Do you dream of turning your passion into a career? This advice may not be as helpful as you think.

The last video I made — the Power of Play — got an unexpected amount of attention. Attention that I’m not used to. And some of the responses made me realize that I made creative careers sound very romantic. And they can be — but I’m not a romantic.

I made a mistake by understating the importance of being practical with creative careers.

First — I want to make it clear that I’m not a licensed anything. Except tattoo artist. I’m not a financial advisor or a career counselor. All I have is life experience, some mentoring experience, and a whole lotta books.

With that said, I don’t necessarily encourage anyone to “follow their passion.” I actually have a very different view. This was hard-won wisdom that nearly cost my family everything.

Passion vs. Practicality

It’s pretty common advice to “follow your passion.” And, to a li degree, I agree.

To be more precise, I believe in following your curiosities and letting passion happen. Curiosities become experiments. Passion is the byproduct when you do an experiment that works.

But passion doesn’t support a family. When my son was born I had a stable job, good credit, and could have supporting my family very comfortably. But I decided to follow my passion because I wanted to be a tattoo artist.

After college, but before I had a family, I’d built a pseudo-successful graphic design business that buckled under my personal problems at the time. So I thought I could make it work again in a different field, avoiding the mistakes I’d made in the past. But I had no idea what I was doing.

I’d already completed my apprenticeship but never pursued tattooing as a full-time career while I was in college. After that huge gap, my first year of tattooing was filled with disappointment, disillusionment and depression.

I worked insane hours just to make ends barely meet and destroyed my credit in the process. Eventually, through trial by fire for years, I made it work.

What I did was NOT practical. It caused an insane amount of stress for me AND my wife and kids. I only made it work because of my amazingly supportive wife and a drive to succeed fueled by grit and a desire to prove “them” wrong. Whoever “them” may be.

What I eventually discovered was a more relaxing path where I relied on referrals from clients, rejected the “hustle” culture of tattooing, and got obsessive over studies and having fun.

I found where I fit in the market, but it took a lot of practice, patience, and experimentation.

The Reality of Finding Work You Love

Yes — finding work you love is possible. And I would argue that it’s incredibly important.

Work you love tends to energize you instead of drain you. That’s something that I’m incredibly grateful for.

But it took time, effort, and (in my case) a lot of stress. Because I did things the hard way.

What I wanted to encourage people to do in my last video was to explore their curiosities and look for WORK that they love.

I think that’s an important element that gets glossed over. You get paid for work.

I was trying to encourage my viewers to explore different obsessions and find a calling through trial and error. Find a way to either get passionate about something you can monetize, or experiment with obsessions and see who will pay for them.

Find the overlap of money and love, but understand that it takes time to find your unique path.

Steven Pressfield, the author of The War of Art, and the ultimate creative hard-ass, had to win through trial and error. He was a trucker, a migrant worker, and flirted with homelessness before “hitting it big” with The Legend of Bagger Vance when he was 52 years old.

Robert Greene, author of Mastery, The Handbook for Evil aka The 48 Laws of Power, and The Laws of Human Nature worked several writing-related jobs in his early life. He worked in a bookstore, as a translator, and as a movie development assistant. He spent years studying subjects like history, literature, and philosophy, and reading countless books.

Eventually, Greene wrote articles for magazines and newspapers, then published The 48 Laws of Power when he was 39 years old.

Stephen King was a high school English teacher who wrote short stories in his spare time.

He was a younger than Greene and Pressfield when he finally “made it” at age 26, but he still had to overcome incredible obstacles for his breakthrough. His teacher’s salary barely supported him and his wife, so he worked in a laundry mat and as a janitor to make ends meet.

Their stories are NOT common, but they illustrate a couple of very important things:

First, there’s real risk involved in “putting it all on the line.” I don’t know how close Greene and Pressfield came to losing everything, but I’m sure they sacrificed SOMETHING in the process.

I know I came dangerously close to losing everything. It wasn’t a pleasant feeling.

Second — it takes experimentation.

I studied studio art, computer science, and graphic design while I flirted with being a tattoo artist.

I finished a mediocre apprenticeship and put tattooing “on hold” for years. Eventually, I made a stupid leap and made it work AGAINST the odds.

I don’t regret my decisions, but I wouldn’t advise anyone else to make the same decisions I did. Especially not if you have a family to support.

I’ve seen and encouraged people to do it the smart way, and it DOES work.

Making (Sm)Art Career Choices

Art can be a viable career path, but it’s important to approach it with a realistic and practical mindset.

You might not be able to eliminate the risk of pursuing a career in a creative field, but you can at least manage it — or figure out what your risk tolerance is.

Are you young, single, and free? Start building your portfolio and finding clients!

Are you in your 30’s with a wife and kids? Don’t quit your day job. And start building your portfolio and finding clients! Think about how you can make a transition and manage the risk of a career in the arts.

Do you have a big safety net that will let you coast for a year? There isn’t much risk involved if you can manage your lifestyle and start looking for paid opportunities. Figure out how you could get back to where you are, then go for it.

Regardless, develop your skills and learn how to monetize your creativity. There are countless options, so do some research into the fields you’re interested in.

Find out everything you can about getting a foot in the door — preferably from people who have real-world experience.

As much as I love educators, experience is almost always a better teacher. Educators will give you a theory that doesn’t work practically. And if you take jobs immediately, YOUR experience usually pays with cash.

It’s all about exploring and seeing what work works!

I hope this helped shed some practical light on the dimly lit romantic room I portrayed last video.

Yes, I love my career. Yes, I believe in the incredible POWER of making your work feel like play. But I would recommend leaving one foot planted in reality while you chase your dreams. 🙂 It actually makes it more likely that you’ll succeed.