Dark horse

My rate of failure may be higher than other people. Failing at a higher rate has meant I’ve ended up looking stupid more often than I would like, but I learn more as a positive consequence. Like the kid in the class who asks a “dumb question” that all the smarter kids lament. 

Growing up I found myself failing classes, never making the cut for teams, getting destroyed in video games, losing schoolyard fights and disappointing my parents regularly. Teachers kicked me out of class and my parents often received calls about my behaviour. 

As I got older I got fired from jobs, my finances were in shambles, long-lasting relationships combusted, failed to manage projects and closed a music studio that I plunged 95% of my savings into. 

At one point, I was hit with a series of failures. I dropped out of university to work at my dream job and make some money. I was fired after 6 months without being told why. I felt devastated, that I would never make it in design. 

A light appears at the end of the tunnel and I score an interview for my dream position at a company I wanted to work at. I thought I nailed the interview. I get a call later that they passed on me because I was “too passionate”. Somehow something that is generally positive, became negative. 

I was now desperately looking for work and in need of money. I went to a temporary staffing agency, hoping I can at least get a job at the factory. The receptionist looked at me from top to bottom and told me “You don’t belong here” and rejected my application. Although it hurt at the time, she was right and this failure was necessary. 

For a while, I began to think that a rainy cloud was hanging over my head. That simply I could do no right. That perhaps I was not deemed worthy of winning. The low-level dread created by the inevitable prospect of failure hardened me, made me stony eyed and created an indifference inside of me towards any outcome - good or bad. This comfortability of standing in the fire of failure would prove to be useful towards the latter arc of my life. 

One of my childhood friends noticed a deep change within me. He began to realize that I wasn’t the cheerful, go-lucky kid he grew up with. He looked at me and said, “You’ve changed”.

I said nothing. I didn’t want to admit it at the time but deep down, I knew he was right. I knew one day, that all these failures would mean something. I won’t win today and perhaps not for a while. But one day I will. Like a dark horse:

a candidate or competitor about whom little is known but who unexpectedly wins or succeeds

Fast forward to today. We as a people have become fixated on the appearance of success and correctness. 

One of the greatest pitfalls is becoming susceptible to confirmation bias. Scrambling to find anyone or anything that will prove your case. 

Take the example of undergraduate university essays. A student introduces the topic, lays out some background information and then slaps down a grand theory of everything - the coveted “thesis”. An intention is made to prove its correctness by penning 3 elaborate arguments, citing credible evidence coupled with deep rigorous analysis. 

After the student has proved themselves right after a few pages it’s concluded with a reiteration of how correct the thesis is and how the due diligence was sufficient for this worldview. An essay worldview held together with overconfidence and duct tape.  

When did we stop and try to create three counter-arguments, source counter-evidence and engage in counter-analysis? After the paper, when did we test our arguments as an experiment? Well if we did that, we would risk disproving our thesis and we don’t want that, do we….

This is a great example of confirmation bias. Staking your claim, seeking out any study that proves your point then reaching a hard definitive conclusion while completely shutting out any alternative viewpoints. What began as a bold claim ends as an exercise of self-aggrandizement. 

Success can draw the wrong incentives: affirmation, compliance, fame, capital and a title to your name. It deeply centers on matters that present the appearance of correctness as the metric of success, rather than a metric that expresses intrinsic value. Even rappers who explicitly seek out money and fame, still know that they have to make music that people will listen to (intrinsic value). 

For example, many people consider MAU (monthly active users) as a strong signal for the success of an app. Apps are valued against this metric because they appear to be an arbiter of truth, even though the definition can significantly vary based on the company, industry and how the company defines its analytics. Activity can range from little as 1 second to as much as 1000’s hours. A user can be an account that’s active, inactive, verified, unverified, banned, blocked, and so on. 

What is supposed to be a simple metric to determine success becomes muddied water of convoluted definitions of users and activity. Despite MAU being so loosely defined, shaky and imprecise it still carries weight because of its appearance.  

