Unlearning the first 20 years of my life

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 realise that there was no answer key.

From the outside looking in, I looked like I knew what I was doing. I landed a project management role at an FTSE 250 company, working at Bank alongside some brilliant minds.

Life as a picture looked bright, but the day to day pixels were grey and dull. Working all day and hoping on the number 8 bus to Shoreditch as soon as my day finished.

I felt the warm glow of society’s approval and yet an emptiness gnawed at me inside.‍

The work of analysing ways to reduce costs and pitching these ideas to category managers 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 in a Charles Tyrwhitt suit.

I questioned how I arrived at this point, and how thousands of people every year clamour 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? Whom 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 to the dissatisfaction of my family, 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 sales, which is a track defined by unbounded outcomes and a real stake in what happens.

Your success is also measured by an individual outcome, not how many late nights you pulled or how well the Category managers liked you.

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