Follow my work long enough, and you’ll start to notice something: I like to revisit my old paintings, recycling visual elements and remixing old ideas. Especially in my personal work, I absolutely cherish the do-over as the antidote to that sinking feeling you get when you put the finishing touches on a new painting only to realize it’s not quite right. Here are some thoughts on the harnessing the power of the do-over, and a look back at a few of my paintings that took a few tries to get right…

Borrowing from your past self


Like most artists, I have mixed feelings about many of my paintings — so whenever I make one that feels “right” — whether it’s a a concept, a composition, or a character that just works, it really stands out to me. Inevitably, though, my skills improve, my medium of choice changes, and my personal vision adapts; my older work starts to become a little embarrassing, and I’m forced to start cycling it out of my portfolio.

Rather than relegating an old piece to the archives, sometimes a repaint can let me “take it with me” as I change. When I first made the jump from digital to traditional media, two of my very favorites at the time came with me. First was Tam Lin (in and of itself a repaint — a quickie I’d sketched for Month of Love, then polished up for a digital “final,” before at last revisiting in oils)…

… As well as an oil painting of another of my digital-media wins from the same era, Sword of Purpose — unique in that it’s one of the few pieces I attempted to replicate as closely as possible in the new version. This is one of the advantages of the do-over: the ability to focus on honing your skills or trying out a new medium without the additional complication of planning out an entirely new illustration from the ground up.

Finishing the thought

Conditions are rarely ideal for making a masterpiece. Some artists are able or willing to shut out the outside world and let their work be their “real” life, but I’ve never been one of them. As a result, my paintings form a sort of geological record of how much attention I was (or wasn’t) devoting to my art at the time I painted them.

My piece Cold Wind (above left) was painted at the 2014 at Illustration Master Class, an environment with a lot going on — lectures, dinners, celebrity artists swooping in — that was frankly a lot more interesting than what was on my easel.

After returning home (and letting the lessons of that week percolate) I took advantage of the relative peace and quiet to paint a second version with a bit more focus — Colder Wind, above right.

Harness the clarity of hindsight

Sometime the road to a finished painting is littered with missteps and regrets. I’ll get three quarters of the way through and think “damn, I should have used a colored wash for the underpainting” or “I really shouldn’t have used such clunky lineart for those tiny details.”

Once such piece is Carrier, painted just last year. When I started this one, many moons of painting monochrome playing cards for Reign of Sin had left me a little shaky when it came to making a full-color piece (case in point, the muted version at above left). The best way to figure things out is by doing; stumbling my way through the painting the “wrong” way once gave me all the information I needed to hit that just-missed-target the second time around.

(You can find a step-by-step writeup of my process for that second, more successful attempt here.)

Technical issues aside, I’m always waffling on my stylistic choices. Sometimes I think a graphic, hard-edged approach with a lot of clean, high-contrast lineart is best; other times I think subtler transitions and delicate lines are the way to go. Very occasionally, a client will get in on the fun! I had the good fortune of receiving back-to-back commissions from D&D on a similar theme, which let me try out a little of each approach. The first was the alt cover for Tasha’s Cauldron of Everything, and the second was the cover of the issue of Dragon+ Magazine announcing the same.


Reinventing yourself

I always start a large-scale project with the best intentions when it comes to careful planning and maintaining a consistent style from start to finish; however, as they say, “time’s arrow marches forward.”

Case in point, the Reign of Sin playing card deck, where a sudden change in vision compelled me to change the look of the decks partway through the project, requiring me to repaint all of the artwork I’d done up until that point. It was a setback (setforward?) that cost me six months of work, but yielded finished pieces I was more enthusiastic about, and (perhaps more importantly) a combination of tools and techniques that wouldn’t drive me completely insane over the course of 30-odd paintings.

Indulging your perfectionism

There’s really no limit to how far this can go if left unchecked. Thanks to a mix of the technical, stylistic, and personal factors above, some pieces even make it to three “finished” paintings before I finally throw in the towel.

All of this probably looks like an exercise in futility from the outside — after all, I’m painting the same damn thing over and over. Sometimes the repaint doesn’t look all that much different from the original. Sometimes it even looks WORSE than the original! Is it worth it?

Totally. Despite the long hours, and the hair-tearing tedium that’s often involved, I’ve never regretted revisiting a piece. There’s always something to be learned or gained from the process — giving me the hope that maybe, one day, I’ll get things right the first time around.