Ryan Putnam

Feb 4, 2023

Ryan Putnam’s following on the popular design community Dribbble is easy to understand the moment you take a look at this work. He’s a talented designer and artist with a playfully creative style. From doodles on a banana peel to beautiful ceramic pieces, his work is youthfully imaginative and just fun.

On a chilly day in San Francisco, I sat down to chat with Ryan at the Red Door Cafe. We told design stories, spoke about our passions, journeys and struggles. This was one of the most therapeutic conversations I’ve had in quite sometime. That day was the first time we’d met and we walked away friends. I’ve been a huge fan of his work for years and was happy to find that he is a genuine and down to earth guy.

Ryan is currently working independently as a freelance designer with great products like Operator. He previously helped to develop the well known illustration style at Dropbox.

Can you tell me a little bit about yourself?

Ryan: I grew up in Colorado Springs, CO.  It’s a beautiful place where you can spend lots of time in the outdoors and nature.  My dad would often take me to the national parks in the area. I grew up skiing and my dad would actually snowboard. Way before it was cool. It’s very homogenized but there’s great people there.

As a young kid I was really into comic books. I was big into X Men and Batman. I started by sketching that kind of stuff. In high school I did fine arts and won some local awards. It was just really fun for me. In college I received a BFA in Graphic Design from Colorado State University in Fort Collins. It gave me a chance to do a bunch of different things like metal smithing.

How did you discover your passion?

Ryan: I don’t actually remember a time that I didn’t draw or make things and I’m not even sure it’s a passion. It’s more of a compulsion really. I feel a passion is something you have some control over. I just can’t help creating things. It actually drives me crazy sometimes. Sometimes I don’t want to create. Sometime I just want to hang out with my son and not have a need to turn everything into a project. Even though it’s a compulsion I still enjoy it. It just not that easy to turn it off.

I know your currently freelancing. Can you tell me a bit about that?

Ryan: Some freelance projects I’m embedded.  A lot of tech companies prefer that.  It helps me actually understand the product and breathe the culture, making the results more effective. Anything that touches the product you really need to have a lot of exposure to the company.

Office life really isn’t my thing though. I feel like there is too much noise and a lot of distractions. I actually don’t think most work environments are conducive for focused productivity. Being freelance affords me the time to get away when I want to.

At this point, I wouldn’t want to work at a company embedded again.  I actually think freelancing can scale and that’s what I’m interested to find out. I don’t have strong ideas about how at this point. Freelancing only gets you so far because I don’t want to manage an agency or people but I actually do want to advance in my career. There has to still be a balance to achieve upward mobility. I’m actually really interested to figure out how I can scale what I’m doing now.

How do you approach your freelance work? What are some of the challenges?

Ryan: I talk about this often with other freelancers, because it could be something beneficial to companies where employees are leaving every few years.

Sometimes I feel more disconnected from the graphic design or interface work. I don’t feel as drained when it gets critiqued. When I do illustration work I get much more invested in the result. Going through a process of design iteration for illustration is much harder for me. I think that’s why maybe it’s hard for me to be part of a company. It’s just easier for me to let go of the graphic design work. I don’t know.

The way to approach illustration in the context of product hasn’t been evolved enough because people don’t know how to talk about it. Early on at Dropbox, when I would take things into a CEO or PM they really didn’t know how to critique it. So now my approach is to take the subjectivity out of it. I have actually started to create a feedback system that helps develop a framework for people at a company talk about the work.

I feel that a lot of agency work is mostly looking at things in a vacuum and they don’t consider the cohesive experience across the brand and product. Building the systems to do this is really interesting to me. I have been building a lot of style guides for companies lately. It’s actually a bit of a challenge to pass things off and build things for companies that stands apart from myself.

I could break away from from line work and it could be shapes overlapping.  The approach to the illustrations should all be consistent and an artists would work within those bounds. There will be some variation in style but you will almost not be able to tell. We were trying to approach it that way at Dropbox. I think they are doing a really good job at it now.

