No business stays the same, because no business OWNER stays the same. The reasons you started your MSP in the first place may no longer be relevant. Your services, target audience, business goals – all these have probably changed. And that’s ok.

Founder’s Guilt and How We Evolve as MSPs

Have you ever looked around your IT business and thought: “How did I end up here?”

Not in a bad way. You’re proud of what you’ve built. Maybe you’ve scaled, brought in a leadership team, or even stepped back a bit. But you feel off. Disconnected. A bit like an imposter in your own company.

Welcome to the MSP Founder Identity Crisis.

I’ve spoken with several prominent Managed Service Provider owners recently about this common issue that isn’t often discussed publicly.

You don’t know what your role is anymore
At first, you did everything. Then you hired people. Delegated. It may have even evolved into something “strategic.” But now? You’re not sure where you add value. And that’s a weird feeling for someone used to being essential. You feel guilty for not enjoying the business
You’ve got revenue, a decent team, recurring income. But you’re bored, frustrated, or even resentful. Then comes the guilt. “I should be grateful—what’s wrong with me?” Nothing. You’ve just outgrown your old identity. You don’t know what’s next
Do you scale up? Sell? Start something new? Become a Non-Executive Director (NED)? Mentor others? The options feel endless—and also terrifying. No one talks about how hard this transition is emotionally.

Things Evolve and Change

If any of this rings true, you’re not alone. I’ve been through it myself, and I’ve spoken to a number of MSP founders who have been through the same transition.

You’re allowed to changeYou’re allowed to not love your MSP anymoreAnd you’re allowed to design the next chapter on your terms

If what I’ve shared has hit a nerve, then start by asking: “What do I love doing now—and how can I do more of that, without blowing everything up?” You might be surprised by what comes up.

To Sell or Not to Sell

So you’ve spent some time thinking about your MSP business and how you think it might evolve. Let’s now consider selling it – or choosing to remain as the owner.

If someone came to buy your MSP tomorrow—could you hand over the keys? No scramble, no panic, no “just give me a few weeks to tidy things up…”

Even if you never plan to sell, building your business as if you were going to can do wonders for your growth, clarity, and stress levels.

An Exit Mindset is Essential for you to Evolve It forces you to get out of the weeds. No prospective buyer is interested in a business that relies solely on your constant involvement to function effectively. Building systems, delegating properly, and documenting your knowledge are all habits that free you up too—whether you sell or not. It shines a light on what’s messy. Messy contracts. Dubious clients. That weird one-off pricing you did as a favour. Viewing things from a buyer’s perspective allows you to streamline and refine your approach. Make it consistent, clean and—frankly—less stressful to manage. It gives you leverage. When your MSP could be sold tomorrow, you’re no longer trapped. You’re choosing to stay. That’s powerful. It creates space to step back, bring in help, or say no to work that doesn’t serve you.

Even if you never leave, you’ll sleep better knowing you could.

This approach worked for me when I sold my MSP business. When a life event happened (in this instance, my father’s death), I was free to follow my passion, sell my business, and do what I’m doing now.

Has any of this struck a chord with you? You can let me know in the comments or *****@********co.uk” target=”_blank” rel=”noopener”>message me privately. I’d love to know your thoughts.

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