Imagine stumbling upon a skill in your teenage years—only to realize, years later, that it could shape your entire career. That’s exactly how Matt Armstrong found his way into design: making websites, playing with pirated Photoshop, and experimenting with Flash animations to help friends and teachers. Back then, he never dreamed that these playful projects would pave the way to roles at Dropbox, Zendesk, and Eventbrite. However, as Matt’s story proves, sometimes the seeds of a lifelong passion are planted in the most unexpected places.
If you’ve ever questioned whether you “belong” in design or felt unsure about how to build a lasting career, Matt’s journey will inspire you to look beyond formal paths. From his self-taught beginnings to navigating high-pressure rebrands, Matt shows that a blend of humility, curiosity, and personal authenticity can bring success—even in the face of imposter syndrome and industry upheavals.
An Unlikely Start: Computers, Forums, and a Flash of Inspiration
A Taste of Tech
Matt was just four years old when his family got their first computer—an ancient DOS machine that sparked a fascination with technology. By high school, he was lugging bulky gaming PCs into school to play Unreal Tournament with friends and tinkering with web design for small local projects.
Yet Matt didn’t see design as a legitimate career path. Instead, he viewed it as a handy hobby—a way to help his school community or create fun online graphics. “I had no idea I could do this for a living,” he recalls. That all changed when he and a friend started a small web design business, tackling everything from a teacher’s local shop website to the high school’s homepage.
Actionable Insight #1: Recognize Hobbies as Hidden Clues
If you find yourself spending hours perfecting layouts or color palettes “just for fun,” you might be onto a bigger opportunity. Ask yourself: Could this be more than a hobby?
From Support Tickets to Surprising Design Gigs
The Dropbox Detour
Not long after college, Matt landed at Dropbox—which, at the time, was still considered a “scrappy” startup with around 90 employees. He wore multiple hats, dabbling in everything from customer support to data science. “I didn’t realize design was even an option,” he admits, explaining that he initially saw himself as a project manager or operations specialist.
As Dropbox ballooned into a company of over 2,000 employees, Matt faced the chaos of hyper-growth: late nights, tight deadlines, and a fast-paced environment in which job titles often felt irrelevant. Though intense, Matt credits that period for teaching him to be flexible and adapt—skills that would soon become crucial.
Finding a Design Role at Zendesk
It wasn’t until he moved to Zendesk that Matt’s creative streak took center stage. Tasked with marketing responsibilities for gaming clients, he designed and coded the company’s booth, posters, and website for the Game Developers Conference (GDC)—simply because no one else was available. His work turned heads. “The design you did for GDC was pretty good,” a program manager told him. “Do you want to do this full-time?”
That seemingly casual offer transformed Matt’s career overnight. He joined the Zendesk design team, eventually working on the company’s broader rebrand and developing its design system, Garden. Looking back, he jokes, “I just got bored over Christmas one year and ended up redesigning all of Zendesk.” Still, there’s no doubt the experience cemented his confidence as a professional designer.
Actionable Insight: Step Up When No One Else Will
If your organization lacks a design resource, volunteer your skills. Even if it’s outside your formal role, you’ll sharpen your abilities and prove your readiness to grow.
Scaling New Heights and Grappling with Self-Doubt
The Call of the Big Leagues
With brand-building accolades under his belt at Zendesk, Matt eventually found his way back to Dropbox and later jumped to Eventbrite, Square, and Meta in varied design capacities. He often focused on design systems, rebrands, and bridging product and marketing teams.
To outside observers, it seemed like a meteoric rise. But behind the scenes, imposter syndrome loomed large. Despite his achievements, Matt questioned whether he truly “belonged” in design. “It’s ironic,” he notes. “I’ve worked on big projects and managed teams, yet I still wonder if I’m good enough.”
Therapy and Genuine Conversations
Eventually, the stress of hyper-growth and constant pivots took a toll. Matt realized that simply powering through wasn’t sustainable. He sought therapy—a move he encourages for anyone in high-stakes fields. “You shouldn’t have to wait until you’re near a breaking point to talk to someone,” he emphasizes.
Through professional help and candid conversations with peers, he learned to compartmentalize his emotions, set boundaries, and stand firm despite shifting priorities. According to Matt, “Vulnerability isn’t a weakness. It’s a tool for authentic leadership that helps you and your team navigate change without resorting to sugarcoating or panic.”
Actionable Insight: Normalize Mental Health Check-Ins
Whether it’s therapy, peer-to-peer chats, or mentorship, find outlets for stress before burnout strikes. Regularly reflect on your feelings about work and ask yourself if you’re still enjoying the journey.
Embracing Collaboration: The Power of “Jam Sessions”
Why Jam Sessions Matter
As Matt’s responsibilities shifted from individual contributor to leading design teams, he discovered the magic of “jam sessions”—casual, co-working times dedicated to tackling a single design problem. By pairing up with team members in Figma, they could brainstorm off-the-wall ideas and question whether the tried-and-true approach was always best.
This environment sparked more innovative solutions and made it easier for newer designers to voice their ideas without fear. “When you’re free to prototype wild concepts, you realize there’s more than one ‘right way’ to do something,” Matt explains.
Creating a Culture of Exploration
While rebrands and product overhauls often come with tight timelines, Matt urges leaders to reserve some buffer room for experimentation. “Otherwise, you end up just repeating the same patterns everyone else has already done,” he warns. For a designer who once taught himself by building forum graphics, exploration remains the heart of creativity.
Actionable Insight: Encourage Low-Stakes Brainstorming
Set aside an hour weekly for your team to co-create solutions—even if they’re initially far-fetched. Breaking out of routine patterns leads to fresh perspectives that can elevate the final product.
Navigating an Uncertain Industry: Advice for Aspiring Designers
The Tough Reality of “Junior” Roles
Matt doesn’t sugarcoat the difficulty of entering design right now. “Companies hire fewer entry-level designers,” he says, pointing out that internships or long chains of contract gigs are increasingly the norm. Yet he believes the industry should champion up-and-coming talent. “It’s on us as senior folks to push for these junior roles—everyone wins when you have fresh perspectives on your team.”
Building Skill and Visibility
Still, self-driven practice can set you apart. Whether posting concept work on Behance or Dribbble, contributing to an open-source project, or seeking design meetups, Matt encourages aspiring designers to show up and share. “Your next opportunity might start with a direct message or casual introduction,” he notes. After all, a spontaneous conversation with Zendesk coworkers catapulted him into design full-time.
Actionable Insight: Create and Connect Consistently
Even if you lack “official” design tasks, build mock-ups, redesigns, or passion projects. Then, share them publicly. Real-world feedback is the fastest way to refine your craft and attract potential employers.
Conclusion: Your Next Step on the Path
Matt Armstrong’s journey—from high school web gigs and gaming forums to designing for some of tech’s biggest names—offers a refreshing blueprint for forging a career in unexpected ways. You don’t have to start sure of your path or hold a fancy design degree. Authenticity, a hunger for exploration, and a willingness to jump into the unknown can carry you far.
If you found Matt’s story insightful, I invite you to dive deeper into our full podcast conversation. He shares more about juggling brand and product constraints, learning to say “I don’t know” when stakes are high, and leaning on therapy to stay grounded in an ever-shifting industry.
Which piece of Matt’s journey resonates with you the most? I’d love to hear your thoughts. Reach out and let me know. Until next time, keep experimenting, keep learning, and remember that the spark you accidentally discover might be your greatest asset.
Ready for more real-world design lessons and candid career advice? Listen to the full interview with Matt Armstrong here.
Feel free to share your thoughts or tag us on social media with your takeaways.
Share this post