Insights from a Rocky Road to Creative Self-Employment

As many creatives embark on their professional careers, we encounter a lot of the same challenges: restlessness with one’s current position, difficulty submitting to authority, insecurity in our abilities. And every day as we go about the minutia of our jobs at agencies or in creative departments, that tortured artist living inside our egos begins to whisper, and then scream loudly, “You’re better than this! You should be working for yourself!” When I got fired for the second time, I really had no other option but to listen to it.

Here’s what I learned.

Be Prepared (with Your Portfolio)

Two weeks after 9/11, I was let go from my agency gig in Lincoln, NE. I had spent the first few post-college years floating around various art departments and agencies. But after the terrorist attacks, the world economy screeched to a halt. I had zero options locally, but I had managed to secure a children’s book deal with a publisher in New York a few months prior to my unemployment. So with my contract and my edition of “Writing Children’s Books for Dummies” (seriously) packed, I headed straight for New York. For what, I wasn’t sure.

The best professional decision I ever made was to forgo relaxing after work and on weekends so that I could build my portfolio. I would come home from my job and get started on my book or anything else that would bolster my body of work. I hustled my portfolio around to the biggest publishers and ad agencies in New York hoping security wouldn’t escort me out. But beefing up my body of work with art that had a very wide degree of styles gave me an edge. I started securing work immediately.

I still commit an enormous amount of time to building my portfolio when I’m not producing for clients. It was the only thing that propelled me forward when I moved to New York, and it continues to open up opportunities for me that are far beyond the day-to-day design jobs. These projects have helped my art flourish, and challenging yourself creatively is essential to keeping your work fresh. 

Illustration work from Greg Paprocki, a creative entrepreneur

Never Become Complacent

After I hit the ground running as a freelancer, I was constantly in search of ways to expand my business. [Do you identify as a freelancer? Check out this post about why freelancers should be called creative entrepreneurs.] In those early days, I stumbled onto the ground floor of stock illustration. At its inception, the stock world was a bonanza for its contributors. I almost abandoned growing my clients to focus my energies on stock. But with any gold rush, those who came looking for fortune found the market oversaturated and tapped out. On the bright side, I had amassed a large portfolio and landed several clients who were familiar with my stock work and who would commission jobs. The boom and bust of stock taught me to never become complacent—the market has a way of shaking you up.

Consider the must-dos below when deciding whether creative self-employment—rocky road and all—is right for you, too.

6 Creative Entrepreneur Essentials

1. Run Your Job Like a Business

If you do choose to strike out on your own, run your job like a business. Incorporate it. Set up your bookkeeping to reflect good practices: proper invoicing, paying yourself a salary, tax payments, retirement planning. Ensure your website reflects that level of professionalism. You may be working in your pajamas, but no one should be the wiser.

2. Protect Your Intellectual Property

Be sure to protect your intellectual property! I cannot stress enough the importance of copyrighting any art or trademarking any brands you try to introduce to cartoon, toy and merchandise companies unsolicited. Make any possible co-collaborator sign a non-disclosure agreement before you begin the conversation. These industries are rife with creative plagiarism, so tread these waters carefully, and if necessary consult a lawyer. I have done this with several of my own properties. My Cherry Bombs brand has had limited success, but my new series of historically themed ABC books for publisher Gibbs Smith and my collaboration with the animation studio Deepwater on a cartoon concept has been among my biggest professional accomplishments.

3. Build Your Reputation

Entering the design world as a free agent also takes a monumental shift in attitude. You need to develop a service-based profile that attracts and maintains your client base. Many of those relationships I fostered 15 years ago in New York are still people I receive work from regularly, and I hope it’s because I have a reputation of producing and being amiable to work with.

4. Choose Flexibility Over Victory

Flexibility is a must. And while, yes, your opinion as a professional is why they hired you to begin with, the buck starts and ends with the client’s vision. If you feel very strongly about a creative choice, be courteous and suggestive, but going to the mat for your opinions may alienate your clients. Sometimes a job is just a job, and kicking it out of the door and collecting your paycheck is far more important than your vision for the project.

5. Keep Tabs on Industry Rates

And though your clients may call the shots, do not ever undervalue your services. Remember, you possess talent that they do not. Have a good grasp on the going rate for design services and charge accordingly.

6. Find Your Confidence

Most of all, have the confidence that you can pull it off! I’m not suggesting that you take on a project that you’re not equipped for, but tune in to that voice in your head that is telling you that you are good enough. Believe in it. Then, it’s likely your clients will too.

Maybe you are ready to take that leap. And if you jump and find the whole endeavor is not for you, agency life really isn’t so bad. I desperately miss venting at happy hour with coworkers. And while it’s great to not have to deal with a commute or a toxic work situations, my office is always just steps away. Work is ever-present and unescapable, even if your kids are screaming at each other while your wife is vacuuming.

So pick your poison.


Greg Paprocki has been a free agent for nearly 15 years. He currently resides in Omaha, NE with his wife and three kids. His clients have included Pepsi, Taco Bell, Mattel, and he illustrates Curious George for publisher Houghton Mifflin. His new series of ABC books for Gibbs Smith’s BabyLit® division are now available in bookstores and online. He credits trusting his gut, meditation and exercise to helping maintain sanity in the chaotic, unpredictable world of freelancing. 


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