Fixing Mistakes and Redoing Artwork

This post is all about messing up artwork, which is something I have a decent amount of experience with. I’m going to share some of my thoughts on fixing mistakes in drawings and paintings, and redoing artwork when it’s just beyond the point of repair. And to go with this discussion, I’ve got a great example of a painting that I just couldn’t fix – the perfect candidate for a complete do-over. As Kenny Rogers said, “you’ve got to know when to hold ’em, know when to fold ’em.” But how exactly do you know?

That’s kind of a difficult question, and the answer is going to depend on the person. I think it also depends on the artistic medium too, though. Before I became so obsessed with oil painting, I mostly sketched portraits with graphite and colored pencils. My preferred approach was to apply layers of color very thickly, pressing hard with the pencils. I’ve always liked a “painterly” look, and found that drawing in this way at least looked less like pencil marks. The down side though was that I almost always used up all of the paper’s tooth – laying down so much pencil wax that there was no surface left to grip more. Bizarrely, in this way, colored pencil is really not very conducive to fixing mistakes. Typically, once I got past the first blending, there wasn’t much I could do to fix major issues.

On the flip side though, to my great surprise, oil paint is incredibly flexible. It’s still amazing to me how much you can mold and sculpt the paint once it’s on the canvass/paper. Working “wet on wet” really allows you to completely reshape major pieces of an oil painting. It’s one of the things I’ve come to love about practicing in this medium. But there are limits, which I’ve naturally run up against as I try to learn. Sometimes, I’ve overmixed and my paintings have become muddy, slippery messes. And other times, a painting is simply not worth the time investment to try to fix versus cutting my losses and moving to something new. Sometimes, you just have to take it as a lesson and cut your losses.

Left: Original attempt, Right: Second attempt. Screen capture from the YouTube video discussion.

During my painting journey over the last couple of months, I had a specific example that really exemplified the “worst of the worst” in terms of paintings going wrong. I started a portrait one Friday evening, with all the usual things – environment, materials, painting set up, and so on. For some reason though, this painting was a disaster from the start. I don’t know if I just wasn’t in the right mood, or had too much other stuff on my mind. Or maybe it was just one of those bad art days, which I’m sure happen to most people. But the underpainting started poorly, my paint was too thin, and I immediately overmixed into a uniformly messy blob.

At a certain point in the evening, I decided to put the brush down and sleep on it. This painting was a disaster zone, but it’s not the best feeling to give up on a painting completely. I woke up the next morning and looked at it with fresh eyes…and immediately decided it was beyond saving. Normally, I would just move to a new subject, but I felt like this wasn’t a particularly difficult scene and I shouldn’t be defeated so easily by it. So, I made the decision to start completely fresh.

A Completely Redone Portrait, Oil on Paper.

Although I usually try to be frugal with my paints and reuse a palette across as many days as I can, I opted for a totally fresh approach. I cleaned my palette and brushes, got some fresh paint, and gave it another try. Otherwise, I approached everything the same way, but with perhaps more dedicated focus. This was originally another effort to practice painting without any kind of measurement, and I must admit the thought did cross my mind to break out the trusty proportional divider. I dismissed that idea quickly though, because I didn’t want to wave the white flag at my effort to practice. Not that I’m opposed to still using pencil – for projects that require a good likeness, I will surely continue to sketch. But I want to push myself, and this is one way to do that.

Also, I realized measurement probably wouldn’t have helped the first version much. Although the underpainting was poor, I think my biggest problems were color mixing and sloppy painting. As I said, it became a muddy mess – thin, wet oils that morphed into an unrecoverable painting. The second painting had better established, discrete zones of color, while the original become a generic blob. As I started this second one though, everything that didn’t work last time somehow worked out fine this time. Even now, I can’t quite put my finger on specifically why, but it was probably just “one of those days.”

So, the second/final version of this painting. I’m quite happy with how it turned out. After finishing, I felt some degree of satisfaction that I’d made the right choice to redo this painting. Some doubt had crept into my mind after failing so spectacularly – certainly some degree of Imposter Syndrome. But I was able to put that out of my mind for now, and felt some vindication (apparently against myself) that I was able to end the piece in a better fashion. Interesting side note: I measured using a proportional divider with the original attempt, but in the redo, I just completely freehanded the underpainting. Logic would tell me that should have a worse result…but painting truly doesn’t always follow my predictions.

As usual, I also created a video to go with the painting. This time though, I did something a bit different. Since I recorded both the good and bad paintings, I put both of them side-by-side for a synced comparison of the processes. I actually found it to be pretty interesting to watch. But perhaps I’m in the minority on that, because it’s not well-liked within YouTube itself. Perhaps people don’t enjoy watching time-lapsed failures? Anyhow, I got a kick out of it. The audio commentary covers a lot of the same ground as this post, but hopefully they aren’t exact narrative duplicates.

Despite the rough first attempt, this painting might also represent a useful milestone. I’ll probably talk about this in more depth in another post, but I am trying to create more from resources that allow me to sell the resulting painting, such as royalty free sites and photos I take myself. So basically, that means less of a focus on movie, television, and video game characters, as well as stock images that would cost money to license. I started focusing more on this aspect, which helps, but I also think the paintings have improved quite a bit. This one might finally be one I could feel comfortable selling or making prints from. Definitely more to come on this topic.

Also, quick mention regarding the last portrait giveaway I shared, which just ended a day or two ago. This one is focused around oil painting, portraits of people, and YouTube. The winner has been randomly selected (by the widget’s magic) and contacted via email! So, perhaps more to come on that at some point in the near future. There is no expiration on these prizes though; in fact the last winner is still pondering. So, it may be some time!


  • I appreciate the discussion of “failures” or as we called them at work, lessons leant. I have 5 efforts to the one that I eventually post. Great stuff.

    • Thanks Omar, I’m glad to hear it was a useful thing to read about! Like most people probably do, I struggle a bit on whether to share the failures and rough patches along with what I’m proud of. I try to share the learning experiences as much as possible, but there have definitely been some that I just had to trash and move on from. I guess that’s part of the whole experience, eh?

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