No More Failure

At the risk of sounding like some sort of motivational speaker, here’s what I believe to be true: failure is a choice.

Well, at least my definition of failure is a choice.

You can solve any problem by simply redefining your terms. Therefore, let me redefine, or perhaps refine the definition of failure allowing you to eradicate it from your life, if you so desire. Failure sounds so negative anyway.

Shoo, failure, shoo!

Merriam-Webster has a few definitions of the word failure up her (book) sleeve:

1. a lack of success in some effort2. a situation or occurrence in which something does not work as it should3. an occurrence in which someone does not do something that should be done

A “lack of success in some effort” assumes at least two things:

  1. Success has been clearly defined upfront.
  2. Our definition of success is immutable.

I have worked on many software projects in my career. How many of them worked out exactly as expected in the beginning? I would say: hardly any. Hashtag fail. This happened for a whole range of reasons. In some cases, it turned out mid-way that our vision of the project made no sense, or was not in demand. So, we changed course along the way. In other cases we underestimated the effort and were forced to either reduce the scope drastically and still deliver on time, or push out the deadline.

Now, depending on your perspective you may label these things as failures: your idea failed; you didn’t managed to deliver the product with all the features you intended on time; you delivered too late. Those would be true statements. However, they ignore a very important aspect: what did we get in return for all of this failure?

When having to pivot or cancel a product, because its original incarnation doesn’t work or make sense: this tended to result in tons of learning. How could we have been so blind, and how do we prevent similar issues in the future? How do we get better at discovering what potential customers want on a more efficient way, without having to waste as much effort again? (Potential answer.)

When having to cut scope to make a deadline you learn a lot about what your product’s real value proposition is. I’ve participated in cutting feature lists by sometimes even two-thirds to make a deadline. While painful, the result was often something much more simple and elegant. Adding features to a “must have” feature list is easy, really cutting that feature list down to its bare essentials is much more educational.

Having to postpone a deadline because you underestimated the effort is something everybody has to go through to learn about the harsh realities of software estimation. Where were the estimates the most off? How do we dig deeper next time and figure such things out earlier next time? There is ample value in the learning whenever this happens.

The beautiful thing is that this is where we always get a choice. We always have the ability to learn when things go wrong. If we choose to, we can analyze, retrospect, deep dive, root cause. More so than when things go right, in fact. If we want to optimize our learning, we better optimize our failing process.

The good news is we’re in luck. We make mistakes all the time. It’s inevitable. And it may well be humanities biggest strength. How many amazing things came out Merriam-Webster’s second definition of failure: “a situation or occurrence in which something does not work as it should”?


My favorite example of this is Stuart Butterfield — the dude that just won’t stop trying to build games and fails in increasingly spectacular ways.

From Butterfield’s Wikipedia page:

In the summer of 2002, he co-founded Ludicorp with Caterina Fake and Jason Classon in Vancouver. Ludicorp initially developed a massively multiplayer online role-playing game called Game Neverending. After the game failed to launch, the company started a photo-sharing website called Flickr.

Butterfield tried to build a game, but failed. On the side, the team had built a photo sharing site. That site was what ultimately became Flickr, one of the biggest photo sharing sites on the Internet for a long time. Flickr was sold sold to Yahoo! for around $25 million in 2005.

Then in 2009, Butterfield tried once again:

In 2009, Butterfield co-founded a new company called Tiny Speck. Tiny Speck launched its first project, the massively multiplayer game Glitch, on September 27, 2011. Glitch was later closed due to its failure to attract a sufficiently large audience.

Luckily, Butterfield and his crew had built another side project that they had been using to facilitate communication among the team. They spun it off into a little company called Slack, which was sold in December 2020 to Salesforce for $27 billion.

I anticipate that soon Butterfield will attempt to build a game again. The pattern seems to be a 1000x increase in sales price for his next side project, so I’m conservatively projecting a $25 trillion exit, give or take.

Get in on his next “failure” when you can.


As the famous philosopher Forrest Gump said: “Life is like a box of chocolates, you never now what you gonna get.”

Forrest was right. However, the key thing is that you do get to decide how you respond the particular “chocolate” you end up getting.

Butterfield could have closed up shop after his game failed the first time, cry in a corner, and move back with his parents. He didn’t. Or maybe he did, I’m not sure. However, after the potential crying and potential moving back-in with parents, he looked what value to extract out of what his team had built and redefined success. After his second attempt at a game he did the same. The result: he earned enough money to run a few more game experiments.

Failure is only true failure if you extract no value out of it.

Whether something fails is sometimes outside our direct control, extracting every drop of value out of that failure is not.

Somebody once told me that the reason Silicon Valley’s start-up scene is so much more successful than the European one is its perspective on failure. In Silicon Valley if you build a company and fail, your perceived value goes up. You failed, so you must have learned a lot of valuable lessons. Chances are high your next attempt would be much better. In Europe, the perception of failed entrepreneurs is much more definite: they had failed before, so why throw more money at them?

Failure is choice. Failure is a perspective.

Yeah... I definitely do sound like a motivational speaker. Move aside Tony Robbins.

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