Hannah Donovan

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I design music products for the web & speak about it.
Want to chat? Get in touch: han@hannahdonovan.com

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Notes from New Adventures

About two weeks ago I went to New Adventures Conference. I’m grateful that I got to go, because it sounds like it might be the last of its kind! Lately I’ve been putting away my phone and laptop at conferences and just listening and taking notes in my sketchbook instead. I’m a shit multitasker anyway, so choosing to ignore the Twitter backchannel (that I can catch up on later) makes the presentations more enjoyable; and secondly I’m a visual learner and remember things about a bazillion times better if I write/doodle them down while I listen. Not surprisingly, this method warrants notes much more thorough than anything I’d previously jotted down at conferences, and notes that I found useful after the conference too, so I wanted to share them in case you find them useful too.

All the talks were excellent. Top drawer stuff all-round. The three talks that resonated to me the most personally – touching on problems and ideas that I’ve struggling with or focusing on lately – were from Jason Santa Maria, Tyler Mincey, and Jessica Hische. This is already verging on tl;dr so I’m just recording what they had to say and the personal lightbulbs that went off while they spoke:

The Nimble Process – Jason Santa Maria

Jason opened the day with a talk about process. I love a good talk about process – as a designer, process is what the outcome of our initial concept has to answer to; it can make or break an idea. When working on a team, it only becomes that much more important, because everyone has to bend their own personal processes a bit to be in synch with each other. Having seen this go awesomely as well as terribly, I’m a firm believer that it doesn’t matter how great your talent or ideas are, if the process sucks, the product is likely to suck. You need all three.

On to Jason’s talk: he began by talking about how we understood the web to have certain constraints, and (for better or worse) our process of making things was linear. As these constraints have evolved, so has our process. He talked about his own personal shift in process as he started working at a start up (Typekit), and how different this had to be from his previous process. At this point he showed a slide of process that looked like a neat line and then another that looked like a bunch of spaghetti. Yup, that’s working in a start-up all right!

At this point I basically just wanted to run up and give Jason a big hug because this is exactly how I felt when I started working at Last.fm in 2006 (having come straight out of an agency background). It’s just super nice to hear your heroes tell you the problems you struggle with are hard and they struggle with them too. 

He had a bunch of great insights about trying to design in the spaghetti process, so for anyone who feels like they’re drowning in a bowl of noodles, listen up:

• Instead of MVP, think MVU ‘Minimum viable understanding’: Find the quickest way to get an idea across and do so – whether a napkin sketch, a prototype, or another way. (I’m constantly asking myself if I’m using the right tool for the job  – why prototype if a sketch will do? Why sketch if lobbing an idea into IRC will do etc. – so this really resonated with me).

• Presenting with clients instead of to them: In a startup, almost everyone you work with is your ‘client’ (in the sense that you need them to trust you, and you need buy-in from them), so this made a ton of sense. Jason talked about the importance of giving clients language to talk about design, and how to show them the pieces of it (so they could understand how it might fit together) instead of what it might look like finished. I admit, this is basically the only way I know how to present to clients. There’s probably a whole other bit of writing in how I do this, but basically I like to show them almost everything, talk through the rejects, give a lot of context and tools. Sometimes I feel like it might be playing with fire, but so far it hasn’t burned me.

• Details are your enemy; as you carry on, everything comes into focus: Totally. I‘ve always thought of this as ‘broad brush strokes first’. When I was in art school, we were taught to paint by using a big brush first and the fine brushes at the end. Obvious in hindsight, but everybody in my class made this mistake at first.

• IDEAS WANT TO BE UGLY! This one goes in all caps because it was one of the most important lessons I learned that day. So many times I’ve apologised to my peers for the scratchy, ugly looking sketches I did in that rushed moment while I tried capture a fleeting idea. Never again will I do that! Of course it’s ugly, it’s an idea. Jason went on to say that ugly ideas invite participation and collaboration, neat ones don’t.

• Mould content like clay: It doesn’t make sense to decide on a grid or other design constraints up front, it’s better to dump all the content onto the page/screen and start moving it around until it starts to feel right, and then pick your constraints. I’ve struggled with this one a lot, especially because its seems like from a development perspective it often makes more sense to have a fixed design constraint (like a grid) in place first… ah, the spaghetti.

