The Curse of Success

Just look at all the successful people around you. Doctors are too busy to see their families. Scientists are so brilliant they won’t change disciplines. Public figures are so popular they can’t change their minds.

One of the problems with success is that it gives us something to lose. As a species not known for risk-taking, it seems after our underlying needs are met, there is little incentive to explore our limits any further. Success for many becomes the acquisition of approval, often through successive jobs — building safety net upon safety net.

In this reality, there is no need for risk-taking; instead, we just become habitual acquirers of safety nets.

That’s not to say this pursuit is necessarily bad; even Einstein talked about how “a calm and modest life brings more happiness than the pursuit of success.”

But what opportunities do we lose in that pursuit? How many world-altering entrepreneurs, academics, artists, and restaurateurs are trapped in institutions of successful stability?

If we are well supported enough to take a risk, do we have an obligation to do so? I suspect many wouldn’t agree — life is hard enough already. Why invite chaos to the tea party?

“Never promote someone who hasn’t made some bad mistakes, because if you do, you are promoting someone who has never done anything” — Philip Fisher

I found myself trapped by success once. After leaving medicine and moving to London to begin my first startup job, I had within six months displaced my manager and was promoted to head of product. Sounds like a great success story, right?

At the time, I felt like a god damn genius. But truth was that this success had more to do with luck than skill. At the director level, I learned you never really know how your choices impact until much later. That’s not great when most of those decisions are being based on first-hand instincts.

The salary was good, the team was terrific, and I was growing into an increasingly lavish London lifestyle. But as years passed, I realized that I was not really great at the things I wanted — still not confident about how to grow a company, let alone a successful product.

In the end, I did the only thing that felt reasonable — I started again. I quit and took a junior role at a company with strong product culture. This would be the fastest way I reasoned to test and learn from my assumptions — see if any of them were true.

Apparently, many in tech feel that the best way to accelerate your career is by attaching yourselves to a growing product. Take it from me this may be great in the short term, but this kind of success is a lousy teacher. Worse, we may start believing in our own success narrative while becoming handcuffed to the lifestyle success affords us. There is less time for honest reflection.

As French writer Charles Augustin Sainte-Beuve once said, “There are people whose clocks stop at a certain point in their lives.” I agree; and we should be wary that with success always comes the risk of stunting personal growth.

The joy of failure

Failure has a strange and remarkable omnipresence that other aspects of our lives can’t quite capture.

French surgeon Rene Leriche once mused that “every surgeon carries within themselves a small cemetery to which they must go from time to time to contemplate. It is a place full of bitterness and regret. A place where they must look for an explanation for their failures.”

See, friends and loved ones may come and go; successes and triumphs are only temporary, but failure for Romanian Philosopher Emil Cioran (whose work on the Heights of Despair inspired this article) was different — failure sticks with you. Each one becoming a scarlet letter we carry.

There are just so many more ways to fail than succeed, and failures are just far more interesting, not to mention funny. So why, Cioran would ask, do we make such an effort to run from failure?

Let’s say you were at a party. Who would you rather speak to — the guy who married their high school sweetheart, studied law, and everything worked out; or, would you rather talk to the person that failed? The person who wanted to be a programmer but couldn’t get their head around functions so they moved to Mexico to pick vegetables but kept crushing the avocados, so they became a crystal healer, but here’s the thing, they know nothing about crystals. Who is the better conversation? The success or the failure?

Though failure is something we strive to avoid, sometimes it’s the fear of failure that singe handily promises it. “People waste years of their lives not being willing to waste hours,” to paraphrase Israeli cognitive psychologist Amos Tversky. So terrified we are of failure that we risk sitting around and never doing anything.

When we make an important decision, we tend to do so in consideration of failure. So it’s worth asking what opportunities we miss through the aversion. What if, Cioran would ask, instead of running from failure, we were to lean into it? Because for all we know, it may be the most important part of the human experience.

“Look, if you had one shot, or one opportunity To seize everything you ever wanted in one moment Would you capture it? Or just let it slip?” — Marshall Bruce Mathers III, “Lose Yourself”

For example, comedians like Chris Rock always perform in front of small crowds before taking their routines to a larger audience. This way, they can observe what jokes prompt laughter and adjust.

