This Entrepreneur Retired In His 30s, But Here’s Why He Hates It

It was time to celebrate. Aaron had just sold a large portion of his startup and his friends had gathered to toast his newfound wealth. What they didn’t realize at the time – nor did he – was that they were also toasting Aaron’s early retirement.

Aaron, who couldn’t provide his full name due to contractual obligations in the sale of his company, had found himself wealthy enough to where he wouldn’t have to work for the rest of his life. Suddenly, the drive to build and grow new businesses – something he had done since joining the workforce – had vanished. He realized, a few months after the celebratory dinner party with his friends, that he had reached FIRE (financial independence, retire early) in his mid-30s. The only problem?

He hated his retirement.

More reading: The Forbes Guide To Fire

Those that pursue extreme early retirement will give up almost anything today, for the promise of a cushy escape from the 9-to-5 in the next five, ten, 15 years. They look upon that moment where freedom will reign as worth the pain of missing out or cutting back in the present. But for everyone that seemingly enjoys the endless days of no obligations, there are others that find the experience stifling, filling them with dread and a sense of aimlessness.

For Aaron, he quickly realized that he wasn’t enjoying having all the time in the world. But it also sapped him of the drive and ambition that had pushed him to his success. It has left him with the sinking feeling that his early retirement won’t last.

Always Wanted Financial Independence

Aaron always knew he wanted financial independence, which he defined as not needing to rely on a job for security. It stemmed from childhood, when money was often tight. “Money always meant freedom to me,” he said.

He came across the idea of FIRE early in his working career and it always clicked with him. While he initially started to try and cull back his spending, in order to upsize his savings efforts, he disliked the monastic lifestyle. So instead, he focused on making more. That wasn’t difficult, since he also enjoyed building businesses.

“A lot of people want to retire early,” Aaron said, but he didn’t think about it much. He liked what he did, enjoyed his coworkers and he had some semblance of control over his position.

After the sale of the business, though, he told himself to take some time off. He got some travel in, visiting places like Japan and Portugal. He caught up on shows and movies he had missed. But the abruptness of the sale, and the lack of another job, made leaving the company feel more like “a divorce,” he said.

He Tried To Launch A New Business

Within months after leaving his company behind, Aaron had already begun planning another company, not out of desire but fear. “I had never been more wealthy,” he said, “and never felt more poor.”

By May of this year, he had developed the idea to the point he began talking to investors and started the early steps to launching the firm, when he suddenly stopped. Despite trying different work methods, like focusing on it for four hours a day, four days a week, he couldn’t summon the energy to pursue the thought more than just as a hobby, he said.

Suddenly he had financial freedom, and “my drive went away,” he added. While he’s still pursuing the idea, there’s little timetable for turning it into his third act.

The Pursuit For Purpose

In a recent Reddit post, Aaron first laid out his issue with adjusting to the ‘retire early’ portion of FIRE. In it, he issued a challenge that he would seek to find his passion again, by fulfilling a series of goals through November. The tasks range from going to the gym at least four times a week, to eating one vegan meal a day or meditating every morning.

While some tasks have been easier, like the gym for example, others have been more difficult, like the meditation. By posting it to the public, though, it “gave me the accountability,” he said.

Without the public posting, he’s not sure he would have had the follow-through to continue pursuing some of the goals. The feedback has been profound he said, as he’s connected with others, pleading for advice on their own startup idea. “[It’s] been a rewarding thing that I wasn’t expecting,” Aaron added.

It hasn’t, however, changed his opinion about his early retirement.

Adjusting To The New Lifestyle

In talking with others that have retired at an extremely young age, whether in their 30s or 40s, they often say it takes at least six months to brush off the sense that you should be doing something productive. It makes sense. When on the job, there’s a constant feeling that if you’re not producing, then you’re falling behind. Once you step away from that environment, your body must adjust.

Aaron, however, has been in retirement for 14 months. “I don’t think this is for me,” he said. But the freedom has given him the chance to take a moment so he can figure out once he un-retires, what he wants to do with his time, unmotivated by the financial factors.

Maybe that’s why in the goals listed on Reddit, he also included one business-focused objective. He plans to vet one of three ideas he has for a new startup. It’s not a full-time job, at this point, but if he finds the right motivation, who knows.

That early retirement very well may turn into a mini one.

More reading: Millennials Love Sabbaticals. Here’s How To Save For Yours

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