#unfiltered #32 How to Win Even When You Lose

Two and a half weeks ago, I wrote about my mental model for confronting fear – the art of running into walls. Inevitably, I’ve had more conversations about fears and how to overcome them since then. And in those moments, I was reminded of a question Seth Godin posed on his recent appearance on The Tim Ferriss Show. Most people ask the question: “What would you do if you could not fail?” And subsequent answers led to wild dreams, achieving the impossible, and often times, still not a step closer to achieving that dream, myself included. I wanted to be an astronaut, a pilot, an Olympic medalist, and more. Instead, Seth posed the counter: “What would you do if you knew you would fail?“

Knowing that I’d fail

Seth cites that most marathoners competing in the Boston Marathon do not aim to win, yet they still do it. Similarly, I work with founders knowing that most will fall short of their dreams. If we’re talking about expected value – the sum of all the dollar size outcomes of each possibility, multiplied with their respective probability of occurring, then:

E(V_{startup success}) << E(V_{most other career paths})

Rationally speaking, the career of a founder is not designed for success. But hell, it’s the irrational founders who do find it. Against impossible odds.

But why?

Why still pursue a career when the odds aren’t ever stacked in your favor?

On the same token, why participate in any contest if you know you’re most likely going to fail? And, I mean contest in the most liberal sense here. Just like a marathon is a contest of endurance and physical prowess, building a startup is a contest of capital, time, and social impact. Confessing to your crush is a contest of love. Sending a cold email is a contest of attention. The more saturated the market – the contest – the more likely you are to fail.

How to Win

In winning, I focus on only one question: What will I gain in this pursuit that’s independent of the result of the contest?

Running a marathon proves that I can push my body beyond its limits.

Confessing to my crush gives me resolution to move on in my life.

Sending a cold email hones my communication and research skills.

I work with startups to build friendships and acquire skills that will transcend the dollar value of the venture. People who are ambitious typically learn fast, and will try again and again until something works. If not this idea, then the next. If not today, then tomorrow. And, if not tomorrow, then the day after. It’ll only be a matter of time before preparation meets opportunity. It’s why we call startups 10-year overnight successes.

So when I take on a new endeavor even outside the exciting world of venture, I look for where there will be a net positive in my life and the world around me, on 3 fronts:

1. The relationships/friendships I will build along the way,
2. The skillset I will develop and/or hone,
3. And the impact the process will have in the lives of other people, particularly my friends and family.

If the above function has a positive first and second derivative, then I know I will win even if I lose.

Photo by Johann Walter Bantz on Unsplash

---

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

---

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!