When the Money's Just Too Damn Good

Be careful how you pay the bills

King Midas and Dionysus (Bacchus)

“We are what we pretend to be, so we must be careful about what we pretend to be.” - Kurt Vonnegut, Mother Night

I’ve tried to seriously pursue writing a few times.

Every time, I’ve given up. Not in an explicit “I SURRENDER” moment of defeat, but through a subtle sliding away.

The kind of sliding where you wake up a year later and wonder “when did I make this decision?” Maybe you’ve experienced that, too. That moment when you realize the current of life carried you somewhere you never fully chose to go.

My greatest professional fear is not that I will fail to write something good, rather that I will keep abandoning writing from short term thinking and shiny object syndrome.

Particularly around money.

II

I used to be obsessed with financial independence and passive income. I read all the blogs and books: 4-Hour Workweek, Early Retirement Extreme, The Millionaire Fastlane, Mr. Money Mustache, I Will Teach You To Be Rich, Money Master the Game. 

I was terrified of my fate if I couldn’t make money independently before graduation. When I talked to graduates who had taken the typical high prestige jobs: Finance, Consulting, Tech, Management, it was clear that they were making huge sums of money but did not love their work. Some seemed quite miserable. I didn’t want that.

Thankfully I have always been stubborn and believed I know better than everyone else, so I was committed to finding an alternate route. And the passive income, FIRE, lifestyle business digital nomad solopreneur #influencer buy-my-courser seemed like the best option. 

In my senior fall of college, I wrote “$2,000 a month” on the whiteboard by my bed. If I could generate $2,000 a month before I graduated then I wouldn’t have to take a job I didn’t like. I could fly to Argentina or Thailand, live off that income, and have plenty of time to figure out what to do next.

That was all I focused on for the next 8 months. The week I graduated, I launched a course with my friend Justin that ended up blowing my “$2k a month” target out of the water.

I did it. I had the financial runway to live the digital nomad life. I didn’t end up taking advantage of it yet, I worked at a small startup in Austin for a bit instead, but I’d laid the foundation for being able to take off a year later.

That was when I decided to try focusing on writing for the first time. I churned out a couple mediocre ebooks, wrote a ton of blog posts on my old site, started a podcast, and tried somewhat diligently to make writing my full focus. 

But then money got in the way again. I’d grown my monthly passive income to around $4k-5k between the course and my app (this app hilariously still makes ~$2k a month), and while that let me live a wonderful life in Argentina, when I moved to San Francisco for a few months money was suddenly a little tight. I could have lived on that amount, but I didn’t want to give up dining out and traveling. I needed more.

I took an inventory of my skills, and tried to figure out how I could make the most money in the least amount of time. That was always my framing for work. Either it’s the fun stuff you’d do even if it weren’t making money, or it’s all about how fat you can get before winter.

The obvious opportunity at the time was to sell SEO services. My site was doing extremely well from SEO, and many businesses were trying to figure it out for themselves. So I sold SEO consulting in 2-3 month packages to a few companies. I made about $41,000 in 3 months, which I left in cash and that was my new “freedom fund” to support any shortage from the monthly passive income. 

Back to writing I went. I think my articles around this time were quite good, I struck some sort of flow in that period. And I was able to do almost no work while Cosette and I traveled around Asia for 7 weeks.

But then we moved to New York, and I once again felt the money pressure. That freedom fund wasn’t going to last forever, so I needed to figure out a more sustainable source of money to live comfortably in Manhattan. And so came Growth Machine, which I worked on for the next three years.

When I stepped out of Growth Machine in late 2020, I could have gone fully back into writing. But Cosette and I were expecting our first child, I didn’t know what the finances would look like, and I didn’t know what life was going to look like once our daughter was born. It didn’t matter that we were completely fine financially, I was still scared of not having enough. So I started programming and got into crypto instead.

That went better than I expected. I didn’t always love the work, but I was making great money, and I wasn’t worried about our post-baby financial situation anymore. I wasn’t writing anything I was particularly proud of though. And I was barely reading.

I hit a point a few months ago where I needed to decide between doubling down on crypto, or trying once again to focus more on my writing. 

It took a while for me to realize that all of this other work was originally just to support being able to write. I started making courses to support writing. I started the agency to be able to write. I went into crypto because I was scared of not making enough money writing.

But at some point I forgot that. I went past the number I needed to justify putting money back on cruise control, and kept accumulating more and more. I got hooked on it.

