On this beautiful early autumn Sunday in the Blue Ridge Mountains, I took the easy walk downstairs, out through the courtyard, and into my semi-finished studio. I pulled up a photo on my phone that I'd taken last week, clipped it to a holder, and started mixing up some lights and darks on my palette.
I put some midtone touches on a small 5x7-inch canvas panel. Just a little study of a waterfall. Nothing particularly interesting or special about it. But this Sunday was the thousandth straight day I had put brush to canvas (or paper).
The streak started at the beginning of 2024, and I had no idea how long I'd go. My thinking was simple: I had started painting inconsistently during the 2020 pandemic. I'd gone in fits and starts but knew I had to log some serious time with a brush if I wanted to get anything out of this hobby — and I felt I owed it to myself to give it a try.
Here's where it intersected with a lot of thinking and learning I've done on habits, discipline, and learning.
There is a theory in the art world that every artist has at least a thousand ugly paintings in them. It's the artist's job to get through those paintings to some (hopefully) really good stuff.
The logic rests on three foundations, which I think apply to almost any pursuit:
1. A Quantifiable Learning Curve: Many are familiar with Malcolm Gladwell's "10,000 Hour" theory for achieving mastery, popularized in his 2008 bestseller Outliers. While the number of hours is oft-disputed, what's not in question is that being good at something takes time — lots of time — and deliberate practice. There are no shortcuts here. You have to do the work. Better to get that through your head now.
2. Liberation from Perfectionism: This is a big one with art. I've talked to so many people who've said some variation of the following: "I've tried it, but I wasn't very good!" After just doing it a few times? No kidding.
Despite how easy things may look in a YouTube video, I can assure you that it will be harder and take more missteps than you realize. Trying to get through "1,000 ugly paintings" essentially removes this mental hangup. The results are predetermined: it's not going to be a masterpiece. Realizing this is strangely freeing. Suddenly there's less pressure. Things that turn out well will feel great, but you won't beat yourself up about the stuff that is, to put it bluntly, bad. But that's the plan. Embrace it.
3. Muscle Memory: Just as a great golfer needs to make hundreds of thousands of swings to develop their best swing, you need time with a brush in your hand. You have to learn how it feels, how to make different brushstrokes, how to control the paint, and how to mix the colors you want to see. Again, there's no way around the reps here.
I also intentionally kept the commitment light. I didn't say I had to finish a piece every time I picked up the brush. Some days I would only have time to put a few strokes down. Some days I had to sneak a few in at a hotel while traveling. Other days I would finish several pieces in a longer studio session.
But just making the commitment to paint something every day is like the old gym advice to exercise for just five minutes (spoiler: you usually end up getting into a groove and going further). Sometimes it's just getting started that's hard.
As the streak grew — first hitting one year, then 500 days, then two years — there was a natural inclination to keep going. There is a habit-building method commonly attributed to Jerry Seinfeld: mark each successful day with a big X on a calendar, and before long you've created a chain you don't want to break.
But the truth is that it has not been that hard to keep it going. Certainly, there are days when it comes more smoothly, but I have been excited to get that work in each day. The feeling of creating, the feeling of getting better, and having tangible results from an effort you sink your heart and soul into is invigorating.
I'm not going to say I'm done with the ugly stage of my painting. I'm not selling my work, and I still don't share as much as I should. Some of what I create is frustratingly bad. But there are glimpses — there is more control, and I can feel the improvement.
I'm not sure how much longer I will insist on painting every day, but I don't expect to stop any time soon. That desire to "not break the chain" is strong, and we're almost to three full years.
I hope to keep writing more about the journey as well. I came to this pursuit later in life than many and am doing my best to catch up. If there is a similar thing you have been thinking of pursuing, please do it. It's not easy, but it is worth it.
