Dear Rob, (name has been changed)
I spent a long while thinking about what I want out of my career, and more broadly, my life. It all came down to one thing. I want to be deeply happy and fulfilled, and I want to feel this way in the day-to-day trenches of whatever I'm doing. To be honest, I've spent my last few years searching for this. I worked at incredible companies like Stripe and Figma, chasing after this feeling. Going into those experiences, my hypothesis was that if I worked at the best companies I could, I would be the best engineer I could be, and thus I would be happy and fulfilled. Over the last few years, I’ve realized that some part of that hypothesis was untrue. I was my happiest when I was thrown into chaos; I felt most fulfilled when given crazy logistical challenges to think about; I felt myself expanding in my human experience most when faced with uncertainty. This wasn't true of my time at Figma or Stripe. These companies were ostensibly startups, but in many ways they weren’t. Stripe, by 2016, had already firmly entrenched themselves in Unicorn territory. Figma, by 2017, had hired one of the strongest engineering teams I’ve seen to date. In that sense, both companies shared one key quality when I joined: the sense of knowing what they were doing, of having Processes and Best Practices -- a byproduct of having amazing engineers and tons of funding from the top VC firms in the world. I believe that Company is in this category. I believe that you will be immensely successful, you will carve out a new pattern for internal communications for thousands of teams, and you will become a billion dollar company at a stunning pace. You will attract amazing people and build fantastic internal culture while doing it. Call me a contrarian, but I think my most direct path to happiness involves something different. I think I need to put myself in a place with uncertainty, unknowns, and deep ambiguity. In the process, I will learn immensely about myself and the world. I will develop risk tolerance: the ability to rise up in the face of danger and stare it down. The ability to fail hard and fast, and grow because of it. And I will gain the skills to start my own company. This means that, for now, I'll have to decline to move forward with Company. Thank you so much for the opportunity to meet you and to glean insight into your world. Shirley
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