Business Owner Near Retirement Reveals Difficulty Of Knowing How Much Is Enough | Road to Retirement

Business Owner Near Retirement Reveals Difficulty Of Knowing How Much Is Enough | Road to Retirement

June 22, 2026 · 45 min

About this episode

The episode explores the challenges faced by pre-retirees, particularly focusing on Shawn's journey as a business owner nearing retirement.

For so many people in their 50s and early 60s, the road to retirement doesn’t start with a perfect plan, it starts with fatigue. That’s where Shawn is today. After decades of running two small businesses, volunteering as a firefighter, and never really turning “off,” he’s finally asking the question every pre-retiree faces: When is enough… enough? This episode dives into the real challenges people face when they’re 1–3 years from retirement: selling a business, navigating healthcare before M...

People in this episode

Host: Ari Taublieb

Guest: Shawn

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