Inside the creative mind of Tymn Armstrong
In the ultra-competitive Bay Area startup and tech scene, designers can so easily get sucked into focusing solely on the work that gives them as much presence as possible. And understandably so.
Bigger projects means bigger audiences, which means a bigger payday at their next job.
But there are so many facets to design that can’t be captured in a single project, or in awards and public recognition. Design in its purest form is the practice of creating joy—of creating not just for a pay off or some extrinsic reward, but to really and truly pass value and happiness onto another person.
Since leaving his successful freelance career (mostly) behind, San Francisco-based illustrator and designer (and Crew member member) Tymn Armstrong has been creating joy through design full time for Dropbox’s 2,000+ employees on the ominously named Black Ops team.
We sat down with Tymn to talk about his role at Dropbox, how he designs for human values, how to use inspiration the right way, and why he doesn’t feel guilty binge-watching Netflix.
Let’s start with the basics: What’s your role at Dropbox?
So I have a pretty unique position in that everything I do is internal.
I was hired by a guy named Jon Ying who started the Black Ops team. Jon had been at Dropbox since the beginning and just recently retired, so I now report to the CEO.
One of our values at Dropbox is this cute little image of a cupcake. This is also our team mission. It basically means the unexpected but thoughtful and delightful thing that comes from a product or company that makes people fall in love with it.
“Our teams main objective is to find creative ways to bring cupcake to the everyday lives of Dropboxers, so they not only have a great working experience while here, but are also inspired to bring cupcake to the work they create. All of this is done through design, communication and social engineering.”Tymn Armstrong
We’re also considered in some senses a recruiting tool. There’ve been instances where people are going through the hiring process and they actually list Black Ops as one of the reasons they decided to join. Claire Pederson, one of our designers on Black Ops, helped redesign our recruiting kit, and she made this cupcake kit, with all the ingredients to make a vegan gluten-free cupcake in the microwave, and it’s actually really delicious.
Tech is such a competitive market. And especially having all the major tech companies so close to each other, the companies cross pollinate so much. You’ll have people that have worked at every single one of them. So while I don’t like reducing us to a recruiting tool that aspect is definitely there.
It sounds pretty exciting. Can you give us an example of the kinds of projects you work on and how your team operates?
Yeah! It’s pretty exciting to come into the office Monday, and people don’t really know what to expect, because we don’t even announce projects until they’re live. So they might come in one day and see a brand new mural on one of the floors, that we either did in house or got a local artist to do.
Recently we also launched this internal project called Gratitude Post. It’s this little pop-up where you write can send a personal note to any Dropboxer at any global office. You write a message on one of the custom designed postcards, put it in a little envelope, and then you can stamp it on put sticker stamps on it and drop it in a little pick up box. At the end of the week, the facilities team comes by and they grab all the cards and then hand deliver them to their desks or even to other offices around the globe. It’s makes the offices feel super connected.
We try to find ways to spread optimism and positivity—to just making people happier in unexpected ways. Because when people love their company, like when they truly fall in love with their company, they feel more part of it and put more heart into their work. There is more ownership and and emotional investment into it. And I think that comes through the product.
It sounds like you have a positive impact on everybody around you, which has got to be such a satisfying feeling at the end of the day, especially when it isn’t a calculated HR sort of project. Are there any sort of boundaries or guidelines that you work within, being part of an isolated team?
Absolutely, the CEO (Arash Ferdowsi) loves the people of Dropbox which is why he leads our team, none of this is coming from HR.
To answer your question, because our projects are designed to speak to our culture rather than our product, we made it a rule from the the get go that we would not develop any type of style guide for the work that we do.
Culture is ever-evolving and we try to guide that process a bit. And there is also the surprise element of what we do to consider. It’s better that people don’t know what to expect next. It’s been really both challenging but also very rewarding to have that kind of freedom.
You have to be consistent at checking you work to see that you’re designing for people and not for yourself. It can be very easy to get really excited about a new design trend and want to work it into your project, but that might not be the most appropriate thing for the project. It’s important that the design choices you make be authentic.
That’s good in a way though because it forces you to really step back and look at what you’re doing rather than just copying what everyone else is doing.
Exactly. When I freelanced I used to try to avoid looking at anything online and just go at each project in a pure sense. But what I’ve found is that can severely limit you. There’s nothing wrong with following trends. Trends keep the industry moving forward. Sometimes you see something and you’re like, “oh, that looks great. That feels like something I could apply to my work. I wonder how they did that?” and it forces you to go and figure it out.
Dribbble and Pinterest are good examples. People definitely plagiarize each other out there. But if you look at any trend as a whole, you can always trace back to their inspirations, and you can see the community has just been building off of each other and evolving that trend over time. Everybody takes part in that whether they’re conscious of it or not.
