Business Exit Planning – Ramp Up to Retirement

Life After the Sale: Designing Your Next Chapter Before You Exit (Ep. 26 | Pt. 2)

By Ramp Up To Retirement | March 11, 2026

What happens when the title you have carried for decades suddenly disappears? How do you prepare for the emotional shift that comes after stepping away from your business?

In this episode, Dan Reese, CFP®, continues the business exit series by focusing on the personal side of transition. He explains why identity, routine, and purpose play such a critical role in life after a sale. Dan shares practical exercises to help business owners design their ideal week, align with their spouse, and prepare emotionally for what comes next. He also discusses research suggesting that many owners experience regret after selling and how intentional planning may help reduce the likelihood of regret.

Key takeaways:

Why identity transition is one of the biggest hurdles after selling a business
How routine and decision-making impact emotional well-being in retirement
The importance of lifestyle design and structuring your ideal week
Why spousal alignment and family communication matter before exiting
How proactive exit planning strategies can help business owners prepare emotionally and financially for transition
And more!

Resources:

Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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Are Business Owners Ready for the $14 Trillion Exit Wave? (Ep. 22)

By Ramp Up to Retirement | December 24, 2025

Most business owners say they feel prepared to step away, but available data suggests gaps in readiness.

In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion of many owners’ net worth tied up in their business, exit planning often involves business, personal, and financial considerations.

Dan walks through common elements often associated with readiness, including understanding business value, identifying wealth gaps, and planning considerations for life after the business following a transaction.

Dan discusses:

The role small and mid-sized businesses play in the U.S. economy
The commonly referenced three legs of exit planning: business, personal, and financial considerations
The role formal business valuations can play in exit planning
The wealth gap and how lifestyle expectations may affect a transition
And more