• A big +1 for Dan Mall’s thought of changing the phrase from “designing in the browser” to “deciding in the browser”. Somehow, I missed Dan saying this the first time round, so listening to Jason explain it, I was like yes, yes, yes! As I’m hyper-conscious about choosing the right tool for the job, I feel that sometimes, the browser is just not the right tool for me (especially when considering the MVU). But, the browser – or the final home for your design (app, object, etc.) is the only place for decision making to happen. Experience trumps everything. And this is true for disciplines as well. Copy, for instance, is impossible to make a decision about until you’re reading it in the context of your product.

• “Shitty first drafts” are your friend: From the book Bird by Bird (a book Relly first recommended to me and has long been on my reading list) is the notion that it’s easier to revise than create. This made me do a bit of a ‘huh’, because I often feel like I’m carrying a certain amount of personal baggage when I’m revising, where as creation feels like a blank slate, but I like this idea in principal and I’m going to give it a go.

Appropriate Tension – Tyler Mincey

Tyler’s talk was the perfect segue, because he mainly talked about what I’d call the pre-requisites for a healthy process.

(Before I get started, a quick note: there was a prevailing message of responsibility for what we should and do create in Tyler’s talk. Personally, I struggle to silence my over-active responsibility gene, so though it would probably better reflect what Tyler said if that aspect were underlined and starred in my notes, I didn’t write it down like that).

Tyler began by talking about how real-world impact requires interdisciplinary teams, and how learning how to be creative in a group isn’t easy. Definitely, I have enough difficulty figuring out how to keep Hannah functioning at max creative strength on an individual basis, let alone with a team.

So, if learning how to be creative in a group is so hard, what should you look for the first place in your group to make this a more attainable goal? 

• People who strive for a high standard and are also held to it

• People who have the authority/autonomy to get their work done

• People who feel the burden of responsibility for their work

• People who are loyal in service to their discipline but ultimately loyal to the product they’re making

He summarised this by saying the ideal place is a small group where you have authority to do stuff and want to sign your name to it. He went on to talk about the levels of experience you should look for within that group. Old dogs have old tricks; young dogs have young tricks, and both are vital. Look for a place with old and young dogs.

The next bit got really interesting for me – that you should look for a culture of respectful challenge. At Apple (where he previously worked), people frequently started sentences with “Help me understand…” when they wanted to prod at an idea. I’ve been working for a long time at how to start those sentences, so that’s a line I’m adopting.

He also talked about the importance of longevity with a team; that you should find people you want to build things with for a long time. You’ll build, break, build, break… eventually you might break through. Products don’t happen overnight. I’ve been working with Matthew Ogle now for nearly a decade, and I feel like we’re only just approaching this ability now.

If you can align all those things, you have a set up for what Tyler calls “deep collaboration”. If you’re going to remember one thing about Tyler’s talk, it should be this: that “real innovation happens by moving constraints, not just designing within them”. Having worked in and around the constraints of the music industry for the last six years, this really resonated with me. For instance, it’s nice if you make a really beautifully-designed music product completely within the existing constraints today, but ultimately it’s not going to change the world. Figuring out – through deep collaboration – how to push the envelope a little and nudge a few constraints is where innovation happens.

Tyler’s last point was about craftsmanship. He told a story about how he and his team were working around the clock to put the finishing touches on a product at Apple, and Steve Jobs asked them: Why do you put all this time into the details, the last 10% of polish? After letting his employees think about this for a bit, Steve proposed that the answer is communication. The details are how we communicate with customers; they’re how we express ourselves in the work we do. They’re how we show we care.

He ended with a plea for all of us to make a better effort to “work together” and start today by talking to each other. Designers/developers; old dogs/young dogs etc.

Procastiworking – Jessica Hische

One of the main reasons I went to New Adventures was to hear Jessica speak. Like many others, I’m a long-time fan of her work, but I also got the sense that she’d be fun and honest person to listen to speak. She was. Like, 100x more than I ever could have expected.

The thing I loved most about Jessica’s talk was that she managed to keep me in that ‘happy learning’ place the whole time. I was listening to her stories, then learning a thing, then laughing at a joke, then learning another thing. That’s incredibly hard to do. Until you sit down and try to write a talk that’s a series of fun and honest stories peppered with wisdom, you won’t realise how much of a total pro Jessica is at this. 

