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Career

Firing Your Most Lucrative Client, and Eight Other Crazy Career Changes That Were Ultimately Great Moves

We asked some of our favorite designers and illustrators to walk us through a time when they drastically altered their course—from launching an agency to quitting a dream job without a plan.


When you launched your creative career, you may have pictured a series of razor-sharp lines leading from one position to the next—a sequence of steps moving irreversibly onward and upward. For most of us, that career path is less like a staircase and more like a hiking trail, twisting and turning organically, and even branching out unexpectedly.

No doubt, change can be terrifying, but sometimes it’s a little less terrifying than the prospect of staying on the same path you’ve been on for years. The next time you’re considering a new direction, keep stories from these nine creative leaders in mind.

Carve out time for yourself.
Kim Knoll and Kyle Eertmoed, partners, Knoed, Chicago, IL

Last year was Knoed’s fifth year in business and one of our most humbling. As a husband-and-wife agency of two, we’ve always prided ourselves on our ability to juggle a lot. And we appeared to have it all—a steady stream of work, good clients, prestigious awards, and active involvement in the creative community.

But behind the scenes, we were slowly suffocating ourselves, working weekends, eating dinners at 10 p.m., and waking up in the middle of the night worried about deadlines. We didn’t realize how much it was affecting us until Kyle (a fit 36-year-old) returned from the doctor with a prescription for blood-pressure medication and a stern warning to make some lifestyle changes.

Leading into 2017, we shifted our perspective away from what we thought we were supposed to do to what we needed to do. After four years of leading the Chicago chapter of CreativeMornings (a monthly lecture series), we handed the reins to a new organizer. We said goodbye to a lucrative catalog client and the thousands of dollars that came with it. We even suggested that one of our favorite clients hire another illustrator to take over our work.

Flash forward six months: Freeing up that space has allowed us to do more of what we love, with some downtime built in. We brought in two new clients with branding needs, and one of our favorite long-time clients agreed to a monthly retainer—a move that would have been impossible with our previous workload. And the new arrangement with the illustrator is working out great. For the first time in years, we were able to take a three-week vacation, renting a campervan from Denver to San Diego and hiking in national parks all along the way. It was heaven.

In the end, we’ve learned that adding “health” and “happiness” to our client roster is important, and sometimes making a big shift is worth it—even if it’s a little scary in the beginning.

Listen to your own voice.
Glen Hilzinger, SVP, integrated group creative director, Leo Burnett, Detroit

Four years of design school taught me one thing: I wasn’t a good designer. Or at least, not as good as I wanted to be. Though my design work was generally well received by others, I was never happy with it. I was my toughest critic.

After a few years at a small design shop, I found myself doing much of my own copywriting. And I found myself enjoying it more than design. Scraping together some writing samples, I landed a junior copywriter job at J. Walter Thompson. My first assignment? A radio spot. Yes, the quintessential copywriter’s assignment. Never mind that I’d never written one before. It was, I felt, the perfect opportunity to prove to myself why I gave up my life as a designer.

Sooner than I would have liked, it was time to present to the executive creative director, a middle-aged man whose three-piece suits underscored his austere, prickly manner. As I stepped into his stark corner office with several other writers, he gestured to a small table that sat beneath a signed portrait of Pat Buchanan hanging on otherwise blank walls. When my turn came, I gave it everything I had, character voices and all. I finished presenting my script, anxious for a reaction. Quietly, the ECD reached across the table, grabbed the script from my hands and slowly wiped his butt with it. Without so much as a smirk, he handed it back to me saying to the group, “Next.”

Surprisingly, even though my first radio script had just been summarily reduced to toilet paper, I wasn’t crushed. Instead, I was eager to get started on a new one.

And that’s when I knew I was meant to be a copywriter. I enjoyed the craft of writing enough that it didn’t matter how tough the critic was.

Honor the work—even if it means butting heads with the client.
Jonden Jackson, co-owner, senior designer, Forefathers Group, Tulsa

For nearly two years, our small agency had tried every method possible when handling clients’ requests for design revisions. From an open-door policy that allowed any revision they wanted (worst idea ever) to additional hourly billing (never fun), all the way down to a limited number of revisions allowed for the project. And guess what? It rarely, if ever, improved project results.

Finally, in the Summer of 2016, we wrote The Declaration—an eBook that we share with all of our clients before we begin working together, which explains our design process and our decision to refuse any revisions that don’t serve the greater good of the project.

It was a risky move, to be certain, but it was one we fully believed in. Forefathers was built on the idea of taking big risks to get to where we want to be, and it was important for us to keep taking big risks to continue growing and learning. And that means pushing our own boundaries to get the best results for our clients.

The Declaration has completely transformed how we work, and has helped bring order to the results-driven design that we pride ourselves on.

