Eat the Damn Fig

If you had to choose between finance job offers, graduate school or joining a startup and had 72 hours to decide, how would you make the decision? A few years back, I faced a similar decision and recently helped a friend make that decision. Today, I will share how I approach career decisions and why I chose to wander down a different path.

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Five years ago, I was torn between accepting an offer for a career in finance or joining a startup. At the time, it felt like the most significant decision I had ever faced. The job offers felt like two diverging paths. The first felt like a well-paved highway — work hard at an investment bank for a few years, then go to business school, then something else. The other seemed like a bumpy, windy road with no known stops along the way and an unclear destination but the promise of adventure.

And with exploding offers, I had three weeks to decide.

At the time, I remembered coming across three particularly helpful things:

• 1) The Start Up of You by Reid Hoffman
• 2) Zero to One by Peter Thiel
• 3) The concept of the Pre-Mortem

These frameworks were the tools I used to build the map that helped me navigate my career crossroads. They are the tools I shared with my friend as well. A few more details on each:

• In Reid Hoffman’s book, I learned about the concept of career competitive advantage. I could create a career competitive advantage if I found where my assets, my aspirations and the realities of the market overlapped. Said simply, I needed to find the intersection of the things I’m good at, what I enjoyed doing and what the world needed. And, like any entrepreneur, I needed to run experiments to get real-world feedback on whether I was actually right or not about the overlap. The whole book is worth reading but Reid Hoffman also wrote a great summary.

• In Zero to One, I came to terms with a reality of the human condition: we seek competition as validation. We want to win the prizes others want to win, often without regard for the other things we value. Zero to One helped me rethink what I wanted and re-oriented me to a new type of thinking. I started to focus more on me and what I valued and less on what everyone else valued.
• And finally, the pre-mortem exercise guided me through the possible future outcomes of the decision I was about to make. As part of the exercise, you imagine different worlds, years from the present. In one world, the outcome of the decision you made was an unmitigated disaster and you reflect on what happened and why. In the other, the decision lead to roaring success and you follow a similar reflective process. By considering the extreme outcomes of the decision, you can plan better. It’s a helpful tool for making big decisions of any type. Farnam Street has a great post on the concept if you want to learn more.

And so I paired the wisdom from The Start Up of You and Zero to One with the structured decision process of a pre-mortem to make a more intentional decision.

I thought about paths in front of me and the futures they would lead to. For me, the hardest part about using Reid Hoffman’s circles is actually knowing what you enjoy doing. So far, I have found it is easier to define the inverse — What do I not enjoy doing?

I reflected on the career experiment I ran as a summer finance intern. I remembered that I found myself checking my watch more often that summer than stock tickers. Counting down the hours until something is over is generally not a sign of passion or enjoyment. So, I followed Reid Hoffman’s advice. I knew I hadn’t found the right intersection since I did not truly enjoy the work. I wouldn’t have a competitive advantage if I competed against those that did.

I decided to quickly run another experiment before I graduated and joined the team at Ring as an intern. I would spend most of my time over the next few months learning what it meant to build and scale a business up close. And, for many reasons, I fell in love with the work. At high growth startups, my skills, aspirations and what the world needed aligned well. I stopped checking my watch and took the dirt road.

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A final thought — at the time, choosing what felt like an unconventional career path was scary and uncomfortable. Most everyone around me took the highway when I got on the dirt road. The highway is not lonely. There are others traveling with you and it is calming knowing you aren’t alone. The unconventional path offers no such benefit. It is lonely to wander and it’s something to prepare for.

Fortunately, I had a fellow wanderer, which has made the journey less lonely. We both interned in New York during the same summer and left with more questions than answers. One day, when we were both struggling with the weight of the decision, he shared a Sylvia Plath poem with me.

“​​I saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked…. I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn’t make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.”

Ever since that summer, our motto became, “Eat the Damn Fig.”

My fig became startups and in many ways, I have been incredibly lucky. The first two startups I have been part of both raised several rounds of funding and the teams grew quickly. Fast-growing startups are wonderful. There are a lot of important problems to solve and not nearly enough talented people to solve them. So, relatively unqualified people get handed very big, important problems and the opportunity to show what they can do. High-growth startups create amazing learning moments and career advancement opportunities for all involved.

I love startups, but I will not pretend to know what is best for you. I can not understand your circumstances as you do. Only you know what exists at the intersection of your circles. I hope these tools can help you navigate the crossroads and continue on your journey with confidence. If you’ve decided that your fig will be a startup, stay tuned for part 2 on how to decide which startup to join.