7 Hard Truths About Building a Creative Career

There’s a harsh truth about getting paid to do what you love that most people aren’t aware of: If you’re not careful you can follow your passion right into poverty.
In all our talk of meaning, purpose, four hour workweeks and lifestyle design it’s easy overlook the reality that people have to pay their bills, keep the lights on, and put food on their tables.
The coconuts, palm trees, and laptops on beaches that litter your Facebook newsfeed are a very small part of the picture. If my Facebook ad showed me sitting in my room, staring at a computer screen, banging my head against the wall, the click through rate on my ads would be pretty low.
Yet, that is a daily reality of getting paid to write books. There are so many parts of creative work that nobody sees. Countless hours and years of deliberate practice going to great creative work. One of the big difference between amateurs and professionals is that that professionals treat their creative work like a job because it is one. They show up every single day because they understand the profound power of consistency.
One of our readers emailed me a few weeks ago and asked me the following question:
I would love to get paid to do what I love, which is to write, to speak, to share my voice and to act/produce. Working a corporate office job is soul sucking for me as I don’t care about job titles and I’m not purely money motivated. But I have no idea where to start.
I didn’t really have a good answer for him. So, I started writing this post and ended up with these insights on getting paid to do what you love.
1. There has to be a Market Demand
In No BS Wealth Attraction, Dan Kennedy attacks the follow your passion mantra in a hilarious way:
I like to lie in a hammock, eat pizza, and bet on horses. I have yet to find anybody who will pay me for this. My passion can multiply and nobody will pay me. Businesses have to be market driven.
If your passion doesn’t intersect with some sort of need in the market that people are willing to pay for, you’re not going to get rich or make a living from it. That being said, if you hate what you’re doing, but there’s a market need, that’s probably not going to make you rich either. (Although, there are probably a few rich investment bankers who hate their jobs and their lives). It’s hard to show up as the best version of yourself when you can’t stand how you spend your days.
Follow your passion has been such a repeated mantra of personal development and entrepreneurship that it’s now become a cliche. Passion follows engagement and meaning follows mastery.
Don’t follow your passion. Find a market need that you can satisfy and fill it.
2. You have to Create Value
If you want to get paid for anything, it has to create for value for other people. As my friend Garrett Gunderson says, “money is a byproduct of value creation.” Value that satisfies a market need falls into 3 main categories: entertainment, education and service.
Entertainment
could be one of the most lucrative ways to create value, but it’s also one of the most challenging. As Jeff Goins brilliantly pointed out, if you want to make a living from it, your creative work needs an audience. You can’t just paint, write, or do whatever it is you desire in a vacuum and expect money to fall from the sky. If there’s no audience for what you’ve created, the likelihood that it will make you money is almost zero.
Education
With creative work there often tends to be overlap between education and entertainment.
- Many authors teach writing workshops and speak. Our team at Unmistakable Creative recently launched a course called Finish What You Start. While our podcast is in the business of entertainment, this puts us in the business of teaching.
- My friend Joe Goodkin who is an amazing professional guitarist also teaches guitar lessons.
Like getting paid for anything, you have to create value for people.
Service
Providing a service of some sort gives you the widest range of options in terms of getting paid for your work.-
- Copywriters, Web Designer, and Freelance Writers all provide a service that increase traffic, conversion rates and in some cases even revenue.
- Airbnb creates value for other people by providing its renters with a way to earn income and guests with a place to stay that’s often better than a hotel.
- Lyft creates value by providing passengers with transportation and drivers an opportunity to earn income.
Whether you entertain, educate, or serve, it’s going to take time to get paid to do the work you love. Start planting seeds today for who you want to eventually become.
3. You Need to Pay the Bills and Reduce Your Overhead
While many people dream of quitting a job to pursue a passion, doing so without any means to survive is a bit like base jumping without a parachute and being surprised that you die. Figure out what your actual expenses are, and build a financial runway. Even in my current situation, I always know how many more months I could survive if I didn’t make a dime.
Another approach is to work at a job that helps you to build transferable skills. After 2–3 failed businesses, a good friend of mine decided to join a startup. His day job is teaching him a whole new set of skills that he’s already applying to his next entrepreneurial venture.
