Most of us can relate to the wistful daydreaming that comes with working a “real job” and while many creatives have mastered the freelance life, many more still clock in, clock out, and devote a lot of time and energy to a job that isn’t necessarily their primary passion. It can be so easy to see your 9 to 5 as a burdensome time-suck that robs you of all creative joy (a bit dramatic, but, right?!?), but it really doesn’t have to be that way. We asked writer Nikki Volpicelli to interview five creatives, each with a day job and a passionate side project. So if you too have to sit at a cubicle to pay the bills, let their perseverance inspire and motivate you to always keep dreaming.

As creatives, we all hear that voice. It tells us to quit our day job so that we can be free and flexible to do as we please, to start that new project, travel and get inspiration for an even newer project, clear our heads, refresh our minds, not have to answer to “the man.” It’s romantic, but it’s also not always the best or most responsible idea. In some cases, your day job can be the very thing that keeps your creative projects flowing.

For many artists, the balance is an art form in itself. It can help you avoid compromising your own work for monetary reasons. It can help you gain new ideas from people, places and things you wouldn’t otherwise be exposed to. It helps you stay competitive and creative. And, you have to be really on top of your shit.

If you’re like most of us and you can’t yet quit your day job for your life’s work, don’t be discouraged. Instead, make it work for you. Here’s some life advice from five talented creatives who have managed to stay on the 9-5 grind while keeping their own work very fresh and inspired.


Manage your time wisely and know what to prioritize.

“I try to set realistic expectations with my side-hustle clients, so I don’t kill myself with being overworked and they understand my limited availability. There are always the occasional deadline crunch or late night, but that’s to be expected. My 9-5 gets priority no matter what, so if I have to push delivery dates with side-hustle clients because I am busy at my main gig, I let that happen and chalk it up to part of the process.” – Tom O’Toole, Art Director at Kamp Grizzly, Co-founder of Pizza Friday, Illustrator

Surround yourself with other motivated, creative people.

“I rely on [my partner] Corey a lot for feedback on my work. We’ll be working in silence for a few hours and then I’ll usually sneak up silently behind his chair and scare the heck out of him by whispering in his ear that his work looks nice. We sit in each other’s chairs and paint over each other’s work to get a fresh take on something we’ve usually been staring at for too long. We’ve done a few collaborations and I always have fun with those, I always prefer working with other people to creating by myself.”  – Jameela Wahlgren, Designer at a publishing agency and Freelance Illustrator

What you’re not getting it from your day job, get from your night job.

“I was once a footwear colorist for a large sneaker company here in Portland. My average day consisted of coming up with colorways for shoes, which was essentially like filling out a coloring book of hundreds of shoes, except I was clicking around in illustrator. The palette I could use was pretty limited, and the political nature of color and people’s opinion about it was something I never expected to encounter. But the work I did in my off time was all trippy drawings and branding projects for a number of restaurants – all of which were super open and free in terms of what I could make them look like. The rigidity of the day-to-day loosened me up, incidentally.” – Tom O’Toole

Keep your creative work honest. Don’t do it for the money.

“Right now I think I’m still developing my ideas in terms of my sweaters and clothing I make. I really don’t want the pressure of survival mixed in with it. I find I start feeling really blocked creatively when all of the pressure is on that one thing to make me money. I’m much more creative and open when I have multiple things going on. And right now my sweaters are my creative outlet for myself–my day job is creative, luckily–but this feels like my personal contribution to the world. And I want that to remain pure for now.” – Jenna Yankun, Art Director at Urban Outfitters, Founder/Designer of Jimmy Sweaters

Always pressure yourself by whatever means necessary.

“I’m finally realizing that I thrive having my hands full. And I also really fear the solo hustle. Having “jobs” to rely on almost keeps me motivated to create more. When I have too much space to create, I have this false feeling that there is no pressure. I think things grow best when you put some pressure on them, whatever that pressure is, and it’s different for everyone.”  – Jimi Hendrix, Real Estate Agent, Designer for Chapter Jewelry, frontwoman of Portland’s dark-pop band Thanks

Conversely, know when to take a break.

“This is something that is actually really hard to remember. Give yourself a fucking break. If you aren’t producing as much as you like or the kind of work you think you should be making, or you feel stagnant, or you’re just super tired, the last thing you need is to be shitty to yourself. Take a walk, a bath, a sauna. Get high. Pet a dog. Eat ice cream. Just reset and be kind to yourself for a minute.” – Jimi Hendrix

Don’t be short-sighted. Remember that patience is just as important as hard work.

“Life is long! Keep in mind that this is just a moment in time in your life, yet what you want from your career is a long lasting. So do what’s necessary (even a full-time job) to keep the fire burning for your projects. Also, what you want to do with your career should be driven by passion, not a desire to make money. Do it because you wouldn’t be happy NOT doing it.” – Vin Shambry, Admissions Counselor at Portland Community College, Actor & Director

Header: Hustle Harder