Photo by Kate Williams on Unsplash

You Have To Make Failing Enjoyable To Win


One of the many reasons I love Munich is that everything is within walking distance. Always. Even after you’ve left the city center, hardly anything will demand more than 20 minutes of exercise from your legs.

Another reason is that those countless little trips from A to B are littered with stunning sights and beautiful buildings. “They don’t make ’em like this anymore,” my friends and I often agree when we look at yet another 100-year-old architectural masterpiece.

I can’t tell you how many times I’ve asked myself, “why don’t we?” but today, after years of scratching my head, I can at least give you the answer. “I wish we still built houses like this,” it turns out, is a terrific example of survivorship bias. Because we do — we just haven’t torn down the ugly ones yet.

For any period of architecture, 100 years later, only the sturdiest and prettiest buildings will remain. By that time, everything else will either have collapsed or been rebuilt. It’s such a simple, perfectly logical, elegant explanation, and yet, it has escaped my mind for years.

That’s the nasty, distorting power survivorship bias can have — and it’s also why we should fight it wherever we encounter it. After all, not everything in life is as laissez-faire as a stroll around town.


I’m not a world-famous writer or bestselling author, but I entered the writing world over 4 years ago — and I’m still here. That makes me, by definition, a survivor. Unfortunately, it’s also enough to make me look like a winner to the budding writer’s eye.

You have an idea, you start writing, you browse the web and, 20 minutes later, you close your laptop in despair, thinking, “my God, where could I possibly find the authority to hit publish? All these people are insanely successful.”

But you never saw any freshly minted writers like yourself. You just screened a portfolio of the victorious cases of evolution. That’s also survivorship bias and it can intimidate you into never even chasing your goals.

The results you see from other people might be an average outcome for those, who make it through the dip, but because you have none of the quitters to compare them with, they look like superheroes.

To combat this, you’ll either have to find some of those quitters, for example in the form of deserted blogs on the web, or create a much more granular picture of each of the winners.

And while I can only speak from my personal experience with writing, I can tell you, man, have I torn down some ugly buildings throughout the years.


Failing on the internet is wonderful. You can just shut down the site, take back the announcement, email a few people, and the books of history are wiped clean. Contrast that with closing your restaurant, getting booed off stage, or telling your investors you lost their money. Yikes.

But just because it’s easier to hide, scrap, and ignore failure online doesn’t mean it never happens. It does all the time. Here’s a tiny excerpt from my personal list of “things that caught fire, just not in a good way:”

  • In 2014, I started a content marketing blog. After two posts and realizing I didn’t know what I was talking about, I shut it down.
  • In 2015, I ran a webinar in which I announced the launch of a paid course called “Do More, Stress Less.” No one bought it and I never hit ‘Record.’
  • In 2016, I wanted to build an app called AniQuote where you could animate your quote pictures. It never came to fruition.
  • That same year, I made a free course to help people love reading again. It’s still online, but the premium course I wanted to make? Never followed.

The list goes on and on. Failed ideas, dead Instagram channels, tanked articles, and those are just the things I saw through to publication. Add everything that never made it out of draft-mode and you could fill a phonebook — another non-survivor, by the way.

In that respect, career failures are much like relationship problems or mental health issues: just because you can’t see them doesn’t mean they’re not there.

A long list of failures is attached to even the most stellar of careers, and the same will be true for yours. It’s important we never forget this.


Will Smith is one of my favorite actors. Not just because of his acting, but because of his attitude. Take his perspective on failure:

“Fail early, fail often, fail forward. Failure is where all of the lessons are. You gotta live where you’re almost certain you’re gonna fail. Practice is controlled failure.”

The reason any thriving career comes with a truckload of failure is that, to even have one, you first have to ditch everything that’s not working — and the best people do it fast and, therefore, often. Even if most of the time, you only find out the hard way — after trying — you’ll come out fine if you react immediately. But as soon as you realize the ship is sinking, jump ship.

Doing this means you’ll leave behind a long trail of sunk ships, of destroyed buildings, but it also gives you a chance to make it to the other side, to be the survivor, not the biased. Failure might be inevitable, but not unmanageable. You want your mistakes to happen early and fast, to be small and contained.

You also want to have fun as you’re crashing. If you can’t happily fail your way to success, will you like it once you get it? I think winning is mostly about making the process of failing so enjoyable that you’ll keep doing it regardless. That you’ll chuck one thing in the trash and start another right away.

Take a walk, maybe. Look at some buildings. Find other people’s failures. Or those of the winners. But then wipe the dust off your jacket, watch a Will Smith clip, and get back in the seat.

Fail early, fail often, fail forward. And don’t quit until we call you survivor.