Failing Efficiently

The foundation of my own narrative

Recently, I have discovered that the public persona I have created for myself comes with some downsides— foremost being my inability to fully control my image. With that lesson learned, my hope is that I can be inspired to write more and share the best version of myself.

Foremost, I will outline my life philosophies as much as possible over the coming months and years. Ray Dalio’s Principles, which I recently read, has been an incredible inspiration (and I encourage everyone to read it.)

The first principle I will lay out is the concept of failing efficiently.

Failure is a part of life. It is the antonym of success.

In fact, I would argue that success is impossible to know without having first experienced failure. Nobody hits a home run the first time they swing a baseball bat and you can’t become fluent in a new language without getting some conjugations wrong at first.

What distinguishes “successful” people from your Average Joe is not fundamentally determined by any hereditary or socioeconomic advantage (though they obviously can help.) “Success stories” permeate every culture and religion. These narratives highlight individuals or groups who overcome extreme adversity as a testament that anybody can succeed on their own merits. The biblical tale of David and Goliath, in which a normal man defeats a Philistine Giant, demonstrates the timelessness of this truth. Thus, instead of attempting to pinpoint any intrinsic qualities, I would argue that the ability to “fail efficiently” is the key to enduring success in life.

But what does failing “efficiently” even mean?

I: Failing Fast

When I use the term failing efficiently, many might think of “failing fast,” a popular mantra in Silicon Valley. Indeed, failing fast is a cornerstone of this principle.

Failing fast means dumping bad ideas as soon as possible, or at least iterating quickly. This is a hugely valuable life skill and integral to failing with efficiency.

In relationships that one is not born into (you can’t choose your family), particularly the most important ones, such as romantic partners or cofounders, failing fast is perhaps the greatest means with which to avoid heartbreak, disappointment, and, potentially, financial ruin. It certainly saves time. Relationships that feel toxic, unproductive, or misaligned should be treated in two ways: termination or identifying and addressing the root cause. Dump or iterate.

My favorite Twitter philosopher

Similarly, when developing a concept or skill, and the results are measurably bad, you have two choices: move on or shift tactics.

Ex 1. When I first got started in tech while in college, many people I met told me I needed to learn to program… so I tried. And boy, was I bad. I could hardly get past the first online courses. It went against the way my brain operates in every sense. With coding off the table, I dove deep into how to make myself invaluable to a technology team and, eventually, even respected by software developers (sometimes).

Ex 2. When I left my position at the first software company I cofounded, I joined a local venture capital firm as an “entrepreneur-in-residence.” The job of an “EIR” is typically to work on a new startup while helping the firm source deals. My first startup idea was a company called “Headshotter” — kind of like Uber for headshots. The concept was that a lot of people have nice cameras that they don’t put to work, and could quickly learn to take professional headshots and make some part-time income from anyone nearby that needs such a photo.

As I began to work through this idea, however, I began to get the hang of venture investing, and the industry I currently worked in began to pick up steam. While I was passionate about the headshot company, it was clear it was not the right direction to take my career. (If someone wants to develop this, I’d be very inclined towards funding the idea, so get in touch!)

Whether it’s because they’re not working, or because there are better opportunities, drop pursuits that are not good directional bets on your future, as soon as this becomes clear.

II: Failing Gracefully

Everyone knows a sore loser — that person who throws a fit when they lose a game of Monopoly, their favorite sports team blows a lead, or they don’t get the promotion they were hoping for. Nobody wants to be that person. If you are that person, stop! But being a sore loser can be more insidious, whether it’s with passive aggressive behavior or undermining friendly “competition” in work or play.

When a job, venture, or relationship does not work out, it can be incredibly tempting to go to social media or get plastered and vent to everyone about how one was mistreated or misunderstood. Don’t do this until after some reflection, and trusted confidants reaffirm that such feelings are truly well-placed (such as with Susan Fowler at Uber and many of the horrifying sexual harassment scandals brought to light recently.) Often upon reflection, and time, it is possible to see the other side of matters, and make peace with such instances.

Ex. My departure from my first software company was abrupt, and turbulent, to say the least. I felt poorly treated by one of my cofounders and that my contributions were disregarded. Fortunately, my other, more even-keeled cofounder, suggested that I step away — that I was fully vested and my contributions would not be forgotten. It helped that I was already in the process of moving on, but I cannot emphasize how detrimental it would have been to let my anger get the best of me— it likely would have jeopardized the credibility of my startup, and myself.

When presented with failure or disappointment, take a step back, breathe, and consult with those you trust. The best course of action is to often just walk away.

III: Failing Thoughtfully

Perhaps the most important component of failing is not the act itself, but what happens afterwards. While failing quickly and gracefully are important to success, failing thoughtfully is absolutely necessary. Otherwise, “those who cannot remember the past are condemned to repeat it” as George Santayana presciently stated.

From my observations and my own life, I have found that in addition to being the most important part of failing efficiently, learning from our failures is perhaps the hardest to do.

In the wake of failure, the easiest route is to believe that we are not at fault. It is more convenient to blame others or factors outside of our control than to take full accountability for our failure. When we do this, however, we learn nothing.

I don’t think this concept requires an example. That being said, most of the misery that I have experienced in life has been brought upon by my inability to learn from past failures. It was only at twenty-two years old did I truly begin to take responsibility for the consequences of my actions. Failing efficiently has been so much easier ever since.

When met with failure — recognize what wrong, embrace reality, and learn from what happened… or risk repeating the mistake.

IV. Moving Past Failure

A perk of failing a lot, as I did growing up, is that one learns to move past such an experience. The upside of failure, particularly when done quickly, gracefully, and thoughtfully, is that it develops resiliency.

In my experience, fear of failure is the greatest inhibitor to success. “Fear” as written in Dune “is the mind killer.” Without fear, we are free to indulge in our most daring intellectual, athletic, or romantic pursuits… and are most likely to succeed.

A journalist recently asked me what allowed me “to be successful at such a young age.” My reply to that cringey question was that it was the lack of expectations set for me. Due to being such a screw-up for most of my life, I posited that nobody, including myself, had high expectations. That, in turn, allowed me to pursue my entrepreneurial endeavors unburdened by what might happen.

In hindsight, I realize this was disingenuous, as I have personally always had extraordinary expectations for myself… just on a longer time horizon given my proclivity for failure. Furthermore, I long ago came to terms with the reality that my expectations for myself are the only ones that matter when all is said and done.

Thus, the better answer to that question would have been “my willingness to fail.” Whether it was getting kicked out of school or thrown into jail, I quickly learned that dwelling on my failures got me nowhere. Perhaps it was because such incidents happened so many times, I eventually realized how little anybody else cares about our mistakes. Maybe the disappointment of our parents, spouses, and children, lasts longer, but for the most part, most individuals are too absorbed with their own lives to care or remember what we have done wrong. And once we recognize that, it becomes so much easier to move on from failure… and to embrace failure as an important part of life.

Everyone fails sometimes. What determines our course forward is how we move on from it. Acceptance that we may fail, gives us the liberty to succeed.

There’s dark, tingling sensation that often plagues me late at night. Last night, in fact, was one of those nights, and led me to finally finish this blog post. The sensation is one of uncertainty — I worry that the longer I go without a major failure in my life, the more likely my next real failure is going to be cataclysmic.

To a certain extent, this post would suggest that I have adapted the strategies necessary to avoid the sort of failures that haunted me as a youth, but only time will tell…