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Risk-Taking

A Road Map for Navigating your Next Crisis: Nine Creative Leaders on Overcoming their Greatest Challenges

We all encounter defining challenges in our careers. It’s unavoidable. But it’s how we handle them that matters most. From career quandaries to financial lows, these creatives explain how they overcame career-defining dilemmas.


We all encounter defining challenges in our careers. It’s unavoidable. But it’s how we handle them that matters most. Whether it’s using unconventional ways to keep the lights on when the bank account is empty or explaining to corporate America that the role you aspire to is ‘Dad,’ the experiences of our subjects will help you traverse your next career challenge.

Being 50 percent excited and 50 percent terrified is a good place to be.
Duncan Wardle, former Head of Innovation and Creativity, Disney

My most daunting challenge was walking away from Disney last year, after 30 years. The moment of realization came when they handed me the bronze Jiminy Cricket Statue for 30 years of service. I had always preached getting out of your own expertise, trying something new, being brave. But I realized that I hadn’t really ever stepped out from my own comfort zone. If I was going to do it, now was the time.

I looked at a few in-house roles and was approached for a few. But one of the key challenges you face is: the more senior you get inside any organization, the more you manage the politics, not the work. I left Disney to create my own startup, helping companies embed a culture of creativity throughout their organization.

The first few months were completely terrifying. I was starting from zero as an entrepreneur after 30 years inside the safety of a corporation. The whole time, I was thinking to myself, ‘I’m bloody mad!’ My greatest fear was: would companies and agencies hire me?

I confess it took longer than I thought, but the last few months, things have taken off. I’m on a mission to prove to everyone that they are creative and give them tools to think creatively. I wake up most days 50 percent excited and 50 percent terrified. I think that’s a really good place to be.

It’s very early days. I’m still finding my way. But I learned that it’s never too late to pursue your dreams. It sounds cliche, but you only get one life. 

Constraints breed creativity.
Adam J. Kurtz, artist

The earlier years of my creative life were about making the most with what I had. Just five years ago, money was extremely tight. My rent was very low in a pretty grimy house with five roommates, but I still had trouble scraping it together sometimes. The first edition of my Unsolicited Advice planner was born out of necessity: I had zero money for holiday gifts. Instead, I looked toward my resources and skillset to make something to gift friends and family. I didn’t have money, but I did have access to free printing from a copy center job.

After a small run of that 2012 Unsolicited Advice weekly planner, I decided to try Kickstarter for a 2013 edition. I wanted to take a risk and see if the project could grow into something more. Turning to Kickstarter was about establishing my own legitimacy on a platform that had more brand name value than I did.

Telling the story, creating a video, and essentially selling myself as an independent creative and trustworthy person felt much more daunting than just printing 25 books at a time. The ‘all or nothing’ goal was intimidating. Even low fundraising goals are sometimes not met, and I was worried and embarrassed about what could potentially happen.

I ended up hitting my goal of $1,600 on day one, and exceeding it several times over ($7,598 total). It was more money than I’d ever had in my bank account at once. I was overwhelmed by the responsibility. I was used to doing small batches of zines, but this was the first time I thought, Wow, I do something that people really like. This might be a future. It seems silly now, but it was a formative moment in my life and career. Taking on some financial, and definitely emotional risk with that first Kickstarter project opened up a new chapter.

My big OMG am I an artist? freakout wasn’t entirely pre-emptive. The next month, I signed a book deal with Penguin Random House. And I created a personal manifesto that’s helped me set my intention and goals for the future. It’s given me something to reflect on whenever I’ve lost my way over the last few years. Knowing what actually matters to you, whether it feels important or a little silly (which is still valid!) enables you to focus on the work and keep you on track.

Be who you are. 
Tea Uglow, Creative Director of Google’s Creative Lab

Doesn’t everyone find life to be daunting? I find life completely terrifying. I am sure there are professionally daunting prospects, but most of my real challenges have been being myself; finding myself, growing into myself, growing out of old selves, closing chapters, turning pages, starting fresh.

