This might be the most impressive career jump of the 21st century.
From “product” at Instacart to helping take ChatGPT from inception to 500M+ users, $13B in revenue, and the 5th most visited website in the world. That’s not a career move. That’s a career transformation. And it started with a decision that probably didn’t look logical on paper.
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Logical vs. Leverageable
Most people think about career moves in terms of what makes sense on a resume. Same industry, adjacent role, incremental step up. Logical.
The problem with logical career moves is that they compound slowly. You stay in a lane. You build expertise in a category that might be less relevant in 10 years. You optimize for a version of success that was defined before you had enough information to define it yourself.
Leverageable moves are different. They put you at the center of something that’s growing faster than you are. The team around you pulls you up. The problems you work on are the problems that matter most right now. The connections you make are with people at the frontier.
Instacart to OpenAI wasn’t logical in 2021. AI assistants weren’t mainstream. The risk was real. But it was leverageable. And the difference shows.
How to Find the Leverageable Move
Here’s the question I’ve started asking when I think about career positioning:
What’s growing faster than everything else right now, and where can I get a seat at that table?
It doesn’t have to be the most prestigious seat. It doesn’t have to be the highest-paying one. It has to put you in proximity to the people, problems, and momentum that will matter most over the next decade.
In 2012, that answer was mobile. In 2016, it was SaaS. In 2020, it was crypto and remote work infrastructure. In 2024, the answer is obvious. It’s AI.
What Most People Get Wrong About Timing
When a wave is obviously large and obviously real, most people think they’ve missed it. They haven’t. The biggest opportunities in any technological shift come 2-5 years after the initial hype, when the early winners are clear and the real applications are just being figured out.
ChatGPT launched publicly in late 2022. The wave is still forming. The people who position themselves now are not late. They’re early for the second phase, which is usually where the real value gets built.
The bottom line? Your next role doesn’t have to be the logical next step. It has to put you somewhere that makes your skills more valuable over time, not less. Look for the wave that’s actually forming, find a way onto it, and do the work to deserve the seat.