Why I quit my job in 2020

A lot of people are questioning business as usual in 2020, literally. I planned my 2020 exit back in 2018, and, as fate would have it, I left in a climate that is more receptive to this decision that ever. Thanks to Alex West for writing this post that inspired my own.


I started my first corporate job after college, and within five months was in full rebellion against the modern American workplace. The required work hours, the stifled creativity, the combination of boredom and exhaustion, the self-censorship that I witnessed from almost every co-worker pretending the situation was the opposite of our shared reality. It was a hellscape where people stretched on a smile and said, “Isn’t the weather lovely today?”

No. It is raining fire you fool–don’t smile, run!

I left after 11 months on the job, and entered into an extended period of precarious freedom, poverty, and necessary recalibration. It wasn’t financially sustainable, because I left my job with almost no plan, $20k+ in student loans, and almost no savings. But it was worth the validation of my knowledge and confidence: the man behind the curtain is a fraud. All that glitters is not gold. The emperor has no clothes. I’m not the crazy one, everyone else is.

Some people call this taking the red pill, but that’s not what it felt like to me. I never went into the matrix in the first place.

I returned to the corporate world in 2017, determined to find a way to live independently. In 2018 the plan was in place, and in 2020 it was executed.


I left my job in legal PR in July 2020 with $20k in savings and a severance package worth about $15k, to be paid out over several months. I made my plan to leave without knowing about the severance package–that was a rare lucky break. I gave myself a year from that point to generate an independent income and work on various projects, and it’s a work in progress.

I left without another source of income in place. I had a lot of ideas and a lot of skills, felt like taking a gamble on myself, and knew I’d get a large psychological, performance-enhancing boost from merely leaving the job. Short of getting hit by a bus twice, there was no way I was going to ruin my life. I might have to start over financially, but…that’s doable. And worth the risk for me.


There is never a “right time” to leave your job. You can always think of reasons to stay.

So why would I leave without a concrete way to make more money? Because of my first round of leaving the typical working world, I knew I would gain:

  • The full use of my creative mind. No more constant email and firedrill interruptions. No more whiplash from a thousand unchosen things to do.
  • My full health. My sleep cycle never played well with the 9-to-5, and leaving work has meant being well-rested for the first time in a long time. That sent epic ripples throughout every domain of my life.
  • Full focus on my personal projects. I no longer have to cram them into the evenings and the weekends. Iteration and improvement are blazingly fast.
  • My level of life satisfaction is 10/10. I am living life the way I want to live it, doing what I choose, and when I choose.

And I did.


I’m doing a lot of things. Some of them:

  • Hosting salons via Interintellect.
  • Building a publishing company
  • Improving my piano and sax playing, in anticipation of performances in 2021.
  • Setting up a lot of little income experiments to see if any of them pay off.
  • Getting better at Twitter, and connecting with great people online.
  • And soon, a podcast and some other things.


I don’t think working for someone else, or for a company, is inherently bad. There are some companies I could see myself working for in the future, both because I love their product and because the corporate philosophy/structure of work seems suitable. Think Stripe, Shopify, Gumroad, and others.

But for now I’m focusing on developing my own skills independently (product development, selling, and more). A lot of people trick themselves into thinking they know how to do things, but they don’t. They’re just plugged into the large machine known as a company that does 95% of the work for them.

Imagine a marketer: slot them into a successful company with a large following, and they might successfully carry out an ad campaign.

Now take them out of the company, and tell them to market a brand new (and good) company with no reputation and no online presence.

If they can do it, they’re a real marketer; they understand the profession and its ways. If they can’t, they never really were. They were just stewarding an audience and other resources that already existed, and probably not getting as much success as they should have, given that. This is like the difference between someone who can plug numbers into a mathematical formula, and someone who knows how to derive it in the first place.

There’s a lot you can learn in the corporate world, and it’s worth working within it (how much depends on the individual). But for me, right now, it’s much more beneficial to be on my own. Maybe I’ll be here for a while–I’m certainly enjoying it. But if I go back to a company, I can rest assured that it will be because it’s a good match for both of us, not just because I need money and it will pay me.

You gotta risk it to get the biscuit.

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