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