Not Done

People have started asking me the question.

Not directly, usually. It shows up sideways, in conversations at industry events or over coffee. “So, 25 years… what’s next?” The question carries a set of assumptions. Guy in his 50s, been at it a while, business is doing well. The script says this is where you start thinking about an exit. Cash out. Slow down. Enjoy the fruits.

I get it. And I’ve watched a lot of my peers follow that script. Some were tired. Some hit a ceiling they didn’t want to push through. Some just saw a good offer and took it. I don’t judge any of that. Everyone’s working with their own set of circumstances, and selling a business you built is a legitimate choice that can change your life in meaningful ways.

But it’s not my choice. At least not right now. And I think the reasons why might be worth sharing.

There’s a common philosophy in business: build it like you’re going to sell it. Get your systems tight, your team strong, your financials clean. Make the thing attractive to a buyer. Here’s what’s funny about that. It’s the same logic as fixing up your house to put it on the market. You finally renovate the kitchen, paint the trim, stage everything just right. Then you walk through it and think… why am I selling this place? It’s never been better.

I think the same thing applies to a business. If you do the hard work of building something that doesn’t revolve around you, that runs well, that creates value for the people in it, you’ve built something worth keeping. The very things that make it sellable are the things that make it worth owning and the things that make it worth continuing.

And I think that’s where some business owners get stuck. It’s not that owning a business is inherently draining. It’s that they built one that needs them at the centre of everything. Every decision, every client relationship, every fire. That’s exhausting after 15 or 20 years. Of course you want to escape that.

But the escape impulse might be a symptom, not a solution. Selling doesn’t fix the pattern. It just ends it.

I’ve tried, imperfectly and over a long time, to build Smart Dolphins so it doesn’t need me in the middle of things. Not because I was planning to leave, but because I think that’s just a better business. It’s better for the team. It’s better for clients. It’s better for me. I get to choose where I put my energy instead of the business making that choice for me.

So when I think about what I actually want, it’s not an exit. It’s flexibility. Working from somewhere warm for a couple months in the winter. Spending my time on things that matter most rather than whatever’s on fire. Still learning, still being challenged by new problems.

That probably sounds simple, but getting there has been the work of 25 years. And I’m still working at it!

Here’s what I’ve come to believe, though. A business built with intention can actually be one of the most freeing things in your life. You have a place to be productive and creative. You’re connected to people you care about. You have problems worth solving. What does selling give you? A blank calendar. Some of the people I know who sold eventually went looking for something similar to fill it.

I’ve watched peers cash out, enjoy life for six months or a year, and then start circling back. Some started consulting. Some got into private equity. Some started new businesses in the same or adjacent industry they just left. Which always makes me wonder: what if they’d just kept building what they originally built?

I’ll be honest. There have been hard stretches where I wondered if I should move on. Big challenges that tested me. Times where I genuinely wasn’t sure I could lead the next version of this company. A growing business asks things of you that you haven’t learned yet, and that gap can feel pretty permanent when you’re in it.

But I think most of those ceilings are ones we build for ourselves. We get comfortable. We mistake familiarity for limitation. The skills and growth required to lead a bigger, more complex business aren’t genetic. They’re learnable. The question is whether you’re willing to do the uncomfortable thing.

And look, when you’ve been at it this long and things are going well, coasting is tempting. Just protect what you’ve built. Stay comfortable. But the stretches I look back on most fondly aren’t the easy ones. They’re the ones that cost me sleep. The ones where I wasn’t sure it would work out. Doing hard things doesn’t feel meaningful while you’re in it. It does after.

Writing 25 insights from 25 years has a feeling of finality to it. Like I’m packaging up the lessons and putting a bow on things. But I might only be halfway through. There’s a lot of runway ahead, and I have a belief that some of the most interesting chapters are still ahead.

I’m not naive about that. The world changes. Circumstances change. Maybe something happens that makes selling the right call. I’m open to that possibility. But I’m not looking for an exit. I’m not building toward a finish line. I’m building toward more of what I already love: a great team, work that matters for clients that matter, interesting problems, and the room to keep evolving how I show up in all of it.

So no, I’m not retiring. I’m not done.

Can’t wait to write 50 insights from 50 years.

What’s this 25/25 stuff about?: 25 YEARS, 25 INSIGHTS – Reflections on Growth, Leadership and Resilience | Smart Dolphins IT Solutions Inc.