I'm Rebranding Quitting

I am an excellent quitter. So good at it that my executive coach Kevin Coale, said to me the other day, "you are great at letting go." It stumped me completely. I had to ask what he meant by that, because I've never considered that to be a talent. He went on to explain that I have successfully quit many things that served as stepping stones to move onto something else. Then Kevin, being profound as ever said, “quitting is choosing again”. I've quit a lot of things in my life. In the last few years every time I quit something I was propelled into a part of life that was entirely unexpected and always better. There are a handful of quits that stick out to me from my adult life that allowed me to see myself in entirely new ways.

I quit snowboarding. I learned how to snowboard when I was 17 and I am not a natural athlete. Somehow while being a below average snowboarder I became the director of one of the biggest college ski organizations in the country. I simply could not keep up with my friends and I hated it. Then, on a trip to Tahoe in 2021 a friend's dad told me that I should try skiing, he thought I would be "less of a hazard" on skis. He ended up giving me a pair of hand-me-down skis and I quit snowboarding immediately. When I picked up a snowboard in high school I had simply chosen wrong, so it was time to choose again. I'm a skier now, and a pretty good one at that! Here's a pic from my trip to Mammoth last weekend.

I quit drinking and San Francisco. These go together because the first informed the second. My decision to quit drinking was an empowering one, but my decision to quit SF made me feel like a failure. After 11 months I packed up my stuff and left with my tail between my legs, or at least that’s how I felt at the time. I left LA after college thinking “I can make friends anywhere” and boy did I underestimate how hard it actually is. I did make friends but what I was missing was friends that felt like family. I needed people to call upon in times of great distress and for most of my time in SF I didn’t have that. I had to quit living there (and my job at the time) in order to choose myself. Making that call to leave and settle into my old home of LA changed everything.

I quit my job (again). If you have ever worked at a startup (I know many of you have) you know that feeling where your work just absolutely consumes you. I was obsessed with my job. I was taking calls at breakfast with my friends, answering requests from clients 24 hours a day, I literally left a date once to go put out a fire at work. Being good at that job gave me enormous purpose, and seeing my impact on the business and bottom line was fulfilling. Then it all came crashing down. I had to leave because of circumstances that were not aligned with my values. It sucked, I felt like I had gotten the rug pulled out from under me. It was a tough moment, but I held tightly onto my integrity. That choice ultimately led me to Operate, which led me here.

I quit a relationship. This was my biggest quit of all and it happened more than half a year ago. I had entirely lost myself in an attempt to make something work. By deciding that I no longer needed that relationship to feel valuable, I was completely transformed. I quit trying to make someone love me and found a level of confidence in myself that legitimately did not exist before. I chose again, and that time I chose me.

I’ve learned that you always have a choice, the results are simply dependent on whether or not you decide to make it. If something is in your way, not working, causing you pain, or just not fun - you can choose again. The only person in your way is YOU. Quit your job, quit school, quit vaping, quit being hard on yourself. Just quit, because you’ll find something better in its wake. Ily, see you next week.

Who inspires me today?

This is Jason Levin, one of many friends I have made on the internet in recent months. Jason is a writer, I discovered him on Twitter then found out he writes one of my favorite newsletters. When I first connected with Jason I didn’t know was that he was such a hustler. Jason has since shared a ton of stories with me about his sobriety, his many business ventures, his failures, and more recently his success as a writer.

The reason I wanted to talk about Jason today is because of a thread he shared on Twitter about what he called his “Graveyard of Failures,” here’s two of them:

Jason, like most American high schoolers, took economics and learned about Sunk Costs and they became a driver for his decision making as he started making bigger career moves.

Towards the end of 2021, Jason was making his money running a Facebook Ads business for Kitchen remodel companies. He was bored, his creativity had plateaued, and he was feeling called to do something else. Against the advice of his parents and friends, he shut that business down to dive head first into twitter. He grew up sharing his life online, and it truly is his super power. Jason’s success as an online creator may look like it happened over night, but he says that the last year felt like a decade. I can see why, his newsletter Cyber Patterns has over 3,000 subscribers, he’s writing for some insanely prominent VCs & Startups, and has 13,000 followers on twitter. Jason is steering a one man rocket ship and it is freaking awesome to watch. Best part? He’s been a quitter too, and he clearly made a great choice.

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