With failure in mind, you may arrive at a different conclusion as to what metrics are meaningful. You’ll start looking at what might be initially uncomfortable: bounce rates, checkout abandonment, drop off and any other metrics that could express symptoms of failure. 

Chasing the appearance of success can amplify confirmation bias, calls the wrong incentives and bruises the ego when proven wrong.

This is why I argue why we should seek failure, rather than success. By seeking failure, we can increase our chances of having a positive second-order effect of success. 

With failure in mind, you become awakened to a new realm of possibilities. Instead of innovation theatre, you begin to run experiments. Instead of an over-engineering process,  you have a low-touch process with no micro-management and increased autonomy. Instead of fake work, you get in the trenches and do hard manual work that eventually can scale. 

The signal is now separated from the noise. Your eyes widen when something fails. The curiosity within you beckons. Eager to pop the hood. Take a gander inside. Tinker. Then pause. Repeat. 

Your senses are heightened and you become more open to different possibilities and casualties. You entertain ideas you usually wouldn’t, and you exchange sober thoughts with colleagues who are similarly eager to be wrong. 

Since you’re detached from your hypothesis, you feel no way if the idea is killed off. You may be the one to suggest that you were wrong. No one shames you for it. Everyone else dwells and ruminates. Tapping into a deeper collective understanding of the problem at hand. 

It’s a civil affair. No leaderboard of who was right, but a score of what has failed and succeeded. You go back to the drawing board and try again. 

The process of elimination is one of the great pillars of failure. I often say “I don’t know what to do, but I know what not to do”.  The process of elimination is an underrated and overlooked way of discovering what works. It’s like trying to hit a single in baseball, instead of a grand slam. 

If we were to think of seeking success as a person, it would be a dictator while seeking failure would be a detective. The former is deeply driven to prove their point by any means necessary, while the latter is detached and hosts multiple opinions that could contradict each other.

Being wrong comes with its difficulties. After a while, it can become demoralizing. You may begin to doubt a lot. But I think if you can survive this trough of sorrow, then you would have built a new coat of armour to weather the storm of incorrectness so you can march forward. 

There are situations where seeking failure could be a grave mistake. There are instances where if the stakes are too high or the mistakes could be irreversible, seeking failure may not be wise.  This is why a person should use their discretion to decide what mindset is right for the situation at hand. 

Or even better, a sandbox simulation that offers a safe space for tolerance of failure as opposed to failing in the wild. A great example of this would be a pilot simulator that helps pilots fail safely, instead of risking the lives of people.  

I’m not proposing that we view everything through the lens of failure, but that we as a people generally over-index on success and correctness including it’s respective optics and aesthetics. By trying to consider failure as a lens we may be pleasantly surprised by the results. 

It’s also very possible that I’m very wrong, about the benefits of being wrong! If that was the case, I would be okay with that. I would be happy that I had achieved a better understanding of the topic.

I’ll end with this poem by Khalil Gibran that celebrates defeat better than I ever could.

Defeat
By Khalil Kibran

Defeat, my Defeat, my solitude and my aloofness;
You are dearer to me than a thousand triumphs,
And sweeter to my heart than all world-glory.

Defeat, my Defeat, my self-knowledge and my defiance,
Through you I know that I am yet young and swift of foot
And not to be trapped by withering laurels.
And in you I have found aloneness
And the joy of being shunned and scorned. 

Defeat, my Defeat, my shining sword and shield,
In your eyes I have read
That to be enthroned is to be enslaved,
And to be understood is to be leveled down,
And to be grasped is but to reach one’s fullness
And like a ripe fruit to fall and be consumed.

Defeat, my Defeat, my bold companion,
You shall hear my songs and my cries and my silences,
And none but you shall speak to me of the beating of wings,
And urging of seas,
And of mountains that burn in the night,
And you alone shall climb my steep and rocky soul.

Defeat, my Defeat, my deathless courage,
You and I shall laugh together with the storm,
And together we shall dig graves for all that die in us,
And we shall stand in the sun with a will,
And we shall be dangerous.