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AUX Design Challenge: Sketching App


My life as an apprentice alongside Brad Sheehan at Fresh Tilled Soil began with a two-week design sprint where we were challenged to design and prototype a product that solves a need in a given category. To kickstart the fun, we drew a category, randomly, out of a hat. I drew “Art and Design”. My initial reaction was “Oh man, how am I going to design for design? This is the most meta design topic ever!” The art and design realm is certainly massive, and if you really think about it, everything is designed. I knew that if I was going to build a meaningful product in two weeks I would have to narrow my focus as much as possible.


mind map

In order to cast a wide net of potential ideas, I drew a mind-map that captured many of my associations with “art & design”. This lateral-thinking exercise exposed many of my own pre-dispositions about the topic and gave me insights into potential problem areas. The bubbles across my map included art galleries, street performances, design thinking, hipsters, photography, sketching, and even mind-mapping itself. There were two that stood out: street performances and sketching, not because they were obvious problem areas but because they were both areas that I was passionate about. If I’ve learned anything about design in my life, its that its nearly impossible to design well without putting your heart into the project.

Failing Quickly

Initially I was set on the idea of empowering street musicians and the people who enjoyed their craft. I had millions of ideas floating around in my head, but I wanted to make sure that I wasn’t delusional, that I was tackling a significant need. I traveled to Harvard Square after work and serendipitously found a guitar player strumming near the Red Line entrance. I sat, got out pen and paper, and observed.

I jotted down everything from the style of music (a mix of Bob Marley and Jack Johnson) to the amount of money donated in the short time I was there (about $5). I was desperately trying to find something that was “wrong”. I didn’t find it. During a break between songs, I approached the musician and asked him some questions. “How often do you play here?”, “How do you figure out where to play?”, “How many people usually give you money?” I was leading him on: “Do you use a smartphone?” I didn’t get any answers that hinted anything was wrong. He played when and where he felt like it, he appreciated anyone who tossed a penny in his cap, even if he made one cent in five hours. He had a smartphone, but he only used it to communicate with his friends (what did I expect?). I was frustrated at first, but I soon realized that knowing what not to design for as helpful as knowing what to design for. I was not going to design for street musicians.

Behavior Change

behavior change chart

I love to sketch, but it’s not something I do regularly. It’s something I do when I’m riding a wave of inspiration or designing a mockup before I go into Adobe Illustrator. I wish I sketched more, but I have trouble coming up with inspiration. I wondered if other designers and creatives felt the same way. Luckily, I could test my disposition with the other designers here at Fresh Tilled Soil. After interviewing a handful of my co-workers, I was beginning to glimpse shimmers of potential. To reinforce my hunch, I found countless blog posts that harped about the value of sketching when it comes to design. I knew I was on to something.

While many of my interviewees said they would love to sketch more, I was skeptical that if I shoved a piece of paper in their face they would be motivated to draw something, let alone do it on a daily basis. There were certainly a lot of factors at play and many could be attributed to the challenge of changing habits.  Habit change is habit change everywhere, and there are plenty of resources describing the most efficient ways of designing for human behavior, whether its going to the gym more or sketching regularly. However B.J. Fogg, a researcher at Stanford, stood out to me as an influential source when it comes to tweaking habits. He developed his own model which points out three key variables: motivation, ability, and triggers. When both motivation and ability are high, the trigger should cause the desired behavior to flow easily. However when either motivation, ability or both are low, the trigger doesn’t do much to encourage the behavior. I aimed to make motivation and ability as high as possible so a simple trigger, such as an email or push notification would lead to a sketch.

I figured that much of the motivation to draw was inherent so I put much of my focus on the ability of the user’s to get sketching as effectively as possible. One of the biggest inhibitors of sketching that I discovered was the lack of a prompt or inspiration. We all know the frustration of staring down a blank page. The key functionality of this app would be to deliver a prompt. But how? And for how long? And what kind of prompt would it be? What would happen when the person was done sketching?

User Testing

drawing essentials

I began to answer some of these questions with simple user testing.  I started with four different kinds of prompts: a recognizable noun (i.e. apple), a personal noun (i.e. your biggest fear), an obscure noun (hilarity), and a specific scene (i.e. a hippo using a vending machine). I shuffled the prompts and gave them to my co-workers with a time limit of one minute. All of the users agreed that the most specific prompt was the most fun to write and this makes sense because it gives the person drawing a creative constraint that was enough to get them to visualize the scene, whereas something like “hilarity” would be a cause for delay as the person thought about what hilarity meant to them. The users also agreed that 60 seconds was an appropriate amount of time to sketch something out without thinking about it too much, but it was long enough for them to put in the detail that they wanted.

With a prompt delivery method in mind, I mocked up some screens in Balsamiq and then opened Sublime to begin coding the prompt delivery functionality as well as some of the other main features. I planned on making the prompts random and found “Cards Against Humanity” to be a great source. I liked the idea of having the person click a “reveal” button that would then display the prompt alongside a one-minute timer. After time was up, the prompt would disappear and another screen would show up that directed the user to take a picture of their work.

The Final Build

prototyping sketches

sketchy home

what you need


ab electrocuter


With my final version in mind, I was able to rapidly code the random prompt delivery, a Javascript timer, and a “take photo” button. Although the new prototype was very rudimentary, I had a much more realistic product to test with users. In my next round of testing, I got some great feedback. Something that I hadn’t considered was the “zero-state” user who is picking up the app for the first time. In all of my user testing, I had been the one to tell people that they needed pen and paper. If this was going to be a standalone app, I wasn’t going to be standing over people’s shoulder telling them what they needed. My advisor for this project emphasized the importance of minimizing the time spent in the app, and maximizing the time spent doing the desired action: drawing. Clicking through unnecessary screens would frustrate the user and prevent them from building a habit. I wanted this app to be something that people looked forward to using. To address what the users would do after they finished drawing, the users suggested that I add in a way to document the drawing in a sort of journal.

In the remaining time, I was able to add in these desired functionalities and style the interface so it was enjoyable to play with and use. There are, of course, many further improvements I could continue to add. These include the ability to share photos, a notification system that pings users when it is time to sketch, and a tutorial that listens to the user’s preferences for types of prompts.

If you would like to see the app in action go to:

Author Will Dickey

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