He did everything right—at least on paper. Built wealth in tech. Amassed an eight-figure net worth. Never drank, never smoked, stayed in shape. But now, at 53, he's looking around and realizing: he's alone. No spouse, no kids, no real sense of meaning. Just money. And regret.
"I let my life pass me by," he wrote in a post that struck a nerve with thousands on Reddit. "I worked 13 hours a day, rejected women, and built a system that's long retired. It meant nothing."
Now he watches young people give up in their twenties, and all he can feel is frustration—and envy. "It makes me sick how 23-year-old men are giving up," he wrote. "I would give it all today to be 23 again."
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He's not angry at them. He's angry at time.
"You become invisible when you get older," he said. "Even women your age don't want you."
Despite having more money than most people dream of, he admits he feels like he missed the point.
He's watched time disappear in a blur of late nights and long hours. He remembers 1994 "like yesterday," when he had just graduated and was working 13-hour shifts in a big-name finance firm. Two of his managers are now dead. The system he helped build is gone. "It meant nothing," he wrote.
Now he's facing what he calls a "lifetime of being alone." No family. No partner. Just the weight of time and a gnawing feeling that he spent decades chasing things that didn't matter. "Hope this post is a wake-up call," he said. "Too late for me."
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But thousands of Reddit users didn't agree. Some said he was still young—53 isn't a death sentence. Others pointed out that people tend to romanticize the past. At 18, they missed being 10. At 25, they missed the freedom of 18. And at 53, it's easy to miss 23. That's how time works—no matter where you are, the last chapter always looks easier.
One user offered a perspective shift: instead of wishing you were 23 again, imagine you're 90 and just got dropped back into your 50s with a second chance. You'd probably do something with it.
Those words snapped something open: the realization that money alone can't fill the emptiness of time wasted or relationships neglected.
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It echoes something Warren Buffett—now in his 90s—once said about what true success looks like:
"When you get to my age, you really measure your success … by how many of the people you want to have love you actually do love you."
Buffett's words cut through the noise: a big bank account is useless if your life is empty of the people you care about.
Plenty reminded him that having money and good health at 53 puts him ahead of more people than he realizes. It's not over. There's still time to build something that matters—not a company or a system, but a life. A good one.
The real tragedy isn't being alone. It's believing you have to stay unhappy and lonely.
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