I mean there’s probably 5-6 illustrators there. The guide is build out so well you shouldn’t really be able to tell the difference in each individuals work.

Speaking of Dropbox, can you tell me about how you joined that team?

Ryan: I was doing freelance in Colorado and Morgan Knutson reached out to me for DBX in 2012. It was the first Dropbox developer conference. Morgan asked me to just come out and help with all of the brand and environmental work. So I came out to San Francisco for 3 months with my wife and son. During that time we created all the visual style and work for DBX. After that, they offered me a full time gig. We really thought San Francisco was cool, and Dropbox was great to work with, so I joined the team. We had about 12 designers. Everyone was really great and at the time we didn’t really have super defined roles. We all just worked on a bunch of different stuff. They didn’t ask me to come in and be a illustrator. I came in as a designer and did product work as well. I worked on on-boarding for Project Aloha. It just so happened that it had some illustration work involved.

I started to do illustrations on a few projects and it became a recurring brand function. For us, it was really a humanization moment for the brand that John Ying developed before everything. We really wanted to carry that into other projects and we thought it could be a defining characteristic of the brand. I worked with Alice Lee early on to create the guidelines and it evolved from there into being a continuous development. I just really started to document it and once Zach Graham joined he really pushed it to the next level.

Ryan Putnam Muni


Dropbox is known for its illustration work. How did that happen?

Ryan: I think we really had a good leadership that saw the value of continuing this kind of work. Now it’s more formalized but when we were starting I think leadership really drove all the investment to continue.

I think the biggest challenge was getting people to talk about illustration in a way that is conducive to get a project out the door. Trying to properly set expectation and how the whole process works. People at the time just didn’t know how to work with it and how it fit in to a product timeframe. I don’t even know if it was something that I was able to fully work through.  That’s something where I’m not the most successful.  Most of that has probably been formalized since I’ve left.

Can you tell me about what it was like for you leaving Dropbox? Any advice to others who are going through that process?

Ryan: Luckily, before Dropbox I was doing freelance for 5 years on my own. Things can never get too bad. The worst thing that can happen could also happen while at a “real company”. I just knew that I wasn’t happy full time and I would be happier on my own.

“You will know when you’re supposed to be there or not. It’s an undeniable feeling.”

If you are younger and at a company or agency, there really is a lot to learn that can prepare you for trying to run your own business. I know people are really eager to go out on their own or freelance but when you’re at your full time gig, eat everything up you can, because when your on your own you’re actually “on your own”. You are forced into doing everything. You don’t just design anymore. Some people think that it’s fun but others really don’t like it. You need to be aware of all the things that come with it.

I think at this point in my career I have an easier time getting more credible clients but I still have to educate in order to get what they really want. I’ve been thinking about developing the who, what, where and why of product illustration to refer people to. I’m starting to notice the continual pain points where I think this kind of information would be really valuable.

Ryan Putnam in SF

You love to explore, can you describe the greatest adventure of your life?

Ryan: My greatest adventure so far is becoming a parent. Being a parent is challenging, eye-opening, frustrating, and I hope, rewarding. Don’t get me wrong, my three year old son Cyan is the most amazing creature ever but the daily slog of being a parent is grueling. Once you get past that it’s amazing to see how he grows and interacts with the world. It’s also refreshing to interact with a human that isn’t trying to hide anything or have any agendas. He is raw and real. I know if he is happy, hungry, or sad.

My trepidation about becoming a parent started when we lost our first daughter Rylyn when my wife was 8.5 months pregnant with her. As you can imagine it was a devastating experience that affects everything I experience today.

Sometimes when bad stuff happens to people there’s some big educational moment that people are better because of that. I don’t think I’m better. I have pain. I have struggle. I think now I recognize more that people’s realities are different. You never know what someone is going through. I think it’s made me more empathetic to everyone. Not just parent, or users. Everyone is going through something and it’s good to recognize and talk about. It’s made me look at everyday like that. It permeates everything and I don’t know if it makes me a better person.

“Having something like that happen makes me think I don’t have to have all the answers. Things could change at any moment.”

