Why 75% of Business Owners Regret Selling Their Business (And How to Avoid Being One of Them)

The numbers are staggering: 75% of business owners profoundly regret selling their company within just one year of the sale, according to surveys from the Exit Planning Institute. Despite receiving what seemed like life-changing money, three-quarters of entrepreneurs find themselves wishing they had never signed those papers. The question isn’t whether you’ll face regret – it’s whether you’ll be prepared for it.

The Hidden Emotional Cost of Success

When most business owners think about selling, they focus on the financials: maximizing valuation, negotiating terms, and securing the best deal. But what they don’t anticipate is the profound emotional vacuum that follows. Your business isn’t just an asset – it’s been your identity, your purpose, and has often been your primary source of fulfillment for years or even decades, in fact it is your life’s work.

The deepest regret rarely stems from the money itself. Instead, it comes from something much deeper: the realization that they weren’t emotionally prepared for life after the exit. The first 12 – 18 months are often filled with decompression, catching up with friends, family, golf, and travel. It is after this period that the voice of regret starts to be heard.

The Six Core Reasons for Post-Sale Regret

1. Loss of Identity and Purpose

While Identity and Purpose are different, For many entrepreneurs, their business introduction has been “I run XYZ Company” for decades. When that’s gone, there’s an unsettling void. They wake up asking: “Who am I now?”

Without the daily rhythm of leadership, problem-solving, and decision-making, many former owners feel professionally and personally lost. The adrenaline rush of building and growing something meaningful is extremely difficult to replace.

Many privately held businesses were started to provide an income and support a family and eventually a lifestyle. The business is often linked to a purpose filling a gap, to solve a problem that the founder perceived. Once they step back the absence of the sense of fulfillment, pride, or mission can make them feel aimless.

2. The Reality of Financial Expectations

The sale price may feel like a victory initially, but owners often discover they:

• Overestimated how far the money would stretch
• Underestimated taxes, fees, and inflation
• Miss the steady tax efficient cash flow their business once provided

Only 5% of business owners report being happy with their net proceeds from selling. Wealth on paper isn’t the same as sustainable income, and many realize too late that their business was their primary wealth-generating engine.

3. Lack of Business Post Exit Planning

The main mistakes owners make in relation to the business:

• Clear definitions of roles and responsibilities to operate independently
• Preparing and testing the team to solve the issues you do day in and day out
• Preparedness for handling an attractive unsolicited offer
• Uncoupling all the lifestyle expenses you run through the business

4. Lack of Personal Post-Exit Planning

According to research, 60% of business owners who regret their sale had no formal personal plan for what would come next. Some think that it is something you do in the final year. They spent months preparing their business for sale, cutting costs, moving things around, but zero time preparing themselves or their family for life after the transaction beyond the catch up on a sport, travel or time with family and friends.

5. Culture and Legacy Concerns

Many founders dream that buyers will honor their legacy, people, brand, and values. When new owners cut staff, change or integrate culture, treat clients or vendors differently, or dismantle what was built, original owners can feel that their life’s work was undone. This emotional pain can be devastating for entrepreneurs who viewed their company as their legacy.

6. Timing Regrets and Second-Guessing

Some sell too early, truly leaving money and growth potential on the table. Others wait too long, holding out for the market to pay a value that the business isn’t worth that they originally plucked out of the air, or must sell under health or financial pressures. These scenarios lead to an endless “what if” loop replaying repeatedly.

Additionally, friends or family members can plant the seed of doubt that your business could have been sold for more, or a better or prestigious buyer could have been found. All of these can be true, but when buyers look to buy and when sellers are open to selling don’t always align. As much as sellers want to sell for maximum value, most are not worth it, for most businesses buyers do not look to pay for top dollar for mediocrely run and prepared operations. One of the common reasons potential buyers withdraw is that the quality of the business doesn’t equate to the sellers’ perceived value expectations and ego.

The Myth of Retirement Bliss

The fantasy of leisurely retirement often clashes with reality. Golf, hobbies, and travel don’t provide the intellectual challenge and sense of accomplishment that running a business did. Many discover they miss even the “fire drills” they once thought they hated.

Strategies to Avoid Post-Sale Regret

Start Emotional Preparation Years in Advance

Begin planning and implementing your exit, mentally, emotionally and activity based as early as possible – ideally 3-5 years before you intend to sell. This gives you time to gradually adjust to the idea and develop and test interests beyond your business.

Define Your “Next Chapter” Before You Need It

Don’t make the mistake of seeing the sale as your ultimate goal. What comes after is just as important. Whether it’s investing in new ventures, mentoring other entrepreneurs, pursuing philanthropy, or finally writing that novel—have a quantifiable plan that excites you.

Build Your Identity Beyond Your Business

Start expanding your sense of self while you’re still running the company. Join boards, pursue hobbies, volunteer for causes you care about, or take on advisory roles. This helps prevent the identity crisis that catches so many former owners off-guard.

Assemble a Strong Advisory Team

Surround yourself with professionals who understand the business, emotional, day-to-day, and financial aspects of your exit, including other entrepreneurs who have successfully navigated their own transitions. Their experience can provide invaluable perspective during challenging moments.

Consider a Phased Exit Strategy

Rather than an abrupt departure, explore options to stay involved through consulting roles, board positions, or retaining partial ownership. This can provide continuity and ease the emotional separation while still achieving your financial goals.

Focus on Your Legacy, Not Just the Transaction

Think deeply about what you want your business to represent in the long-term. Clear legacy and financial priorities help guide decision-making and can reduce regret about how new owners handle your company.

The Path Forward: Preparing for Success

The entrepreneurs who successfully navigate their exit share one common trait: they treat selling their business as a life transition, not just a financial transaction. They understand that preparation extends far beyond financial statements and legal documents – it requires emotional readiness and a clear vision for what’s next.

Remember, 76% or more of an owner’s net worth is typically tied to their business. This isn’t just about maximizing the sale price and its bragging rights at the country club, it’s about maximizing your life satisfaction afterward.

The choice is yours: join the 75% who look back with regret, or be among the 25% who successfully transition to a fulfilling next chapter. The difference lies not in the deal you negotiate, but in how well you prepare yourself for the person you’ll become after signing those papers.