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Eli Woolery
This is an audio version of the Brief the Design Better newsletter that takes you deeper into the insights we've uncovered through hundreds of interviews with creative thinkers. I'm Eli Woolery. Stop specializing Live a multidisciplinary creative life if there's one thing we've learned from the multitude of people we've interviewed for Design Better, it's that the most innovative creators of our time share an unlikely trait. They refuse to stay in their lane. While conventional wisdom pushes specialization, these multidisciplinary minds build careers by following curiosity across fields from nuclear engineering to footwear design, from video games to graphic novels. In my own career, it took me many years to realize this, and in some ways, my journey began the day after my son was born. I remember that day as unseasonably hot, September 2015 on the Monterey Peninsula, the kind of clear, warm day that follows long stretches of coastal fog. After leaving the hospital where my wife, Courtney, was recovering with our newborn, I grabbed a quick wife sanctioned surf. The clear horizon promised a month of record warmth ahead. At home, I checked email before setting up my autoresponder for two weeks of paternity leave. Near the top of my inbox, a message from our startup CEO. Not quite what I expected. The gist we're sorry, but our co founders had a fight, the company's splitting up and we have to lay you off. I panicked. Losing my job right after our second child wasn't the plan, especially since we'd just moved to the Monterey Peninsula in an era before remote work was widespread. I delivered the news to Courtney at the hospital, along with her Starbucks coffee, and I couldn't find anything comforting to say. She ended up reassuring me we were going to be okay. And we were. It became a rare chance for me to spend real time with our newborn son, young daughter, and Courtney. Time to reflect on what came next. And I had a secret weapon, something I hadn't always considered a strength. Design Better is brought to you by WIX Studio, the platform built for all web creators to design, develop, and manage exceptional web projects at scale. Learn more@wix.com studio living a multidisciplinary creative life before college, I loved drawing and thought I'd become an illustrator. My parents and I remember this slightly differently, but as I recall, they encouraged a broader education, and I'm grateful they did. I studied product design at Stanford, where I now teach, but in the late 90s that meant physical products, and with my love for the outdoors, I hope to design climbing or camping gear. But companies didn't know what to do with me? They wanted an industrial designer or a mechanical engineer. Product design, at least Stanton's version blended both, but emphasized human centered design as its foundation. Frustrated and unable to land a real product design job, I took an internship in Bermuda, running to scuba dive and helping researchers. This led me to Light in Motion, a manufacturer of underwater camera equipment and bike lights. As a design engineer, I learned the harsh realities of manufacturing products that protect electronics under high pressure and corrosive seawater. And I destroyed a lot of expensive camera equipment in the process. Photography also grabbed me during my time here, along with marine biology. I went back for a master's degree in marine science, discovered I was a terrible scientist, although I love the field work, and decided to start an underwater photography magazine with a Stanford friend. Three years of producing a beautiful magazine, world travel, and basically no money. Around the time my daughter was born, I was a freelancer creating websites and apps for clients, but wanted to try entrepreneurship again. I got into a startup accelerator at Eric Schmidt's venture firm, Innovation Endeavors. Our team received funding to try different venture ideas. All of them crashed and burned. As Courtney and I discussed having a second child, the pressure for another real job became, well, very real. Trying to make sense of my winding career path in a way that I hoped would appeal to potential employers, I created a timeline of my work since graduation in the 90s up to 2015. But what it demonstrated most convincingly was my short attention span, who moves from physical product design to marine biology to magazine design to photography to apps to teaching in just over a decade. Companies wanted specialists in tidy boxes, not jacks of all trades. After months of contracting and proving that I could be a productive employee, I eventually landed the startup job that imploded right after my son was born. Then I went to Envision, where Aaron Walters saw promise in my scattered career path. We both shared an interest in people living multidisciplinary creative lives, and Design Better became our place to explore those stories. Most of our guests who have lived multiple creative careers didn't plan it out that way. Rather, they let curiosity lead them. Jordan Mechner, creator of games that many of us who grew up in the 80s and 90s loved, like karateka and Prince of Persia, reflected on how lucky he was to have this chance.
