The Emotional Journey of Selling Your Business: Identity, Grief, and “Now What?”

Show Notes

Selling a business isn’t just a financial decision; it’s an emotional one. You’ve built something from the ground up… so what happens when it’s time to let it go?

In this episode of Moolala: Money Made Simple, host Bruce Sellery speaks with Jonathan Bennett, Executive Advisor at ClearlyThen Inc., about the emotional side of selling a business, the part most entrepreneurs aren’t prepared for.

While conversations around selling often focus on valuation, timing, and deal structure, this episode dives deeper into the identity shift, emotional challenges, and psychological impact of stepping away from something you’ve built.

In this episode, we cover:
👉What it really feels like to sell your business (from someone who’s done it)
👉The emotional stages business owners may go through, similar to the stages of grief
👉Why identity loss can be one of the hardest parts of selling
👉How to manage the emotional toll during the transition
👉Tips for preparing your team for a business sale
👉Advice for entrepreneurs who are selling but feel stuck or afraid
👉How to approach the process with clarity, confidence, and support

Whether you're planning an exit strategy or just starting to think about selling, this conversation will help you navigate the human side of entrepreneurship, not just the numbers.