I think that’s the trick; you want to take risks on failing, but never a failure so spectacular that you never recover completely.

“The optimist sees opportunity in every danger; the pessimist sees danger in every opportunity.”- Winston Churchill

True success may be the ability to look back a year from now, and not being able to believe how ignorant you used to be.

What success never gives us

Being blessed with success is like carrying a torch in front of a lamp — it casts an ever more powerful light on those around you.

We are drawn to such individuals hoping to learn their secrets. Trouble is, those with success are never great storytellers.

In fact, the stories we hear of success are pretty similar (just watch any TED talk). Typically they follow a hero’s journey of desire, discomfort, overcoming the odds, sacrifice, then returning victorious and better for the experience. We easily fall prey to this narrative fallacy, which offers what our minds crave: logical chains of cause and effect.

Now our philosopher in residence Emil Cioran would understand all this, and I think he’d probably say, “Hold on a second … are we focusing on the wrong part of the story?” Cioran would ask, “What is it that you always get from failure that you absolutely never get from success?”

The answer? One thing failure never fails to do, is give us an honest picture of who, at this moment, we actually are.

I love the following analogy from Stephen West which I think describes this idea nicely. Imagine some middle-aged dude who drives down after work to the local primary (elementary) school. He puts his exercise headband on and challenges all the 10-year old’s to a friendly game of basketball.

He’s taking jump shots, ripping the ball, blocking all their shots, trash-talking. When it comes to basketball games against school kids, he’s the best in the biz. But here’s the thing, if Lebron James goes down to the very same school, he too would be the best in the biz. So if this is the only sample to work from, who is to say who is truly the better player?

How can the middle-aged dude ever honestly know how good he is at basketball until he dares to challenge himself enough to fail and see where his limitations are?

Though success is desirable, Cioran described how “failure reveals to us to ourselves” whereas “success distances us from what is most inward in ourselves and indeed in everything.”

By playing it safe or focusing on past accomplishments, we inadvertently create obstacles to our personal development in the present.

Success has many fathers, but failure is an orphan — Possibly George Washington

When listening to stories of success, take them for what they are — stories.

Favour narratives of failure over success, experimentation over storytelling (data over anecdote), experience over history (which can be cherry-picked), and knowledge over grand theories. Success narratives should be an opportunity for sharing honest reflections.

If you find yourself living through previous successes, remember that it’s what you’re doing now that makes the difference.

Failure and failure narratives should be a voice of reason that keeps us honest about who we really are.

Repeated success has a nasty habit of making us lose interest and stop trying as hard. I think the founder of Intel and father of the OKR, Andy Grove, was right when he said, “Success breeds complacency.”

Yes, success can bring great rewards; yes, it is desirable, but it also increases our anxiety and fear of future failure.

Our pursuit and maintenance of success becomes the enemy of personal freedom. We can be coerced into doing what is defendable rather than what is necessarily right.

“When you have reached the top of a mountain, its hard to keep climbing.” — Buddhist proverb

Author and business coach Jim Collins would suggest that Regardless of the outcome, we should always focus on developing qualities that enable long term success and happiness: passion, perseverance, imagination, intellectual curiosity and openness to new experiences.

There are two things I believe we can do to help achieve this:

Celebrate past successes in moderationEnsure self-awareness prevails — “Know thyself”, as the Greek aphorism proclaims

“Success is not final, failure is not fatal: It is the courage to continue that counts.” — Churchill

Taking time to slow down and examine our failures and successes can be emotionally unpleasant. Failure is arguably easy to reflect on, but being honest about our successes is challenging — it requires setting aside ego and putting our self-esteem on the line. A true test of our intellectual curiosity and openness.

Next time you are successful, ask yourself: Why should my current achievements make me believe I deserve repeated victory?

“Trying to make a consumer product successful without an existing distribution advantage can instill more professional humility in a product person than anything else I know.”- Shreyas Doshi, Product Advisor, Twitter

They say beware the person with nothing to lose. But I say we should envy that person; for I suspect that success and failure no longer inhibit their actions. In a way, they alone are free.

“ If you’re laughing, you’re winning.” — A psychiatrist I heard once

Further reading

Episode #156 … Emil Cioran Part 2 — Failure and Suicide (Philosophize This!) — Podcast, Steven West

Previously published here.