The Long Game: How 20 Years in Design Taught Me What Really Matters
For over two decades, I've navigated the ever-evolving landscape of design, from creating precise technical drawings for financial signage to developing graphics for video games, from designing web interfaces to managing design teams. This journey has taken me through multiple industries, teaching me invaluable lessons and shaping both my professional approach and personal philosophy.
The Foundation: Precision and Craftsmanship
My career began in 2002 in New York, where I designed signage for major financial firms, including Chase and Merrill Lynch. This wasn’t just any design work—every measurement had to be precise to within 1/16th of an inch. These technical drawings were fed directly into machines that would create the actual signs, leaving no room for error.
This experience instilled in me a meticulous approach that remains with me to this day. Every design I create, every pixel I place, is measured and perfected. It’s a standard of craftsmanship that has served me well throughout my career. During this time, I even had the opportunity to design a proposal for the 9/11 memorial—though our proposal wasn’t selected, being part of that process was deeply meaningful.
It was also during these early years that I taught myself web development and design. The web was emerging, Flash was king, and there were no formal prerequisites for this type of work. I learned through trial and error, developing skills that would prove invaluable as the digital landscape evolved.
The Dream Job and the Reality of Corporate Life
In 2006, I moved to Florida and eventually landed what felt like a dream job at EA Sports. As a lifelong gaming enthusiast, the opportunity to work in the video game industry was irresistible. What started as a three-week contract turned into five years, thanks to what my managers called my "can-do attitude."
The work was grueling—we'd spend months working 65+ hour weeks during crunch periods. This was simply part of the culture in the gaming industry at the time. Despite the exhaustion, I loved it. We worked hard and played hard, and I was part of an exceptional team that supported each other through the demanding periods.
However, like many good things, this came to an end when I was laid off. This experience was a turning point in my career and mindset. I had been devoted and loyal to the company, but the layoff taught me a harsh lesson about corporate loyalty—it doesn’t always flow both ways. From that point forward, I stopped investing so much emotionally in companies and began viewing employment more pragmatically.
Rapid Transitions and New Challenges
The job market was different then—I was able to bounce back within a month, landing a contract role for a morning news show. This meant 4 AM wake-up calls and creating graphics under intense deadline pressure. I worked during major news events like the Boston Marathon bombing and the Aurora movie theater shooting, which added another layer of stress to an already demanding schedule.
The silver lining was that this high-pressure environment made me incredibly efficient with Photoshop. I developed numerous shortcuts and customizations that allowed me to create complex graphics in under 30 minutes—a skill that has served me well throughout my career.
From there, I moved through various roles: a small gaming studio called Nspace (which unfortunately went under), an AAA studio (where I learned about responsive design during its early days), and Novatus, a contract management software company, where I gained my first experience with B2B design.
Leadership and Mentorship
At Novatus, I had the opportunity to direct company conferences for two consecutive years, creating intro videos and collaborating with lighting teams to set the mood for events. This was my first foray into broader creative direction, and I discovered a passion for color theory and visual storytelling. This also helped me gain my initial experience in the UX field as I interviewed and researched users for the application.
Later, while working on golf course management software at NBC Sports, I encountered a situation that would define my approach to problem-solving. A major client was dissatisfied with an iPad application I was involved with and was considering switching providers. Instead of panicking, I conducted extensive user research and applied UX principles, ultimately redesigning the application to meet the client's needs.
This role taught me the importance of good management. While my direct manager wasn’t always supportive, other leaders in the company showed me what great leadership looked like—they cared about their teams, helped people through difficult times, and understood the importance of the work we were doing.
The Leap into Management
My last corporate role took me into an entirely new industry: government contracting. More significantly, it marked my transition from individual contributor to manager, overseeing a team of six designers across graphic design, UX, and UI disciplines.
Managing this team while overseeing 20 different applications was one of the most challenging yet rewarding experiences of my career. I learned that great teams aren’t built on technical skills alone—they’re built on personality, collaboration, and mutual support.
When hiring for our internship program, I focused less on portfolio perfection and more on personality. Anyone can be taught technical skills, but you cannot teach someone to be a good person or a good team player. This philosophy paid off when I hired an intern who went on to become an exceptional full-time designer.
The team I built came together from different backgrounds—most didn't know each other initially—but they formed an incredible bond. They supported one another, never said "that’s not my job,” and approached challenges collaboratively. We made decisions as a team, and they taught me as much about leadership as I taught them about design.
Current Reflections and Future Focus
Today, I find myself among the many talented professionals currently seeking new opportunities. While unemployment brings stress and uncertainty, I choose to view this period as an opportunity for growth and learning.
Rather than spending energy worrying about job applications and rejections, I’m focusing on health, education, and building new skills. The rapid advancement of AI in our industry means continuous learning is essential, so I’m dedicating time to understanding how to work effectively with these new tools.
Lessons Learned
Looking back on this 20-year journey, several key lessons emerge:
Craftsmanship Matters: The precision and attention to detail I learned in my first job continue to distinguish my work. Excellence in fundamentals never goes out of style.
Adaptability is Essential: From signage to web design to video games to government applications, the ability to learn new industries and adapt to different challenges has been crucial to my career longevity.
Corporate Loyalty Has Limits: While it’s essential to take pride in your work and do your best, remember that employment is ultimately a business relationship. Don’t sacrifice your well-being for companies that wouldn’t do the same for you.
Teams Beat Individuals: The best work I’ve ever been part of happened when teams supported each other and worked collaboratively toward common goals.
Personality Trumps Perfect Portfolios: When building a team, look for individuals with good attitudes, strong work ethics, and collaborative spirits. Technical skills can be taught; character cannot.
Good Leaders Make All the Difference: Whether you’re managing others or being managed, remember that leadership is about supporting your team, making collaborative decisions, and caring about people’s growth and well-being.
Moving Forward
Every negative experience in my career has ultimately been a learning opportunity. The layoffs, difficult managers, failed projects, and stressful deadlines have all contributed to making me a better designer, manager, and person.
Life isn’t always supposed to be easy or perfect, but it’s what we make of it. Each challenge we face shapes who we become and prepares us for what’s next.
As I look toward the future, I’m excited about the opportunities ahead and grateful for the journey that brought me here. The question I leave you with is this: What has your journey taught you, and how have you grown from the challenges you’ve faced?
