Twenty years ago, when I was trying to figure out how the hell to get out of debt, I was fortunate enough to find two silent mentors from which to learn financial skills: Dave Ramsey and Vicki Robin.

I say silent mentors because I didn’t have any actual relationship with these people. I read their books, and for some reason they connected to me, and that was enough for me to find my way and, eventually, to become a mentor to others who needed help with money.

Today, almost exactly twenty years later, it’s not money that I’m interested in but art. And I’ll be damned if I haven’t found a couple of silent mentors in the art world: James Gurney and Stan Prokopenko.

James and Stan == Dave and Vicki?

Why do I like these two? I don’t know. Something about the way they teach just connects with my brain. And that’s how it was with Dave and Vicki. The way they talked about money made sense to me. I’d read ten or twenty personal finance books before finding The Total Money Makeover and Your Money or Your Life, but those were the two books that actually clicked.

And that’s how it is with James and Stan. There are many other artists from whom I’m learning (via YouTube or books or what have you), but it’s Stan and James — especially James — that have a sort of dedicated line into my brain.

James Gurney is perhaps the most inspirational and interesting person I’ve ever found on the internet. His books and blog and YouTube channel and courses are all top notch. He’s just a guy who loves art and wants to share that passion with others. There’s zero bullshit. Love it. I hope that I’ve been to personal finance as Gurney is to art.

Stan Prokopenko has perhaps the very thinnest layer of bullshit, but only to the extent that he’s monetized some of what he offers. And that’s not really bullshit, right? If you’re good and you have something to offer, then sure, ask for payment. He still offers tons of free material, but James is on a whole other level.

I like James and Stan so much that I’ve sent money their way. Sort of. I spent big bucks to buy an out-of-print book that James produced with his college roommate, Thomas Kinkade. (Yes, that Thomas Kinkade.) And I bought several of Stan’s online courses. They’re great.)

Anyhow, I didn’t really start writing this to share these two professionals. I started writing this to share my own progress.

Getting Started with Art

In a relative sense, I’m still very much at the start of my art education. I know that. I respect that. I’m fine with that.

But after roughly a year of dabbling with this stuff, I’m just now beginning to produce stuff that I like. This might be a long way from producing stuff that others like — although there was the fellow student who wanted to buy one of my paintings last fall, even though I thought the painting was crap — but it’s good enough. Really, my aim with this art journey is to be able to produce material that means something to me. And, at last, I’m able to do that.

Just to be clear, most of what I produce is still crap, and I know that. That’s what I expect. But just as with my photography 25 years ago, I’m beginning to produce stuff I like now and then.

I had zero background in photography when Mac and I started taking classes together in roughly 2000 or 2001. My photos were like most photos: poorly composed, poorly exposed, etc. But after a year of classes, I could make photographs I found interesting. And after a few years, I was able to make photos that others found interesting. I was even able to sell a photo to a Audubon Magazine, which I guess makes me a pro photographer.

For my own edification, I thought it might be fun to document my progress so far. It’s not great progress, but it’s progress. (My friend Tanja Hester — from Our Next Life — has made amazing progress with her art over the past 18 months. I wish she’d share it publicly. Her stuff is terrific.)

Documenting My Progress

To start, let’s look at where I was in late 2022. Here’s my first-ever watercolor painting (which is so so bad) and an early attempt to draw my dog.

First painting

First drawing

Next, here’s an example of where my skills were after two weeks of watercolor class last September.

Bad trees

Progress, right? Instead of looking like a painting from a six-year-old, it looks like a painting from a twelve-year-old.

I spent three months with twice-weekly watercolor classes. Because I’m a people-pleaser, I’d paint each homework assignment three or five or eight times. By the end of November, I could paint this:


Much better, yes?

At this time, I realized that much of my problem was that I couldn’t draw. Intellectually, I understood the principles of good design and composition, but I couldn’t actually convert that understanding to practice. So, I signed up for two drawing classes. I’ve been in them for about a month now. My progress has astounded me.

Here, for instance, is a drawing of my dog made after a week of drawing instruction.

Rough drawing of my dog

That’s a lot better than what I’d done thirteen months before, right? But wait. There’s more. Here’s the same drawing (based on the same photo) after a month of drawing classes:

Good drawing of my dog

Wow. Again, I know it’s not great, but it’s good enough for me.

Now, what happens when I combine what I’ve learned about drawing and what I’ve learned about painting? Well, here’s a painting of my dog (over a drawing of my dog).

