When success stops feeling like success
An exit strategy for accidental agency founders
There's a moment, usually around 3 AM on a Tuesday, when you find yourself staring at your laptop screen, surrounded by the debris of another "urgent" client deadline, wondering how the hell you ended up here.
You never set out to build an agency. You were just good at something: design, development, marketing, whatever. People kept asking you to do more of it. So you did. You hired someone. Then someone else. Before you knew it, you had a team, an office lease, and a business that looks impressively successful from the outside.
Congratulations. You've accidentally become an entrepreneur.
The problem is, success without intention is a peculiar kind of prison. Your agency pays the bills, employs good people, serves clients reasonably well. By most metrics, you've "made it." Yet here you are, Googling "how to sell my agency" at ungodly hours, feeling like a fraud for wanting to exit something that's supposedly working.
The liminal space of successful misalignment
If you're reading this, chances are you're caught in what I call the liminal space of successful misalignment. It's that uncomfortable middle ground where you've built something that works, but it doesn't feel like yours. The business has momentum, but you've lost yours. You're successful, but you're not energised.
Think of it as being stuck between two rooms. You can't go back to the simplicity of freelancing because too many people depend on you now. But you can't move forward either, because you're not sure where forward even leads. So you hover in the doorway, successful but suspended, accomplished but adrift.
This is what transition experts call "the messy middle." It's the second stage of any major life change, sandwiched between letting go of what was and embracing what's next. The problem is, you're struggling to let go of your current identity as agency founder, and you have no idea what the new beginning might look like.
The cruel irony is that staying feels impossible, but leaving feels terrifying. What comes after? Who are you without this thing you accidentally built? What if you walk away from the best opportunity you'll ever have?
The exit that wasn't
I know this space intimately because I lived in it for years. My business partner Laurence and I had built a successful digital agency. Good clients, talented team, steady revenue. From the outside, we had it figured out. From the inside, I felt increasingly disconnected from the work, drained by the endless cycle of projects that paid “well” but didn't light me up.
I'd been so busy being the technical director as well as the agency founder. I'd created an identity of being the technical expert. But that identity wasn't really mine. It was something that I thought I should do.
Eventually, we made the decision to close the agency. On paper, it was the right move. We even had a vision for what came next: The Happy Startup School, helping other entrepreneurs avoid the trap of building businesses that owned them instead of serving them.
But here's what I didn't anticipate: even a "successful" exit can leave you completely lost if you haven't done the inner work first.
When we closed the agency, I thought I'd feel relieved. Instead, I felt adrift. I'd been so busy playing a role that I'd forgotten who I was underneath. I knew what we were building next intellectually, but I couldn't connect to it emotionally. My energy scattered. My focus wavered. I struggled to channel my time and attention towards anything meaningful. I kept on asking Laurence for the plan.
The only reason I didn't completely spiral was that Laurence was more attuned to listening to his gut. He had clarity about what energised him, what he wanted to create, how he wanted to spend his days. I could follow his lead whilst I figured out my own. But it was a struggle, one that could have been avoided if I'd had an honest conversation with myself before we shut everything down.
Looking back, I wish I could have sat down with my past self and said: "Before you figure out what to do with the business, you need to figure out what to do with you."
Why traditional exit strategies miss the mark
Most exit planning treats the business as a separate entity that can simply be transferred or shut down. Fill out the forms, find the buyer, sign the papers, walk away. Clean and transactional.
But here's what those approaches don't account for: you didn't just build a business, you accidentally built an identity. For a decade or more, you've been "the founder." Your days, your energy, your sense of purpose (however reluctant) have been wrapped up in this thing you never really chose.
Strip that away suddenly, and what's left?
The standard advice sounds reasonable: "pursue your passion," "start something new," "enjoy your freedom." But it falls apart when you realise you've been so busy running something you didn't design that you've forgotten what you actually want. The muscle memory of desire has weakened.
This is why so many agency exits lead to either immediate regret ("I should have kept building") or existential drift ("Now what?"). Without doing the inner work first, you're just swapping one form of misalignment for another.
The real exit strategy: starting from the inside out
The most important exit strategy conversation isn't with your accountant or business broker. It's with yourself.
Before you can figure out what to do with the business, you need to figure out what to do with you. Not the you that accidentally became an agency founder, but the you that exists underneath all that. The you that had interests and energy and curiosity before it got channelled into client work and team management.
This isn't therapy-speak. It's practical. Because whatever you do next, whether that's selling, transitioning, or even recommitting, needs to be aligned with who you actually are and what you actually want. Otherwise, you'll just end up building another beautiful prison.
The questions that matter
Here's where it gets uncomfortable. The real exit strategy begins with questions that business school doesn't prepare you for:
What did I care about before I got so good at serving other people's needs? When did I last feel genuinely excited about my work? What would I do if I wasn't afraid of disappointing my team, my clients, or my own expectations of success?
If I could wave a magic wand and be doing anything in three years, what would that be? Not what should I be doing, or what would be smart, or what would maintain my current lifestyle. What would actually energise me?
What are my actual needs? Not just financial, but emotional, creative, physical. How do I want to spend my days? What kind of impact do I want to have? What would make me feel alive again?
And perhaps most importantly: What am I afraid will happen if I stop being who I think I'm supposed to be?
These aren't questions you answer in an afternoon. They're questions you live with, sit with, let percolate whilst you're doing other things. They're questions that require space and patience and a willingness to not know for a while.
Permission to not know
Here's something nobody tells accidental founders: it's okay to not know what comes next. In fact, it's necessary.
You've spent years being the person with the plan, the one who knows what to do next, the one responsible for keeping everything moving. The idea of stepping into uncertainty feels like professional suicide.
But uncertainty isn't the opposite of success. It's the precondition for authentic choice.
You don't need to have the everything figured out before you can start moving away from the current thing. You just need to create enough space to remember who you are when you're not performing the role of founder.
Think of it as clearing the static so you can tune into your own frequency again.
The path forward (there is one)
The path forward isn't about finding the perfect exit or the perfect next chapter. It's about developing the capacity to make choices that feel aligned and alive.
Maybe that means selling and taking time to rediscover what you care about. Maybe it means restructuring so the business runs without you whilst you explore other interests. Maybe it means recommitting fully, but to a version of the agency that actually reflects your values and energy.
Whatever you choose, making that decision from a place of clarity, rather than burnout, will always serve you better than running on autopilot or reacting out of old habits and hidden pressures.
Begin again
If you've made it this far, you're probably someone who cares deeply about doing good work and serving people well. Those impulses are worth honouring. But they don't have to trap you in a life you didn't consciously choose.
The business you accidentally built doesn't have to become your permanent identity. It can be a chapter, a phase, a thing you did well for a while. What comes next is up to you, but only if you give yourself permission to figure out what you actually want that next thing to be.
The space between who you've been and who you're becoming doesn't have to be a prison. It can be a doorway. But you have to be willing to walk through it consciously, with your eyes open to both what you're leaving behind and what you're moving toward.
The real exit strategy isn't about leaving something behind. It's about moving towards something that's actually yours.
The work begins now. The work begins within.
If this resonates, you're not alone. And you're not stuck, even when it feels like you are. The way forward exists. It just starts in a different place than you might expect.
I learned this the hard way, but you don't have to. The version of yourself that knows what you need and want is already there, waiting. You just have to create the space to listen.