Overcoming my denial about my sexuality, my gender dysphoria, and face blindness have been a 40-year-long program of assembly, delusion, disassembly and reconstruction. The singular most daunting part of that is: how do you communicate to everyone a truth about yourself that you’ve never told anyone? Not a lover, not a therapist, not even a pet.

The whole ‘project’ ultimately became the consolidation of everything I never wanted to admit, unpacked into a series of open letters. It wasn’t an act of bravery. It was an act of obligation, to myself and the people around me who I desperately wanted on the journey: my creative team, my colleagues, my professional collaborators and my friends. I wrote 350,000 words during the first two years of my transition. Most of it was garbage. Three thousand words made it to my first open letter—a coming out letter. Two further letters followed.

I’ve learned that letters are a far better way to share information than blog-posts or social media. They scale way better than trying to tell everyone. I learned that the internet is fickle. I have learned never to read the comments. I’ve learned that sometimes, it’s useful to insist people ask ‘How are you today?’ rather than ‘How are you?’

I’ve learned that people do want to hear from you, your story. I’ve learned never to trust a newspaper sub-editor. I’ve learned the average time-to-burn-out for a truly supportive friend (about 6 months). I’ve learned what a mess clothes sizing is for women, and how broken or under-acknowledged many female-oriented systems and models are. I’ve learned to love getting my nails done, and to take a certain pleasure in being occasionally objectified. I learned how to use Tinder. I learned loads of stuff.

I’ve mainly learned that however much you think you know yourself, your mind, your beliefs, or your history, that the world can flip on a dime. And you cannot even try to be ready for it. But you shouldn’t try to stop it when it does. I’ve learned that the human mind is incredibly powerful, and incredibly fragile and that you should look after it. Exercise it, support it, nurture it, love it.

What to do when your project has a lot of friends but is low on funds.
Vince Kadlubek, CEO, Meow Wolf

Opening the House of Eternal Return [Meow Wolf’s art experience in Santa Fe] was definitely the most daunting challenge I ever faced. Prior to House of Eternal Return, the biggest project I’d worked on was about one-fifth the size and one percent of the budget. And it was temporary. House of Eternal Return was the first time we ever got into business. None of us understood business. We kept running out of money. We were sleep deprived. And we were working around the clock to finish it on time.

I can’t do this came up all the time. And then it was followed with, ‘Yes, I can.’ We operated for a year with a constant pressure of running out of money. We never had more than two weeks worth of cash on hand. One time our bank was overdrawn and I had 100 artists to pay; $75,000 was needed. I had to make some really difficult phone calls. I called existing investors to ask them to very quickly invest more, with the transparent knowledge that we were out of money. That’s the most difficult and leveraged position a business can ever be in.

It was nuts.

The project was really rough at times, but there was a collective creative high that we were all riding. We all just wanted to make amazing art, and that’s what we were doing. There was always this really exciting thought in the back of our heads saying, ‘What if we really pull this off?’

During the build, we had over 100 artists working together, volunteering their time, and staying late. Every single person involved was absolutely crucial to the project’s success. We could not have pulled it off if we had not been working together as a collective every step of the way.

This project really made me believe that I, and the rest of the people at Meow Wolf, are capable of anything. No matter how daunting the project may seem there is always a way to make it happen.”

When corporate America doesn’t buy that your favorite title is ‘dad.’
Jason Mayden, CEO, Super Heroic

The most daunting challenge I faced was transitioning from my position at Nike to the more purposeful role of full-time stay-at-home father. At the time, my son was facing medical challenges that were greater than the ones I faced designing products for athletes. So, I decided to step away and use my gifts and talents to help him heal, both emotionally and physically.

I expected difficulties to come from the day to day tasks of being at home. But the real difficulties lay in the skepticism from my peers in the design industry. People had trouble understanding my choice to leave a prominent position in corporate America for the sake of the wellbeing of my child. Some speculated that I was going to a competitor. I felt shunned by the industry, discarded, even seen as a traitor.

I know that their judgmental perspectives were bound to a lack of knowledge. I was confident that my decision could endure a temporary rebuff from an industry that I deeply love. I decided to remain centered and calm. Ultimately, it was the right decision for our family. It helped me to focus on what mattered to me most: the preservation of childhood creativity and innocence. I decided to focus on building stronger children, rather than fixing broken adults. I decided to dedicate my life to the protection and well-being of all children—not just my own.