That’s what I’m scared of happening again. Of hitting some slump with writing, or hitting some brief financial stress, and chasing after the next shiny thing instead of sticking with this path until it works.

III

My ideal work life is to write about whatever I want, however I want, and be able to turn that into a comfortable living.

Unfortunately that’s not easy. Your options reduce down to selling books, selling articles, and selling paid newsletter subscriptions. I’m already working on the former and latter, and don’t want to sell articles (I’m stubborn and want to own my content as much as possible), but then there’s the question of whether that can be enough money to be comfortable.

Obviously there’s a lot we could unpack on the “be comfortable” idea. Much of it comes down to lifestyle creep and what you can be satisfied with. But it’s also a real question of how much money you can make purely from writing. And that’s where it’s easy to get distracted.

The nagging itch to try something else comes from some sense that I could make more money, faster, from chasing another path. And THEN I could return to writing what I want to write about.

When you’re afraid you can’t earn a sufficient living from the thing you want to do, you find something else to earn that money for you. But then it’s hard to balance the two, especially if the money is really good. Success can be its own failure. You start a lifestyle business to fund your passion, then the business takes off and now you’re stuck managing employees and a Shopify store.

Once upon a time your options for “selling out” were more limited and at least involved doing the thing. If a fiction writer churned out a few pulp novels to pay the bills they were still writing fiction. But if you want to be a fiction writer now and you’re stuck in the suck, it’s easy to think “I should make a course…” It’s fine if that’s your jam, but I didn’t get into writing to become a course creator.

Or maybe you do stick with the thing but you give up on your style. Threads are all the rage on Twitter, maybe you should become a threadboi. Oh now people are talking about mental models. Everyone’s focused on SEO. Now Twitter. Now TikTok. Instead of sticking with your style and who you want to be you find someone with clout to copy. Is “The Philosophy Guy” taken yet?¹

Worse, the more you succeed at how you’re paying the bills, the harder it will be to go back to what you were trying to fund doing! You almost want to have mediocre success in your bill-paying pursuit just so you give up on it and get back to THE ART as soon as possible.

These detours are also a symptom of an underlying fear, a very primal form of procrastination. Steven Pressfield talks about it in Turning Pro: 

“Sometimes, when we're terrified of embracing our true calling, we'll pursue a shadow calling instead. That shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.” 

If you told me at 80 that I never launched a great course, or never built a great crypto app, or never built a billion dollar business, I would not give a fuck. I would care a lot though if you told me I never wrote anything great. That’s what I’m most afraid to fail at. So why do I allocate so much time to the other things? 

It comes back to money. Slogging through the long period of failure before you hit success with the art you want to do is brutal. And if you’re strapped for cash, you will try anything to solve that problem.

That’s what ended up scaring me with crypto. If you’ll forgive the absurdity of this statement: it was too much money. It started to change how I was thinking about finances, lifestyle, work, everything. It was absolutely, totally corrupting. Very fun! But it fucked with my head. I’m glad I took a step back. 

IV

There’s a moment when I wake up at 6:00 to go running where I really, really don’t want to go. 

Bed is comfy. Bed good. Running bad. I just want to turn the Eight back down to negative 5 and pass out for another hour.

But if I get through that moment and put on my running clothes, I’ll get outside and start running.

And then it still sucks. Running is boring. This podcast is boring. Why is it already 80 degrees out? Jason needs to stop interrupting Sacks. Why didn’t we go somewhere else for the summer? Is someone sleeping at the bus stop?

But if I get through that part, sometime around mile three or four, it clicks. I know this is how the mental cycle of running plays out, but I have to endure it every time. Knowing what’s coming helps me get through the suck though. It just took a lot of runs to realize.

I now understand, too, my mental cycle with writing and money. I don’t regret the past diversions: they’ve given me a much better starting point than most people who decide to take their writing seriously. But now that I know it’s how my mind works, I can better guard against future diversions. Future distractions by other people’s success. Future desires to “just go make some money for a little bit.” And hopefully, once I’m in the flow for long enough, the little voice in my head to go do something else will go away.

I’m not afraid of failing. But I am afraid of getting distracted by money, and telling myself “I can always come back to it later.”

Be careful what you do to pay the bills. You might just succeed at it.

Thank you Saint Louis Art Museum for the painting.

1. I believe David Perell came up with this branding originally, and it was a fantastic way for him to distinguish himself on Twitter. It’s a shame everyone copied him and turned it into a meme. UPDATE: Apparently Nik Sharma came up with it first.