How to Become Rich as Hell With Your Art

Lately I’ve been feeling the pull toward even more creative work.

You know, the kind you feel guilty for doing?

The calligraphy, the macrame, the oil painting. Okay fine, not the macrame. Am I even spelling that right? What even is macrame? Is it like a dreamcatcher? If it’s like a dreamcatcher, that can stay right the hell away from me, do you know last night I dreamt that there were men trying to kidnap me from my house—and I ran out the back door because, well, they weren’t too bright, and I lost my phone trying to army crawl through a thicket of bushes (“thicket of bushes,” definitely a 3-pointer), and somehow ended up running all the way to Newport, Rhode Island, where I found myself still trying to outrun these masked ninjas who were trying to pretend they WEREN’T masked ninjas, because nice people in nice outfits in Newport were giving them the side eye??????

Shoot, maybe I do need a dreamcatcher. Is that the point? To catch the freakshows in my dreams?

ANYWAY, what’s weird about being 41 and wanting to do more ‘arts and crafts’ — insert deep, bottomless eye roll — is that, by now, you’re supposed to be a MORE serious person, not less.

A serious person.
With a serious job title.
And a serious resume.
And a serious portfolio.
And, you know, a serious life. The kind of person who irons her suits, and cleans the toilets on a schedule, and autopays her homeowner’s insurance, and has a color-coded list of all of the plants in her garden, and which days they get watered.

Oh god. There is definitely someone out there doing that. There is definitely probably a business selling notebooks for this very thing! Do I dare Google it? I might have to Google it.

I GOOGLED IT. IT IS REAL. I AM A FRAUD ADULT. I WILL BE OVER HERE TRYING TO TIE MY SHOELACES.

Anyway, I suppose it’s this air of formidability that feels expected, by now. And, haha, somehow hand-lettering absurd things in Sharpie markers overtop of sober-looking paintings feels a little more like, “hey, want some Playdough, too, you childish scab???”

So, I’ve been thinking about this, and how stupid it all is, to even think that ‘making art’ would somehow be a downgrade. But then I realized where that tension in my brain was coming from:

It means you have to be even more f*****g vulnerable.

I’ve always talked about how running your own business is sorta kinda like a giant personal development exercise because you have to have SO MUCH FAITH in yourself in order to even so much as respond to a new client inquiry because even you, sometimes, are going, “Do I really deserve that rate? Or am I a total tit monster?”

You’re selling your ideas.
You’re selling your concepts.
You’re selling your mind.
You’re selling your abilities.
You are selling YOU.

And, that can be hard at first, because assigning value to yourself can be awfully subjective. I can’t tell you how many creatives I’ve coached through that mental fiasco. But, if you’ve ever heard me talk about my ‘hot dog theory of money,’ then you know the business! 🫵

Here’s an excerpt from my book, THE MIDDLE FINGER PROJECT, where I talk about this:

IT TOOK ME A LONG TIME TO GET GOOD AT THIS. I had no problem at the magazine when I was selling someone else’s product, but when you’re selling yourself? There’s so much room for self-­ doubt. And that’s precisely why I decided that self-­ doubt could no longer be a part of the equation. Hence why I created The Hot Dog Theory of Money 🌭💰.

(a) Because hot dogs are hilarious; and
(b) They make the subject of money simple.

It goes a little something like this: if you were a hot dog vendor on the Jersey Shore—­ I’ll let you decide if you’re wearing a gold chain or not—­ and a customer approached you and asked you how much a hot dog costs, you aren’t going to start sweating and stuttering and tell them that, urrrhhhh, you’d be happy to work within their budget.

No, Darla! You’re going to tell them how much the damn hot dog costs. You aren’t going to feel guilty about it. You’re not going to automatically offer discounts and start charging a pittance for a hot dog, just to relieve the pressure. You aren’t going to negotiate the price of the hot dog, either. The hot dog costs what the hot dog costs, and it costs that much for a reason.

And so do you.
And so do your talents.
And so does your energy.
And so does your mind.

In this hypothetical scenario starring the Oscar Mayer Weiner, you can’t start arbitrarily assigning different prices to every customer, taking a crapshoot at whether or not you’ll turn a profit that day—­ and you can’t do that in real life, either. The price is the price, and it exists for a reason. Beyond everything else, one really important reason—­ *cue angel harps*—­ is profit. Women feel guilty about profit, but it has to be factored in. If you don’t factor it in, you know what you have? A nonprofit.

