American entrepreneur Logan Chierotti, recently named the EY Entrepreneur Of The Year 2026 Mountain West Award winner, has revealed why retiring at the age of 32 turned out to be one of the biggest mistakes of his life.
In a video shared on Instagram, Chierotti reflected on life after selling his business and achieving financial independence. Although he retired with several million dollars in the bank, he said the experience quickly became emotionally draining.
“Freedom without purpose = boredom,” Chierotti wrote alongside the video.
“I retired at 32 with a few million bucks in the bank. It was the worst mistake of my life,” he said.
The entrepreneur explained that after stepping away from work, he struggled to find meaning in his daily routine.
“I was sitting around, gardening, playing with chickens, trying to figure out stuff to stay busy to kill the day.”
At the time, Chierotti had a one year old child, and his wife was expecting another baby. Because of those family responsibilities, he said constant travel was not a realistic option.
“I have done it, it’s not that fulfilling,” he said while explaining that even extensive travel eventually loses its appeal.
Search for purpose led him back to business
Chierotti admitted that the financial success initially felt rewarding.
“Initially after I got the money it felt good. I remember feeling ‘I made it’.”
However, the excitement faded as he realised that complete freedom without meaningful work created an unexpected sense of emptiness.
“I was going crazy. I was driving myself nuts.”
He tried several activities to fill his time, including day trading, but nothing gave him the same satisfaction he had experienced while building a company.
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Eventually, he realised he missed solving problems, creating new businesses and working with talented people.
The entrepreneur decided to leave retirement and launch another company.
His experience reflects a growing conversation among business leaders about the psychological impact of early retirement. Research has shown that many entrepreneurs strongly identify with their work, making sudden retirement emotionally challenging despite financial security.
Social media users share mixed reactions
Chierotti’s video sparked widespread discussion on social media, where many users shared similar experiences while others defended early retirement.
One user 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 commenter wrote, “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 person added, “Hey Logan, thanks for sharing. I relate a lot. Exiting a CEO role at 33, and yeah, freedom without purpose is definitely boring.”
Not everyone agreed. One user argued that retirement offers opportunities beyond work.
“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.”
Chierotti’s story has resonated with entrepreneurs around the world by highlighting that financial success alone may not guarantee long term fulfilment. For many founders, purpose often comes not from reaching the finish line, but from continuing to build, create and solve meaningful problems.
