting to hand down.
If the thing keeping you from thinking seriously about your exit is a version of that imagined judgement, it deserves a hard look. You may be protecting yourself from a reaction that doesn’t exist.
My exit wasn’t exactly what I imagined it to be
Now for the part of my story that surprises people.
After all those approaches and all that guilt, nobody bought the agency I ran. We got close a few times, letters of intent, formal offers etc. None of it materialised for a bunch of good reasons.
Well, someone did. My co-founder. He bought me out in 2024 and the agency carries on under his ownership today, without me. That’s my exit. No acquirer, no earnout, no announcement photo. The exit I had was the one I needed at the time, not the one I’d spent years imagining.
In truth, I’m thankful to my co-founder (and always will be) that he enabled me to make a change in my life that I needed at that moment in time. I have regrets of course, but it’s hard to look back on this and say it was a mistake based on what I knew and most importantly, how I was feeling at that time.
I share that because the dream version of an exit, the big trade sale with the life-changing number, is the only version most founders ever picture. And it’s one option on a much longer list. Founders sell to acquirers, yes. They also sell to their co-founders or their management team. They move the business into an employee ownership trust. They step back from running it whilst keeping their shares and stay involved only in the parts they love.
I’ve spoken to founders that have done ALL of these and things have turned out fine for all of them.
Some of those routes come with a smaller cheque than the dream. Some come with a better life than the dream. Almost none of them look like the version in your head and if you only ever prepare for the imaginary one, you’re not actually preparing at all.
The feeling of wanting out is universal. The mechanism almost never matches the dream. Both things are worth knowing early.
What to actually do with the thought
If the leaving thought has arrived, however quietly, here’s what I’d do with it if I did it all over again.
1) Say it out loud to someone safe
Not your team and probably not your spouse as the only audience. A peer who’s been through it, an advisor, another founder, even your therapist. The thought does its worst damage when it’s carried alone as a shameful secret. Spoken, it becomes a plan you can examine and make more sense of.
2) Work out what you actually want
“I want to sell” is often shorthand for something more specific. Sometimes it’s the money. Often it’s actually the pressure, or the boredom, or a role you’ve outgrown. Those are different problems with different answers, and one of them can be fixed without selling anything.
3) Learn the options before you need them
Know roughly what agencies like yours go for, how earnouts work, what an MBO or an EOT involves. Not because a deal is close, but because you make better decisions about a menu you’ve read.
Also, if you have a co-founder, talk to them about this too and understand that you can actually both do different things – your exits don’t have to be 100% identical or happen at the same time. The same goes for an earnout – you can negotiate different routes based on what you both want or need.
4) Build it to be sellable whether or not you ever sell
A business that could be sold, with revenue that doesn’t depend on you, documented ways of working and a leadership team that runs the week, is also just a better business to own and an easier one to live inside. None of that work is wasted if you stay.
When you first actively look to sell, you’ll probably engage an advisor who will take a look at your agency and “prep” you to sell. If you can have all of this stuff done in advance, you’ll have a much more robust and valuable business anyway.
The bit we avoid saying out loud
One caveat before the uncomfortable truth. Sometimes the wanting-out feeling isn’t about ownership at all. It’s about the job you’ve built for yourself inside the agency and changing the job fixes it. Stepping back without stepping out is a real option, a topic for another issue and for some founders it’s the whole answer. I’ve seen it done a few times very successfully.
But if it really is the exit you want, here’s the cost of sitting on the thought.
Every good exit, whatever shape it takes, is years in the making. The businesses that sell well, or hand over well, or transition to their teams well, started preparing long before the decision was made. The founders who suppress the thought, because it feels like a betrayal to even have it, are the ones who end up trying to leave in a hurry, from a weak position, with a business that was never made ready.
The guilt doesn’t protect your team. Preparation does.
So if the thought has arrived, stop treating it as a confession. Take it seriously, quietly and early. Wanting to leave the thing you built isn’t the end of caring about it.
Sometimes it’s the start of finishing the job properly.
