Career odyssey
Issue 264: Lessons I shared with MFA Design students
An odyssey is a long and eventful journey. My own has taken me from fine art studios to startups, from mobile consulting in Seattle to design leadership in San Francisco, from making apps for others to building products and teams of my own. The thread that ties it together is curiosity about new materials — whether that meant paint on canvas, iOS as a new medium, or AI as the latest shift in how we work.
I recently had the pleasure of guest lecturing for the School of Visual Arts’ Design MFA program, where Randy Hunt is the chair. Hunt, who is Head of Design at Notion, is a friend, and I was honored to spend time with his class of bright students. I decided to share lessons from my career odyssey, a story of a very non-linear path of trials and tribulations before figuring out what I wanted to do, and who I wanted to be.
Though history doesn’t repeat itself, it certainly rhymes. There are many parallels that I experienced when entering the job market in the 2000s, which I hope will bring optimism to people navigating their early careers in an unstable time. I’ll share parts of my lecture with you on a bit of my story and the five lessons I learned along the way.
My career hasn’t followed a straight path. I co-founded a consultancy, pivoted into iOS engineering, joined healthcare and design tool startups, and moved from Seattle to New York to San Francisco. Each move looked like a detour at the time, but in retrospect, they form a coherent arc. That’s the essence of an odyssey: you don’t always see the map until you’ve walked the path.
Setting out
I studied Studio Art with an emphasis on Drawing and Painting. But I was restless with the boundaries of traditional media. I started taking computer science courses and experimenting with ActionScript, which at the time felt like digital alchemy.
Upon matriculation and entering the job market in 2006, it was during one of the worst times. The Great Recession (2007–2009) was the most severe global economic downturn since the Great Depression, triggered by the collapse of the U.S. housing bubble and the subprime mortgage crisis, which led to widespread bank failures and a credit crunch. Its ripple effects included massive job losses, plummeting consumer confidence, and government interventions like stimulus packages and bailouts to stabilize the financial system.
Our graduating class expected to change the world after earning our degrees. In reality, many moved back with their parents to figure out how to earn a living. It was an extremely volatile time. At the same time, in 2007 at MacWorld, Steve Jobs announced a new product Apple was working on. It was a Phone, an iPod, and an internet communicator.
iPhone.
Act I: Mobile
I often tell people the iPhone launched my career, and it was true. It’s not because of the device itself, but rather the moment it unlocked. The art department I studied encouraged multi-disciplinary courses. My core classes of painting, drawing, and sculpture were paired with electives in business, philosophy, humanities, and computer science—quite the mix!
Though mobile computing existed before the iPhone, this moment introduced a new surface: a 320x480 pixel-perfect screen with multi-touch gestures to design for. I didn’t have professional experience as a designer, but I did have thousands of hours learning software such as Adobe Photoshop and Flash. I also learned to use the materials of code to build websites with CSS (including the z-index trick to style my MySpace page) and make things move with ActionScript.
These skills applied allowed me to get my first tech role, start my own product design consultancy, and work at Black Pixel—a mobile agency I really looked up to in my early career.
Mobile design in that era required new approaches — node-based prototyping tools like Quartz Composer and Origami, as well as writing code directly in Objective-C and Swift. I wasn’t just designing; I was learning how to think with a new material in my hands.
Lesson 1: Emerging technologies during economic downturns can be equalizing moments.
Act II: Startup hyper-growth
If Act I was about learning new material, then Act II was about scaling companies. After living in Seattle, Barcelona, Paris, and New York in Act I, the next phase brought me to San Francisco, California. In this phase, I spent eight years working at two companies. I went from an individual contributor to being the Head of Design, a much different lifecycle than my previous roles.
At One Medical, I experienced what it meant to design for behavior change in healthcare. It was here that I went from a user of tools to a maker of ones for people to use. I discovered my passion for tooling and workflows to help people get their work done. At One Medical, it was for clinicians, admins, and patients. At Webflow, it was for helping people create on the web without the need to learn code, but still respecting the needs of developers.
These roles demanded design craft but also required team-building, systems thinking, and navigating the turbulence of fast-growing startups. I realized that optimizing your role isn’t about climbing titles, but about aligning your work with the purpose you care about.
Lesson 2: Optimize roles for the impact and purpose you care about.
Act III: AI
The pandemic years marked a turning point. On November 30, 2022, OpenAI released an early demo of ChatGPT, the AI chatbot that quickly went viral and went on to be the fastest-growing product ever. Suddenly, people went from talking about baking sourdough bread, Tiger King, and trying to buy the US Constitution to looking at AI as a big shift moment.
At Replit, I saw firsthand how the loop from idea to application was compressing. “Vibe coding” wasn’t just a meme but a signal that software creation was becoming more accessible, playful, and social. At Atlassian, the focus shifted to scale again, but in a new way: how AI can help teams make sense of fragmented knowledge across their organizations. Rovo, our AI-powered knowledge platform, is one example of this shift.
Time will tell how AI will affect things, but there is a high possibility that it’ll change how things work. AI made me hit the career reboot button; however, with a lot of familiarity. The materials keep changing — from paint to code to AI. But the intangible skills of a designer remain constant: imagination, empathy, and the ability to navigate ambiguity.
Lesson 3: The materials change, but the intangible skills of a designer will remain.
Act IV: (Unwritten)
I've always had the mindset that my current role will be my last to remain ultra-focused on the mission. I don't think too far ahead in terms of career ambitions, but I do think about where I want to be spending my time and energy.
Whether I own my own business, work at a startup, or a larger company, I believe in entrepreneurship as a differentiator. This is why angel investing and advising became a natural interest; a way to remain in the innovative startup ecosystem and give back time, talent, and treasure to the next generation of builders.
Lesson 4: Entrepreneurship is not a job, it’s how you live your life.
When it’s all said and done, I want to look back with fond memories and contribute to a small part of the next generation—there is no success without a successor. I reflected on Denzel Washington’s framework of Learn, Earn, and Return.
Lesson 5: The hard work you put in the beginning is an investment that accrues career equity over time.
Remember to experience the odyssey
Recapping the five lessons I learned:
Emerging technologies during economic downturns can be equalizing moments.
Optimize roles for the impact and purpose you care about.
The materials change, but the intangible skills of a designer will remain.
Entrepreneurship is not a job; it’s how you live your life.
The hard work you put in the beginning is an investment that accrues career equity over time.
Despite two decades passing, my interests remain the same: art, culture, technology, and business. What’s changed are the materials and how I applied those interests. What began with sketchbooks and canvases evolved into mobile apps, design tools, and AI platforms. In many ways, my career has shaped the way it is because I was not rigid about it; I allowed serendipity and timing to guide me.
An odyssey isn’t a straight line. It’s an arc designed as much through chance encounters and economic cycles as through deliberate choices. The challenge (and the opportunity) is to shape that arc with intention, to populate it with sparks and serendipity, and to treat each chapter as preparation for the next. Remember to enjoy the journey.
Hyperlinks + notes
Agentic AI tracks at Fellows Forum 2025: AI Summit – Where Unicorns Meet Giants! → I’m excited to be speaking on the panel on Designing Platforms for Collaborative AI
Full Tutorial: From Design to Code with Claude Code | Meaghan Choi by
Philosophy for Designers 2: Parts and wholes and moments, oh my! by Sean Voisen
Everything we announced at Webflow Conf 2025 → Congrats to the team, another successful Webflow Conf with great product announcements
Great read David!
Thank you for sharing your journey so far. What a fabulous adventure!
I am curious do you create art? Or plan to? I know design of products, teams and a career is a type of art, but I am curious about your art art.