I’m back from London after getting many tattoos. I spent the majority of my birthday in the air—I had my flight from Heathrow at noon and from JFK at six.

The time served as a solid reset. I spent little time working on art or thinking about art; most of the days were spent freezing while walking to the tattoo studio, getting blasted by needles for 6 hours, and zoning out. I spoke with my artists and watched the other tattoo studio-goers and let my mind wander.

I met Saskia in the concrete building for Sans Patrie. She helped me place all of the stencils for my patchwork vision; her pieces in conjunction with Koblin’s.

We spent much time discussing books and art while I was in the chair. I later went to their launch party for the tattoo studio— it reminded me of the popups that I’ve seen in San Francisco with mixed appeal: tattoos in the corner, art hanging, haircuts and shirt sales on the other end. I wallflowered for most of this time. Cool cats at these popups: they wear all black or at minimum use black accents and silver jewelry and all have sick hand tattoos.

The event felt like Pancakes and Booze, but a bit more organic. It was like if the artists were not emerging artists, but not quite professionals from their painting—somewhere in between. They are professionals, after all—just for tattoos.

I drank my Drip water on the way out of the venue. I wondered about my relationship with La Croix as a statement about being an introvert— the call to wander the streets opposed to hanging out inside, mingling with people who I would fly away from in a few days. Europeans on the street smoking cigarettes in groups of three. People who are huggers and not hand-shakers.

I thought about other jobs and roles to do which might boost my creative output by adding routine into my life. In addition, they may offer me some skill development—learning to work with wood to build frames, or upping my manual dexterity which might translate to painting, or improving my Spanish speaking.

On one hand, I consider this a good idea, and on the other, I think it may distract from my true vision. Ultimately, I want to take advantage of the time that I’ve given myself to become this vague mixed-artist-hybrid. If I’m not taking advantage of this time, am I succeeding?

I consider how to find the exact iteration of “thing that I’m uniquely best at in the world.” I learned about this concept in The Almanack of Naval Ravikant, where the author describes how Naval thinks that you should iterate on “what it is you do” until you’re the best at it. As I redefine my life as an artist (and all the things adjacent), I consider that I need some skill development in other areas as well. I wonder about working in sales for a short while.

I met Koblin on the 4th floor (5th for us Americans). This spot was far more industrial, over in Fish Island. Koblin slapped stencils on me and I laid on the bench and watched the crane at the top of the building opposite of us. The crane moved every so often so it kept me occupied. There were a few others getting tatted— Koblin’s partner was doing a bird holding a fish in its mouth, and a guy behind the mirror kept glancing at his iPad to check the reference for a forearm tattoo. There was a woman tattooing another woman who had tons of tattoos already—they worked almost the same amount of time that I did, but they left just before we finished.

I lay in the tattoo chair and consider that I am content. I’m glad to have all of my needs met, and then some! I’m able to travel and get tattoos and buy art supplies and eat good meals with friends.

As of today, I’m about halfway through my year-long experiment to see if I’m able to craft a sustainable self-employed endeavor.

I spent this time in London to consider if I’m on track. But what is “on track” anyway? Am I measuring my progress based on income? Or some inexplicable change in my painting ability? I’ve certainly spent a lot of time with friends, doing restorative work on my shoulder, and practicing jiujitsu.

I left my job under the assumption that I should really know if it’s viable to pursue self-employment by a year, but it was never just about being self-sustaining. My goals for the year were to prioritize myself and my development, learning new skills, and working to utilize my time effectively. No low energy, corporate America zombie time.

Still, I’m trying to be strategic. I’m making an attempt to follow Dan Koe’s plan for making money as someone self-employed. He says to consider that how you make your first dollar won’t be the exact same as your first $10k, nor will that be identical to your road to your first $1m. I’ve already made a dollar here and there—I’m hoping to scale that up to $10k, and from there I’ll need to identify what else to add or subtract to pivot to making even more than I was in software.

I think it makes sense to continue to run experiments on social media and on my marketing and production. I feel like Flex and Paint is getting a touch stale—I want to run different approaches to the setting, content, and hook of each post. If you have ideas for how I could iterate on my content, please let me know!

Some other thoughts that I’ve had lately on how to make some scalable income:

Use affiliate links for promoting painting materials which I like
Write up My Only Friend La Croix into an ebook
Continue on commissions

I’m sure in time, I’ll need to pivot—offer paintings of higher value with all the bells and whistles—framing, shipping, so on. I’d also like to learn direct sales and how to identify arbitrage opportunities as an art dealer; I want to buy art which I think has value and see about reselling.

As of today, I’ve made very little cash but I’ve leaned into a completely new style of painting. The best thing that I had painted in San Francisco was probably my big yellow or big purple piece (or maybe My Only Friend La Croix), and now I feel like I’m churning out pieces which I am enamored with at a regular basis. “Churning” is probably an overstatement—I think I’m making pieces at a solid rate, but it doesn’t ever quite feel like enough. Perhaps I feel this disconnect because my paintings don’t leave—I paint them, and they hang out in my apartment. I’m hoping that once I prioritize finding shows and moving volume, it’ll feel a bit more like traction.

Here are my goals for March:

Get into more art shows, popups
Paint more & paint larger
Start some stone sculpture
Finish my painting course and follow online leads—experiment with affiliate marketing
Make more fitness content on Flex and Paint
Devote more time to painting resources at hand, improve my technical abilities
Set up printing apparatus/relationships
Focus on my own fitness, get more swole

Patreon has gone well, but it’s not really covering much yet. I aim to keep doing it—I’m in this for the long-haul and I have to consider that even at six months, I can’t expect to be on the positive end of exponential growth. Things are slow-going to start.

I’m eager to determine if people want to buy my courses. Some said that they were interested—perhaps I need to do more marketing. I’m aiming to have it all filmed and available on my website within the next few weeks. Experiment, experiment, experiment.

As for the next six months, I’m not certain if I should re-evaluate with a higher level of scrutiny. I think that what I’m doing makes sense for now—at the very minimum, I’m enjoying the process, and I think it’s a bit too early to tell if what I’m doing will be sufficient for income. I have some leads on the software side of things as well, so that can always bump my time along.

I’m hoping to crank out work and videos for the next few months and I’ll do some travel in the summer when it starts to get hot. I’d like to visit Seattle again, and I want to check out Jared’s setup in Boise. I’m also considering something in Mexico.

Life is on the up and up, despite the feelings that I have every so often that I’m confused on my path to what feels like success. I remember being happy in San Francisco, knowing that I had a good life, but that I wanted something different. I told myself that I was happy with what I had built, and what I was doing, but it just wasn’t the life I wanted. Something about it was wrong. Have I migrated away from that and into something that I chose deliberately? I can’t say, but it feels like it.

London had different birds than Phoenix, and it made me want to paint some grackles.

Thoughts into March

paintings in february