Chicago Camps

Hannah Donovan (Video) — Prototypes, Process & Play 2015

Hannah has done a number of outstandingly cool projects, from to This is My Jam and clearly has found her path through music. She’s also found out, the hard way, what it’s like to deal with burnout, and has some great lessons to share with you.

We hope you enjoy Hannah’s presentation, “Sometimes You Need to Draw Animals” and don’t forget to get your tickets for Prototypes, Process & Play on August 11th and 12th!

Hannah Donovan

VP Product Design, Ripcord

Hannah Donovan is a designer and speaker based in New York City. She’s worked at the intersection of music, design and technology for the last decade, making digital products in music and entertainment. She currently leads product design at Ripcord.

Previously, Hannah co-founded This Is My Jam with incubation from The Echo Nest, led design at in London, and designed for youth-focused brands in Toronto.

She’s a classically trained cellist who loves hip-hop and R&B, as well as a classically trained graphic designer who loves bold patterns, clashing textures and type. She also loves tigers, but isn’t classically trained to tame them.

For more, keep up with Hannah at or on Twitter as @han.

Sometimes You Need to Draw Animals

This is my story of going to the edge of burnout and back again. When I quit my first startup job in 2011, I did so thinking I might not be able to make anything ever again. Since then, I’ve devoted most of my personal time to working on this as a design problem.

As people who make things, burnout – and the inevitable sequel to it, maker’s block – is something we all face. It might be big, it might be small, mine was pretty big. I’ll share my favourite tools for solving and preventing burnout, as well as what factors contributed to it in the first place.

(There will also be drawings of animals.)

Presentation Transcript


Hannah Donovan:

Thank you for the lovely introduction Russ and thank you for having me here Chicago. This has been amazing. I don’t think I’ve laughed so hard at a conference before, before I get on stage. Normally I’m laughing at my own jokes here. You’re going to be an awesome audience. I’ll put these online for you later and you can enjoy the many hours I spent on Photoshop. [Laughter] Now you can see a little bit of it. It’s too dark for the video camera. I work specifically in music and culture. These are some of the places that I have worked. And I will tell you a little bit about some of the stuff that I’ve done so you can put a face to it. I worked at Last FM for a long time. I was the design director. I did stuff like this and we made crazy newspapers. The whole point — whoa, what just happened? Everything went dark. Did the display turn off? This is cool! Cool story. Huh. Does anyone in the tech booth know what is going on? Well while they fix that I’ll tell you about what Last FM was.

Russ Unger:

They’re on it.

Hannah Donovan:

Okay, cool. It’s okay, I don’t need my slides. It was a precursor to Spotify. It was the first music service out there to track what people listened to and give them recommendations back on what they were listening to and what other people were listening to. Collaborative filtering. The wisdom of the crowds. When you buy something on Amazon it’s like “You might like this other thing too.” On Last FMI did all kinds of crazy stuff. I’ll skip these slides. This is the part of the talk where I show you guys my work and you can’t see it.


It’s sort of the part of the talk where I show you my work so you know that I’m actually a somewhat credible designer because then I tell you these stories about feelings and burnout. And I feel like if I just came up on stage and did that and didn’t show you this other stuff, it would be like how do we know if she’s legit. Now you have no idea if I’m legit or not. Because we don’t have a display right now! [Laughter] Hold up the laptop. Other projects you might know me from. This is my Jam where I was cofounder. It was also in music, really fun. But a completely different approach to Last FM. We did almost exactly the opposite thing there. Instead of being big data and let’s figure out what we can recommend to people, it was just all about hand‑picked music and human curation. We essentially asked people one very simple question, which we honed in on asking people other years about music taste and user research.

And we asked them what is your favorite song right now. And when we asked them that question, what happened is we got basically a much higher quality than song selection happening and much better conversation around those songs, too. It wasn’t just about the music, it’s also about the conversation around the songs. And in doing this, in this very high‑touch, special, hand curated way, we ended up stacking the deck. When we plugged them into a play list engine, it was really great. It was so great, because if anyone has tried to make a play list here, you’ll realize it was hard. The reason it was interesting was because the data we were feeding it into was lovely, hand selected stuff.

