Unlearning the first 20 years of my life

Ups and downs of abandoning the social script

Something interesting happened between finishing school and starting my adult life. For the first time in 20 years, I did not know what to do next. I was searching for the “right” answer only to realize that there was no answer key. 

From the outside looking in, I looked like I knew what I was doing. I landed a consulting job at a prestigious consulting firm, working in the heart of San Francisco alongside some brilliant minds. 

Life as a picture looked bright, but the day to day pixels were gray and dull. I felt the warm glow of society’s approval and yet an emptiness gnawed at me inside.

The work of making 300-page decks packed with catchy words and airy numbers was deeply unrewarding. We were in the business of output and perception, not real outcomes. There was no true skin in the game. And when you don’t have skin in the game, you don’t actually know whether you’re any good, or just another empty suit. 

I questioned how I arrived at this point, and how thousands of people every year clamor for the opportunity I now dreaded. 

Our education system rewards memorization, answer-seeking and the pursuit of brand names to signal we are valuable. We are taught to hack bad tests in order to get good grades. However, the hacks we master in the first 20 years ironically lead to a sense of emptiness in adulthood.   

It’s like learning how to drive while always being told exactly where to go and when to get there. Suddenly, you’re handed the keys, and the ability to choose both the answers and the questions. Where do you want to go? What are you willing to give up? Who do you bring along? 

The easy choice is to stay on the race track, and not ask the hard questions. Society will never stop you from pursuing the hedonic treadmill.

But if you want to explore doing something meaningful, you do need to ask the hard questions. The process of waking up from a decades-long slumber is uncomfortable but rewarding. 

For me, it’s meant going off script, prematurely leaving my job in consulting, and trying other things. It’s meant paying the price of trailing off the beaten path: higher highs and lower lows. It led me to product management, which is a track defined by unbounded outcomes and a real stake in what happens.

You’re creating new solutions for customer problems. The spectrum of outcomes can range from cricket chirps to resounding applause, and even a place in the history books. Your success is also measured by the outcome of your product, not how many late nights you pulled. You get a pat on the back for a valiant effort, but the only real prize is building something that other people want.

It’s led me to starting this newsletter, where I hope to share my journey with you.

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