What if selling your business didn’t bring the fulfillment you expected? While most discussions around business exits focus on valuation, deal structures, and financial freedom, few address the emotional toll that follows. In this episode, Jerome Myers, America's leading exit authority, unpacks the silent costs of selling a business—the identity crisis, emotional void, and six centers of doubt that can leave founders feeling lost. He shares why 75% of entrepreneurs regret their exits and reveals a four-step framework to help navigate post-exit life with clarity and purpose.

If you’re planning an exit or struggling with what comes next, this episode is your guide to designing a fulfilling next chapter.

[00:00 - 01:15] Introduction: The Emotional Toll of Selling Your Business

• Exiting a business isn’t just financial—it’s personal and emotional
• Many founders feel lost, questioning their identity after selling
• This episode uncovers what happens emotionally after an exit

[01:16 - 03:09] The Six Centers of Doubt Every Founder Faces

• Self-Image: “Who am I without my business?”
• Relationships: “Do I still belong if my network was tied to my company?”
• Work: “I need something to do, but what?”
• Health: “I sacrificed my well-being—can I fix it now?”
• Prosperity: “I have time and money, but am I using them wisely?”
• Significance: “What is my impact beyond the business I built?”

[03:10 - 04:44] Why 75% of Founders Regret Their Exit

• Without a clear post-exit vision, many founders fall into one of two traps
• A company doesn’t automatically bring fulfillment—it must be intentionally designed

[04:45 - 06:00] The Four-Step Process to Exit with Clarity

• Nourish: Take time to recover and reflect
• Explore: Identify what truly excites and fulfills you
• Evaluate: Test new paths before committing too soon
• Transcend: Step thoroughly into your next chapter with confidence

[06:01 - 06:54] Taking Action: Designing Your Next Chapter

• The key to a successful exit is preparing beyond financials
• Jerome’s Exit Readiness Assessment helps founders determine if they’re genuinely exit-ready
• Instead of suffering in silence, founders should proactively plan for their next phase

Key Quotes:

“The moment you sell, you’re not just exiting a company—you’re exiting an identity.” - Jerome Myers

“You either design your next chapter with intention or drift into regret.” - Jerome Myers

Ready for your next chapter?

Start Your Assessment Now 👉 https://theexitparadox.com/assessment

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You sold your business… now what?

No one warns you about the identity crisis, the void, or the doubts that creep in after the deal is done. 75% of entrepreneurs regret their exit but it doesn’t have to be that way.

In this episode, I break down the hidden costs of selling and share my four-step framework to help you navigate what’s next with clarity and purpose.

Don’t let your exit become your regret.

🎧 Listen now:

#BusinessExit #LifeAfterExit #BeyondTheDeal

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