American founder Logan Chierotti, recently named the EY Entrepreneur Of The Year® 2026 Mountain West Award Winner, opened up about the psychological toll of retiring at 32 and what ultimately drove him back into the business world.
“Freedom without purpose = boredom,” Logan Chierotti wrote on Instagram while sharing a video of him recalling the time when he retired from working.
“I retired at 32 with a few million bucks in the bank. It was the worst mistake of my life,” the CEO says. He adds, “I was sitting around, gardening, playing with chickens, trying to figure out stuff to stay busy to kill the day.”
He recalls that at that time he had a one-year-old kid and his wife was pregnant, so extensive travelling was not an option. However, he says that travelling all the time gets boring after a point. “I have done it, it’s not that fulfilling.”
{{/usCountry}}He recalls that at that time he had a one-year-old kid and his wife was pregnant, so extensive travelling was not an option. However, he says that travelling all the time gets boring after a point. “I have done it, it’s not that fulfilling.”
{{/usCountry}}Chierotti continues, “I was going crazy. I was driving myself nuts.” To keep himself busy, the founder tried different things, including day trading, but nothing could hold his interest.
“Initially after I got the money it felt good. I remember feeling ‘I made it’,” Chierotti shares. However, he soon realised that the sudden absence of work left a profound void. While he had always craved absolute freedom, achieving it without a clear purpose only resulted in deep boredom.
He also missed the thrilling journey of building something and being around smart people. Eventually, he came out of retirement to start another company.
How did social media react?
An individual asked, “Thank you for sharing! And how are you feeling today? After all of this?” Chierotti responded, “I started another company and that has filled the void for me.” Another commented, “This is incredible. What a story to help remind everyone that it’s not about the destination, it’s the journey that gives true fulfilment. Thank you so much for posting this.”
A third expressed, “Hey Logan, thanks for sharing. I relate a lot. Exiting a CEO role at 33, and yeah, freedom without purpose is definitely boring. Cheers, Alex.” A fourth wrote, “Retiring is the best thing that has happened to me... at 32. Purpose can mean different things. More time for family, more time for God. Fun activities, etc. You'll still have the same problem at 65 when you retire, and by then it'll be worse. The body is fatigued, perhaps lifestyle diseases, who knows. The purpose needs to shift from work.”