Why success is a lousy teacher

Earlier this week, I finished the final draft of my forthcoming book. It’s a huge milestone, and I’ve been delighted with the feedback I’ve received from my agent, publisher, and trusted early readers (one said, “Fucking incredible! Thank you for creating a masterpiece to help the world grow. No matter what the ‘outcome’ is with this book, it changed the way I choose to approach the world”).

Although I’m happy with the early feedback, I’m also taking the time to pause, reflect, and think through the mistakes I made along the way.

I’ve learned the hard way that success is the wolf in sheep’s clothing. It boosts egos and drives a wedge between appearance and reality. When we succeed, we believe everything went according to plan. When we’re popping champagne corks to celebrate successes, we avoid a reckoning. When we think we’re destined for greatness, we start blaming others if things don’t go as planned. Success makes us think we have the Midas touch—that we can walk around turning everything into gold.

As Bill Gates says, success is “a lousy teacher” because it “seduces smart people into thinking they can’t lose.” “Whom the Gods wish to destroy,” wrote Cyril Connolly, “they first call promising.” The moment we think we’ve made it is the moment we stop learning and growing.

But it’s possible for bad decisions to lead to good outcomes. You can win a poorly played poker hand if luck intervenes. A badly shot soccer ball can end up in the goal if it ricochets off another player. A bad trial strategy can produce a win when the facts and the law are on your side.

The early readers that enjoyed my book are seeing only the final product. They’re not seeing the ghastly first drafts, the pages and pages of material I cut out because I was too embarrassed to even look at them (let alone print them), and the numerous bad decisions I made along the way.

Here’s one example: I had about 12 months to finish the book, and I spent 5 of those months on the first chapter I wrote (leaving only 7 months to finish the remaining 10 chapters!). My perfectionism kicked in, sending me down a rabbit hole as I attempted to read everything that was conceivably related to the chapter—including the entire Routledge Companion to Thought Experiments, a 600-page tome that was largely an excruciating read and ultimately produced zero usable material for the book. This made for a less-than-pleasant 7 months as I scrambled to finish the remaining 10 chapters by my deadline. This was a major time management failure—one that I won’t be repeating for my next book.

Here’s another example of learning from mistakes after a success, from the National Football League (NFL) draft. For my non-American readers, the NFL draft is an annual spectacle where football teams pick new players for the upcoming season. Each team gets to select one player in each of the seven rounds.

In the sixth round of the 2000 draft, the New England Patriots picked up a player who would go on to become one of the greatest quarterbacks of all time. Tom Brady would win five Super Bowls with the Patriots and pick up four Super Bowl MVP awards—the most of any player in NFL history. Brady would be dubbed the “biggest steal” in the 2000 draft, and the Patriots leadership would be praised for its brilliant strategic maneuvering in scooping up a player of Brady’s caliber at the tail end of the draft.

That’s one interpretation of the events.

Another interpretation is far less forgiving of the Patriots leadership. The Patriots had their eye on Brady for a long time, but they waited until the end of the draft to pick him up (he was the 199th pick of 254 total players—almost as bad as getting picked last in gym class).

In an alternate universe, the same process could have generated a very different outcome. Another team could have drafted Brady before the Patriots. Brady may not have realized his full potential if injuries hadn’t crippled the Patriots’ starting quarterback Drew Bledsoe, moving Brady into the starting line-up. In this alternate universe—which was inches from the actual one—the Patriots management would have been branded buffoons, not visionaries.

The Patriots management had gotten lucky with Brady. Instead of patting themselves on the back about their “biggest steal,” they treated the Brady incident as a scouting failure and focused on fixing their intelligence mistakes.

So the next time you’re tempted to start basking in the glory of your success while admiring the scoreboard, stop and pause for a moment. Ask yourself, What went wrong with this success? What role did luck, opportunity, and privilege play? What can I learn from it? If we don’t ask these questions, we’ll keep upping the ante, but our luck will eventually run its course.

Just because you’re on a hot streak doesn’t mean you’ll beat the house.

[The story of Tom Brady is based on Ryan Holiday, Ego is the Enemy].