We firmly believe that guiding clients to think in terms of results and urging them to ask themselves, “Will this revision improve a user’s experience with my business?” gets them more deeply involved in the design process and helps them start thinking more like their customers.

Be willing to walk away from something good, for the chance to launch something even better.
Claudia de Almeida, principal and creative director, o Banquinho (The Tiny Bank) San Francisco

In 2013, I finally landed my dream job: WIRED Magazine. I honestly thought I would be there for 10 years; after all, the content was amazing, and the opportunity to do great design felt limitless. It was immensely gratifying to bring stories to life with the help of editors, writers, photographers, illustrators, type designers, and letterers—being an art director felt like coaching an all-star team.

But things don’t always goes as you plan. I stayed at WIRED for close to two years and made wonderful friends and work that I am proud of. But when you work for a company, there are things that you cannot control. Change is often good, but sometimes it can be disruptive; ultimately you need to decide if you’re still having fun and doing your best work. I decided to move on.

The demanding deadlines at WIRED made it nearly impossible to plan my next step, so I just left, and figured I would find my way. My good friend Carl de Torres told me to establish myself as a brain + hands: “Let people know you’re a contractor, consultant and a maker.” When you work for yourself, people often assume that you’re just a pair of hands. So I teamed up with my WIRED colleague and pal, Margaret Swart, and we launched a studio as a way to protect ourselves.

I now do all kinds of projects. From consulting to magazine redesigns, logos, type audits, teaching, and sometimes in house work with agencies and companies. I definitely have a long-term plan for my career, but I’ve learned to be flexible.

You don’t need to rush to get to your ultimate goal (and truth is, that goal might change, because life is unpredictable).

For now, I’m most interested in making great stuff. Using the skills I learned from all the amazing people I had the opportunity to work with; eventually, I’ll get where I am going. I think of my career very much like a design project: It’s a process, and you need to learn to love the process.

Pour your passion into self-initiated projects.
Claire Dawson, co-founder, creative director, Underline Studio, Toronto

Back in 2014, our studio was doing well—we had great clients, challenging projects, and a solid team—but we felt a lack of energy and enthusiasm. Creatively, we needed more experimentation and more collaboration.

We realized the solution wasn’t about changing anything, but simply adding to our work through more self-initiated projects.

For our first project, we designed team posters for the 2014 FIFA World Cup, debuting one as each country played its first game. Everyone in the studio participated, designing 16 different posters that were sold online and at an event in a Toronto bar where we celebrated the end of the campaign. Sales of the posters covered some of our costs, but, more importantly, the project energized the studio in a big way. We had no intention of influencing future work or connecting with new clients, but somehow we did.

Months after the campaign launched, Google’s head of marketing in Canada reached out to us, told us he loved the posters, and asked us to design a lookbook celebrating the creators of Youtube—the first of several projects we’ve completed for the brand.

We continued the initiative with two more poster series, and then we decided to make an impact in a more meaningful way: We designed a newspaper series to commemorate the victims of massacres that took place during the civil war in El Salvador, the original home of my co-founder. A corresponding Kickstarter campaign successfully raised $16,000 for Pro-Búsqueda, a Salvadoran human rights group that searches for children who disappeared during the conflicts, from 1979 to 1992. It’s been a wonderful way to collaborate with poets, writers, artists and photographers to support a cause we believe in—and we’re just getting started.

Showcase the type of work that you really want to do—and get rid of everything else.
Justin Mezzell, UI/UX designer, Pluralsight, Salt Lake City

A few years out of school at the University of Central Florida, and fresh off a failed startup in New York, I returned to Orlando and found myself feeling directionless. Although I’d dabbled in illustration while putting myself through college—doing work for friends, family and the occasional church or nonprofit—I had no real experience within the larger design community. I was fortunate enough to land a gig at a small agency focused on branding and more traditional marketing initiatives, but the job wasn’t terribly inspiring. I found myself returning to the blank Illustrator canvas in the crevices between work and the demands of daily life, but I wasn’t sure how to pivot to another career path.

Things started to fall into place when I realized that being unknown meant I could become whoever I wanted to be. If no one was going to ask me to produce the work I wanted to do, I’d do it myself and hope the clients followed.

I created a new portfolio with a focus on illustration, and removed the work that I didn’t want to do anymore (mostly print, branding, and marketing collateral). Every morning, I woke up and produced new work before heading to my day job; that pattern helped me establish a new rhythm.

Over time, the requests began rolling in. A trickle of inquiries eventually became a steady flow, allowing me to leave my day job and dive into the world of freelance illustration with both feet. As time went on, I had the opportunity to apply my illustration skills to UI design, and I fell in love with the interdisciplinary approach that combines illustration, layout, brand, and traditional design principles. That eventually led to a full-time gig at Code School (now Pluralsight) and a healthy dose of freelance illustration on the side.