How are we doing back there with the projector? Any signs of life? Yes, no? Wavy hand.

Russ Unger:

It’s kind of like in Star Trek when they call down and Scottie is going crazy. They’re doing all of that in the engineering room at the moment.

Hannah Donovan:

Cool. This is fine. I understand this. Because this morning I was sticking a few last slides into my presentation. The one I would be on right now is where I was telling you guys about Drip, which is the new place where I just started working at two weeks ago. It is super fun. It’s also a music company. But music and culture. Drip is a little bit like an online fan club. Like a really cool fan club. Not like the one you remember that was like kids from the ’80s. Or it could be. But a way that you can connect with artists and creators that you admire.

Here we go! We’ll go back to Last FM. I did things like made newspapers with big data. And somebody let me video tape Moby and write a script and we put on parties and we lived in a crazy office like that.

This is My Jam. These are the types of songs that people picked and how it works. Simple and paired down, a complete reaction to what was happening at Last FM. This morning when I went to go get the screen shots off the website at 10 o’clock, 9:30, I was sticking these into my presentation. And of course guess what happened? This is interesting, the site’s not loading. I hopped onto Slack, and I realized all the developers are freaking out. Of course. On the day of my talk. It’s fitting that the projector the failing. This is what Drift is all about. You can connect with artists and creators that you care about and have a really close relationship with them where you can get all of their content for lack of better words and more importantly the community around them in a really fun closed way. It’s like a closed social network.

That’s what I’m working on at the moment.

And of course there’s also stupid stuff that I made like this, which may kill you and I take no responsibility for. You can’t choose what people are going to remember you for. Those titles had 80 million page views and it mixes drinks for you based on what you’re listening to. Again, I take no responsibility for this.


So highly important things that you need to know about me for this talk. This is all about establishing me being legit. This is about establishing that I’m not an adult. I have five younger sisters. They keep me young and they keep me honest. My spirit animal is the tiger. Another highly important thing you need to know about me because I’m like 15. My favorite film is Monsters inc. I’m a classically trained cellist. But I also love hip hop. So I’ve played in groups like this and this. My favorite thing is Power Clashing, and if you don’t know what that is, you should look it up because it’s really cool.

This is basically my favorite picture on the internet. I model all my hair styles off of these guys.


We should have a real talk now. I’m going to talk to you guys about feels. I’m going to talk about some now. I’m going to go back to a time in my life when I was totally burnt out. As makers, burn out is something that we all face. It might be big or small. Mine was pretty fucking big when it happened. I’m going to share my story so the route I took to turn my creative tap back on might be helpful, too. So I’ll start with the stories and we’re going to go back in time to design school.

I went to a traditional art and design school. It was a little bit like this. I’m not going to lie. It was a little bit like this. And a little bit like this. And like this. And I put these things up here because actually I’m really grateful for this experience now looking back on it and how much I had to learn about, you know, really understanding myself and understanding my own creativity and getting through things like creative block and figuring out how to address these issues.

If I hadn’t had these sorts of lessons in art school, I’m actually not sure I would have been able to get through what was in store for me later. It made me think a lot about how our community at large, especially the engineers that I work with don’t necessarily have this experience to fall back on. That’s one of the reasons that I want to share this story today.

So after art school what happened? It was good actually. My parents were pretty happy with me because I got a design job so that was nice. Then I moved to like a better design job in a better city for design. And then to another one. And this was all trending upward in a very nice way and then it was really not trending upward in a very nice way at all.

What happened? I was totally burnt out. I was just at that point in my career with Last FM. At this time it was 2011. Broken, depressed, frustrated, exhausted. I really felt like I couldn’t pick up a pencil and draw at all. That wasn’t me. Like you do? I quit my job and ran away of course. Fast forward to Hong Kong. I’m hanging out there with a friend. I have been traveling for a while. I thought running away for a bit would fix it, but of course it doesn’t.

That tap of creativity that I was always able to turn on that made me happy wasn’t turning on at all. What is worse about not being happy is also that’s the only way I know how to make money. So that’s also kind of bad. Shit, this is a real single point of failure for making a living. We better fix this.

