This Is For Those Of You That Don’t Realize When Enough Is Enough

“Whoever is not in his coffin and the dark grave, let him know he has enough.” — Walt Whitman
image - Unsplash / Caleb George
image – Unsplash / Caleb George

Back in undergrad, I met the founder of a successful brokerage company, Mark. He was in his late 50s, and by all accounts was the definition of success — at the top of his industry, had more than enough money, and was a nice guy.

At the end of our conversation, however, he admitted he was miserable. Some of his buddies from business school were making tens of millions of dollars — even hundreds — working at hedge funds, and despite the success of his company, he couldn’t keep up with them. He told me he’d been wanting to retire for many years, but he felt he had something to prove. The only way, of course, was to make more money than his colleagues. Retiring would mean that he had lost.

This made no sense to me at the time. For one, I was a fresh faced 18-year old who would have been happy to retire off of a fraction of what he was worth. But really, here was a guy who seemingly had it all and yet wasn’t satisfied. His idea of money as a measuring stick for success simply didn’t allow for him to retire, despite his waning interest and old age.
When I think back on this now, I’m reminded of a story Kurt Vonnegut recounted about his fellow writer Joseph Heller, author of Catch-22, while they were at a party hosted by a billionaire hedge fund manager.

“Joe,” I said, “our host only yesterday may have made more money than your novel ‘Catch-22′ has earned in its entire history.”

Joe said, “Yes, but I’ve got something he can never have.”

“What on earth could that be, Joe?”


It’s a beautiful story that reminds us of another perspective, that there is indeed more to life than the sole accumulation of money. I’ve seen this sentiment echoed by many millionaires and billionaires who reached the same conclusion after amassing great fortunes themselves. Peter Peterson, founder of the private equity group Blackstone, committed $1 billion to his charity foundation with the words “I have far more than enough.” Felix Dennis, publishing legend and self-made entrepreneur, regretted not stopping earlier in his pursuit of money. He writes, in his book ‘How to Get Rich’:

If I had my time again, knowing what I know today, I would dedicate myself to making just enough to live comfortably as quickly as I could. I would then cash out immediately and retire to write poetry and plant trees. But like an old, punch-drunk boxer, I couldn’t quit. I always craved just one more massive pay-day. It’s no excuse, but making money is a drug. Not the money itself. The making of the money.

Up to just seven years ago I was still working twelve to sixteen hours a day making money. With hundreds of millions of dollars in assets I just could not let go. Like I said, it was pathetic. Because whoever dies with the most toys doesn’t win. Real winners are people who know their limits and respect them.

Knowing what I know now, I’d send Mark this article if I could. To let him know that he had enough, that he had nothing he needed to prove. That he could and should retire in peace, with the knowledge that he had already made his dent in the universe.

Unfortunately, Mark is no longer with us. I’m not sure if he ever did retire, but I hope that he enjoyed the time he still had left. So while I can’t tell Mark now, I can still relay the message for myself and to others. I write this now as a reminder that one can always have enough money, but never enough time.

And if I ever do fall prey to the money bug, my only hope is that I’ll remember this post I wrote when I was 21, fairly broke, a bit naive, but happy with all I had. Thought Catalog Logo Mark

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