Painting of my dog

I don’t care if anyone else likes this. I like this. I can’t believe I produced this. I know I have a long way (year and years) to go yet, but seeing that I can produce even this small painting is like paying off my first debt. It’s like the beginning of my debt snowball. It gives me confidence. It helps me to understand that if I keep doing the “right” things, I’ll get better and better results.

I’m not going to lie. My proudest moment so far as an artist is this: In last night’s class, my instructor sat and looked at this painting for a couple of minutes. She had constructive criticism, sure, but she was also wrapped in it. I count that as success.

Final Thoughts

Last night in my Ink Pen + Watercolor class, I was able to produce this with almost zero effort and zero thought while BSing with the other students (all 70+ year old women haha).

My turtle painting

Again, this inspires confidence. It makes me want to make more art. In fact, it makes me want to set aside everything else to focus on my drawing and painting.

It’s also a bit scary, though. For three years now, I’ve been able to kind of set aside my ambition because I didn’t have the skill to match it. I know I want to draw comics (or a graphic novel or something similar) about Penny Short, but I haven’t had to flesh out a story because I’ve been a long way from being able to draw it. Well, now I see that I’m not so far away from being able to at least rough something out.

I’m a long way from being able to produce something like James Gurney’s Dinotopia series. In fact, I’ll never reach that. I don’t care. I’m enjoying the process of learning about art. More than that, I can see that it’s possible (probable?) that I’ll be able to produce some sort of artistic narrative fiction in my lifetime.

8 Replies to “Learn art slowly.”

  1. J.D. Roth says:

    So, here’s a weird thing about weird me. I often associate X with Y, when I’m particularly focused on Y.

    For instance, Kim and I took a long drive to Sacramento eighteen months ago. During the drive, we listened to The Courage to Be Disliked. Now I associate that book with the drive, and that drive with the book.

    When I draw and/or paint, I tend to put on music or movies or videos in the background. Now I’m finding that that secondary media is burned on my brain when I look at the art I produce. That detailed drawing of Tally? Makes me think of You Can’t Take It With You. The painting of the couple in the rain? Blade Runner. And so on.

    A little strange, but I like it.

    • Josh says:

      I do this with running and podcasts/audiobooks. I listen to them when I run and later when I drive or walk by the same spots I ran I associate them directly with whatever part of the book/podcast that was playing while I ran in those spots.

      It’s odd how strong the association gets burned into your brain.

    • Julie says:

      When I was in college our dorm was so noisy at night I put on instrumental Windham Hill records while I studied to not be distracted. When I took a chemistry or biology exam I would hear the music in the “background.” The two types of memory were very linked.

  2. Jason says:

    Your two people on a walk painting is hauntingly beautiful. I found myself lost in it for a dew minutes. Really enjoyed it and this entire post

  3. Lluviata says:

    I’m on a similar journey, starting watercolor painting as an adult, learning very slowly, and enjoying the heck out of it. Thank you for the two resources.

    Your post inspired some musing about the production of art for art’s sake. You say that you’ll never reach a particular level of quality or skill. It made me think about the immense quantity of mediocre-skill art produced by people like me and you, and how I used to think of it as worthless or near-worthless. Like clutter, distracting from “worthwhile” art. It’s coming from a very money-based view (if it’s not great, no one will buy it, and therefore it’s not worth making.) But now I think how wonderful it is that we have the ability to do things for the love of doing them. And maybe the art itself is proof of people deciding what matters to them and doing things for no other reason than that they want to. So every piece of mediocre-skill art is a reminder of the beauty of living.


    • J.D. Roth says:

      I love this comment! And it reminded me of a realization I had yesterday.

      For months, I’ve been flailing around trying to find a project to focus my efforts. I have some ideas that I’m moderately excited about, but nothing that’s a “HELL YEAH!” that could be propelled by intrinsic motivation.

      Then yesterday I came up with the perfect project, one I’d love doing. I’m going to create drawings/paintings of key photographs from my life. Then I’m going to write out stories about those photographs and why the people, place, things, and ideas in those photos are important to me. My first one will be the photo I often share of the trailer house I grew up in. It’ll be relatively easy to draw and paint, and it’s a perfect starting point. Very excited to make a first attempt at it. It’s a way for me to do both writing and art at the same time!

  4. Emily says:

    I’m also starting to learn watercolor as an adult. Your progress is exciting to see; I’m just beginning and would be thrilled if I could see similar progress a few years from now. I hope you’ll continue to share your work.

    This conversation reminds me of Ira Glass’s comments on trying to become an artist/creative person who produces “good” work:

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