16: Writing Should Never Be Like Brain Surgery

Happy Monday!

Hope everybody who celebrated had a great Easter. Last week I published a massive guide on my website “How to Make Money on Medium (and Is It Worth it?)” If you’re interested in the platform, that article covers pretty much everything I know.

Speaking of which, this week’s newsletter is all about writing and making money. Kind of.


In the fall of 2016, I’m sitting at the corner table of a small coffee shop in the heart of Arlington, VA.

It’s about 10 am, most of the morning crowd has shuffled out, and I’ve been sipping the same small, black coffee since I first got there at 7. Breakfast would’ve been nice, or maybe something a bit more fitting for the Arlington vibe (like a latte), but quitting your job on a whim to chase your dream of being paid to write has its drawbacks.

I was on my sixth 500-word article of the day. At $25 a pop, it wasn’t a gig I was particularly thrilled about, nevertheless $150 in one day was enough to survive. Not quite the $130,000 salary I had flushed down the toilet just a few months prior. But hey, I was living my dream!

Normally, a 500-word article would be child’s play. I’d written at least 50 for this particular client in the last several weeks, but on that morning the work felt like torture. I drudged my way through the final 100 words, submitted the finished product, and told the guy we could close the contract.

I was done writing crap I hated…or so I thought.

For a brief period of time, I did awesomely. I got back into full-time engineering work and wrote on the side for fun. But less than a year later, I (yet again) found myself writing for money instead of pleasure. Medium’s Partner Program opened up and I saw an opportunity to make some extra money.

That’s when things changed pretty quickly.

  • Every day that passed without publishing felt like a missed opportunity
  • Writing became a chore — something I had to do — instead of a hobby
  • I slugged my way through articles I didn’t care to write because I knew they would perform well on the platform

Money is a horrible primary motive for writing. It ruins the magic. Writing is supposed to be fun, creative, and exploratory. When you write for money, it starts to feel more like brain surgery. Every move becomes calculated and precise. It works extremely well, but it’s painstakingly tedious.

“This title will get more clicks.”

“A listicle would be better for piquing people’s interest.”

“Morning routines are bleh, but they’re ‘in’ right now.”

Playing this game sucks. You play the field instead of what’s in your heart. Writing should never be like brain surgery. It should be fun. If it’s enjoyable for the writer, it’s almost always enjoyable for the reader.

I’d rather write less if it means enjoying more of my work. That’s exactly what I’ll be doing here and on my personal site from now on.

Have a good (no, GREAT) week.