No-one wants to reject the Legible Career

When I was leaving McKinsey & Co, I knew that I wanted to build a startup.

I was, and still am, very ambitious. I like working hard and know whatever work I do, I want it to be central to my life. In fact, I’m not sure I know how to live otherwise. I had strong conviction that being a founder would be the best way to realise my ambition and to get deep satisfaction from my career.

But instead of founding a startup, I got a job offer.

Why?

  1. My peers’ response to me saying I wanted to be a founder was that “most startups fail”, and
  2. I had been offered a job at Google and my peers were impressed with the offer.

I was accidentally falling into the trap of the Legible Career path. I had a clear and easy to understand career ahead of me. I knew what I would be doing both now and possibly in a decade’s time. I knew how much I’d be earning and when I’d be promoted. I knew what I’d learn and from whom. My peers could also evaluate my path ahead and confirm that they were impressed by it. It was low risk with a known reward. 

However, that didn’t appeal. I couldn’t get as excited about the Legible Career path as the people around me. I was letting my peer’s risk preferences and life expectations dictate my own. I was validation seeking – unconsciously being directed towards the path that would get me the most kudos from those I respected.

The world is full of legible career paths that are peer and parent approved. A Legible Career path means that your network can assess:

  • How prestigious the role is (and therefore assess your ‘quality’ as a person)
  • Your earning potential
  • Your future career path and opportunities

For example, you get a job as an analyst at Jane Street. Your peers are impressed, they know that this is a selective position and you go up in their estimation. Your parents are impressed, they can understand your earning potential and how your career will progress. The Legible Career path makes you feel good as the people around you will be constantly validating your choices. 

Matt Clifford had been working on the early idea of Entrepreneur First for a month. We’d talked about founding something together in the past and he asked me to join him to build EF. I couldn’t say no – I thought of Jeff Bezos’s Regret Minimisation Framework and knew I had to join him. So, on the day I was meant to be signing the contract for Google, I ended up becoming Matt’s co-founder. 

The Founding Career is one where you disappoint and challenge those around you. You disappoint your parents as you end up taking a path they cannot understand. You challenge your peers as you are rejecting the status quo that they have bought into. And finally, you challenge yourself – as Arnaud Schenk says “You are attempting to settle conflicts between your past and your aspirational self, as well as between how you perceive yourself and how others perceive you.”

The Founding Career is unstructured and uncertain. For me, that felt liberating and exciting; I thrive in chaos and ambiguity. I now cannot imagine taking another path, but I am amazed at how close I was to falling into accepting the Legible Career path.   

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