As I’m hanging out there, I get this text from a long‑time colleague that I had worked at Last FM. He was saying are you going to be back on the grid soon because I really need a designer? Looking at my phone, making nothing again would have been possible. But saying yes is what a commitment to a creative life is. Even though we feel like we can’t do it, we have to say yes. Because there’s only one way out. It’s to keep making. So I said yes. And I went back to London, which is where I was living at the time. And I started working on this. But enough of me. Why does this matter to you?

Okay, well the reason it matters to you I think and possibly also your colleagues and I hope that you share this with them. Just tuck it away in your brain for some later date because you probably will need it at some point. There’s ways. There’s ways to deal with this stuff. Those ways, they’re fun, they’re school. But they’re not super effective in the long run. As makers, you would think that one of the most important things would be for us to learn how to take care of ourselves and our ability to make things if it makes us happy and it makes us money, seems pretty important. But I’m not actually convinced that this happens in our field. Especially in the startup industry. I’m not convinced this happens. The reason is we don’t really talk about this much. It happens to everybody around me. I see it in all the places that we’ve worked. But no one ever talks about it. They just kind of run away and then they reappear one day. When we do that, it’s completely self‑reinforcing. We’re like this dude. This sheep running around with a bucket on his head. A little bit, doesn’t work too well.

So I’m going to go back to this story about Hong Kong here and finish it up and tell you about how I got out of this particular situation here. And I’m going to talk about it in the context of sort of thinking about it like tools. We’ll get to it in a sec. I just signed up for this job that I don’t think I can do. The job happened to be by the way being the cofounder of This is My Jam. How did I dig myself out of this situation?

So years later, these are the methods that I think worked for me to overcome my maker’s block. And continue to do so. Recently I had to lean on some of these tools again just a few months ago actually because I moved from New York to London in December. And within three months, my job completely melted and I discovered I was in a brand new city and you have to find a brand new job very quickly. All of these things are kind of challenging things to somebody who makes things. But I had also been running myself into the ground for the last two years before that, working on my own startup and figuring out how to move to the states. I was pretty exhausted before those things hit. Let’s go back to the tools and let’s get through this. It wasn’t a really fun time. But I got out of that, obviously. I’m here today. But I used these tools again for the second time in my life. I can say now they didn’t just work for me once, they worked for me twice.

What works for me might not work for you. This is not a five‑step self‑help guide. I’m not into that stuff at all. I don’t want to be the creativity lady. These are just five tools for your tool kit. And as a designer, I talk about tool kits a lot with the people I work with. I feel like often people ask me what is your process for getting from A to B? Do you go a sketch first and then do a wire frame? Something like that. They want to hear a clear, linear process for getting things done. Does anyone else experience this? Yes, I am seeing some nodding. I say I don’t know. It depends on the problem. Sometimes I might do a back of the napkin sketch and hand it to a developer. Sometimes I might to a high fidelity mockup. Because that’s what we need. Sometimes I might shoot a bit of video on my iPhone. It completely depends on what I’m making. It’s about choosing the right tool for the job. And I think with designers, with the more experience that we gain, with that ability we’re able to select that tool quickly and a sharp tool that is very practiced that we can use with ease. It’s not about any specific, prescriptive process. It’s just about tools. That’s really all I got for you today guys. Here are some tools that might work for you. They might not work for you. They worked for me.

So let’s get going. The first one here — wow that’s bright — is learning when to stop. So we or at least I come from a world and a generation of things that don’t have an end. For example like when a record finishes playing it has a really definite end. But now I just press pause on my phone. I don’t even press stop to stop the music. I press pause and then it stays paused until I want to play it again.