I don’t have to have all the answers right now. I don’t know what my career will be in a year or if I’m going to be a good father because anything could change on a dime. This has just been hard for me to grasp. I can’t candy coat it. I could maybe glean good things from it but it’s just awful and a lot of people have those experiences. It’s fine for that to manifest in different ways.

My eyes have really been opened to the world. I’m generally a really up beat person but the world is starting to look grim. Look at the guns, police brutality, religion, racism… it just doesn’t end. It’s hard for me to believe that there can be something better.

“Maybe that’s why I draw. Not to make it better but for me to escape it and create some kind of order. Because who knows what’s going to happen.”

I totally agree! I feel that a lot of the issues stem from us having a lack of understanding. I don’t think we spend enough time gaining the skills to understand one another.

Ryan: There’s a lot of focus on craft level or execution at work. The things we are talking about are so much more important than anything. They don’t really teach that. We geek out on the new Sketch app but we don’t geek out about understanding one another. But my son’s school is teaching right now about emotional intelligence.

“I wonder if this will all amount to something. Will people become more aware that empathizing for your fellow man is just as important as understanding a hard skill?”

Especially in what we do. Building products for millions of people. If you only have 25 year old white males building these things, how can we be representing the lives and opinions of all these people. It’s hard because especially in San Francisco we are in this heavy cloud.

I’m a pretty pessimistic person. I’m a bit neurotic but I feel that humans want to survive. We will come up with ways to ensure our survival and eventually do what’s best for all of us.

Even with us historically being greedy, my hope is that the individuals needs will be joined by others.

As designers, we are typically pessimistic and by making order of a particular thing we feel better. But I think people often lean too far and say as designers we can do no wrong and fix everything. I think it’s important and helps people but change takes everyone. There is opportunity for some of us to do more but we aren’t all changing the world.

How do you deal with adversity and challenges?

Ryan: I’m still trying to figure that one out. I tend to use the adage “kill them with kindness” and it works pretty well for little challenges and annoyances but the bigger stuff I am still working on. I’ve recently started to practice mindfulness and meditation and that helps my neurotic disposition. I have the luxury of being a white male so in this culture I don’t face the adversity that women, african americans, homosexuals, and the countless other disenfranchised groups face. Because of that I try to be honest, open, and empathetic to others. I think that makes me a better design and more important, I hope it make me a better person.

What will be the biggest challenge for todays youth as they enter the workforce?

Ryan: My dad worked at the same company for his whole life. That’s crazy! The longest I’ve stayed at a full-time gig was three years. That seemed like a lifetime for me. I’m an independent designer and illustrator now so I don’t work with a company longer than six months. This isn’t exactly reflective of the rest of the workforce outside of Design and Tech but it’s starting to be more prevalent in these industries. When working for a varied set of clients and people it’s a challenge to have to manage skills outside of your expertise. You kinda of have to be a Jack of all trades.

What movie/documentary/podcast or book has inspired you the most and why?

Ryan: That’s a hard one. I think the most inspirational movie for me was The Neverending Story. I loved it when I was younger. It was dark, magical, and it fueled many of my doodles and drawings. I remember watching it at my 10th birthday party and everyone hated it. It just made me love it more. I felt like I had something to call my own and didn’t need the approval of anyone else. I try to carry that feeling into everything I do now.

You started to sell your work. How has that process been? 

My initial goal is to have my own thing that was separate from Dropbox. It’s not a primary focus to make money. I’m not looking to make a big brand like Benny Gold or something. I just think it’s fun and I want to try out some different printing techniques. If I want to make a hat I make a hat. Maybe one day I would like to not do client work but again I really don’t know what my life will be like.  What if I start to go down that road and just hate it.  I’m trying not to be over critical of myself. I’m kinda learning how to sell my work as I go. I’m learning how to ship things and do things efficiently. It’s a natural process for me.

“You can miss a lot if you’re always looking at what’s next.  I’m just trying to be ok with being ok.  It’s not always easy. But right now I’m really happy.”