Not built to do cool stuff

Welcome to issue #1 of my newsletter! It’s so good to have you here. Hit subscribe for the next issue to be delivered straight to your inbox :)

I’m 26 years old and I know three things about myself:

• I pathologically dislike asking for favors.

• Reading books brings me joy.

• I have insecure tendencies.

I recently discovered a fourth: I am deeply pessimistic.

All my life I’ve believed that great things are not for me. You might be wondering what I mean by great things. I’m talking about the wonderfully outlandish stuff childhood dreams are made of; about experiences that fill a meaningful, extraordinary life. That’s the high-brow, pretentious version. Here’s one that’s probably easier to understand: great things = cool stuff. 

So, what is cool?

I think going down reddit rabbit holes about dead authors is cool. You may not agree. The specifics will inevitably vary—but there is indeed a universal measure of what’s cool. The one that made sense in high school, and that still makes sense today. It comes down to some combination of: 

• Being different

• Being an expert

• Being free

I have always believed that doing great things is reserved for others. I didn’t think I’m built to do cool stuff. I never had crazy dreams as a child. I spent a lot of time preparing for the other shoe to drop. I made the safest bets. This was so ingrained in my worldview that until very recently, I didn’t recognize it as pessimism. I thought it’s just the way I am, the way I’ve always been. 

This pessimism informed most of the “big” decisions in my life. 

• I was an English nerd in high school. Especially creative writing. I filled diaries with stories written in pencil, and when I was old enough to use a computer, I made an anonymous account on writing.com. To a 15-year-old me, earning a living through writing would have sounded like a dream. But I assumed that being a writer was too cool or “artsy” a career path for me to pursue. I don’t think I ever shared this goal with anyone at the time.

• Fast forward a few years: in law school, I participated in an international trade law moot court. The question of law I was dealing with was the meaning of a “developing country” (cool fact: the WTO definition of a developing country does not exist). I went pretty deep on the issue — it was a fascinating combination of law, geopolitics, and economics. I decided I wanted to be an international trade lawyer. But when I started looking for summer internships, I realized that international trade is a very niche field. I didn’t think I could cut it. So I chose a normal, slightly generic i.e. safe career path instead: corporate law. 

Clearly, this has been a pattern. Every time I’ve made life decisions in the past, my mind sees a limited set of things as achievable or possible. Things of a specific shape, size, and color. I’ve gone through most of life operating in this self-constructed box. That I would always operate inside it was an unsaid, fundamental assumption I clung onto. 

A few years after my ill-fated tryst with trade law, I graduated from law school, and got a job as an M&A associate at a law firm. I took pride in the work we did because it was interesting. It challenged me, made me think. I was also lucky to work with a great team. But as you may have guessed, it wasn’t all rainbows and sunshine. We often worked long hours under stressful deadlines. I was frustrated because I never felt in control of my own time. I was nearly always on edge. Two years in, I didn’t enjoy what I did anymore. 

Around this time, I took a ten day break to visit my boyfriend who was living in Spain. He had just finished a music business masters and had stumbled into a freelance writing career. Two things stood out to me after the trip: (1) he enjoyed what he did and (2) it enabled a meaningful lifestyle. 

I still wasn’t sure if I could earn a living through writing, but I had direct access to someone who was doing it. (Side note: Yash also happens to be the warmest, most optimistic, and empowering human I have ever met.)

I was ready to test the waters, slowly.

While still working full-time at the law firm, I drafted and sent out a bunch of embarrassingly long cold emails. I wasn’t dialed into the Twitter/X network so I used lists like this to find people who might need writing or editorial help and have the budget to pay for it. 

An unknown number of silent rejections later, I got a 2 hour/week gig copyediting a newsletter for a non-profit. I was working with a passionate team scattered across the globe (incredibly grateful to the folks at Persuasion for taking a chance on me!). It was a small role that paid only a fraction of my rent. But something fundamental fell into place — I had hard proof that if I called into the ether enough times, I would eventually hear back.

I’ve told the rest of the story many times, across loud restaurant tables, in Spanish class, and at the gym. I plan to get into the details over the next few essays, but for now, here’s the short version: I quit my job and moved to Valencia, Spain. I’ve been writing for a living for around a year, working with a bunch of wonderful, smart individuals. Most recently:

• building a library of business case studies with Cedric 

• working with Jason on his book about startup pivots

• helping Paul with his strategy consulting offering

I also occasionally research and write scripts for history podcasts, a fun side hustle that indulges my creative, geeky side. This is my favorite episode yet, about a failed assassination attempt on the life of Adolf Hitler. 

All this to say, I discovered I was a pessimist, just as I stopped being one.

Thanks so much for reading! If you have any feedback, questions, or just want to say hi 👋, you can reply to this email or get in touch on Twitter :) 

Warmly,

Rhea