How Law Practice Killed My Creativity (And How I Got It Back)

Law practice killed my creativity ... for about 6 years.

When I started lawyering in 2008, it got harder to play music, write for fun, draw, etc. I used to speak German and some Japanese. That slowly faded away too.

It was a gradual and insidious decline. It took a ridiculously long time for me to notice anything was wrong. A few years into practicing law, I just became uninspired to pick up instruments or paintbrushes in the evenings.

As far as I can understand, there were two main culprits: conflict and identity.

First, conflict got to me. The U.S. legal system is supposed to be adversarial. It makes good sense when stakes are high and you need to get to the bottom of things. “Due process” is the legal term.

A NYT article titled The Lawyer, the Addict explains, "[i]t would be like having another surgeon across the table from you trying to undo your operation. In law, you are financially rewarded for being hostile." The hostility crippled me with a feeling of inadequacy, even with things completely unrelated to law.

Second, identity was trickier than I expected. I've always hated defining anyone by their credentials or a job. It was unmistakeable though, passing the bar changed relationships. Interactions became different. Over time, I regressed toward some lawyer stereotypes (many of which I'm secretly proud of). Overall though, it wasn't a creativity-inspiring reality.

Creativity slowly started feeling impossible. It felt like law fried the imaginative parts of my brain. Probably did. 1

Creative Resuscitation

Thankfully, creativity responds well to resuscitation. I didn't quit law either, though that's always an option.

I just gave myself permission. Permission to go out on limbs. Permission to fuck up. Permission to start over. Permission to be cool with ambiguity. Permission for whatever, really.

Rehab started in a guerrilla garden in a North Portland alley. And several years of weekly, old school, on-the-couch psychoanalysis.

With time and lots of hard work, I'm happy to have a creative pulse.

The Intergalactic Network

Code is one of my main creative outlets. I absolutely love working with interactive information. And connecting with amazing people throughout the world. Unlike legal work, which largely confines me to physical jurisdictions, I can code with friends anywhere, anytime.

I've written code for as long as I can remember. I started by building a website for a rock band I was in. The earliest piece of code I was able to track down was from 2001. And I know I started at least a couple years before that.

My first legit web project was in 2004. I DIYed a nonprofit art sales website and scaled it to tens of thousands of users. I built one of the first online lawyer referral applications in the U.S. and Groupon before Groupon. I was also proud to write the code for Marlee Matlin's' MySpace page.

Then I turned down a full-time job offer as a web developer and traded Wisconsin winters for law school in Southern California. After that, I landed in Portland on New Year's Day 2008.

Coding took a backseat to legal work for several years. Dark times. I kept quiet about code around my law colleagues. Trust me, vanishingly few lawyers want to hear about Debian Linux.

Knife to the Neck

A "plunging ranula" (cyst in my neck) shook things up in 2016. While recuperating from surgery, I stumbled back into programming via Ruby on Rails.

I couldn't do client work and—in a dumb fit of workaholism—decided to build something to automatically gather court records. Ruby turned out to be a good tool for the job.

I was down a sublingual gland. And up a programming language.

The Majestic Monolith

Ruby led me to Rails. And Rails led me to an insanely supportive community of visionaries, contrarians, artists, and educators.

I flew to RailsConf Phoenix 2017 on a whim. There, I discovered Rails is actually a nondenominational open source software community that goes to great lengths to lift each other up.

I usually tell people I'm a "self-taught" programmer. Truth is, the open source community connected me with some of the best teachers on Earth.2 Rails enabled me to steadily level up my existing coding skills without abandoning my legal career. Accessibility endeared me to the framework. It showed me a powerful approach to learning, collaborating, and creating.

I've since picked up other frameworks. But Rails will always have a special place in my heart.

So What Changed, Exactly?

There's no Do-This-One-Thing-to-Jumpstart-Your-Creativity takeaway here. It was a combination of bigger themes that kept me going.

First, repetition. Committing and shipping code with git commit -m and git push. The repetition of pushing code broke something loose. In cycling, we say "junk miles"—that is, riding without any specific short-term goals. You can productivity hack all day long, but there's no shortcut to putting the work in and shipping your code.

Second, and completely without knowing it, I put myself back into a kind learning environment—where I could get immediate feedback on my work. Musicians will know this feeling from when you play something awesome, the hair stands up on your arms, and your bandmates all start smiling, laughing, and high-fiving. It's a little more subtle in programming. You typo your code and it throws an error. You edit it. It works. The feedback is immediate, obvious, consistent, and clear.

Third, programming kills ego. A complier doesn't care where you went to school, the certificates on your wall, or your membership in fraternal guilds. You ship the code. It's valuable, or not. You iterate. No hard feelings.

Finally, there was a larger purpose. This may sound like something from a 12-step program (it sort of was), but I needed something bigger than myself. Rails provided an ethos that I clicked with. Programmer happiness, provide sharp knives, push up a big tent, etc. were deeper moral concepts that kept me in a code editor. It isn't about inventing the next YouTube and getting rich. It's about limitless creativity.

These things all combined to keep me going. About 1,200 commits in, I woke up and felt creative again. There was no AH HA! moment. Just lots of repetition.

When Two Become One?

In the last few years, I've worked on a variety of legal technology projects, including internal tools for my own practice, workflow prototypes for, a free online database for creativity-related U.S. work visas, and an automated tool to improve access to public court records.

And law practice continues.

Honestly, I still haven't fully figured out where my law and programming sides meet back up. My legal work definitely benefits from a renewed sense of creativity. I'm looking forward to seeing what else I can build.

Writing Online

Before the pandemic hit, I hadn't been doing much online writing. A few things here and there, mostly for my legal practice. I quit Facebook, Instagram, and LinkedIn back in 2016 and haven't missed them. It was time to branch out.

In April 2020, I finally rallied and fired up this personal website. I made it to share, build, write, and connect with new people. I've been inspired by so many great online writers and wanted to participate in the conversation—even if I'm still relearning how to talk.

So far I've written mostly code tutorials. I feel obligated to pay it back to the open source communities that welcomed me so warmly.

I'm part of a great group of writers at Compound Writing, where I'm constantly learning more about writing, editing, sharing ideas, providing value, and building community.

Under the Hood

This site is built from scratch in Rails.

I write in Ruby, Slim, JavaScript, and Sass in a Vim text editor. One great thing about a personal website is doing experimental stuff without worrying about scaling.

Everything you see here is fully versioned in Git, test-backed, and continuously deployed on Heroku (home of Ruby's chief designer, Yukihiro "Matz" Matsumoto).

I don't track visitors, so don't worry, I'm not peering at you on a dashboard.

Not a Gadget

Despite my love for programming, I actually try to stay off computers as much as possible.

My life straddles Portland, Oregon and Walla Walla, Washington, where my partner is a healthcare provider in our rural community. I've worked on legal cases throughout the State of Oregon—from Coos Bay to Ontario—and always enjoy visiting hidden corners of our region.

I volunteer and spend as much time outside as possible. I garden, backpack, bike, and hang with our two rescue dogs, Milo and Gus.

1 A good book on this topic is Behave by Robert Sapolsky.
2 I owe a debt of gratitude to David Heinemeier Hansson, Jason Fried, _why, Michael Hartl, Ryan Bates, Chris Oliver, Derek Sivers, Jamis Buck, Aaron Patterson, David Black, Martin Fowler, and many others for helping me consistently push code again.
Huge thanks to Stew Fortier, Dan Hunt, Zachary Zager, and Joshua Lelon Mitchell at Compound Writing for reviewing drafts of this post!