If the people around you aren’t on the same page, turn the page.
Matt Wegerer, owner, creative director, Whiskey Design, Kansas City, MO

I love the creative industry. We get to cook with art, commerce, data, bravery, and showmanship, and watch it congeal into a crazy pile of weirdness and (hopefully) success.

But after a few years as a senior art director at a small agency, my excitement was waning. The reason? I’d been busting my ass to produce work that was unique, attention-getting and smart, but too often I would hear, “What if this scares the client?” or, “How could we ever pull this off?” or the dreaded, “I don’t feel that this represents our agency’s core values.”

I saw dozens of great ideas smothered by a mound of fear, laziness, and a peculiar need to worship a list of words on a wall—none of which said, “Do great work.”

Moments like this made me go on my own in 2009. Yes, that 2009—the one with the Great Recession making everything shitty. I knew I had enough freelance work to keep me busy for a year—a year where I could work on exciting projects with smart and ballsy clients. Don’t get me wrong; it was scary. I was giving up a solid paycheck in the middle of the worst financial crises in 50 years. But at the end of the day, I was more sickened by the idea of another year of unsatisfying work than the possibility of failure.

That one year has now stretched into eight. Whiskey Design’s roster of clients is diverse, and every day our clients challenge us to make amazing stuff. And, maybe most important, we’ve become a shop where other crazy-ass designers want to be. Now I work side by side with a small collection of creatives whom I would take into battle against anyone. And at the end of the day, I hope they all know that mediocre excuses for mediocre work will never have a home at Whiskey, as long as blood and bourbon are pumping through my veins.

Team up with a partner who complements your strengths.
Eli Horn, partner, Fivethousand Fingers, Montreal

I’d always wanted to work for myself. I started freelancing in school and tried to keep it up following graduation. My design studies included a business class, but for a young designer more inclined towards painting than entrepreneurship, I had no clear path to starting out on my own.

It took me a year to realize how arduous and lonely freelancing can be; while I managed to get gigs, learning how to maintain client relationships and ensuring that I got paid was a full-time job, in addition to doing design work I was proud of.

Lexane Rousseau, a friend I’d met while studying at Vancouver’s Capilano University, had similar sentiments as she went in and out of agency positions and pursued her own freelance work. Eventually, we started bringing one another into our projects, and learned how to collaborate; when there is no hierarchy or defined positions, it’s up to each person to check their ego, discover how to give and take criticism, and make sure the work is fun and inspiring.

After a few false starts, quickly abandoned names (and business cards), and misguided positioning (limiting ourselves to progressive clients didn’t quite pay the bills), we picked a direction, stuck with it, and began to work together in earnest. The benefits were immediate: Representing ourselves as a larger entity instilled more trust in potential clients, and our individual strengths and weaknesses were balanced—Lexane now focuses on strategy, communications and client relationships while I excel in web development and more technical work. Most significantly, stresses and successes were shared, and we gained a moral support not possible when working alone.

We’re constantly adjusting our direction to pursue new goals, but that evolution from two freelancers to one design studio is well behind us. It was a gradual change, but the most consequential of my career.

Recognize when it’s time to move on to the next big thing.
Emily Sander, advertising department chair, SCAD, Savannah, GA

After more than a decade of hustling through the halls of advertising agencies, working my way up from a junior copywriter to a creative director, there was one question I couldn’t shake: Now what? Armed with a desire to do something more meaningful with my life, I left the world of Brooklyn brownstones for the world of academia in Savannah, Georgia. My new clients were college students, and my new challenge was to help them realize their future.

My focus shifted from creating brand stories to instructing others on how to do the same—a task that proved to be surprisingly difficult.

For so many years, I was caught up in the sheer act of doing, and I never stopped to consider how one actually does.

When I recognized that my ability (or inability) to break through to my young audience could reverberate through our industry for years, I gained a deeper appreciation for every teacher I’d ever had. So I started with the 30,000-foot perspective of a creative director, and tried to see the work from 30,000 feet higher. I spent hours reading materials about the processes I had unwittingly employed for years. I formulated my own charts and graphs and templates to breakdown the lessons I’d learned while sweating every detail of million-dollar ad campaigns. But compared to the seasoned professors who had crafted lectures and moved about the world of academia with precise choreography, I was deeply behind in a new role that left little room for failure.

I scrambled to keep up. I lectured, graded, learned, advised, wrote, and analyzed. On the last day of class, a student approached me, and, reaffirmed my decision, with the smallest gesture: He simply thanked me for leaving NYC to become a teacher. Looking at him, I saw what I had been missing from the most successful campaigns and client meetings. I experienced my direct impact on one person’s life—not his buying habits, hashtag sharing, or general viewing pleasure, but something much more meaningful.

Scott Kirkwood

Scott Kirkwood is a freelance copywriter and creative director in Denver, with a focus on nonprofits and “do gooder” brands. His editorial work has appeared in Communication Arts, Eye on Design, HOW, and Modern in Denver.


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