Retiring in your early 30s is often seen as the ultimate success story. Build a company, make enough money, walk away from work, and enjoy life. That is why a founder’s recent admission about his own retirement has caught the attention of social media. Instead of calling it the best decision he ever made, he says it became one of his biggest regrets.American entrepreneur Logan Chierotti, recently named the EY Entrepreneur Of The Year® 2026 Mountain West Award Winner, spoke about the phase in an Instagram video. Although he had enough money to retire at 32, he said the excitement wore off much sooner than he had expected, leaving him with something money could not solve.
“Freedom without purpose = boredom”
While sharing the video, Chierotti wrote, “Freedom without purpose = boredom.”Explaining why retirement did not turn out the way he had imagined, he said, “I retired at 32 with a few million bucks in the bank. It was the worst mistake of my life.”He described what his daily routine had become after leaving work.“I was sitting around, gardening, playing with chickens, trying to figure out stuff to stay busy to kill the day.”
He says even travelling was not fulfilling
Chierotti shared that he had a one-year-old child at the time and his wife was pregnant, so travelling extensively was not really an option.He also said that, in his experience, travelling all the time is not the answer.“I have done it; it’s not that fulfilling.”The lack of meaningful work slowly began to affect him.“I was going crazy. I was driving myself nuts.”
The feeling of “I made it” did not last
Looking back, Chierotti said earning enough money to retire initially felt like a major achievement.“Initially after I got the money it felt good. I remember feeling ‘I made it’.”But that feeling did not stay for long. According to him, once work was no longer part of his life, he realized he missed building something new and being around smart people.He even tried day trading to stay occupied, but he said nothing held his interest.
Social media users shared different views
The video prompted many people to share their own thoughts on retirement and purpose.One person asked, “Thank you for sharing! And how are you feeling today? After all of this?”Chierotti replied, “I started another company and that has filled the void for me.”Another user 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 wrote, “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.”Another user had a different opinion and 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.”Disclaimer: This article is based on a viral social media post. The opinions shared are personal experiences and do not represent universal outcomes or professional financial or career advice.Thumb image: Instagram