What led you into design?
In high school, I played bass for local bands. There was a stint where our guitarist got really sick and we couldn't play shows, but I wanted to stay involved with the community. One of my friends was looking for someone to make a lyric video, so I volunteered. It only paid $20 and free admission to shows, but hey, it was a start.
From there, more opportunities popped up and it ended up morphing into a very relaxed freelance practice with chances to make videos, album artwork and merch. It taught me a ton about negotiating with clients and protecting myself and my work, and it paved the way for my career in design.
Initially, I wanted to study music business at university but ended up switching to art with an emphasis in design. From there, I started working with agencies and ultimately ended up working in product.
TL;DR - The Colorado Springs music scene got me into music.
What does a typical day look like?
This is what most days look like:
5-6am: Wake up, do the whole morning routine thing
6-8am: Free time to read, exercise, work, email, whatever
8-9am: Shower, get coffee, get ready for the day
9-12pm: Work and meetings
12-12:30pm: I have this whole ritual where I make a sandwich almost exactly at noon. So good.
12:30-1pm: Open Calendly slot where I'll talk with designers who book it. It can be about career, portfolio, or whatever.
1-4pm: Work and meetings
4-5pm: Wind down, sometimes go on a walk
5-7pm: Chill, eat dinner, play Rocket League
7-10pm: Usually end up working, be it Square or a side project
____
My work schedule is pretty fluid. I find that I'm most productive when I have a 3 or 4 hour stretch of uninterrupted time. Those are hard to come by, so the best work often happens at night.
What's your workstation setup?
Where do you go to get inspired?
This is going to be a very non-designer answer, but most of my inspiration comes when I'm not designing or even thinking about design. Might be helpful for me to break this down by category:
When I need to think: Go on a walk
For web design: thegallery.io, SiteInspire
Product stuff: Product Hunt and HackernNews
Money things: Bloomberg and WallStreetBets
Art: Basquiat, Cy Twombly, Kash Ashford, Wesleigh Byrd, anything minimalist or neo-expressionist
Food: Cooking with Brad!
I put these in categories but that doesn't mean that art only inspires me in an artistic way. For me, it's been helpful to observe inspiring things in a super broad range of topics and then see how some of the underlying principles or ideas can map to other things. That's kind of abstract, but it's how my brain works ¯\(ツ)/¯
What product have you recently seen that made you think this is great design?
This is probably overdone, but I really like Dispo. My fiancée and I were on a trip recently and it was really easy to snap a photo and then forget about it until the roll developed the next day. Really fun product.
Another one that comes to mind is the Soma water pitcher/filter. I've been using a Brita for forever, and I love how with this you don't need to open a lid. The center thing just opens up and lets you pour water in and then closes once you stop adding water (very technical I know).
Last one, Bowflex adjustable weights. My folks have these (I need to buy a pair). They are so sick. I remember lifting weights in high school and being so annoyed by how long it took to change weights. These are pretty expensive but they solve the problem.
What pieces of work are you most proud of?
Two projects:
Kapsul
I got to work with a few other super talented people on Kapsul, a distressed D2C brand that was making a high-end AC unit. It's my favorite logo I've ever made, and the app and website turned out really well too. Such a fun project that I had a lot of ownership on.
Square Online Checkout
This is what I'm currently working on. It started out as a really simple and lightweight way to take payments, sell items, or collect donations via a link, and it's evolved a ton since then. Since I'm the only designer on it, there's a ton of autonomy and a fair share of challenges (which I'll talk about in the next question). All that to say, I really enjoy striking a balance between meeting near-term design needs and setting a longer-term vision/strategy for the product. It's been really rewarding to work with sellers to create something that helps their business succeed during a pandemic.
What design challenges do you face at your company?
First off, let me say that Square is awesome because there's less red tape and corporate politics than I thought there would be at such a large company. Part of that is also due to my team (y'all are awesome).
Two design challenges come to mind:
Design systems
I am responsible for a native and web product that has both a seller and buyer-facing experience. There are multiple different systems converging into one on the seller side, so it can be a challenge to design for a future state where everything uses components that don't currently exist in production. That said, my engineering team is great and they make my life so much easier. It's also a cool opportunity to participate in the optimization of a new system.
Working remotely
I have worked remotely before, but in that case I met my coworkers at company retreats and work trips. I've been at Square almost a year and have never met anyone. It's been impressive to see how well we operate remotely, but communication is so nuanced that it can be difficult to get a read on some people when you are talking on Slack or a video chat. Also, my coworkers seem cool and it would be nice to spend time with them at lunch or coffee. Those in-between moments are often when great ideas end up happening.
What music do you listen to while designing?
Any advice for ambitious designers?
Five things:
Don't assume
Time and time again, I've come into situations at work or with side projects where I think I know more than I do. Be humble. While it is good to be confident in your abilities, don't let that confidence compromise your willingness to ask questions, seek the perspective of others, and really get to the root of problems when you're designing.
Obsess over craft
Unless you go to a fancy school or have an in with a big company, your portfolio is the thing that speaks the loudest. Hone your skills. Study typography, balance, composition, color theory, pace, and other basic fundamentals of graphic design. Documentation like Material Design and Human Interface Guidelines is a great start, but the great designers I've gotten to work with had a really solid understanding of their craft.
Aesthetics and storytelling matter
A lot of bootcamps and design education programs I've seen over-index on process while failing to educate students on how to tell a compelling story that is visually appealing. People who don't know you (especially recruiters and design leads) need to see work that has a high level of visual quality. Study advertising, writing, and marketing. There's a lot these disciplines can teach designers about how to present their work both in a portfolio and in the workplace.
Learn how to talk (and write)
I'm becoming increasingly convinced that most of design is learning how to communicate. If you can coherently present your work, rationale, and thought process in both a spoken and concise written format (think presentations) you will be leaps and bounds ahead of other designers. I challenged myself to do more writing this year and it's paid dividends. You'll think more clearly and be more articulate.
Be nice
Treat people with respect, show empathy, and be kind to the people you come into contact with. You have no idea what those around you are experiencing in and outside of work. The world is small.
As you get into the design world, it will start to get even smaller.
Anything you want to promote or plug?
I write a weekly newsletter about design and tech. It's pretty fun. Here's the backlog and sign up info:
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