Now, I am the CEO and cofounder of Super Heroic, with the mission to entertain, delight and surprise every child in the world through interactive and imaginative play. We seek to encourage a spontaneous, active lifestyle.

As a CEO, I try to embed the spirit of what I’ve learned in how we work with and reward our teammates. We have an open, healthy dialogue that’s focused on promoting work/life balance. We have to play with and enjoy our families, in order to embed joy in the work that we do. It’s imperative that we live what we speak.

Don’t get promoted to micromanager-in-chief.
Emily Collins, Creative Director and Partner, Mighty Oak

The most daunting challenge I’ve faced as a creative director has been learning to step away from the process of making. I am instinctively drawn to making things with my hands. As a kid, I drew and invented characters inspired by people with crazy shoes, dogs, and wild patterns. Mighty Oak focuses on hand-made work, so the temptation to create is abundant! At first, it was very difficult to pull myself away from executing on my own.

The first time I stepped out of the weeds was for a project for Don Julio Tequila and the New York Times. It was the biggest team I had directed and I had to focus my energy on working with people and hearing their ideas. Our work is innately collaborative and needs a combined set of skills and hands. By reminding myself that we hire people for a reason and that I can not physically do all jobs helps keep micromanaging inclinations to a low for me (or at least I try!).

Once a task is someone else’s responsibility, I let them work it out and do check-ins regularly to make sure we’re on the same page. I fight the inclination to micromanage by highlighting my most important duties for the day—and doing them well—before I consider meddling with someone else’s. If my duties include checking in with people I schedule a couple of check-ins, but I don’t do their jobs for them.

I’ve found outlets to make things with my hands on my own time. Often just drawing at home at night quenches my desire to work with my hands and keeps me feeling fresh. I discover a lot of new ideas by opening up a drawing pad after 9 p.m. and seeing where my hand takes me.

My advice to those facing a similar situation would be to embrace the idea of collaboration. A multitude of artists can create much more work than a single maker, and that work is often enhanced by the collaborative process. Remember to be clear with your ideas while communicating with a team—have notes, sketches and examples ready to share. I’ve found joy in working with a group of amazing artists, and seeing so many of our ideas coming to life simultaneously.

Two designers gave up their salaries for a dream project could yield career-defining results. 
Dan Kuhlken and Nathan Goldman, founders, DKNG

The most daunting challenge we have faced in our career was our first independent solo show. The concept was 50 different screen printed designs, each paying homage to a favorite TV show or film. We called the show ICON, which represented the iconic nature of the properties we were celebrating and the iconic style each illustration would encapsulate.

Prior to this project, the largest series of prints we had ever tackled was…three. Creating 50 designs for a single event? That was completely new to us. Each design was as a limited edition of 100 prints. That meant 5,000 prints would have to be produced and ready to sell.

We thought, ‘With enough time, creating the entire series will be manageable.’

We allowed ourselves two years to create everything. But time went on, and we gave priority to more and more unrelated projects. When push came to shove, we realized we had six months remaining until the opening. And we only had a handful of designs completed. We had to create 45+ designs, including printing and shipping time. When we did the math, we realized that we needed to create three to four designs a week to get this done.

That meant we had to shut our doors to client work. We knew that the potential success of the solo show could bring us enough income to sustain our business, but in order to get to that point we needed to buckle down and execute. We made the conscious decision to forgo our salaries for four to five months.

This was the first time that we had ever used a credit card for credit, meaning not able to pay off the balance in full. It’s ironic that, when we probably needed a vacation the most, or a reward in the form of a fancy dinner, we didn’t indulge in order to stay within a reasonable budget. It wasn’t really until after the posters were being sold online, a month after the show opening, that we splurged.

It was the strangest fiscal year we’ve ever experienced. From a yearly stand point, anyone could say we did great. But if you looked at the year in detail, our company made nearly no income for four to five months. The work we created was some of the most fulfilling work we’ve ever done, but it came with the price of delayed gratification and uncertainty. Long story short, the solo show was a huge success and truly paid off. Our ICON work has landed us jobs from several large clients, including Nickelodeon, USA Today, Lowes, and Marvel.

