I don’t really have role models in the sense I think most people choose role models, as “favorite successful people”. What I have is a small, constantly rotating cast of people in the periphery of my life who inspire me creatively and show me new ways I might think about my future. To me, role models aren’t like favorite colors or favorite desserts. You don’t really choose them yourself – they come into your life, and light something inside you. It’s up to you to keep that flame going.
What follows is a snapshot of that cast of people on my mind today.
Some people on this list happen to share some professional or creative interest with me, but I think that’s more coincidence than intentional. The big questions I’m grappling with these days aren’t about how to advance in my career or how to get better at what I do, but instead how to design a life that balances a focus on craft with broader fulfillment, and balances depth of experience with exploration. My “role models” – at least as the list exists today – are people who offer me different interesting answers to these questions. Each person here has woven their creative, professional ambitions into their day-to-day motions in their own ways, ways that I find worth studying.
Most of these people appear here because I think they share the values I hold closest to my life, so looking at the way they’ve navigated their lives gives me clues about how I might grow in the future myself. Some people are also on here because they show me the unexplored envelope of life – what’s possible to do in a lifetime that might not be obvious for me from my current vantage point.
Bret Victor
Bret Victor is a former designer and engineer at Apple, having worked on products like the iPad and the Apple Watch. But he is best known for his phenomenal talks about computer interaction design sprinkled with tasteful and catalytic demos. He currently leads up Dynamicland, which I might crudely describe as an HCI research lab.
His life is interesting to me because of the way he found his professional focus early in his career – inventing better human-computer interfaces – and has almost obsessively focused his career onto this problem with an enduring sense of relentlessness, even as his ideas and projects and implementations have changed. He is guided by that focus more strongly than any employer or career path aspiration. He says,
I’ve spent a lot of time over the years desperately trying to think of a “thing” to change the world. I now know why the search was fruitless – things don’t change the world. People change the world by using things. The focus must be on the “using”, not the “thing”. Now that I’m looking through the right end of the binoculars, I can see a lot more clearly, and there are projects and possibilities that genuinely interest me deeply.
And I think this reflects on his work only more accurately over time.
A mention of Dynamicland and alternative computing media would not be complete without mentioning Omar Rizwan, whose creative ideas about better, more interesting, more tasteful computing interfaces inspire me on a daily basis. Omar earns an honorable mention on this list.
Hundred Rabbits
Hundred Rabbits is really two people, Rekka and Devine, who are open-source developers and musicians living on a sailboat afloat the Pacific. They’ve been building small pieces of beautiful open-source software from their boat, Pino, sailing from Japan to New Zealand to the French Polynesia and many places in between. During the COVID-19 pandemic, they’re stationed in Victoria, British Columbia, Canada.
I first met 100r at XOXO in Portland in 2019, and fell in love with the idea of the small life. Writing small software for small systems in a small boat, but against the backdrop of the ocean and the wider open-source software world. Hundred Rabbits to me is a quintessential “outside the envelope of the obvious life” story. Despite their constraints (or perhaps fueled by it), they manage to build some pretty cool software and share it with the world, which inspires me to do the same.
And they do it all while living on a boat, which as far as unconventional life experiences go, is pretty high up my bucket list.
Hank Green
Hank Green is a Montana-based entrepreneur, author, web developer, musician, and a little-bit-of-almost-everything-else-person. He’s also known as the creator of a cavalcade of educational YouTube channels, including SciShow, Crash Course, Healthcare Triage, and The Art Assignment. I first found Hank as one-half of Vlogbrothers, a YouTube channel running since 2007 between Hank and John Green (John Green being the well-known young adult author of The Fault in Our Stars fame).
Even before Hank was a published author and the showrunner of a dozen YouTube channels, he was a serial entrepreneur. Not in the sense that we view entrepreneurship in Silicon Valley, as the technical puppetmaster behind a massive scale-up company raising millions in venture capital, but as someone who gathers a small team to build a business that brings interesting, sometimes useful, sometimes heartwarming, sometimes simply unique things to people around the world. I followed Hank start initiatives like Vidcon and Pemberly Digital and the Project for Awesome closely, and was moved by the impact that small-scale initiatives created with good taste and empathy can have, especially when fueled by a great community.
Over time, I find myself pulled more towards this kind of intimate, community driven process of making things more than the scale and impact of the tech giants and unicorns. Hank’s life serves as an enduring reminder in my own life that entrepreneurship isn’t just the jargon-filled capital-fueled bungee jump into the fire that it sometimes feels like in the Valley.
Neri Oxman
Neri Oxman is a designer and researcher at the MIT Media Lab. She’s known for her portfolio of experiments and projects around nature-inspired architecture and materials design.
What I find most stunning about her career, though, is the way she got to where she is today. She was born in Israel, and served in the Israeli Air Force before attending two years of med school, then pivoting to study architecture in Israel, then the UK. Her work then brought her to MIT, where she earned a doctorate and joined the Media Lab. And now, she leads some of the most unique, creative research projects in the lab, even by Media Lab’s high standards for inventive design thinking.
I’m inspired by the path she took to get to her place today, and also by the way her research projects challenge the core assumptions we all hold about the reality of how we make things so essential to life, like buildings and homes and the basic materials of construction.
Bryan Cantrill
Bryan Cantrill is a software engineer currently at Oxide Computer Company, but with a storied career across Sun Microsystems and Joyent working on open-source systems software. He’s best known for his contributions to the Solaris lineage of operating systems and the DTrace tool.
He’s an experienced and respected engineer, but beyond that, I’m inspired by the way he thinks about both the business and the craft of building software, and about the challenges of building software together – software as a collaborative enterprise. Bryan is a celebrated speaker, and two of his favorite talks of mine are about the importance of principles in engineering culture and oral traditions in software engineering. While being a subject-matter expert in the nuances of the technologies he builds, he also manages to be eloquent both aloud and in writing, and consistently thoughtful about what truly matters beyond the technical systems we built as programmers. More importantly, he seems to live by his personal principles as faithfully as anyone I’ve seen, and I think that is a rare trait worth learning by heart, especially in the fast-and loose Silicon Valley milieu.
On his blog, he writes concerning the challenge of software engineering:
Software engineering is an almost paradoxical juxtaposition of collaboration and isolation: successful software engineers are able to work well with (and understand the needs of!) others, but are also able to focus intensely on their own… They must be able to build castles of imagination, and yet still understand the constraints of a grimy reality: they must be arrogant enough to see the world as it isn’t, but humble enough to accept the world as it is.
To date, it’s one of my all-time favorite paragraphs I’ve read about the field I’m in.
Kicking off this year, I wrote:
I like thinking of planning life as a game of exploration. What kinds of lives are possible outside of the ones you’ve grown up knowing? If any of them appeal to you, how can you venture off trail safely without making a dumb mistake?
One way to explore my options is to follow the stories of people who share my values and curiosities, and see how they’ve fared in their exploration. At the moment, these are some of the people whose lives I’m watching for inspiration, to illuminate some of the futures that might be possible ahead of me. Their stories are the light by which I try to peek ahead into my future. And between the diversity of these people and their work, I find much to learn about how I should think about my own life and work, and how I can weave them together without getting too tangled up.
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