Note: This essay is not relevant for more than commissions. But commissions are what I have experience with, so I’m writing about them.

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You can buy a beautiful, custom-made piece of art—like a painting—with just a couple of hours and a few hundred dollars. 

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A few years ago, I traveled to a new country every few months. So many of the places I ended up staying in looked like what the default Modern Apartment Template would look like if you made a bad video game about interior design—which is to say boring, minimalist, and uninspired as hell. It was often even more depressing when they did have decor, because what you’d find were the kinds of things you accidentally walk by as you make your way towards the Ikea checkout.

And so a couple months back, I got the idea that it would be cool to pay a real artist to paint something for me. But somehow I had the idea that commissioning paintings was only something that rich and pretentious people got to do. I mean, how many people do you personally know who have commissioned artwork? Probably not many. Unless you’re one of the aforementioned rich and pretentious people.

As I started to research, I realized two things:

• Commissioning a painting is way more accessible than you think. You don’t have to spend thousands of dollars if you don’t want to. I paid someone $400 (in their local currency, the purchasing power would be much higher) to do a large oil painting. If you have at least a couple hundred dollars that you’re willing to spend, you can commission a painting. If you have more money, even better—artists getting paid is good!—and you can definitely find ways to spend it.

• The hardest part about commissioning a painting is finding an artist you like. But there’s no great guide to finding artists you like. This makes the process of commissioning a painting a bit more daunting than it should be.

I found commissioning a painting to be one of the more fulfilling side quests I’ve embarked on in life in a while. So here’s the simple guide I didn’t have when I started the process.

Finding an artist you like

Here are a bunch of tactics you can use to find an artist you like. I ultimately found the artist I paid via the second artist on this list, but found great artists with all of these methods. 

• Find artist residencies and look at their alumni. Getting into an artist residency is hard. While there are a few different formats (fully-funded, self-funded, etc.), it tends to be true that if someone was accepted to a quality residency, they are good at what they do. What’s more, most of these residencies are proud of their alumni and will show lists of artists who were there in previous years. Start clicking around until you find people you like, and note them down.


The best way to start is by going local. You can search something like “Artist residencies in [your city]” and scroll through. But you can also expand to the rest of your country and to the entire world, as long as you’re comfortable receiving packages from abroad and paying the associated tax (depending on your country’s laws).

• Dive down the social media rabbit hole. My impression is that the majority of artists share their work on social media. Here the art is not filtered through the opinions of a residency or a gallery; you get to look at all the options. My favorite tactics were the following:

• Find the account of an artist you like (via the first or third tactics here), or just find the account of any artist that does the style of painting you want. Then look at who they follow and start scrolling through those accounts.

• Find the most popular hashtags for the painting style you want. Then spend an hour or two scrolling through a bunch of posts with those hashtags. You can combine this with the first tactic for a near-infinite rabbit hole.

I would be shocked if you did this for a few hours and didn’t find at least one artist you like.

• Go to galleries and browse their websites. Find work you like and contact the artists directly. Galleries can be a great way to get exposure to work that resonates with you. Many of them have websites with the current paintings on offer, so you can quickly browse 100s of artists without even having to go to a gallery in-person (if you prefer online). A quick Google search of the artist’s name will usually lead you to a personal website where you can find their email.

There are other ways to find artists, of course, and plenty of websites where you can find and buy art from people. But for me, part of the fun was being intentional about the search, looking at 1000s of artists until I found styles that I liked. Some of the artists I contacted had 50 Instagram followers, some had 50 thousand.

Commissioning the painting

You can usually find an artist’s email within 30 seconds of Google searching. If you can’t (for example, if they don’t have a personal website), then DM them on whatever social platform you found them on. Not everyone will respond, but that’s why it helps to have a few in mind.

Note: If you don’t want to commission something, you can just see what art they have available and buy one of those pieces. This is a very normal thing to do—just buy it from the artist’s online store, if they have one, or reach out to them directly and make the purchase.

If you want to commission something, it’s a bit more complicated. Here is the process:

• Reach out to the artist and ask if they do commissions (not everyone does).
• Decide how much instruction you want to give them.
• My personal advice—remember that the artist is the expert.
• In my case, the person I commissioned specialized in landscape oil paintings. I asked him to paint a landscape oil painting of a particular region of the world I have a close connection to.
• I gave no instruction other than that. No photo reference, no specifics, nothing.
• I was (and am) in love with the final result.
• Tl;dr: let artists do art! I think the more constraints you place, the worse the outcome.

• Agree on a fair rate.*
  

• Wait for them to finish the art.

*If you have a small budget, like I did, here is where you can get creative. Good artists in high cost-of-living places tend to charge a lot, which is fair. And underpaying them or aggressively negotiating with them isn’t an ideal path to take. Instead, you can find an artist who lives in a lower cost-of-living region (Latin America, for example) and hire them.

It’s a win for you, because you can pay less for a high caliber of artist. It’s a win for them, because in their currency what you paid is what a high-caliber artist makes. There’s nuance here, but that’s the gist.

Not being an asshole

It’s a lot easier than you think to be an asshole—more politely, a bad client—when you commission a painting, especially if you don’t have any experience hiring and paying freelancers. (If you do, you might still be doing some things wrong, so read on.)

One thing I heard from the painter I commissioned was that sometimes people are fixated on having the painting exactly replicate a photo they have. Every little detail. In my view, this is just kind of dumb. You already have the photo. Just frame the photo. And if you want to basically just add a painting filter to a photo you have… There are easier ways to get that now.

Other things you do to avoid being an asshole are:

• Pay some money upfront if you can. Most artists don’t get paid well. Even those that do deal with shitty clients. One little thing you can do is paying something like 50% of the rate upfront. Avoid this if you have some good reason to distrust the artist (but there’s always going to be some level of human decency and trust involved with a transaction like this).

• Don’t frequently check in for status updates. Most art takes time. The person you’re paying has a life and a bunch of other things they are probably doing. One helpful thing you can do is just let them take their time. You’re going to have this piece of art for, like, 50 years and then it’ll continue existing for 100s of years after that. So you can wait another week.

• Don’t go back on your word, and don’t ask for a re-do. If you find an artist you like, commission a painting from them, and then decide you don’t like it (and no longer want to pay for it), then that sucks for you—because you still need to pay them. Also, don’t ask them re-do the painting if you happen not to like it. It’s kind of your fault if you went through all the work to find an artist and then decided later on that you don’t like the artist. This happens a lot to writers, too.

Enjoy your painting. (Or other beautiful work of art.)