Creative career advice: Relatable lessons from 6 successful creatives


A career in the creative world can feel like a long, lonely road. The field is competitive, and as a creative, it’s all too easy to begin comparing your work to others’ in a way that can seriously harm your growth and your confidence.

Something that helps: knowing that you’re not the only one. Since these struggles are almost universal, we compiled advice from six creatives who made it big time to see what they have done to remain mentally fresh and confident as a designer or creator.

Jessica Walsh: Find what you’re passionate about
and do it

Jessica Walsh is somewhat of a design prodigy. From coding and launching her own website as a teenager to being partner at an esteemed design studio by her mid-20s, Jessica’s fingerprints are all over the design world. Her advice for any young, budding designers out there? Discover what you’re passionate about and do it.

"Follow your heart and create things you love and truly believe in” - Jessica Walsh

“My grandfather always used to repeat a famous quote: ‘When you do what you love, you never work a day in your life.’ I think that is the best advice, to follow your heart and create things you love and truly believe in,” says Walsh in an interview with Elle

“It takes a lot of time and persistence and failures to produce great work, or to create a great business or brand. So it can’t feel like a job, and you have to believe in what you are creating.”

Leon Bridges: Don’t depend on others to be creative

Leon Bridges has come a long way in the past few years. From open mic nights in cramped bars to an ultra-successful opening album, Coming Home, Bridges’ silky smooth vocals and throwback style have delighted listeners for the past few years.

“Over time, I grew tired of depending on others to be creative, so I decided to buy a guitar and write songs on my own” - Leon Bridges

In an intimate interview with the Great Discontent, Bridges opens up about how he first started singing. Beginning by singing with his buddies in the cafeteria at his local community college, Bridges began to feel the urge to create more.

“Over time, I grew tired of depending on others to be creative, so I decided to buy a guitar and write songs on my own,” says Bridges. “I knew I wanted to do something different with R&B, but I hadn’t found a connection to soul music yet.”

This path took Bridges from tiny coffee shops to smokey dive bars for a couple of years before finally being approached by someone about creating a record, and the rest is history. But none of that happens without the confidence and ambition to pick up a guitar and create something on your own.

Shea Serrano: Shoot your shot

Shea Serrano is a high school teacher turned blogger. Okay, these titles are a little bit misleading. By blogger, we mean Staff Writer at the popular sports and pop culture site The Ringer. We also forgot to mention that he’s a two time New York Times’ Best Selling Author for The Rap Year Book, and Basketball (and Other Things).

Harder to give a title to, though, is Serrano’s unofficial position as the head of a rapidly growing band of Twitter users who dubbed themselves the FOH Army. Sure, army is in the title, but the crew isn’t exactly here to fight.

Inspired by Serrano’s unrelenting encouragement and motivation, the group's purpose is to urge people to, in their words, shoot their shot.

Whether it be applying for a dream job, asking for a raise, or asking someone to marry you, the FOH Army is here to celebrate with you if it works, or lift you up if it doesn’t. And hey, also in Shea Serrano’s oft-repeated words: “someone’s gonna do the thing you wanna do — it might as well be you.”

Aaron Draplin: Have fun, keep it fun

Designer, Founder, Author –– there are a lot of titles Aaron Draplin can go by. The guy has created a ton of awesome work in his lifetime. Not only is he the founder of his own successful brand, Field Notes, but he’s also worked with big names like Patagonia, Nike, and Burton Snowboards, to name a few.

"I tell kids to have fun, to keep it fun" - Aaron Draplin

“I tell kids to have fun, to keep it fun,” Draplin says in a wide-ranging interview with Adobe. “Just so you know, there’s going to be a lot more people who make things un-fun than there are ones who make it fun,” Draplin continues, “So just be aware of that, and don’t be so jarred by it.”

Debbie Millman: Don’t be afraid to go after what you want

Debbie Millman is an established designer, author, and host of the popular design podcast Design Matters. Before Millman became the voice of authority that she is in the design world, her career arc looked really relatable. 

For almost 10 years after graduating, Millman bounced around between jobs, wanting to make great work, but not having the courage or confidence to dare to go after the things she really wanted to do.

In an interview with AIGA, Millman was asked about the biggest challenge she’s faced. Rather than describe an outside circumstance, she began to speak about her mentality in her younger years.

“I wish I knew enough to not to be afraid of going after what I really wanted” - Debbie Millman

“I wish I knew enough to not to be afraid of going after what I really wanted,” said Millman. “But I didn’t — I thought that if I didn’t get into one graduate school or one art program that I wanted to go to, that I wouldn’t get into any. And I thought that if I didn’t get that one job that I really wanted, I would have to settle for whatever came my way, otherwise I would never get any job.”

The lesson here: go after what you want to go after, and know that if success isn’t immediate, that’s okay, because things that are worthwhile often take more time.

Seth Godin: Quit waiting to get picked

Seth Godin is a marketing guru. He’s had his hand in many companies and projects throughout his career, but what Godin is perhaps best known for is being a public speaker and author of multiple best-selling books on marketing and entrepreneurship; Tribes, Linchpin, and Purple Cow, to name a few.

In an interview with the Great Discontent, Godin is asked what advice he has for someone who’s just starting out, and he goes on to tell a story about a recent graduate who had the words “Hire Me” written on their graduation cap.

If you’ve been to a college graduation in recent years, this shouldn’t sound shocking. But Godin recognizes a serious problem here. The notion that students are putting themselves in massive debt so someone could pick them just doesn’t sit right with him.

“Quit waiting to get picked; quit waiting for someone to give you permission; quit waiting for someone to say you are officially qualified and pick yourself.” - Seth Godin

“That’s ridiculous. It really makes me sad to see that. The opportunity of a lifetime is to pick yourself,” says Godin. “Quit waiting to get picked; quit waiting for someone to give you permission; quit waiting for someone to say you are officially qualified and pick yourself.”


Like we said, a career in the creative world isn't easy, but it helps to know you're not the only one! Even these successful creatives had to fight for it early on. So continue to create the work you believe in, knowing that it pays off in the long run.

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