In this post I want to share a rule that I find useful in making art as a hobby: avoid the kinds of good/bad/should judgments that get in the way of making art.

This post is solely about your own personal practice, not the kinds of professional decisions that a working artist must make for their business, audience, and reputation. Although I also don’t believe in simple “good”/”bad” judgments in art in general, but that’s a whole separate discussion.

This post was spurred by many conversations I’ve had recently and over the years, especially with colleagues who draw or paint as a hobby and often feel insecure about it (as I have done as well).

I’m trying to write more blog posts that have less editing, so this post is not currently edited much, but still it took awhile.

Making judgments

For people who have the time and enthusiasm to make art, I believe that | the biggest barrier to making art are judgments: judgments like “I’m not a good artist” or “I shouldn’t do X” or “Good art is X.” | As soon as you start calling things “good” and “bad” and “should” and “should not”, you put up walls that could prevent you from making stuff that you enjoy, and learning and growing in the process.

The first judgment to banish is “I am not a good artist.”

Whether or not you are “good” or not does not matter. All that matters is whether you benefit from practicing art. Do you enjoy it? Do you learn something from it? Is it meditative or calming? Does it help to connect you with other people? Those things all seem worthwhile.

I’ve never thought I was all that great as an artist, and can point to hundreds of flaws in everything I draw. But I still keep going, and I even try to embrace the flaws as a good thing.

Anyone can draw. If you want to improve your skill, it takes practice and experience, and, ideally, some kind of training or practice or feedback. Practice, practice, practice. But if, along the way, you say “my drawings are bad” you risk demoralizing yourself into not doing it more, and more practice leads to more experience, and hopefully more enjoyment and better skills.

There are certainly good reasons not to keep working. Sometimes it doesn’t feel that rewarding, or you’re just too busy. Sometimes I’ve learned a new skill and plateau’d and then decided that the rewards of extra practice weren’t worth the extra effort. The first several improv classes I took were a wonderful, valuable experience, but, after that, additional classes stopped feeling worth it. Whether or not it’s worth pushing through a wall depends on your motivation, time, and other constraints. Fear of failure is not a good reason to stop working, though, since there’s really no such thing as failure in making your own art, apart from whatever arbitrary rules that you impose on yourself.


You have to make individual decisions all the time when you make art. Which brush will I use? Will I draw in color? Will I work from a photograph?

When I started drawing again in 2019, I confronted this a lot. I thought that drawing from a photograph, instead of drawing from life, was “cheating.” I thought that drawing digitally on an iPad, instead of using real, physical media was “cheating.”

Sometimes those decisions, too, get corrupted by judgements: “I shouldn’t work from a photograph”. Like we have a sense of how we should or shouldn’t make art, based on some vague value-system about good or bad art that we can’t quite articulate.

In psychology-speak: “‘Should’ statements … are a common cognitive distortion or ‘unhelpful thinking style’. ‘Should’ statements are characterized by imposing fixed ‘rules’ on how the self, others, and the world should operate, coupled with overestimations of how awful it would be if these expectations are not met.”

If you feel these “should” or “good” or “bad” judgments strongly, it’s worth asking yourself where they come from. What would really be so bad about not doing what you “should”?

If I listened to my judgement that I’m not a good artist, then I would never make art. If I listened to judgments about what I should or shouldn’t do, then I would end up never making art.

The value of constraints and exercises

One time when I was learning to ski, the instructor told us to go down our slopes, without using our poles. This scared me—going downhill without supports to lean on? But there was a point to it: to discover and practice how skiing requires controlling your body movement and, especially, feet, and the poles aren’t really necessary. The exercise helped me understand skiing in a way I wouldn’t otherwise.

Likewise, drawing classes involve all sorts of exercises. You often warm up with fast sketching exercises; I recall life drawing classes where we had 60 seconds to sketch a person that touched at least 3 sides of a giant page. These exercises break you out of habits, especially the habits typical of beginning artists.

So, it’s not that I shouldn’t work from photographs, but it’s useful to me not to do so.

In short, no technique is cheating but it’s often very useful to deliberately limit yourself.

(It would be cheating if you deceived people, say, painted from a photograph and then told people you painted from plein air).

In fact, it’s often said that imposing artificial constraints is an important—or necessary—step in making art.

Drawing from real life is an immensely valuable practice. It’s really hard. It forces you to think make many more decisions and choices, rather than just leaving them to the camera to make. It’s really valuable experience. When I first got back into drawing in 2019, and tried drawing from a photograph, I found the drawings to be dull and lifeless But, now, 5 years later, and I think my drawings from photos really improved, largely because of my experience drawing from life.