Jordan Mechner
I've been lucky to have the chance to do things on my own terms. Going back to Karateka, you know, when I was 20 years old, you know, the year that I finished college and graduated. That's the time in life when usually you're like, okay, how Am I going to live? I'm going to get a job. What kind of a job can I get? And because I had just published this game that was a bestseller and was bringing in royalties, I was 20 years old and I didn't have to get a job. I had the luxury of thinking, okay, well what do I want to do? Because the royalties are gonna fund me for the next few years. I could get a job if I wanted to go to film school. I was also dreaming of becoming a filmmaker. That was one possible path. But making another game was appealing too, because after making Karatek, I had all these ideas and, you know, I had met all the people at Burterbuns and other people in the game development industry, and I kind of wanted so having the luxury to choose for the right reasons and not just because this is the best among so. So options that I have at the moment. That's a chance that so few people get in life. So I think I was really lucky to be the age that I was to have that first success with Karateko, which then gave me the freedom to do, you know, what ended up being Prince of Persia, which basically. Since then, one opportunity has led to another and I've never had to say, okay, I hate this project or I hate this job, but I have to take it. And I know how rare that is.
Eli Woolery
Natalia Shelburne, who worked at the New York Times when we interviewed her, has led several different creative lives, including as an art director, an instructor, and a front end developer. Here she describes how her curiosity led her to learn to code and how she views the skills she has gained as an accretive process.
Natalia Shelburne
In college, I majored in fine art and psychology. And right after I started teaching design and eventually became an art director at a nonprofit. It was a school basically started by teachers who said, we can do better. And by the end, we were running four summer camps. I did basically everything you could possibly do, from sitting on the board to teaching macrame one semester digital illustration. Just anything that would grow the creativity of both the students we had as well as the community around. The idea here was I wore so many hats trying to make up a program and make up this organization. So I had to build things, figure things out. So it wasn't a really big transition to doing that with code. I had to solve the problem of how do I enroll people in the summer camps I started and my budget was zero. So I basically looked online, like, how hard could this be? I built some geocities and dabbled around with front end stuff. When I was a teenager, a lot had changed, but I found that it really was an extension of everything I was doing, and so I started learning more and more about it. I got deeply curious about how things worked, and one year I just said, I'm going to go try a startup. I'm going to just see where this path leads. And I never lost or put down any of the things I was doing. It just felt like growing and adding to it.
Eli Woolery
Build your curiosity muscles. Here's a few things you can try Cross Pollination Fridays every Friday Consume content from a field unrelated to your work. A woodworking video. A finance podcast. A biology article. Notice what idea has Transfer the skills. Stack journal. Keep a running list of every skill you learn, no matter how small. Track how they connect and build on each other. Like Natalia's Accretive process. The Curiosity Calendar Block one hour monthly to dive deep into whatever random question has been nagging you. Give yourself permission to go down rabbit holes. Prototype before you pivot before making any major career move, find a small way to test it first. Volunteer. Freelance. Take a class. Shadow someone for a day. We'll get into this last idea more in the next section because in addition to letting their curiosity lead the way, many of our guests found ways to prototype a new career before investing in it. Fully prototype your way forward in my career, many of the transitions or side hustles I developed came through prototyping. For example, I thought I might want to teach later in my career, perhaps closer to retirement, but I didn't know if I'd like it or or if I'd be very capable. So I took on a coaching role at Stanford in the product design program where I'd done my undergraduate degree. The class was the capstone project for graduating seniors who come up with a product idea and make it real in the world. I did well enough as a coach that I was asked to become a lecturer the following year, and I've been helping teach the class since 2013. Many of our guests took a similar prototype first approach to their career. Jordan Mechner knew he wanted to develop a graphic novel at some point and began developing his sketching skills in his journal.