She also set up just the right amount of context for her stories through Jessica-land at the beginning – which is something I’ve often noted speakers (including myself) struggle to do well. You don’t want to talk about yourself for too long, but you also need to give some amount of context or the whole talk might not make sense. ‘I introduce myself’ is an easy first slide to skip over practising when you’re preparing a whole damn talk, and plus, that first minute on stage is always the worst. It’s usually after that minute has passed that the nerves calm down that things really get rolling. Jessica nailed this in a way I’ve never seen before, and gave us just the right amount of who / what / where / why up front.

Then, she explained “procrastiwork” – the work you do for fun: side projects, scratch-your-own-itch, for-the-love-of-it kind of stuff. Work that you’re not getting paid for right now, but will lead you to getting paid for it eventually. There’s the work we do for money, and the work we do for love. If that’s a Venn diagram, we want those circles to overlap as much as possible, right?

This was really unexpected and downright positive to hear her say. I always kind of assumed that those circles couldn’t overlap much, which is ridiculous, because looking back on my career so far, I’ve done a pretty decent job of doing what I love and getting paid for it. When I was younger though, I heard a number of people tell me those categories of work were fairly mutually exclusive, and I believed it. Nope. Jessica says those circles can overlap as much as you want them to.

From here, Jessica dove into how you find what you love to do. This is hard shit guys, figuring our what you love. I mean, what you really love. It means constantly asking hard questions. I’ve been trying to figure it out since I started designing. And it’s a moving target. As you mature, it changes and moves; it’s a life-long quest. To hear Jessica speak about this subject with such astounding self-awareness was really something to witness. What I’d love to know is how she learned to be so in touch with herself to articulate this stuff in the first place.

She began with the phrase “What do you love doing?” and then inserted words so it read: “What, about the work you’re currently doing, do you love doing?” I’ve always though that through experience, you find out what you definitely don’t want to do (and discovering what you don’t want is easier than, or is perhaps the first step towards, figuring out what you do want), But this process of elimination takes a while, and life is short. Jessica words this in a much more positive and concentrated way. 

She went on to say that the best way to do what you want is to have work on-hand to show people when they ask you for some. Otherwise, they will always point at what you did before and ask for that. Those requests are a nice compliment, and might be a good way to pay your rent, but they’re probably not going to make you happy.

She urged us to take notes on what we like, and delegate away the stuff we hate. It seems obvious but it took me way too long to figure this out. This was not the last time during Jessica’s talk that I wished I’d heard it, like, ten years ago.

She said she often answers questions about how she avoids creative burnout, and that the answer is having enough on your plate. (This reminded me of art school lessons again: I had a painting teacher who told us we should never work on only one painting at a time, because when you got stuck on it, the only way to get unstuck is to turn around and have another canvas on the go to work on). Procrastiwork is a way to keep enough on your plate at all times, ensuring that you have another project to turn to and unstick yourself.

Also, the projects should be diverse. Jessica explained that procrastiwork should be as varied as you want to make it. You’re not getting paid for it, so why not try all sorts of stuff you don’t know how to do (yet)? Too much of one thing is boring and will lead to burnout. She used a funny but pointed metaphor of her spouse to illustrate this. You’re not going to get 100% of your happiness from one person, that’s bonkers. You could reasonably expect to get 51% of your happiness from that person (as she described her relationship), and the rest of it comes from other things. That diversity for happiness is just as critical with your work.

Lastly she talked briefly about the nuts and bolts of her process a bit: the importance of having a personal understanding of the content you’re designing for (for her series with Penguin books this meant reading every one of the classics in the series!) She talked about the values of doing word association before sketching, because words are easier to throw out and if you start sketching too soon you get too precious. Also, it’s hard to capture the tone and setting you require for sketching without some words first.

She ended by saying that the things that make her happy don’t make you happy, you need to go find those things. She told us to focus on the now – what about your current work makes you most happy? Once you know what that is, try and do more of that thing. Don’t be discouraged if you still find yourself dissatisfied – that is bound to happen along the way – but to fill in those gaps of dissatisfaction with procastiwork.