7 Regrets of Business Owners—and How to Avoid Them

For many business owners, exiting their company is one of life’s most significant events of their lives.

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Yet too often, that exit is marked by regret. Whether due to lack of planning or poor execution, these missteps can derail not just the transaction, but also the legacy an owner hopes to leave behind.

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Below are seven of the most common—and avoidable—exit regrets:

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1. Wrong Team: Many owners underestimate the complexity of exit planning and fail to assemble the right advisory team. A successful transition demands coordinated input from legal, financial, operational, and emotional intelligence advisors.
   
   
2. Wrong Numbers: Without a clear understanding of the business’s value and personal financial needs, owners are often blindsided. Too many rely on hearsay or gut feel instead of objective valuations, leading to mismatched expectations and undervalued exits.
   
   
3. Wrong Structure: Poor entity structuring, outdated shareholder agreements, or tax-inefficient deal terms can strip away wealth at the finish line. Last-minute planning can cost owners millions in unnecessary taxes and legal disputes. Legal and financial planning should be proactive—not reactive. 
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4. Wrong Capital: Owners may be unclear about the kinds of buyers or capital partners best suited to their goals—whether family, private equity, ESOP, or strategic buyer. Lack of alignment here can result in an exit that funds the future, but leaves the owner feeling disconnected from the outcome.
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5. Wrong Identity: Too often, the business is the owner’s identity. Without a compelling next act, many owners struggle to find their post-exit purpose. A successful transition includes purpose beyond the paycheck.
   
   
6. Wrong Timeline: Timing the exit for market highs or personal convenience—without preparation—leads to regrets. Value Acceleration is a process and built over time, not captured overnight. Planning should start years before a transaction.
   
   
7. Wrong Focus: Owners who chase income over enterprise value often leave money on the table. Exit planning is about building transferable value—shifting from being the center of the business to building a business that thrives without you.

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The good news? Regret is optional. 

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With the right preparation, execution, and mindset, you can turn exit planning into a strategic advantage—and a legacy-defining decision.

For a deeper dive into avoiding these regrets, join four expert in this "Top & Regrets" webinar as we unpack key lessons in exit planning.