Jordan Mechner
I wanted to do some kind of story or memoir about my dad's childhood adventures, and his father. He grew up in what Stephan Zweig calls the world of yesterday. You know, that central Europe of the early 1900s, this sort of nostalgic golden era that was wiped away by the First World War in 1914-1918. That, of course, was also the setting for my 1990s adventure game the Last Expression, which is set aboard the Orient Express on the last journey across Europe right before World War I breaks out and destroys that world forever. So I wanted to do something along the lines of a memoir. And the idea of writing and drawing it as a graphic novel. I wouldn't have thought of doing that a few years earlier, but because I had been sketching from life in my sketch journal and sort of getting better at it over the years, by the time that I was really ready to do a replay. And as I tell in the book, it's a moment when I had moved to Europe. I had actually come here to do a new Prince of Persia video game project, which ended up getting canceled. But the cancellation of that project kind of gave me like an open space to decide what do I want to do next. I decided what I wanted to do next was to do this family story. And I knew it would take me a couple of years, but I thought that my drawing ability had gotten just to the point where I felt able to tackle it.
Eli Woolery
And Kevin Bethune, who transitioned from a career as a nuclear engineer to designer at Nike, prototyped his design career by dedicating early nights and evenings to developing his skills.
Kevin Bethune
There's something to this stretch assignment approach. And then fast forward. I happened to meet Duane Edwards, who was at the time the footwear design director of the Jordan brand. He's now the president of Penn Soul Lewis College, one of the world's only footwear design academies dedicated to the industry. But at the time, he met me over a coffee chat where he saw this very curious creative person that had a title that was very business oriented. He gave me a little bit more time to understand my backstory, to realize there was more to my story than just the title. I showed him my raw creative drawings for hobby, and he said, you know what? You have raw skill. I can work with it. I have too many briefs, not enough designers. If you come meet me in the mornings, like 6am he was one of the early risers at Nike, but we would meet at 6 in the morning. We would commiserate on the couple briefs that he had. We would then go do our day jobs, and then I would work on his stuff to the wee hours at night. And we worked that way for the better part of a year. We got two shoes with my design credits under his mentorship.
Eli Woolery
Try these prototyping experiments. Morning evening apprenticeships like Kevin Bethune's 6am meetings and late night work sessions. Find someone in your target field willing to mentor you outside regular hours. The Skills Journal Prototype Start doing the thing you want to get paid for, but in your personal life first. Want to teach? Start a blog? Want to consult? Help friends with their projects One small client experiment Take on a tiny freelance project in your area of interest. Low stakes Real experience. Actual feedback from a paying customer. Volunteer your way in. Find ways to volunteer that give you hands on experience in your target field. Coach. Organize events. Help nonprofits with projects. Test the daily reality. Shadow someone for a day or week in your target career. Experience the mundane parts, not just the highlight reel. In an era where the career landscape is like quicksand under our feet, the future belongs to those who could connect the dots across disciplines. Start small, follow your curiosity and prototype your way forward. To read and share this episode with friends and colleagues, visit designbetterpodcast.com and while you're there, you can become a premium subscriber, which will get you access to the brief newsletter in your inbox every month, plus ad free episodes, extra episodes every month, and so much more. Just visit designbetterpodcast.com.
Episode: The Brief: Stop Specializing—Live a Multidisciplinary Creative Life
Host: Eli Woolery and Aarron Walter
Release Date: June 11, 2025
Sponsored by: Wix Studio
In the episode titled "Stop Specializing—Live a Multidisciplinary Creative Life," co-host Eli Woolery delves into the advantages of embracing a multidisciplinary approach in creative careers. Drawing from his personal experiences and insights gathered from interviews with various creative thinkers, Eli emphasizes the importance of curiosity and versatility in fostering innovation.
Eli Woolery shares a pivotal moment in his life that steered him towards a multidisciplinary path. On September 2015, shortly after the birth of his second child, Eli was unexpectedly laid off from his startup. This event prompted him to reflect on his diverse career trajectory, which spanned product design, marine biology, underwater photography, and web development. He realized that his ability to adapt and explore different fields was a strength, not a liability.
