Connecting the dots 🔵 ⚪ ⚫

attempting to appreciate our inability to forecast the future

Aug 18, 2023

A few close friends recently left their current gig and are taking some time to examine what they want to do next. While I’m excited for them (there are so many cool things in the world right now to work on!), I understand that it is a stressful process. High performers are terrified of making the wrong decision. They juggle loss aversion, sunk costs, imposter syndrome, and so much more.

Andrew Chen recently shared a framework to think through career decisions: The Next Next Job. It’s a great read and a simple framework:

TLDR: Ignore this next job you’re considering for a second. What do you want to do after that job (your “next-next” job)? What are the gaps between today and this next-next job? Now look at the options you’re considering for this upcoming job. Which of them will best set you up for your next-next job?

This makes sense. Companies do this exercise all the time (five-year plans, path to $100M in revenue, OKRs, north stars, etc.). However, as someone who has spent countless hours building growth forecasts at these companies, I can assure you that there is more “hand waving” than “data science” involved. We smirk at each other as we draw lines “up and to the right”.

However, unless you know exactly what your dream next-next job is, this exercise really just exists to scratch an anxiety itch. It doesn’t leave much room for the most important variable: spontaneity. When I look at my own career (psychology major, finance internships, marketing analytics consulting, data science at a fast-growing startup, to ultimately launching my own startup), I’m humbled by how little I purposefully orchestrated.

I could tell you that my psychology classes and finance internships during undergrad made me interested in the analytical side of user behavior. This is why I took a job in marketing analytics consulting, where I developed a technical skillset in data analysis tooling and coding. After two years of consulting, I knew I wanted to stop “consulting” and start “building”, which is why I joined the data team Lyft focused on growth. Lyft opened my eyes to the world of building successful products, which is the experience I wanted to go out, fundraise, and start my own startup.

Sounds legit, right? In reality, each and every career step felt like walking into the unknown. Sure, like most of us Type-A control freaks, I hate the unknown and attempt to plan out my next-next-next-next-next job and work backward it.

It feels wrong to talk about career planning (or any planning, really) without appreciating the role of spontaneity. Focusing on the inputs (working hard, facing challenges head-on, gracefully failing every now and then), may be a better exercise than only trying to define the outputs.

Let’s not forget the advice from the ultimate control freak, Steve Jobs:

“You can't connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something - your gut, destiny, life, karma, whatever.”

Happy weekend,

Raman at Rhetoric