Selling Your Business: Why 75% Regret It and How to Be in the 25% Who Don’t

Sellling your business is supposed to feel like freedom.
The big payday. The clean slate. The “you’ve made it” moment.

So why do three out of four business owners say they regret selling just one year later?

Because selling a business isn’t just a transaction. It’s a transition.

And if you don’t plan that transition carefully, you’re not just selling a company, you’re selling your identity, your sense of purpose, your daily structure, and maybe even your peace of mind without realising it.

Here’s how to avoid that trap.

The Broker’s Blind Spot: Maximising the Deal, Minimising You

When it’s time to sell, many entrepreneurs hand the process over to a broker.
After all, they’re experts at getting the best price, right?

Yes, if all you care about is the number on the cheque.

But here’s the problem: brokers are paid to close deals and maximise today’s value.
What they rarely ask is:

Will this figure actually fund the lifestyle you want for the next 20 years?
Are you emotionally ready for life without the business that’s been part of your identity?

Without those answers, you risk waking up the day after closing not liberated, but lost.

Why Money Alone Doesn’t Buy Happiness

There are two common oversights that lead to regret:

The Temporal Mismatch

A lump sum today feels like financial security. But five years from now, without careful planning, that pot can shrink faster than you expect, especially if you haven’t mapped your lifestyle costs against your financial resources.

Identity Loss

Running a business gives you purpose, structure, and community. Sell without a plan for what’s next, and you might feel like you’ve lost the anchor that grounded you.

The Holistic Exit: Planning Beyond the Price Tag

The goal isn’t just to sell for more money.
The goal is to sell with more clarity.

That’s where an exit planner comes in, someone who isn’t just focused on the deal, but on your life after the deal.

They’ll ask the bigger questions:

✅ What does “enough” really look like for your future lifestyle?
✅ What will you do with your time — travel, start something new, volunteer, invest?
✅ How will you maintain your sense of purpose and your community?

An exit planner bridges the gap between transaction and transition, ensuring you step into your next chapter with intention, not uncertainty.

Selling Should Feel Like a Beginning, Not an Ending

When you plan your exit holistically, you’re not closing the book, you’re turning the page.

Instead of drifting into post-sale regret, you launch into a new phase already anchored by financial stability, personal purpose, and a clear vision.

True wealth isn’t just the sale price.
It’s knowing who you are, what you want next, and having the means to make it happen.

If You’re Thinking of Selling in the Next 2 Years

Start now!
Not just to prepare your business for the best price, but to prepare your life for the transition.

Don’t be part of the 75% who wish they’d done it differently.
Be part of the 25% who sell with clarity, confidence, and excitement for what’s next.