I remember how empty my Phoenix apartment felt, navigating around the space in the candlelight at night. I would paint watercolors on my French easel in the early mornings, as my oil painting setup remained in California with the rest of my stuff. I rose from my camping sleeping pad and would make a coffee in my V60 (I lugged my coffee setup along my road trip, obviously) and would lift kettlebells as the morning light filtered into the vacant space.

It all felt like the start of a new beginning, joyous and light. I didn’t know what the next year would hold for me, so I traipsed into the unknown, confident and peaceful.

Exactly one year ago, I was still a software engineer. Now I’m an artist and a personal trainer—a creative in a few different ways. I had been working in tech since graduating from ASU with a degree in Computer Science. One year ago, I made the decision to leave San Francisco and search for something new. I packed my things into a storage unit and left for a long road trip, north then south, eventually settling back in Phoenix. I secured an apartment while I was still working and I began iterating on the concepts for the future.

Long ago, I recognized that I wanted something other than software and salaried. I didn’t know exactly what the answer would be—I had dabbled in art curation, considered becoming a fitness influencer, climbing coach, or even an art dealer. I wanted something that considered two essential goals: first, I would shape my lifestyle first, then find a way to make money, and second, I would prioritize things that exposed me to unlimited upside.

In my ideal lifestyle, I spend a large amount of time painting and I maintain full control of my schedule and flexibility. Additionally, I’m helping people, primarily with their health—I consider physical fitness and emotional wellness as some of the main things I can offer. Art is good for the soul (as it is for the brain) so I wanted to share the benefits that I’ve gained from creative practices and art in my environment.

As for upside, I knew that being salaried only maintained limited upside. Maintaining control over your own production and distribution offers greater upside, I considered. I saw people succeeding on the internet (to levels I consider near-absurd) and thought that I could put my own spin on it.

Articulating the Vision

Between the time of “long ago” and “one year ago,” I didn’t know anything about the implementation. I had a vague sense of the direction I was moving towards—it took a long time to fully articulate the vision of my future life to settle on the path I’ve chosen. I read books like Antifragile and authors like Naval Ravikant and internet gurus like Dan Koe to formulate my plan. I wrote often and knew that I wanted to share my ideas, both through writing and art, and I hope that I’m on the path to sustaining myself from this knowledge work.

Just over a year ago, the seed had been planted that I could succeed as a full-time creative, as I had sold some paintings. I considered that enough—after saving up for “runway,” I settled in Phoenix and began iterating on what felt like it would strike the goals above. I decided that I would use social media to promote my art and fitness businesses, ideally finding a way to stay engrossed in the work, and have a list of clients who would be happy to engage in what I’m offering.

Removing what doesn’t work & Bad Paths

Over the past year, I’ve dabbled in many different endeavors in these domains, trying to find something that sticks. Above all else, I try to remove things that I don’t want to do, so that I’m able to retain positive momentum.

The main reason I pivoted was because I looked into the future—what will I be like at 50, if I keep doing what I’m doing?

I didn’t want to be stuck behind a computer all day, and I didn’t want to work on too many disjointed tasks. I wanted to stop working on projects which felt like they didn’t compound.

Back in October, I started using TikTok more extensively. I livestreamed my process of lifting and painting, which worked well for both painting productivity and finding clients. I was able to sell some original work through the mail, and I connected with many great individuals who have supported me and offered me encouragement.

However, much of the engagement was from people interested in explicit content from me—although I’m not philosophically nor morally opposed to this type of work, it isn’t what I want to be doing when I’m 50—it’s just not how I want to spend my time. I’m happy to keep the trend of “flex and paint” because I believe in the underlying value of body awareness, and I have no problem with body positivity and confidence.

I’m not sure that the methods I’m using to source clients are the best ways. I’ve been spending a lot of time in Instagram DMs, and I had a period where I was manually messaging every new follower, trying to see if they want help with their fitness or artistic needs. There has to be a better way (and I will find it).

Improvements in Painting, Training, and New Paths that work

I made many paintings which I’m proud of. I’ve seen my painting skills expand, both through original work and commissions. I consider it a win that I’ve expanded my surface area for interactions with my community—as a software engineer, I felt siloed and stifled. There was no real way for me to expand my connections and opportunities within one company.