So unless you’re planning on starting the next Make-­A-­Wish Foundation, profit must be a line item. And anytime you feel guilty for that line item? I want you to imagine telling a local contractor that you bought alllllllll of the supplies to build a house, and you’d like him to do it for free.

You know what he’d tell you, right?

So, if selling your ideas is a thorny affair, then selling your art is even thornier. 🌹

Ideas, at the very least, are ‘useful’ in that sort of pragmatic, justifiable way. I can give you plenty of smart business ideas. I can give you plenty of punchy brand name ideas. I can give you plenty of addictive newsletter ideas. And, all of those things will make you significantly more money than you had before.

Direct correlation to 💰 = easy to sell.

But art?

That’s not a ‘need-to-have,’ it’s a ‘nice-to-have.’

And, selling things that are merely ‘nice-to-have’ require a whole new playbook.

How do you convince someone that they should spend $100 on one of your prints? How do you convince someone that your photography is worth that much? How do you convince someone that great beauty is worth good money?

Well, I have ideas.

A few ideas that, hopefully, will help you inch closer to taking a weird and awkward leaps over to your artistic side. Because my contention is this:

Your art can make you rich as hell.

So long as you know how to sell it.

Here’s art’s #1 problem (that keeps you broke):

It doesn’t mean anything to anyone. That very nice basket 🧺 you weaved just sorta sits there. That painting of that zebra 🦓 is just, well, a painting of a zebra. That photo of Edinburgh castle 🏰 is just another photo of Edinburgh castle. (On the surface, anyway, you know what I mean.)

When a consumer has no meaningful way to differentiate one object from another, that object loses value.

It becomes a commodity.

And it’s really hard to make money selling something that can be bought just down the road for less. Competing on price is a literal DEATTTHHHHH SENTENCEEEEEEEE, doesn’t matter what you do for a living.

Which means that the artist’s #1 job?

Is to create meaning.

(Not just art.)

Here are some ways you can do that:

1. 🖼️ Work in core themes. Instead of creating a hodgepodge of art that has no common thread—and, therefore, feels random—consider creating by theme. This month, your theme is democracy. Next month, your theme is reproductive rights. The following month, your theme is immigration. Do you see how, by piggybacking off of topics that are important to people, your work can become important to people?

2. 🫦 Become a living f**king legend. Notice how those themes all tie together themselves? This is how you build a reputation, create an “era,” and become known for something. In this case, you could easily be labeled a political artist, because remember: rich artists like being put in boxes. Of course, you could also center your work around completely different core themes that lead to a completely different sort of reputation. Maybe your core theme is romance, like I talked about with Emily Henry. Maybe your core theme is music. Maybe your core theme is satire. Maybe your core theme is rebellion.

3. 👀 Don’t look at me like that! I know you’d rather paint a toe fungus one day and a sunset the next, but if you confuse, you lose. Should we get that on a tote bag? The fastest way to becoming unmarketable is by being unrecognizable.

4. Stuck on what theme even, UGH, interests you? Don’t think of it like a theme, think of it like a question.
   Forget: “I just make what I feel like.”
   Try: “I’m currently exploring [insert obsession] across all mediums.”

   Examples:

   • “I’m exploring how nostalgia corrupts memory.”

   • “I’m obsessed with manmade objects pretending to be natural.”

   • “I’m documenting the slow collapse of American charm.”

   🧠 This instantly elevates you from a hobbyist to a conceptual auteur. And guess what you find there? Meaning.

5. Monetize like a cult leader. Once your world is established:

   • Merch becomes wearable art from your thesis.

   • Paid community = secret society of people obsessed with your worldview.

   • Workshops = your disciples pay to learn your way of seeing.

   • Licensing or collabs = outside brands borrow your vibe to be cool.

   
   This is how artists become cultural entities. Think: Miranda July. Tyler, the Creator. Jenny Holzer. These people don’t “dabble”—they curate universes.

Sure, being serendipitously creative has its charm—but branding deliberately around themes, imagery, or eras is what transforms creators into cultural powerhouses with serious wealth.

It’s funny, really: at the end of the day, being an artist isn’t just about making art. It’s about making connection.

And—haha, jokes on me—it’s still about selling your ideas.

It’s about connecting your art to topics people care about.

It’s about provoking a response.

It’s about making people think.

It’s about saying something that’ll give ‘em whiplash.

It’s about having an opinion.

It’s about causing a ruckus.

It’s about making a statement.

It’s about making things not just for the sake of making them, but for the sake of saying something.

This is, perhaps, is the biggest difference between the artist who struggles, and the artist who becomes prolific:

They have something to say, even if it’s not with words.