I make really different pictures when I draw from photos versus when I draw from real-life. They have a really different look. It’s a different style. Both techniques have their place.

The same goes for almost any other constraints. For a long time, I didn’t use layers in my drawing app because it felt like cheating. It was good experience to work without them. But then I started using them, and it was worthwhile. Now I don’t use them nearly as much as I could; I see them as a tool but they also take extra time to manage, so I use them sparingly. And, the style of a picture made with layers can be noticably different from one made without. The experience of forcing myself to work without layers was really valuable. I came to embrace digital painting as its own medium, distinct from physical paint.

I miss painting with physical media. I think I benefited a lot from working with real paint, and I would benefit from going back to it. But the practical difficulties are just too much; being able to pick up my iPad anywhere to draw, whether in a park or an airplane, and be done in less than 10 minutes start-to-finish, it’s so valuable compared to all the practical difficulties of real paint. I might never pick up a real brush again; it’s just not important enough to me to grow further in that direction.

Sharing with an audience

So far I’m just talking about your own practice. But sharing with other people adds a bunch of considerations.

First, I do think that sharing with other people is really valuable. Even when the process and benefits feel solitary, I really believe that art is a social practice..

I think that, when I got back into drawing in 2019, had friends largely shrugged when I shared my plain initial drawings, I probably would have stopped. I’m really grateful for all the positive feedback and encouragement I’ve gotten. Likewise, I’ve tried to be positive and encouraging in the occasional cases when a friend shares their own art online, especially if they start out with “I’m not very good, but…”

So I encourage you to share with trusted friends and colleagues, and to be supportive of your friends that share. It doesn’t have to be professional-quality.

I do also pay attention to what people say when I share things, e.g., do they like some types of drawings more than others. I don’t let it determine what I do—I also pay attention to what I want to do, and my intuitions about what to do. But getting feedback that people care about what they’re doing, and what they like, is helpful.

I do suspect that people care about how something was made. When I first showed some of my drawings to colleagues in 2019, two different colleagues asked “what algorithm is it?” Peoples’ impressions really depend on whether they think you drew it yourself, whether you designed an algorithm to do it, or just ran some algorithm off the web.

The impacts of AI

In several conversations I’ve had recently, people said they had stopped drawing because of AI. They said things like “why draw pictures when an AI can do it.” I was unable to probe these people with enough questions so that I felt like I really understood where this was coming from. I certainly do not relate: if I just wanted pictures that looked real, for example, I’d just use my smartphone camera. Does the fact that there are professional artists mean you shouldn’t paint, or the existence of LLMs mean you shouldn’t write? In one case, I think I helped by pointing out that the reason to draw isn’t to make the “best picture ever,” it’s for the personal benefits, and for sharing with other people. Your friends are going to care a lot more about a hand-painted gift rather than one generated by DALL-E.

(With the existence of diffusion models I occasionally worry that people will think that my drawings were done by “AI.”)

The mythology around creativity

The Romantic art movement created a powerful mythology around art that persists and distorts our perceptions today:

  • art should be pure.
  • the artist should work from their inner inspiration and talent.
  • art should be uncommercial, original, and unique.
  • artists should not care about their audience.

Banish these “shoulds.” Instead, figure out what the real concerns they represent, and pay attention to those. There are often good reasons to follow some of these rules, but sometimes they get in the way. For example, I think there’s useful signal in listening to how other people respond to your work. But I think it’s dangerous to only do what other people want, or to internalize every bit of criticism. You might miss opportunities or trying the things that are most helpful for you.

Neil Cohn has argued that some of these “shoulds” have harmed generations of art students. For many years, art students were told they should be creative and not learn by copying. But copying is a really valuable practice for training, and he describes a real fall-off in drawing progress in Western countries with this creativity focus versus Japan where copying is not discouraged.

Practicing skills of creativity

Drawing and painting help us practice some of the actual skills of creativity. Which brush should you try? Which scene should you try? Is it worth spending more time on this drawing, or give up on it? Maybe it’s finished? Maybe it’s time to take a break, or maybe time to work harder? Do the thing that’s easy and appealing to explore it more, or force yourself to do something difficult?

You constantly have to make decisions, and these decisions almost never have clear answers. You need to experiment, explore, and develop intuitions. You need to be comfortable with uncertainty, and without the kind of judgments that kill exploration.

You need to be open to new experiences and ideas, to try things without judgments.

Improv is another real exercise in immediate openness to new ideas, and accepting and welcoming the unexpected without judgment, and seeing where it leads.

These experiences can help in other parts of your life as well. For example, so much of my research ideas and blog have been informed by my art experience.