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Career

10 Ways to Lead a More Fulfilling Creative Career

What is the secret sauce to looking back on a job well done, a satisfying career, and a portfolio that makes you proud?


We have gathered wisdom from some of the most iconic creatives on how to walk out each day and do what you love. Whether it’s Debbie Millman’s advice to invest in yourself or Amos Kennedy Jr.’s advocacy for setting your own values, these lessons act as a guide toward living a wonderfully fulfilling creative life. 

Play the 88-year long game.

We love immediate gratification and recognition. We want to be a prodigy and make the 30 Under 30 list. But being a shooting star isn’t the key to a lifelong career. Take abstract artist Carmen Herrera. She painted for more than 60 years before her work was widely recognized and, at age 101, her work was finally shown in a retrospective at the Whitney Museum of American Art. The takeaway? Nothing says your creative career is over if you’re not recognized early on. Remember to play the long game. Even if it takes close to a century. As Herrera herself put it, “Patience, darling, patience.”

Carmen Herrera in her New York studio. Image courtesy of Herrera.

Pursue personal projects.

Louise Fili has made a career crafting understated and elegant graphics, first for Pantheon Books and then for her own studio, Louise Fili Ltd. But her advice for a fulfilling career lives outside of the workday 9-5. “I feel very strongly that every designer has to have his or her own personal projects,” says Fili. “Because it’s the only way that you really grow and find your design voice.” The designer started with an Italian art deco inspired book, based on years of collecting material for fun. That little book grew into a design series that led Fili all over the world. “You have to combine graphic design with something you’re passionate about,” she says. “I wouldn’t be the designer I am today if I hadn’t done my own projects.”

Fili in her New York City Studio. Photo by Franck Bohbot.

Make confidence a part of your practice.

Animator Floyd Norman has been in the business a long time—since the days when an animator’s top pitch priority was to make Walt Disney himself smile. But his advice to young creatives has never gotten old. The secret to a good pitch? Fearlessness. “If you’re hesitant about your work,” Norman says, “this will show in your pitch. If you feel like you’ve delivered the goods, then you can pitch with confidence.”

Floyd Norman started working at Walt Disney Animation Studios in 1956.

Think in systems, not pixels.

A brand isn’t only a logo you hand off to a client, according to MetaDesign founder Erik Spiekermann. A designer must take command of the big picture: strategy, implementation, a plan to put the pedal to the metal. “You can design anything, but if the rubber doesn’t hit the road,” says Spiekermann, “the client won’t call you again.” So, show up not just with color and a typeface, but a vision for how it fits into your client’s environment and business plan. That’ll put you right in the drivers’ seat.

Spiekermann in his studio in Berlin. Photo by Robert Rieger.

Act like you belong until it’s clear that you do.

President Reagan and President Obama White House Photographer, best-selling author, and Instagram sensation, Pete Souza, has his own twist on getting into ‘the room where it happens.’ The photographer earned President Obama’s trust while covering the then-Senator before he reached the White House. That might get him into the family’s Christmas morning celebration, but how about past security at G20 summits? “My approach was to sneak into rooms I wasn’t supposed to be in and act like I belonged,” says Souza. “I wasn’t successful every time, but it became a game to me.” His ‘fake it till you make it’ strategy eventually paid off. Souza’s Instagram documentation of Obama became so popular that ultimately, gatekeepers learned to wave the photographer in.

Souza walks with former President Obama.

Set your own values.

Master craftsman Amos Kennedy Jr. left a lucrative job at AT&T for the tempest-tossed road of starting a letterpress studio. At 60, the printer isn’t just an expert in type, he’s an expert in ignoring social pressures that whisper we must prioritize security, snazzy cars, and early retirement. “Personal responsibility is first for your happiness,” says Kennedy. “That freedom that we so long for is, basically, an ability to express ourselves and just be happy.” Where does that happiness come from? According to Kennedy, it lies in finding and following internal peace.

Sync your schedule with the work style that inspires you.

Sign painter Norma Jeanne Maloney has lived many places, but in every location, she schedules her studio hours like she’s in farm country. “I get into the studio at 7a.m. and leave at 6 p.m.,” she says. “Sun up to sun down, like a farmer.” The schedule isn’t just about an honest day’s work.  It reinforces the idea of Maloney’s studio as a handcraft tradesman’s paradise, versus a 24/7 graphic design mill.

Maloney in her studio. Photo by Matthew Johnson.

Respect the tradition while designing your own spin on it.

Mira Nakashima may come from a rockstar family of woodworkers. But instead of giving her an inflated ego, that lineage has given her a humble sense of tradition and respect for previously tried-and-true techniques and designs. The result? A craft that blends personal inspiration with historical knowledge. “One usually builds on what one has learned in the past that works well and resonates from within,” says Nakashima. “In Western culture, following a tradition is not a respected path, but in most Eastern traditions it is the only way to go.”

Nakashima in the studio with her father. Image from the Nakashima Foundation for Peace.

Pitch ideas you’ll defend to the end.

George Lois made a name with his big ideas (and bigger personality) across ads, TV campaigns, and the covers of 92 editions of Esquire. “Any problem that you get as a designer, a communicator, the answer has to be surprising, shocking, maybe outrageous,” says Lois. “You want to show your creation to anybody and have them go, ‘You can’t do that.’ That is the story of my life.”

Debbie Millman

Debbie Millman. Photo by Julian Mackler

Invest in yourself.

It’s hard to get behind any kind of spec work, much less paying for an opportunity. Debbie Millman’s design career was taking off when Voice America offered her a podcast show…if she was willing to pay the fee. But, Millman reasoned, the paycheck from her big corporate job offered her the chance to invest in herself. “If you aren’t able to do the kind of work that you want to do at your day job, consider creating something of your own…Think about taking some of that money that somebody’s giving you and invest in something that you can do for yourself to make a difference in your own life.” The investment had exponential returns: Design Matters has become one of the top 100 podcasts on iTunes.

Emily Ludolph

Emily Ludolph writes about business, history, and culture. She has published in Quartz, Narratively, TED Online and Design Observer. She is the host of a live show and podcast called Dedicate It


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