Worried About Seller’s Remorse? Exit Your Business with Confidence
When the time comes to sell your business, it’s huge. But here’s what most business owners don’t plan for: that creeping feeling of seller’s remorse.
Why Seller’s Remorse Happens
You expected more money — “I thought I’d walk away with more after all those years.”
Taxes hit harder than you thought — “I didn’t think the tax bite would leave me with so little.”
The buyer changes things too much — “They’re running things in a way I didn’t expect.”
You lose your identity — After so many years as the owner, stepping away leaves a hole in how you see yourself.
When you don’t prepare for these emotional and practical shifts, regret can creep in — sometimes weeks or months after the deal closes.
How to Avoid Those Regrets
Plan your life after the sale. Think about what you will do once you’re not running the business anymore. Your identity, your schedule, and your energy will shift. Give yourself the time and space to adjust.
Ease out of your business gradually. During the sales process, start stepping back bit by bit so you can get used to the idea of life without the day-to-day responsibilities.
Understand your finances. Get clear on how much you need from the sale to keep your lifestyle going, pay taxes, support family, and fund next steps. Regret often comes from realizing the dollars don’t stretch as expected.
Consider the people who matter. Think about your employees, your community, your customers — the ripple effects of your exit. Executing a transition plan that respects them helps you walk away feeling proud instead of unsettled.
Allow time for the transition. Don’t rush. Give your business at least 6 months (or more) of preparation before listing, and find the right buyer rather than accepting the first buyer.
Selling your business isn’t just a financial transaction — it’s a personal transformation. Planning well, thinking ahead, and giving yourself a roadmap for after the deal are just as important as getting the headline number. Do that, and you’re much more likely to sell with confidence, peace of mind, and minimal regret.