Most business owners regret selling within a year — not because of the price, but because they weren’t prepared emotionally or strategically. To avoid regret:
Get clear on your “why” for selling.
Prepare your business to avoid leaving money on the table.
Choose a buyer who values continuity and legacy.
Plan your role (or exit) after closing.
Consider what life looks like after the sale.
You’ve spent decades building your company. You find a buyer, negotiate the deal, sign the papers — and suddenly, it’s not yours anymore.
For some owners, that moment brings relief. For others, it brings regret.
According to the Exit Planning Institute, 75% of owners regret selling their business within a year. Not because of the money — but because they didn’t think about what would happen after.
At Sixty74, we’ve talked to countless owners who’ve wrestled with this. Some got it right. Others wish they’d done things differently. This post pulls together the lessons we’ve learned — so you don’t become part of that 75%.
Seller regret usually comes down to five factors:
Lack of preparation: Rushed financials, weak management, unresolved risks.
Wrong buyer fit: Choosing a buyer who cuts staff, disrupts customers, or dismantles culture.
Unrealistic expectations: Believing the business is worth more than the market says.
No post-sale plan: Sellers realize they don’t know what to do with themselves.
Emotional unpreparedness: Underestimating the identity shift of no longer being “the owner.”
One of the biggest causes of regret is not knowing why you sold in the first place.
Was it purely financial?
Was it about retirement?
Was it a health or family decision?
Was it because you were burned out?
When the “why” isn’t clear, regret fills the void.
Action Step: Write down your top three reasons for selling. If they don’t feel strong enough, it may not be time yet.
Owners who rush to market without preparation often sell for less than they could have. That leaves them frustrated later when they realize they left money on the table.
Preparation checklist:
Clean, normalized financials.
Reduced owner dependence.
Diversified customer base.
Documented processes.
Legal and compliance issues resolved.
See our post on 5 Steps to Make Your Business Sale-Ready Before Retirement.
We’ve heard this story many times: a seller takes the highest offer, only to watch employees get laid off and the brand disappear within a year.
How to avoid it:
Ask buyers about their long-term plans.
Talk to other sellers they’ve worked with.
Decide what matters more: maximum cash or legacy protection.
Our post After the Sale: Why Sellers Choose Stewards, Not Just Buyers explains why this choice is critical.
Some owners regret selling because they left too soon. Others regret staying too long.
Options include:
30–90 days of transition support.
6–18 months in an advisory role.
Board or governance positions.
Retaining minority equity.
See our post From Operator to Advisor: Staying Involved Post-Sale for details.
The hardest part for many sellers isn’t the sale — it’s waking up the next day without the business.
Questions to ask yourself:
What will I do with my time?
Do I want to start another business?
Do I want to serve in my community?
How would I like to spend time with my family?
Tip: If you can’t answer these before the sale, you risk post-sale regret.
Seller’s remorse is real. But it’s not inevitable. With preparation, the right buyer, and a clear post-sale plan, you can walk away confident — not second-guessing.
At Sixty74, we help owners avoid regret by protecting what matters most: their employees, customers, and legacy. The goal isn’t just a transaction. It’s peace of mind.
If you’re thinking about selling and want to avoid regret, let’s talk.