We also come from a time of being able to tweak things continually. I got into this industry because I love to fix things and change things and keep on tweaking things. But it’s really important, and I think that makes it even harder to know when to stop. And with the physical world, it’s much easier I think to learn this lesson because it comes at us much more harshly. And in fact with the digital world. The first time I learned this lesson was actually in painting class in university and we learned about overpainting which is that point where your painting was better yesterday than it was today. So now you have to throw it all out again. Overpainting was when it was done but you kept ongoing because you didn’t know when to stop. It’s an important that everybody learns in art school. It’s a harsh lesson the first time you learn it and you don’t do it again. But it’s really hard with digital stuff to know when to stop. Because it’s less apparent sometimes that it was better before. And of course with design, we know what this feels like. It’s like tweaking and perfecting and polishing something instead of releasing it like we should be. And of course with coding, it manifests itself as over-optimizing and over-architecting. It’s applicable when you’re working on a small part of a system and also applicable in a big picture. I had to learn the hard way when to stop working at Last FM. When to quit my job for instance. My brain is quite small, I don’t know about yours. This is all it does every day. It does these three things every day. If any of these three things gets blocked, it gets all jammed in and nothing works. I can’t do three things at once. I can only do one thing at a time.

It starts with ideas come in and I have an idea, and it’s like cool. I have to make it to jettison that idea to get it out. If ideas stay in there and rattle along for a long time, it just fits up with ideas and there’s no space for more things to come into my brain. That’s like my metaphor for how it works. It’s very simple. [Laughter] I hope there’s no doctors in the audience.

But what happens sometimes when you can’t make the ideas? Then they just get stuck, right? And we’ve all had, I’m sure we’ve all had that point on a project where we stagnate or for whatever reason the system around us prevents us from getting stuff done. And there’s stuff rattling around in there for whatever reason you can’t get it out. It’s stuck. So at that point I think the only way to deal with it is to just be like "All right. I’m out of here. I’m declaring like. I’m just going to jettison these ideas." Clean slate to make space for new things.

It’s really hard to do this with digital stuff. Especially if we are responsible for something. Especially if we’re taking care of a system or infrastructure. How many people have in the audience have a side project that they wish they didn’t have to babysit in their free time? We’ve all got those. As being good product, good UX designers, it’s important to think about does it make sense for me to keep doing this? Does this project still make sense for the context that I’m in right now? Is there a way that I can get myself out of so I don’t have to keep babysitting so I can do new things. Otherwise it ends up-taking up time in this circle here.

It’s critical not just for this project, but it’s so critical in the long run. At least for me this has to keep flowing all the time. The second thing, start with something shit. When we feel like we can’t make things, we’re on a steep slide to feeling like everything is shit. We have this additional barrier to entry to overcome. We heard about this earlier today when Jen was saying you all have 100,000 bad drawings in you. Just get them out right away. It’s the same principle. Just knowing that the first thing that you’re going to make is probably going to be bad is a lot easier to get over that first hurdle. And in fact, actually for years now what I’ve been doing with my sketch books, this is embarrassing, but the first page I just draw and scribble something on it and I can get on with my work on the next page because I’ve done something terrible on page one that I can start working with it after that.

And I did this with This is My Jam, as well. This is embarrassing. This is the first prototype. It’s ugly and embarrassing and I would never have this out in the world. But we used this to test the riskiest bit of the concept that we were trying to design and it worked, so we made it better. I still hate this because I pretty much hate everything I make 24 hours afterwards. But it’s all right. It works I suppose.

So this idea of just getting the shit thing out faster so you can iterate onto something good is really not something I can take credit for. Many people have talked about this. And anyone who is creative knows this deep down inside. Ann Burt calls upon writers to write drafts. My mom is a playwright and as a kid I remember seeing stacks and stacks and stacks of papers in her offices. Now I see why you do 26 rewrites. Or Fred Brooks, the author of the Mythical — plan to throw one away because you will anyhow.

Knowing that lowers that barrier to entry and makes thinks a lot easier.

Third thing here. This is my polar bear. He’s cute and upside down in the water. Let action create motivation. So taking that first small step. Making that shit prototype that no one will see but you will motivate you to do more. So often I think people think it’s the other way around. This is something that Julia mentions in her book, The Artist’s way, which is a good book on creativity, too. People think it’s a magical process where there’s this bolt of lightning strikes. Oh, I have an idea! I’m going to go make it! And then you have to get motivated and then you have action, when actually it’s the other way around. This is so prevalent that I’ve had so many journalists ask Matt and I ask about how did you come up with the idea for This is My Jam. They always want an answer of we had this idea one day and we made it. Of course it doesn’t work like that.

