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From Getting in the Sales Trenches to Being You: 99U’s 10 Best Tips for Trusting Your Gut

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From Getting in the Sales Trenches to Being You: 99U’s 10 Best Tips for Trusting Your Gut
Published December 12, 2018 by Emily Ludolph

Confidence, experience, and your own special brand of authenticity all come together to make that intangible authority: the gut check. But trusting your instincts can be hard. Never fear. We’ve collected the best advice from Louise Fili, Adam J. Kurtz, and other 99U thinkers on how to have confidence in your decisions.

 1. Know how to manage your own clients.

For an up-and-coming illustrator or designer, it may seem like getting an agent is the surest ticket to stardom. But the shrewder move may be to start out by going it alone. Learn the ropes of the business side —from negotiating fees to sorting out licenses—so you know what an agent should be doing for you. “There’s a certain amount of satisfaction that comes from handling it all myself,” admits Laura Callaghan, an Irish illustrator working in London who’s been freelance and agent-free for the past seven years and counts Adidas and Nike as clients. “I enjoy dealing directly with clients and getting a sense of who they are and what they need.

2. Study the numbers, but trust your instincts.

Data can give us a lot of the answers. But it doesn't possess every answer because the insight we get from our mysterious subconscious is its own kind of data. “Our guts have a wealth of past experiences and rational decisions that we can combine with digital data to make amazing experiences for our customers,” says Adam Morgan, author of the upcoming book, Sorry Spock, Emotions Drive Business: Proving the Value of Creative Ideas with Science.

Designer Jessica Hische photographed in the Bay Area by Jennifer Michelson. Jessica Hische photographed in the Bay Area by Jennifer Michelson.

3. Redefine success.

Designer Jessica Hische, author of Tomorrow I’ll Be Brave, has aimed for enough pie in the sky projects to know that the thing to fear when making big plans is your own sense of confidence. To that end, she’s re-jiggered her own metrics for success: “Achieving is great, but the real accomplishment is pushing through the initial fear to actually start doing something,” says Hische.

4. Try a crazy career move.

Sometimes, the fear of scaring big-name clients can lead to safe but lackluster proposals and atrophied creative muscles. That might be the sign it’s time to try a crazy career move. Matt Wegerer, more afraid of another year of risk-averse creative work than of failure, left his cushy agency role to found Whiskey Design. Now, he leads his team with the motto: no mediocre excuses for mediocre work.

Louise Fili photographed sittingon a floral couch in her New York City studio. Photography by Franck Bohbot. Louise Fili in her New York City studio. Photography by Franck Bohbot.

5. Pursue personal projects to experiment with new skills.

Build spaces outside of work, where your main goal is to develop not only a portfolio you’re passionate about, but also a point of view that is uniquely yours. “I feel very strongly that every designer has to have his or her own personal projects,” says designer Louise Fili. “Because it’s the only way that you really grow and find your design voice.”

Photographer Scott Rinckenberger captures snowy mountain scenes in Washington. Photographer Scott Rinckenberger captures snowy mountain scenes in Washington.

6. Venture off the beaten track.

Find ways to bridge the great passions of your life with your hunger for creative growth. For instance, adventure photographer Scott Rinckenberger used to practice the high adrenaline sports that he now photographs. The former semi-pro skier bridged his lifelong passion with photography when he felt himself wanting to try something different. “I needed a new creative stimulus to keep my mind sharp and engaged,” he says. “I needed some new input and photography offered that.”

7. Prepare ahead so you can live in the moment.

As a travel photographer for the New York Times, Susan Wright often has only a few scant hours on location to shoot her images. That means there’s no time to ask questions or second guess. To get herself in the right state of mind, Wright visualizes the shoot ahead of time, so she can trust her gut in the moment. “Get in a meditative state and think about a location. Feel it. You get visions in your mind: the image that would be truly beautiful to capture…I give myself a shot list and then time to live in the moment.”

8. Be you.

At the end of the day, a successful career isn’t about talent, connections, or fancy tech capabilities. In the inimitable words of the artist Adam J. Kurtz, “We all have the tools and skills. Being yourself is the difference.”

Big Spaceship CEO Mike Lebowitz and illustrator Ping Zhu talking at an AIGA NY event. Photo by Tony Tailor for AIGA/NY. Big Spaceship CEO Mike Lebowitz and illustrator Ping Zhu talking at an AIGA NY event. Photo by Tony Tailor for AIGA/NY.

9. You have more options than you think you do.

There are bound to be moments in your career when you feel like there are no good options. Those are the moments to remember you have the greatest power in the world: the power to walk away. Yes, there are real and important responsibilities, like families or employees, that may impact your ultimate choice. But even in the moments when you feel like the least powerful person in the room, remember, you always have the power to say no.

10. Do the worthwhile thing, not just the measurable thing.

“We’ve all been there where there’s a good idea on the table. We know it would improve the experience, but it would be hard to measure. So, it gets killed,” says Lyft Director of Product Design Audrey Liu. Go to the mat for those ideas that you know will have impact beyond the hard numbers. It may be more worthwhile than you ever imagined.


More about Emily Ludolph

Emily Ludolph is a director at West Wing Writers. She has published in The New York Times, The Atlantic, Artsy, Airmail, Eye on Design, JSTOR Daily, Quartz, Narratively, TED Online and Design Observer. 


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