Exiting a business is one of the most significant milestones in an entrepreneur’s journey, yet many owners reach this point unprepared, often paying a steep emotional and financial price. Research from the Exit Planning Institute reveals that 76% of business owners who sell their companies experience profound regret within 12 months of their exit. Even more concerning, between 70 to 80% of businesses listed for sale will never sell, according to Buy Then Build. This underscores the importance of planning not only for the sale itself but also for the legacy, personal identity, and lifestyle changes that follow.
One of the most damaging mistakes is failing to start planning early enough. 58% of small business owners have no succession plan, according to USAToday. Without proper preparation, owners are often forced into rushed, reactive exits that typically result in lower valuations, unfavorable sale terms, and deep personal frustration.
Another critical misstep is misunderstanding the true value of the business. According to CNBC, 98% of small business owners didn’t know the value of their companies. This disconnect between perceived and actual value can lead to either overconfidence (resulting in unsold businesses) or underpricing (leaving money on the table). A professional valuation conducted years before the intended sale can help avoid these costly misunderstandings.
Regret can also arise in how employees are treated during the transition. Research from U.S. Bank shows that only 34% of family business owners have documented succession plans that address employee continuity, leaving many loyal employees uncertain about their future when a sale occurs. For owners who have built close, family-like teams, failing to protect their people can lead to lasting guilt and disillusionment regarding the legacy they’ve left behind.
With thorough planning, clear valuations, personal readiness, and attention to employee welfare, business owners can transition with confidence—reaping the rewards of their hard work while avoiding the regrets that plague so many entrepreneurs. Exit success isn’t accidental; it’s intentional, data-driven, and deeply personal.