You know if the idea is like a bolt of lightning then what happens before the lightning? The sky needs to get dark and stormy and interesting? How does that happen? By playing around with things, by taking action. By experimenting. Matt and I had both been working in music for five years before we had the idea of This is My Jam. We had been both working in the constraints of the music industry. We had been talking to people, consumers every single day. We learned a ton about that domain. With all of that stuff, we never would have been able to do This is My Jam. We needed the sky to get dark ask stormy first and that spurs you to take more action.

When you’re in the pit of despair of maker’s block, this action can feel small and silly or maybe in a completely different field. I was living in a house in the East End in London where there is actually some green space. I had a little garden. I thought I would try growing things. It’s a fun old lady hobby. It felt like design in a way. You make something and it’s technical. It was just enough to inspire me to design again. Maybe I’ll start drawing some of them and then I was sketching some of them and before I knew it I was having ideas to make stuff again. It doesn’t need to be something that feels really serious. In fact, it may even be better if it isn’t.

Number four. This sounds funny, but I’ll get to the point in a sec. I need to talk about habits for a sec. Firstly, there’s these habits that our industry places a lot of importance on. Team process, agile. We’re familiar with processes that hold us together when shit hits the fan when the going gets rough. Those are cool, that’s great. We should all do that.

And then there’s a second kind of habit which are like personal habits. These are things that we do for ourself to keep ourselves inspired and to keep our tools sharp on a daily basis. Twila Tharp, who is a choreographer. She talks about her personal ritual of getting into a yellow cab and going to her gym. That’s her personal ritual of staying in shape. For us it may be reading a favorite blog or looking at something regularly to stay sharp. Those habits are good, too. But there’s a third, and much more elusive habit. And this third habit, it’s a bit YOLO, actually. It’s about creating patterns for personal serendipity. Creative work needs the unexpected in our lives, otherwise it’s always going to look the same. You need to put yourself out there and do stuff that is different and uncomfortable. I enjoy doing that. I do it regularly. But what’s hard is finding the time to do. This often I’ll discover that when I’m busy or on deadline I’ll have been working for 2‑3 weeks solid and I haven’t given myself an hour or two to do something unusual like take a walk. That’s out of the ordinary. How often does this happen to people in the audience? Oh, you’re pretty good. Okay. Cool. So you’re good at having this time to do things.

But I think it’s important to have these regular pockets of time for unusual things to happen. And realize, also realizing that when you schedule these pockets of time that you don’t really know what’s going to happen. Sometimes it might turn out brilliantly and you discover something you need to know. Other times it won’t be that profitable, because that’s how these things work. You can’t make it happen.

Actually when we were working on Jam as a decentralized team, we realized we needed to shake it up a bit. I planned a series of retreats for us to go on where we would get together for a week and we would work on a feature and build it. This is one that we did in Spain. Oh, no!


All right. Well, okay. It’s good to be up here with you guys. Again. So anyway, we went to Spain. It was beautiful. You want to go in the ocean. But we were in London at the time so it was a lot more close. It’s a lot less romantic than it seems when you’re here. It was just a cheap place to go in the summertime. The way it inspired us to do our work and create the features that we were working on — oh, there we go thank you! — it just turned out very differently than in our London studio. Sometimes I journal. Sometimes I use this thing. 750 words. It’s a chance for me to get thoughts out and do different things than I would expect. When I lived in London, I used to walk around my neighborhood and pick people’s moss that is growing on their fences because I’m really into moss and textures and nobody seemed to mind that it was gone.


All right, so I guess my point is it can be silly and stupid and fun and playful. It doesn’t have to be as extravagant as going to Spain. It can be stealing your next door neighbor’s moss.

Do something different! I think this is probably the most important lesson that I can talk to you about. Going back to art school for a sec. The same painting teacher said you can always have two canvass on the go at any given time. When you get stuck on one, you can turn around and work on the other canvas. It unsticks you. And as soon as you do that thing you realize this is how I solve that problem over here. Especially if we work in house or at a startup, it’s sometimes difficult to do this.