"Companies wanted specialists in tidy boxes, not jacks of all trades."
— Eli Woolery [00:02]
This realization became the foundation for the Design Better podcast, where Eli and Aarron Walter explore stories of individuals who thrive by not confining themselves to a single specialization.
Jordan Mechner, renowned for creating classic games like Karateka and Prince of Persia, discusses how early success afforded him the freedom to pursue his passions on his own terms. He highlights the rarity of having multiple options and how each opportunity led to another, allowing him to explore various creative projects without feeling constrained to accept just any job.
"I have never had to say, 'Okay, I hate this project or I hate this job, but I have to take it.' And I know how rare that is."
— Jordan Mechner [04:41]
Jordan’s approach underscores the value of leveraging initial successes to explore diverse creative avenues, fostering a rich and fulfilling career.
Natalia Shelburne, former art director at The New York Times, recounts her transition from fine arts and psychology to front-end development. She explains how her role at a nonprofit required her to wear multiple hats, which seamlessly led her to learn coding as an extension of her creative endeavors. Natalia emphasizes that her diverse skill set is the result of an "accretive process," where each new skill builds upon the previous ones.
"It just felt like growing and adding to it."
— Natalia Shelburne [06:21]
Natalia’s story illustrates how curiosity-driven learning can organically expand one’s capabilities, enhancing both personal growth and professional versatility.
Kevin Bethune shares his journey from being a nuclear engineer to becoming a designer at Nike. He attributes his successful transition to consistent prototyping and mentorship. By dedicating nights and early mornings to developing his design skills, Kevin was able to demonstrate his potential to Duane Edwards, Nike's footwear design director.
"We got two shoes with my design credits under his mentorship."
— Kevin Bethune [10:43]
Kevin’s experience highlights the effectiveness of proactive learning and mentorship in navigating career shifts and achieving professional aspirations.
Eli Woolery provides actionable strategies for cultivating a multidisciplinary creative life:
Cross Pollination Fridays:
Allocate time each week to consume content from unrelated fields, such as woodworking videos, finance podcasts, or biology articles. This practice encourages the discovery of new ideas and perspectives.
Transfer the Skills - Stack Journal:
Maintain a journal to track every skill you learn, no matter how small. This helps in identifying how different skills interconnect and build upon each other, fostering a cohesive skill set.
The Curiosity Calendar:
Block an hour each month to explore a random question or interest. Allowing yourself to delve into diverse topics can lead to unexpected insights and innovations.
Prototype Before You Pivot:
Before making significant career changes, experiment on a small scale. This could involve volunteering, freelancing, taking a class, or shadowing someone in your field of interest. Prototyping provides real-world experience without the high stakes of a full commitment.
"In an era where the career landscape is like quicksand under our feet, the future belongs to those who could connect the dots across disciplines."
— Eli Woolery [11:46]
Eli further elaborates on methods to prototype career transitions:
Morning and Evening Apprenticeships:
Similar to Kevin Bethune’s routine, find a mentor willing to work outside regular hours. This dedicated time fosters skill development and professional relationships.
Skills Journal:
Engage in activities related to your desired career in your personal time. For example, start a blog if you want to teach or consult on friends' projects to gain experience.
One Small Client Experiment:
Take on a freelance project in your area of interest to obtain low-risk, real-world feedback from paying clients.
Volunteer Your Way In:
Offer your skills to nonprofits or community projects to gain hands-on experience and test the daily realities of your target field.
Shadowing:
Spend a day or a week shadowing someone in your desired career to understand the routine and challenges involved.
The episode underscores the significance of embracing a multidisciplinary approach to foster creativity and innovation. By following curiosity, experimenting through prototyping, and building a diverse skill set, individuals can navigate the evolving career landscape with resilience and adaptability. The stories of guests like Jordan Mechner, Natalia Shelburne, and Kevin Bethune serve as inspiring examples of how refusing to specialize can lead to a more fulfilling and dynamic professional life.
For more insights and to listen to this episode, visit designbetterpodcast.com.