AMA, sold biz/Next Chapter

Job

After 35 years in business, I sold my independent dealership 16 months ago to a national chain. I’ve stayed on to run the new entity, but it’s entirely “joyless”. Money, benefits, PTO are great. Going from a “rockstar” lifestyle to working for the man seems pointless, but I’m having a hard time deciding whether to move on to write my next chapter. The biggest issue is, after working 80 hour weeks as the owner, I’ve forgotten how to take time off and enjoy life. For reference, over those 35 years, I got married, raised a family, created generational wealth, became a servant leader to my work family, took great joy in paying my team at top of industry $, played 3000 rounds of golf, visited 27 countries and 49 states, drank and partied like a rock star, and…worked way to much. But I loved it all. Now that I’ve sold to a joyless large company, all I do is work. I’m not sure why I can’t move on. I don’t hate it, and I don’t love it. Everything seems kinda pointless. Even looking at my finances is blah. I definitely am not ready to retire If this post (my 1st) sounds privileged, trust your instincts. AMA, and I’ll ask yall: should I quit and start a new chapter (company)?

Posted Aug 31, 2025, 12:11 AM UTC

01
Loading comments…