Why Most Business Owners Regret Selling Their Business (And How to Avoid It)

← Back to Our Blog

Most owners are surprised to learn that 75% {The Exit Planning Institute, Emotional Considerations for Transitions https://blog.exit-planning-institute.org/emotional-considerations-transitions} of business owners regret selling their business within twelve months. That alarming statistic stems from research conducted in 1999. But while the data is admittedly quite old, it’s still widely cited and likely accurate—simply because the human truths behind it haven’t changed.

Business owners go into a sale hyped up, convinced that once the deal closes they’ll be free to move on to their next chapter. They imagine freedom, travel, philanthropy, and new ventures only to discover disappointment, disorientation, and regret instead. Why does this happen so often, and how can you avoid it?

What Drives Regret After Selling Your Business?

The regret that owners so commonly feel after transitioning out of their business stems from several key factors.

1. Loss of Identity

Selling a business isn’t just a financial transaction; it’s an identity shift. Owners don’t always realize how much of who they are is wrapped up in the business.

For decades, they’ve been “the owner.” In the community, in their family, even in their charitable activities, their identity is linked to the business. They’ve employed people, funded causes, and provided stability for others. When that disappears, they’re left wondering, “Who am I now?”

It mirrors what retirees so often experience. Just as corporate leaders struggle when their career ends, business owners typically feel a void when their company is no longer theirs.

2. Lifestyle Shortfalls

Some owners realize only after the sale that the proceeds aren’t enough. I’ve seen owners who had to go back on the job, take on consulting work, or even start another business after selling because they miscalculated what they needed. Nobody likes to feel like they failed financially, but without planning, it often happens.

Too many owners underestimate what their business is really doing for them. Beyond salary, many live on distributions, K-1s, and lifestyle subsidies that they don’t even recognize because they run these expenses through the business. When the business is gone, all of that income and invisible financial support disappears. Unless the sale proceeds are enough to replace it, regret usually follows.

3. Deal Fatigue

Exiting a business is exhausting. There are countless documents, negotiations, fees, and advisors to coordinate. Owners often reach a point where they just want to be done. In that fatigue, they accept terms or valuations they later regret. Desperation to get out of a stressful and demanding situation culminates in disappointment once the real-world consequences of that decision hit.

4. No Next Chapter

Not planning for life after the sale is another huge factor behind post-exit regret. Owners who haven’t defined their next chapter are especially vulnerable. Without a clear purpose and defined goals to pursue, they feel lost. Intentionally designing your next chapter prevents a void that could diminish or replace the fulfillment you expect to feel after selling your business.

The Data Behind Regret

Other statistics reinforce the reality behind exit regrets:

Between 80 and 90 percent of a business owner’s net worth is tied up in their company. (Exit Planning Institute, “Understanding Exit Planning,” January 9, 2023, https://blog.exit-planning-institute.org/understanding-exit-planning-epi-and-maus-partnership).
And yet, only fewer than half (41%) of business owners have written up a plan for their life after the business. (https://exit-planning-institute.org/hubfs/Member%20Center%20Resources/2023%20National%20State%20of%20Owner%20Readiness%20Report.pdf)

These numbers matter. Owners spend their careers focused on growing the P&L and driving EBITDA. But when the exit comes, most are underprepared both financially and personally.

Blind Spots That Lead to Regret

The biggest blind spot is failing to calculate what you actually need to maintain your lifestyle. The business may be funding not just your personal spending, but philanthropy, parents, and children as well. Without planning, all of those commitments are at risk.

For women owners, the challenge is compounded. Many women run lifestyle businesses that depend on their leadership and personal networks. They often don’t engage financial advisors early, unless already have investable assets. That lack of preparation means they only meet advisors after the sale, when it’s too late to shape the outcome.

And for all owners, the daily demands of running a business make it easy to ignore exit readiness. But ignoring it guarantees regret, rather than preventing it.

How to Avoid Regret

Avoiding regret is possible, but it requires intentional planning. Follow these steps for an exit you won’t regret:

Know Your Number. Identify how much you need to get out of the business to fund your lifestyle. This means running wealth gap calculations, not relying on a “big number” in your head.
Create Optionality. Start building value now so that you can sell when you want to, not when circumstances force an unplanned sale. Optionality equals power.
Build Transferable Value. Businesses that depend on the owner are far less salable. Make sure your company can thrive without you.
De-Risk Early. Clean financials, strong contracts, diversified customers, and key-person protection all increase value and reduce risk.
Assemble a Full Team. Owners who avoid regret don’t take the first offer. They engage investment bankers, attorneys, CPAs, and a financial quarterback to orchestrate the process. Yes, it costs money, but it saves far more in the end.
Plan Your Next Chapter. Don’t wait until after the sale to figure out who you are. Work with advisors who can help you define your next chapter in advance.

Getting it Right When the Stakes Are High

Exiting your business is a big deal — it’s a transaction that ushers in a new identity — and you only get once chance to get it right. If you sell for too little, or without a plan for your life afterward, you can’t go back. The deal is done. You can start another business, you can consult, but you can’t undo a sale that didn’t give you enough to fund your future.

Two things are critical.

First, build value now so that when you do sell, you get what you need.
Second, start working today with someone who can help you emotionally prepare for that next chapter.

Mentally frame your exit not as the finish line but as a transition. Make it one you won’t regret by preparing both financially and personally.

You can’t control the market. But you can control whether you are one of the 75 percent of owners who regret their exit, or one of the 25 percent who move forward with confidence.