How to Become Rich as Hell With Your Art

Surprising Tip #1: Don't Just Create Art. Create This, Instead.

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):