If you’re worried about how to put a roof over your head, food on the table and keep the lights on, your mental bandwidth for creative and entrepreneurial endeavors will be hijacked.
4. Treat Your Current Situation As a Learning Experience
In my mid 20’s I had a sales job and a boss that I couldn’t stand. So I started submitting resumes and lining up interviews. A CEO of a web analytics startup that didn’t make me an offer said the following to me:
We’re not going to make an offer. But you should know that working in sales is invaluable experience. It’s something that will come in hand throughout your career.
That advice came full circle 13 years later. When I stand on a stage I sell. When I persuade people to participate in my creative ideas, I’m selling. As Robert Greene said to me, no experience in your life should be thought of as wasted.
If you’re unable to walk away from your current situation, search for every opportunity you have to learn and grow. Give yourself an education that kicks the crap out of the one you got in school.
5. You need to Develop the Habits of a Professional
Steven Pressfield says the difference between amateurs and professionals is in their habits. Don’t wait until you’re a professional to develop professional habits. You want to be prepared when opportunity knocks.
By the time musicians and actors get their first big break, they’ve been auditioning and practicing for years. They’ve developed the habits of a professional.
I was writing 1000 words a day 3 years before I had the opportunity to write my first traditionally published book. Because I’d cultivated a habit, I was able to finish a 45000 word manuscript in 6 months.
Professionals treat time as the most valuable asset at their disposal. They optimize their lives for deep work and they spend at least some small part of their day on whatever adds meaning to their life.
On a related note- if creating powerful habits or being more productive is important to you, you’d love my newsletter. You’ll receive a weekly article like this as well as immediate access to a swipe file, where you’ll get my best tips on honing your daily habits, productivity, and creativity. I’ll also send you a guide on finding the courage to carve your own path, rather than following someone else’s footsteps. Get it here.
6. You must commit to Mastering Your Craft
I was fortunate enough to get a review copy of Ryan Holiday’s newest book The Perennial Seller: The Art of Making Work that Lasts. It’s an important and timely message for a generation fueled by clickbait, life hacks, and impatience. If there’s one thing that I truly appreciated about Ryan’s new book, it’s that his view is long term.
By the time one book comes out he’s already working on the next one. He’s truly focused on the process not the prize, and understands that your cumulative output is more important than any individual piece. If you want to build a career, not just get paid once for your work, commit to mastering your craft and building what Ryan would call a Perennial.
7. There Are No Shortcuts
When the reader who inspired this article wrote me, I was a bit frustrated that despite reading 100’s of books and interviewing 700 people, I couldn’t point him to any one resource that would be the solution. That’s because there are no shortcuts. Everybody’s path will be different. I know plenty of people who have started later than I did who have surpassed me in revenue and audience size. But once I started to compare less and create more, that’s when I started to gain momentum.
The Failure Points for All Creatives
According to Steven Kotler, there are 3 major fail points for aspiring creatives:
1) They can’t endure the poverty: Being poor sucks and it’s not easy. Many people quit they’ve had enough of living on ramen and sleeping in less than ideal circumstances. And to be honest there’s nothing wrong with that. If your dream is making you hate your life, perhaps it’s not the most worthwhile dream.
2) They can’t develop the skills: In a world with this much noise, the quality of your work matters. Becoming skilled at what you do isn’t an option, it’s a necessity.
3) They can’t evolve and adapt: When you reach later stages in a creative career, and you’re getting to do work for other people (i.e. publishers, web sites, etc) you have to learn to evolve and adapt. A lot of what got you to where you are will no longer work the way it once did.
When you finally do get paid for the work you love, you haven’t made it. In fact, the work is just beginning. The stakes are higher. Suddenly your work is no longer just about you. Editors, agents, business partners, and customers are all counting on you. The myth of that I’ve made it moment causes people to forget that creative success is an infinite game.
The only question is whether or not you’re up for it.
If you enjoyed this article, you’d love my newsletter. You’ll receive a weekly article like this as well as immediate access to a swipe file, where you’ll get my best tips on honing your productivity & creativity, as well as a guide on finding the courage to carve your own path, rather than following someone else’s footsteps. Sign up here.