Some of our biggest successes still come from our biggest project to date. In order to make big changes in our career, it took an even bigger leap of faith. For anyone facing a similar challenge, create a schedule, and hold yourself accountable to it!

Win office politics by walking away.
Mona Chalabi, Data Editor, the Guardian US

For over a year, I worked in an office with people who didn’t take me seriously. My colleagues weren’t all prejudiced, nepotistic, or dumb. They simply weren’t into what I had to offer.
“There are plenty of areas of my life where I doubt my abilities. But work was always different. Whether I was working in a clothing store or in a newsroom, I’d always felt like I could see what I needed to do to be ‘good’ and then could work fast to get there.

All of a sudden though, the rules for success seemed foreign. We’d all file into a meeting room and the boss would say ‘Hey man,’ ‘Hey man,’ ‘Hey man,’ then ‘Hello Mona.’ I’d never understand their sports analogies. I’ve always found it easy to talk to new people (I think that’s why I went into journalism). But now, my self-confidence was decimated.

What made it worse is that I couldn’t leave the job. There was a clause in my contract saying that if I left before 18 months I would have to pay the company a sum that I couldn’t afford. Plus, for an immigrant on a visa, switching jobs is always difficult.

My internal thought process went something like: I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid, I am stupid, I am stupid, maybe I’m not stupid.

I realized that I was fighting a battle that couldn’t be won (or, where winning meant sacrificing my sanity). The time to stop fighting was when I didn’t feel like myself anymore. So, I channeled my energy elsewhere.

I started to draw.

The illustrations looked like sh*t but they forced me to suspend my judgement of myself, to create and create until I had the strength to be critical in a way that wasn’t destructive. I finally got to a place where I could look at something and think, ‘Wow, that’s bad’, shrug and try again.

You can fight and fight and fight to be seen. Or you can walk away and try something else. I could never be one of that team. The thing that took the most time? Realizing that I didn’t want to be. Jobs are like relationships, the hard part is working out how long to fight for them.

How to get the job done when the client wants everything redone at the last moment.
Jon Burgerman, Artist

My publishers had signed off on the final version of my book, How to Eat Pizza, and my brain was sipping a beer, lying on the sofa, and cooling down with a self-congratulatory glow. That little switch in my head that said ‘picture book for April’ had turned off. Then, I received news that one of publishers wasn’t happy. The book needed to be completely revised in time for an important book fair in two weeks.

Wait, hadn’t they read any of the previous drafts? It’s not my fault! It was a real shock. But it would be awful to turn up at the book fair with a story with no ending. I had to rewrite half a picture book in two weeks.

There was no time to be annoyed. Normally, everything is slow and delayed in publishing; no one expects you to deliver the pages when you say you will. But here was a solid, no excuses, if-you-miss-it-you-might-as-well-not-go-to-the-book-fair deadline.

I was of two minds as I tackled the challenge. One was: This is stupid. I should just put my foot down. Everyone had access to the drafts, they should have voiced their concerns earlier. But then, I thought: What the hell do I actually know? I should listen to people who actually work in publishing. I’m lucky they’re even allowing me to make a book.

Rather than fight the issue—which would have been futile—I tried to understand where the publishers were coming from. They wanted the book to be more ‘Burgerman-y.’ I didn’t really know what that meant, but I was probably the best person to resolve it. There’s no magic spell. I just worked really hard. I swallowed my pride, opened up my sketchbook, my computer, and my brain and went about it.

I learned that even when a book is ‘finished’ that doesn’t mean it’s finished. Always keep good documentation of your drafts. Organize everything clearly, so if you need to look up old notes or artwork you can find them quickly.

Trying to understand the root of the problem is key to tackling it. Often, we only acknowledge the changes themselves and not the thoughts that prompted them. Once you can frame the issue for yourself, it’s much easier to solve it. And lastly, keep an open mind. In the end, everyone wants to make the best thing possible. Sure, publishers want that ‘thing’ to sell—and you know what— so do I.

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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