Artist Entrepreneur


Article by Allison Wojtowecz

If you consider yourself solely in one camp or the other here, slow your roll for just a second. Have you ever considered that both artists and entrepreneurs have extremely similar values and personalities?

How can I even say that? They’re super different, right?

I’d actually argue the opposite: these two groups are incredibly similar in many ways. But one thing sets them apart: their core motivator.

This is by no means a blanket statement on either side, but the core motivating difference I’ve noticed among these two groups is that:

// Entrepreneurs do something they love and look for the best/fastest way to scale it and create revenue.

// Artists don’t give a shit if the money comes — they’ll keep doing the thing anyway.

Now, as a person who identifies as both things here, let’s just throw out the point that the amount of work you see artists put into their passion is inspiring beyond measure. It’s painful to see artists who grind away and are never able to make a living off of their art alone.

Likewise, it’s sad to see an entrepreneur begin a company with all the love in the world for the niche they’re in, only to see the passion disappear as the company scales and the bottom line becomes evermore important.

Let’s explore the differences here and see how the similarities need to be talked about more — and how the two worlds can each learn from one another.

Artist Entrepreneur
Photo by Kat Yukawa on Unsplash

// In defense of entrepreneurial values

One huge bummer that seems to have been a theme of artists throughout time is that they both love and hate money.

There’s an incredibly confusing attitude toward it, which I think is rooted in the fact that it takes artists so long to monetize their work in most instances.

That relationship looks like this:

  • The artist has every hope of making money at what they do
  • They get a “day job” that they don’t need to put much thought/energy into so that their creativity is saved for the off hours where they can work on their craft. (This also allows for easy mobility and no promise to the company that they’ll be a long-term employee when things take off in their craft, thus perpetuating the stereotype that artists are extremely resistant to corporate structure)
  • They begin to resent their day job because it probably sucks and isn’t the thing they want to be making money at
  • Making money begins to be associated with situations they hate
  • They begin to push back at business ideas surrounding ways to monetize or promote their art.

This last point is the strangest part of the phenomenon to me — but I think it happens because money begins to feel dirty, since the artist has been draining their soul for so long at that day job.

Having money starts to feel dirty, and the people who opted to “go corporate” are associated with not having the strength to grind through the early days with low income to hopefully reap the benefit of making money at art later in life.

Promotion of projects feels sales-y, which also feels corporate.

And the artist ends up shooting themselves in the foot, trying to make money at something that they’re not promoting or interested in learning to scale.

So they resent the fact that no one is reaching out to them to offer to pay for their art or book them on a show… because no one knows what they’re up to. And then the cycle goes on.

// Artists need to be okay with talking money and promoting themselves.

There’s something to learn from the entrepreneur’s drive for finding how to make things profitable.

If you want to make money at your art, great! There are more opportunities now than ever before to do so.

But don’t let the suffocation of a shitty day job prevent you from being willing to talk money when the time comes. And don’t let the sales-y feeling of sharing your work become associated with self-indulgence.

It’s not self-indulgence. It’s marketing. If there’s one thing to learn from successful entrepreneurs, it’s how to properly market yourself and find your “niche.”

If you don’t market yourself, you won’t find the people who will pay you and you won’t get booked. Or commissioned. Or hired.

There is not going to be that magical moment where you happen to be at an open mic and a Hollywood booker is there.

Give yourself every possible advantage of being discovered by being willing to go out and meet people in the industry you want to be in. Maintain those relationships. People will notice you when you keep showing up and clearly making an effort to be in the space.

Not to mention: we have the internet now. Use it — that’s why things are so easy now!

And when you become open to this fact, don’t reject suggestions for how to monetize that podcast, or sell your albums, or find someone who will spend money on that painting.

People are out there who will appreciate (and pay for) your work — don’t be afraid to put yourself out there and find them.

Artist Entrepreneur

Photo of Russ (Hip-Hop Artist / Entrepreneur)


// In defense of the artistic eye

Okay entrepreneurs… your turn to listen up.

You are probably the typical over-achiever who thinks every above-average thing they do isn’t good enough. You’re great at what you do when it comes to monetizing and scaling your passion-business. You’re incredibly creative, but maybe in a way that’s not normally recognized as “art.”

And you probably started a company in the area you did because you

  1. Cared about the niche, and
  2. Noticed a need that wasn’t being fulfilled, so you figured out a way to successfully serve it.

But when does the desire for money and scaling and corporate need start to take over?

I think it’s different for everyone.

But far too many entrepreneur friends of mine fall into the trap of disliking the very thing they created because it grows into something they’d never expected.

They get the money. They get the success. They get the speaking gigs to talk about “how to make it.”

And their creative hunger is absolutely all they can think about.

The focus of business takes over somewhere along the journey of building a company, and suddenly that passion project is totally hijacked into feeling like the type of grind they thought they’d avoided by not going to work for someone else.

This trap is the one you fall into when the only goal of a passion is to figure out how to monetize it. The joy of simply doing it to do it is never considered enough, and before long, the entrepreneur can’t even enjoy doing the thing anymore because if it doesn’t make money, it doesn’t feel “worth it.”

Artist Entrepreneur

Photo by frankie cordoba on Unsplash

// There is benefit to creativity with no goal of income.

This is where entrepreneurs can learn from artists.

As much as artists resent money and have a lot of grudges against their financial situation with that day job, they light up around their art. Have you ever seen a depressed comedian hop onstage and suddenly come out of that shell of theirs?

While I acknowledge that I just gave artists all this rah-rah about “do XYZ to make money at your art,” the truth is that they’re going to keep doing their art whether they get paid to do it or not.

Artists never lose their passion because they stop making money on it, because they never went into it for the money in the first place.

As an entrepreneur, whenever possible, please remember why you started.

You’ll be a better business owner, boss, and person when you remember to focus on the cause or passion behind that company.

Your life will feel more fulfilled, you’ll be happier, and potential clients will see that you’re genuinely excited about the thing and the money will come. You already know how to monetize — so chill out and make sure that creative tank is filled so you can serve your people to the very best of your abilities.

Why the two are better together

Hopefully this point is already clear, but it’s worth stating: artists can learn that money isn’t bad, and entrepreneurs need to make sure they retain their passionate roots.

By blending these two mindsets — one of constant creativity sans income and one of income due to a solid business strategy — artists and entrepreneurs will be able to upscale themselves significantly.

They’re both extremely driven. They both have more to offer the world than they are ever given credit for. And if they look to one another for advice on the things that make them different, they can each grow exponentially and realize they’re not so separate after all.

Artist Entrepreneur

Mike Rubendall of Kings Avenue Tattoo. Photo by Sonic Highlark

Like what you read?

I’m an actress/comic based in Austin, Texas. I have a weekly newsletter from my company, Flabs to Fitness, that focuses on complex mental and physical health topics and breaks them down. Some are more philosophical (like this), and some are more scientific. If you’d like to subscribe, click here.

Featured photo by Nicole Harrington on Unsplash

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