How to Handle The Terrible Pitfalls of Success

How to Handle The Terrible Pitfalls of Success

January 19, 2018

Sloane Stephens lost again last night.

If you’re a tennis fan, you know that last year Sloane Stephens somehow won the U.S. Open. To say that her winning a Major was a surprise was the understatement of the century. Stephens was unseeded when she won (almost never happens) and had lost in the first round of two of her previous four tournaments.

Not to mention that 2017 was the most parity-stricken year in women’s tennis history (as many as 8 women had a chance to finish the year #1) and the seeds fell down in front of her all the way through the draw. Stephens didn’t play a seed higher than #9 the whole event.

Incredible unlikeliness aside, the real question is: What would Stephens do after this unexpected windfall?

After all, we know that bad things happen to people who gain tremendous success:

  • 70% of lottery winners go bankrupt within a few years.
  • 78% of NFL football players are bankrupt (or in dire financial stress) within 2 years of retirement.
  • 60% of NBA basketball players go bankrupt within 5 years of retirement.

So what has happened to Stephens since her Major win?

She’s lost her last 8 matches in a row. She literally hasn’t won a match since she won the U.S. Open.


For lottery winners, a huge problem is that they feel they don’t deserve it. Most of the time, lottery winners aren’t already rich. When a winner, who was poor, suddenly becomes rich, it’s very uncomfortable. So they spend and spend and spend until they end up right where they were before winning the lottery.

And balance is restored.

If you think you’re not exceptional, being called exceptional can be an awful burden. You can feel hollow inside. You can feel like a fraud. And the best way to get rid of those awful feelings to become not exceptional.

If you feel like you’re really a poor person, then consciously or unconsciously you’ll make investments that will end up going bad. Would a confident billionaire invest in an inflatable raft company (like a bankrupt baseball player once did)? Probably not. Would a confident billionaire turn over control of all of his investments to unqualified family members or shady fast-talkers? Probably not.

But the lack of self confidence leads to decisions that are desperate or ill-informed. If you believe that riches belong in your bank account, then the riches will stay right there. If you believe you’re just a poor person who happened to make it, and that other people are the ones who deserve to handle the money, then the money will go away.

If we want success, we have to first believe we deserve it. The mindset must come before the winning.

Without the proper mindset, success goes away and may not come back. There’s a reason Stephens has lost 8 matches in a row. She doesn’t believe she’s a Major winner.

Until that changes for her (or for us), success will always belong to someone else.


My book is called The Inevitability of Becoming Rich, and you can find that here.