


Keeping to the theme of last week’s opening, I will start with a conversation I had with my manager last week, side-eye abstained. We discussed some avenues where my writing could go. Should the series be, completely random, a continuous proclamation of sorts to inspire the masses? I’m still toying with my vision for this, but Joe asked a question that gave me some direction: “what do you like to read”?
In my head, the immediate answer was a jumbled genre of sci-fy-historic-action-romance-fiction-esque-empowering-biographies. When I thought about it for .5 more seconds, I concluded what reels me in, from a non-fiction POV, are the stories of silent tenacity.
I love a tale of perseverance, especially those tales that are often not told. What I mean by this is that I find it fascinating to uncover stories that people share long after their trials have become triumphs. I enjoy these stories so much because they are rooted in failure, and reading about someone else’s failure makes me feel less bad about my own. It also begs the question of whether “failure” is really a stagnant state, given that it often is the predecessor to something exciting.
I think these seemingly stagnant states of failure are often felt by each party in our ecosystem, investors and founders alike. Founders are more boisterous about it because, let’s face it, failure makes for a great come-back narrative, and everyone loves a relentless founder who “defied all the odds.” Investors, to everyone’s surprise, experience these stagnant states as well.
There are a multitude of scenarios where the F word came into play in my life. There are almost too many stories to share, but the one that’s the most profane is the failure that would morph into my first paid job. In Common App style, let’s go down the rabbit hole of my ambitious attempt to become a professional athlete.
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For some context, my juvenile and collegiate career as an athlete was decimated by relentless injury. I had a back fracture, an ACL tear, foot ligaments stretched, another ACL tear, a pilonidal cyst (steer clear of that google search), ankle problems, and to top it all off, another ACL tear. The sports gods granted me the grace of finishing my sport while still standing, and in response I decided to keep pushing my luck. I turned down a full-time job to pursue a career where a key prerequisite was being healthy: professional soccer. Needless to say, my phone was not blowing up with offers. In the interim, to earn some money, and to distract myself from my phone not ringing, I joined a startup.
Joining the startup didn’t feel like a monumental decision, and yet it was the first domino to fall in a series of serendipitous developments that led me to the venture space. To save some time, I’ll condense the journey, and relay that joining the startup led me to working at an accelerator which led me to my first VC role which would subsequently lead to my current VC role. All due to being a terrible ROI in the eyes of pro scouts.
The failure to make it professionally has since paved my way into a career I'm still navigating, where failure is viewed almost as a rite of passage. I’m not sure if I’m as comfortable with failure as I want to be, and I’m also not sure if that’s necessarily a bad thing.
Losing a game, or losing your ability to walk without crutches, is a form of failure that, in a weird way, is short-term. You know there will be other games, and you hopefully have a great PT specialist that will get you walking in 4-6 weeks. Failure in career ambitions does not always have that near-term light at the end of the tunnel. You’re often left thinking “what now?”, and it can be months or years until that next path forward presents itself.
Professional failures are disheartening, and often lonely. They’re definitely not something you want to reflect on immediately, write down, and read the next day!
But perceived failure, whether good or bad, ultimately culminates in a future state that is (hopefully) better than the present.
To that point, I’m going to advise my three readers to start thinking of professional failures like ACL tears. Extremely painful and exhausting to manage but, in the end, a temporary stagnant state, a short-term detour. But at the same time, recovery is not straightforward, and in that process you may end up in a completely different destination than you intended. This can be a good thing. To the dreaded “F word” that derailed all my plans: a delayed thank you, for the nudge to trade in my cleats for term sheets.