Instead, I’ve been able to paint pieces for those who saw my livestream. I made a piece for my neighbor who saw my work. I consider this to be just the beginning—as I continue to expand my area of exposure, more opportunities will flow in my direction.

I consider my abilities in painting to continue to compound, along with my skills in marketing, sales, and media creation. These endeavors build on each other, and I was able to use my new following to continue to offer the value that I know—I worked with clients who asked me about my physique to provide insight into their own fitness.

For one of my first clients, we worked to address his goals—he went from being incapable of doing full bodyweight pushups to now doing over 25. We worked on some elements of his posture to where he can now lay on the ground comfortably and reports that he gets out of bed with no real aches. Moments like these alone account for much of the satisfaction in my journey.

On the painting side, I offered a painting course concept to TikTok and Instagram. Someone reached out and we arranged for a time to paint within my studio. He and I painted for four hours and he reported that it was more comprehensive than his previous classes and that it was absolutely worth the trip and the money. I’m eager to do more courses like this.

Additionally, I remember the first time that I got an email that someone bought one of my prints—I was ecstatic. It felt “real.” It took me a minute to even get the operation running, but I hope that I can continue to make things and share the vibrancy that they bring to spaces.

Sharing what we make

I kept creating freely, and I wanted to share insights into my process, so I started a Patreon. I’m grateful that so many people want to support me and view the internals of my creative process and my life. The creative juices kept flowing—I dabbled in figure drawing, portraiture, and new artistic styles—I consider that I now paint something a bit closer to Impressionism.

I was able to host some events as well, and it has been slow-going in terms of getting my work out into the local community. I ran an event at my apartment complex and at Luanas Coffee & Beer, which went well! I’m eager for the next few months as I will be going to more shows, promoting a higher skew towards local interactions as opposed to those from the internet (although I still see the internet as my main potential for upside).

Continued Uncertainty & the Brass Tacks

You might be curious how things are going financially—I’m still at the point where there’s a lot of uncertainty. My payment processor on my website was actually broken all the way through April, so I wasn’t able to collect direct orders (and thus I only sold commissions via PayPal). I checked the Abandoned Cart page on my Squarespace, saw that I had left over $3000 of lost revenue on the table, and kicked myself consummately. However validating, I saw that I could post things to the internet, have people see my work, and at least be interested enough to “almost buy it.” This removed some uncertainty, at the very least.

Through April, I made maybe $800/mo. In May, I was able to hit my goal of $3000/mo. I have been floating around that for the past few months (although September has been a slow month). I will say that I’ve been grinding far more than I’d like, prioritizing less and less deep work and painting in search of opportunities and income.

Only recently have I hired out for some help. I investigated opportunities in how to scale my fitness coaching business, but I’m not sure this is the right avenue to endeavor. I also thought about enrolling in a program for artists on social media, but it felt a bit too MLM for me—much of the advice was stuff I’m already doing. I’ve dabbled in running Instagram ads and marketing, but I don’t know anything about it, so I’m excited to work with a marketing specialist.

Looking Forward

What does “grinding” mean to me? I don’t consider hours spent painting or writing (or even recording content) to be “grinding.” I’ve been spending more time within social media apps, talking with prospective clients and responding to inquiries. Much of this fragmented attention detracts from my vision, my ideal lifestyle, so I want to consider what I’d like to be doing for the next year.

Again, in a perfect world, I’m prioritizing work that I enjoy and work that offers upside. Thus, I’d like to:

Devote more time to painting and writing every day.
Offer a way to help the most people with their fitness. I think individual coaching offers less of this—I don’t want to hold anyone’s hand and I’d rather strategize with them. I think an online course or set of materials to really move the needle with fitness is the main initiative.
Teach more people how to paint (and practices to be creative). I have a lot of insight into why my painting style has evolved, how I’ve learned to make pieces that I enjoy, all from remaining focused on subjective qualities and the process itself.
Deliver paintings directly to my local community. I don’t hate shipping, but I don’t enjoy it. I’d much rather paint something and deliver it directly to its final home.
Prioritize scalable opportunities like prints (and online courses as mentioned above).
Find ways to use social media and my email list to make the most of the above.

There’s still so much to discover, so much to paint, and so many people to help get in shape (physically or creatively). Again, I’m doing my best to honor where I am in the process—I’m excited to see where I’ll be when I make this recap again next year.

Thanks for reading,

—Kevin

A Year in Review