What led you into design?
I played guitar in a ska band when I was in middle school. One day we needed flyers to promote an upcoming show. We had no money to pay someone to make them, and I was the only band member with access to a cracked version of Photoshop 7.0 on my dad’s PC. After a few Abduzeedo tutorials and a distastefully copious amount of lens flares, I guess you can say I got my start “designing.”
Later, in college, I fell in love with web design in a Flash (RIP) class as part of my Advertising degree at Boston University. I would obsess over these zany Flash-based websites like 2Advanced, Get The Glass, and Red Agency that were effectively unusable by today’s standards, but were so mind-blowingly rad back in 2009.
This class is where I met AJ Vaynerchuk, who would later co-found the digital agency VaynerMedia with his brother Gary Vaynerchuk. AJ saw how huge of a nerd I was about weird sites and elaborate loading spinners, and offered me a job as the first designer at VaynerMedia. I think I was employee #1 or #2. Now that company is like 1000+.
What does a typical day look like?
I used to never be a morning person, but living bicoastally between Portland and New York helps bump my bedtime back 3 hours while visiting the west coast. Now I friggin’ love mornings.
My ritual on a good day looks something like this:
- Wake up (ideally)
- Write my Morning Pages
- Exercise (compound exercises, weight training or running)
- Cold shower (ala Wim Hof)
By then, I’m usually ready to hit some work. When in Portland, I ride my bike to our office. When in New York, I’ll either work from home or at a coffee shop like Hungry Ghost or A/D/O in Williamsburg.
I’m the only designer at our tiny startup Oak Meditation right now, so my day changes constantly. Typically, once I get through any admin stuff, I’m focused on our product in some shape or form. One hour I may be talking to users or digging into analytics, the next may be focused on strategizing, spec’ing, working through flows, building out prototypes or shipping designs! I’ll break up the day with a mid-day rock climbing session, meditation, or by playing guitar. Evenings are a total grab bag.
What’s your workstation setup?
Where do you go to get inspired?
Inspiration comes from everywhere, really. Conversation, travel, art, architecture, books, albums, movies, industrial design, cars, watches, graphic design, and fashion. Inspiration typically strikes from unexpected collisions of the above, applied to software.
Early in my career, I used to be inspired by purely beautiful things. Now, I’m more inspired by usefulness. Instead of spending hours or days getting an interaction perfected, I’d rather invest time in finding the right problem to solve, quickly shipping a solution, and iterating. Without function, form does very little for me. That said, hitting the sweet spot of that intersection is just the best.
But hey, to give less abstract answers to your question:
Layout and art inspiration: I love stopping into Iconic Magazine in Soho to dig through magazines
Web stuff: https://www.siteinspire.com/
Mobile patterns: https://mobbin.design/
Interaction ideas: https://uimovement.com
Typography: https://typewolf.com, vintage watches, car gauges
Color: Travel, being in nature, walking around Williamsburg and Manhattan
General design and business advice: Twitter
What product have you recently seen that made you think this is great design?
I’ve been blown away by the products coming out of a New York-based company called Ecovative. Specifically, by their MycoComposite packaging and their use of mycelium (the root structure of mushrooms) to create a eco-friendly alternative to plastics.
Mycelium is fascinating for many reasons, but MycoComposite packaging is incredible design because it solves a very real widespread problem efficiently and sustainably, using low-cost materials that are not just low-waste, but are actually healthy for the environment.
The MycoComposite mycelium packaging requires 12% less energy than plastic production, produces 90% less carbon emissions, drastically reduces our reliance on fossil fuels, and even decomposes in 30-90 days! How sweet is that?
Excited to see big retailers like Ikea and Dell adopt this tech. You can check out more of Ecovative and their products here.
What pieces of work are you most proud of?
Prior to Oak, the design of the lifestyle brand, Hodinkee.com, and the Hodinkee Shop, on iOS and Web. Both projects were a huge undertaking that made some big waves with a passionate niche audience.
As a side-project, I’m proud of myself for learning enough Ruby on Rails and Twilio to build an SMS-based gratitude journal I call, Grateful.me. It’s simple– I get a text once a day: "What are you grateful for today?” and my response saves to a private web-based journal. It’s a daily reminder for me to express gratitude, which can go a long way towards greater happiness and mental health.
Lastly, in my free time, I’m super excited to be working on an app that uses a VR headset to help eye doctors perform low-cost eye-exams in developing countries. I don’t have much to show yet, but I’m excited to share more on that soon!
What design challenges do you face at your company?
Helping people make meditation a habit. I often hear from users “I want to meditate, I just don’t have time to do it”, or “When I’m busy and stressed, l forget to meditate.” A) You do have time, you just aren’t prioritizing it right now and B) Busy and stressed is the best time to meditate! My job is to develop systems that make healthy habit formation as frictionless as possible.
Luckily, there are plenty of studies backed with neuroscience and cognitive behavioral research on habit formation. Those papers are a great place to pull product ideas, game mechanics and inspiration from.
What music do you listen to whilst designing?
Any advice for ambitious designers?
I used to be a big believer in the phrase “fake it till you make it.” And I still am, to a certain degree. To me, that means you should take on projects just out of your comfort zone because through that hard work and struggle, you’ll grow. However, now that I’m older, I’m a fan of the phrase, “face it till you make it.” Face your fears, face your shortcomings with persistence until you transcend them. Invest time into getting to know yourself.
Taking a page from Jason Fried here. Don’t take advice from people who are 20+ years past you in their career. Instead, take advice from someone who is just above where you want to be. Especially in our insanely fast-changing field, relevance is key.
Relationships = everything. In my 10 years of professionally designing, I’ve never gotten a job by directly cold applying to it. I’ve always either been recommended by a friend or reached out to directly. Seek out people you admire on Twitter. Go to events, meet people.
98% of things aren’t worth stressing out about. Relax. You’re going to die someday.
Anything you want to promote or plug?
Sure! If you’re looking for a free alternative to paid meditation apps, check out Oak Meditation in the App Store. Also, folks can follow me on Twitter and Instagram. Always down to connect with and help good people.
Sending love to my infinitely-creative partner @jordannshoe, and these designers who inspire or influence me, massively:
@pasql, @han, @jasonfried, @allanyu_, @walkertovin, @elirousso, @lilrogalski, @3dfordesigners, @jgebbia, @pemberton, @kylebragger, @dburka, @dtrinh, @jhodsdon, @addison, @kevindavidcrowe, @officiallyrad, @thethese, @jeremylv, @lansdaza, @gracelarosa, @milesfitzgerald, @vanlancker, @neilsarkar, @joulee, @cesart, @davejohannes, @bartonsmith, @pkattera and many more I’m missing.
Thanks for reading! 🙏