I’ve never tried to pigeonhole myself aesthetically and just do like, one specific style. I think it’s more important how good your ideas are. Have you ever read Austin Kleon’s Steal Like an Artist? It’s great, it’s all about the creative process and being aware that nothing is truly original. Everything’s a remix. And there is a very distinctive difference between inspiration and plagiarism.
There’s nothing wrong with following trends. Trends keep the industry moving forward. Sometimes you see something and you’re like, “oh, that looks great. That feels like something I could apply to my work. I wonder how they did that?” and it forces you to go and figure it out.Tymn Armstrong
Plagiarism is being inspired by one this and copying it word for word or pixel for pixel.
Inspiration is being inspired by many different things and mashing them together. For example, if you want to write a story, take 5 different authors (or painters, directors, etc) that you love, and take away one specific technique you love about each of them, then try to imagine if they all collaborated on a book together and each brought that specific technique to the book. Then write THAT book. It applies to any type of art. This is a great way to find your voice.
It just becomes an awareness I guess, where you can say, yes, I’m inspired by these sources, or these trends, or this technique inspires me. Versus just being kind of arrogant to say ‘this is totally original’ and making that assumption?
Yeah. Also, when somebody comes up with some new take on a technique or idea that just blows me away I feel like, “Aw, I wish I would have done that,” or “I wish I would have thought about that,” It’s so inspiring and motivating. I love that. We’re all fans of what we do first.
How has your work has changed compared to when you were doing branding work or public-facing projects? Do you ever feel that itch of wanting more public exposure?
Honestly, I was kind of wondering about that when I first joined Dropbox. I suspected that switching to internal only, the stakes wouldn’t be as high. That maybe my work wouldn’t have as large of an impact. But what I found is that it actually is more fulfilling for me personally, because I get to see the impact that it has first hand. And in a company of two thousand people, where things can get overwhelming, it’s really, really great to hear directly from people that your work had an impact on. Before Dropbox, I was freelancing with a lot of big brands in other cities and sometimes countries. A lot of my projects I never got to see the physical product.
Also what’s interesting is that by influencing how people understand and interpret our culture, it naturally starts to bleed into the external product. So even though my team doesn’t work on anything external, per say, we still sometimes see tidbits of our influence there, which is really, really cool. For example, the new style of our product illustration was influenced by some internal illustrations Black Ops had done.
Aside from things like Dribbble and other designs, where do you turn to for inspiration? Does the atmosphere at Dropbox create a vibe where you just feed off the optimism, or do you have something that you like to get away to?
Oh yeah, good question. I often read away my weekends at the park, especially on warm days. That’s definitely kind of the getaway for me. And also, I love Netflix. I like to binge-watch shows and listen to a lot of music.
It’s funny. I was really into photography for a minute, but I haven’t really been posting a lot in at least the last six months. I’m getting more into making music currently.
I tend to jump between things. I get really, really interested in new creative outlets and then get to a point where I’m really happy with the results I’m getting and then I kind of lose interest and move on to something else. I wish I could get it to a point where I get really good and then I do something with a new skill, but then again what you learn inevitably manifests itself in your work in other ways.
But you have worked on a number of your own side projects lately. How do you carve out time for personal work? Also, what do you look for in a freelance gig or opportunity that makes something stand out?
This year especially a lot of projects I’ve been taking on the side have been for friends that I just want to help out.
I also just wrapped final artwork on my first illustrated picture book with Chronicle, a publisher in the Bay area. It’s a nonfiction picture book written by Lola Shaefer. It’s all about dangerous animals and what to do if you encounter them in nature. I’ve been working on it for about a year and I’m really excited about it coming out.
One of the reasons that lead me to step back from full-time freelance work and go work for a company was that during the last year on my own, I found myself taking on projects that I knew I could just complete really fast. When you’re freelance you’re often just hustling and trying to get as much done to pay the bills. I was starting to get really down on the work I was producing because I just didn’t feel like it was to the caliber that I thought I could deliver and I felt like I was relying on crutches that I knew I could produce quickly and that would get approved.
For whatever reason, at one point in my career I attracted a lot of dentists. I think it was because one of my first big break projects was for a paediatric guy. Anyways, because I had worked with so many dentists, and they’re all kinda the same, I basically learned a bunch of different visual things that I knew would be approved. So if I had any kind of hang ups, where I just wasn’t finding anything unique about the company, I knew I could just pitch some of these concepts and they would be approved.
When it starts to get to the point, it’s time to do something different. And Dropbox provided that opportunity for me. So now the freelance opportunities I look for are ones that I haven’t worked on before that will have new challenges or new industries to learn about. I’m mostly interested when I see something that I just haven’t done before. Not just the type of project, but also the type of company.
Keep up with all of Tymn’s great work on Dribbble, Instagram, and Twitter.