When I used to work at an agency, it was easier. But as soon as I was working on one project, 100% of the time, I didn’t have this doing something different in my life anymore. So another thing they did is I started working on some different stuff during this period. I did some design that was in a completely different medium for me. I started doing some print work, which was like I hadn’t done that in maybe ten years or something. I think that taking the skills you have and trying them in a different medium or a different paradigm or a different language is actually pretty useful. I worked on this comic with a friend. Collaborated on this comic and did the typography for it. I did some identity design for my friend’s bar. I did more work in comic since then. I really like it. It’s a lot of fun, that industry.

Doing something different is the best way to just remind yourself that you can make stuff again because I think it puts you in a position where you don’t know so much about the thing you’re working on. And it’s easier to make mistakes. And it’s easier to kind of get over those hurdles of making something bad first perhaps. And it’s also just more fun because it had nothing to do with my regular stream of work. I didn’t feel like I was being judged on it as much, I suppose, as well.

So I really think that doing something different is one of the best things. And more to that point I think diversity is really inspiring. Because what I realize now is it wasn’t about doing something different. It was actually about being someone different too. In my case I found the field of tech and the situation I was in at the time, working in London in a big tech startup was really quite homogenous. And I’m sure other people have experienced the same thing. I stifled a lot of things about myself, like fashion, which I find to be an inspiring visual input. Instead I tried to assimilate bits of this culture they was working in that weren’t native to me. Try to wear it and assimilate it. It didn’t feel right for my personality and who I was as a woman and how I express myself with that design. Stifling that self‑expression was one of the best things I could have done. Trying really hard to fit in. The reason why it was one of the best things I could have done. Here’s another diagram of Hannah’s brain. When I get inspired by something, I need to express it. And I don’t get inspired again unless I can express that thing. So just by not being able to express myself by something that I was inspired about, it kind of got blocked out by that other cycle that I showed you. It’s like oh, I don’t though what I’m inspired by anymore.

So I guess my message to you with this is to embrace diversity in your workplace. Everybody gets inspired by different things and expresses themselves in different ways. This makes the world more beautiful, more fascinating, more interesting and helps the world get unstuck.

It’s this homogeneity and trying to fit in that can be problematic.

Last but not least, once you figure out what works for you, codify your methods, write them down and talk to your colleagues about them. If you have a quirky habit and you need to walk around your neighborhood and go steal moss, tell your coworkers about it. They’ll be like I understand. That’s what you need to do to keep yourself creative. Like diversity, we try to shove ourselves into these systems for ourselves that maybe don’t make a whole lot of sense for how we like to work.

So give yourself permission to be different. It’s okay. Everybody needs something else to keep themselves creative.

We’re nearly at the end here. And I wanted to let you go a little bit early, because I think you all want coffee. And I think I heard there were going to be donuts, too. So don’t say I told you.

I’m sure you’re wondering at this point what was up with all the animals. What was this all about? Well I guess in like 2011I drew this little otter and I had a lot of fun doing it and I started sketching more and more and more animals. And later on I got really obsessed with owls for a period. And I got to hold this owl named Duster who is an African Spotted Eagle Owl. He was the softest thing I ever touched. And I realized just how much I loved animals. I thought why don’t I incorporate them into my work more. Animals and music aren’t usually things that overlap, although I should do a project about that.

And then I got this magic pen that lets you record on paper and do the strokes and record in digital. But I needed a project to help me learn how to use this pen. Otherwise it would have sat in the drawer. And I also wanted to talk about maker’s block. But I needed to get the energy from somewhere to do it. I needed an action to get this motivation rolling. And I also needed an unusual element. I needed some personal serendipity. I needed something different, which is why of course sometimes you need to draw animals.

Thank you very much.


Chicago Sponsors Camps

  • Rosenfeld Media
  • Simplecast
  • Lead Honestly
  • Columbia College Chciago
  • MOMENT Design

Code of Conduct

All delegates, speakers, sponsors and volunteers at any Chicago Camps, LLC event are required to agree with the following code of conduct. Organizers will enforce this code throughout the event.

The Short Version
Full Version

Be respectful of other people; respectfully ask people to stop if you are bothered; and if you can’t resolve an issue contact the organizers. If you are being a problem, it will be apparent and you’ll be asked to leave.