What I Learned From 100 Doodles In 100 Days

Steve Portigal
The Overlap
Published in
13 min readJun 9, 2015


Here’s an admission: I can’t act. As a kid I thought I might grow up to be a actor (or maybe a stuntman), but I never did. However, that hasn’t stopped me from studying and teaching improv. Another confession: I can’t sing. I do sing in the shower and in the car, of course. I’ve recorded a few songs with friends and I even did karaoke for the first time last year. Also, I can’t build stuff, but last year I made a ramp to help our aging dogs go from our back porch to the lawn to do their business

And finally, I can’t draw. But I made a comic book in grade 8. I teach workshops where I encourage people to develop their ideas visually (and as I learned from Kate Rutter, just calling it “making marks on a page.”) I am surrounded by designers and visual facilitators but I’m well aware that I’m outside my creative comfort zone here as well.

Maybe it’s uncomfortable to read my declarations of what I can’t do. Can’t is considered a bad word. But let me reclaim it here and acknowledge its role in demarcating the edge of a comfort zone. Drawing is outside my comfort zone. But I’m going to tell you how I explored that boundary and the territory beyond.

The Inspiration

Last November I sat in the audience at the HOW Interactive Design Conference as Jim Krause spoke about “Habitual Creativity.” He talked about breaking out of unconscious habits (e.g., driving to work the same way each day and never really “seeing” what was around you) and creating new habits by taking on new behaviors. At some point during his talk, I made a note that read simply “100 doodles in 100 days project.”

The idea of taking something new and doing it deliberately and repeatedly appealed to me. I was even reminded of other efforts like Rachel Hinman’s 2008 project “90 mobiles in 90 days.”

After making the note, I set the idea aside, eventually deciding to kick the project off in the New Year. As I reflected on what I would actually do, I confirmed my initial supposition that “doodle” was the right level for me to focus on, imagining this hierarchy

  • Scribble
  • Doodle
  • Sketch
  • Drawing
  • Art

By focusing my effort near the bottom, I was framing the task in a way that was safe for me. No, don’t worry, I’m not drawing, I’m not even sketching. I’m just doodling! Doodles aren’t of consequence, they’re little visuals you do mindlessly in the margin of your notebook to keep your hands busy while talking on the telephone. They aren’t intended to be “good” (whatever that means).

I made a quick selection from my piles of empty notebooks and pens. While optimizing the pen and paper selection might make sense for some, I wanted none of that — that’s knowin’-how-to-draw talk. With very little thought I grabbed a BIC GripRoller and a Japanese wire-bound B5 (about 7 x 10) notebook with dot-grid pages. I went through the book and numbered and dated the first 100 pages, thereby committing to a project that would run until April 10. Finally, part of this new habit would be to publish the doodles as I made them (on Twitter, as well as Facebook and Flickr).

At HOW, Jim Krause told us that new habits could make me more creative and that informed how I framed this experiment. My goal was not to become better at something by practicing but rather to do it and look for the side effects. If this was science, we would identify ahead of time what it meant to be more creative, do a pre-test to establish a baseline, do the experiment and then do a post-test to see if it “worked.” I had no passion for that; as with all these decisions I was ruthless with myself about eliminating barriers.

The Doodling Begins

Clock faces, from memory

As I began on January 1st, I continued to refine my problem statement for this daily doodling task. I wanted to make the rules for myself explicit. Since I had committed a page for each day already, there would be no tearing up a day’s doodle-in-progress and starting again. I would not practice a particular doodle idea outside the notebook so that the doodle is somehow better. I would try to use the whole page (although the notebook was much larger than that what I assumed a “doodle” needed to be, I stuck with it). If I was drawing something specific like clock faces I would not go online to see exactly what a sundial or alarm actually looked like.

I soon discovered that trying to draw — to represent a familiar thing so that someone else might recognize it— was a challenge. Even further, If I began the doodle with an endpoint in mind, I was not going to be able to get there. (or I would need to set the bar awfully low). On Day 12 I drew a big ‘ol question mark, dotted with question marks. That may have begun with a line or two but it quickly became a specific idea and I worked to execute it. But the more abstract my intention was, the more likely I was to be able to do it. If I tried to draw a dog, it might end up looking like some weird animal. Doodling aliens or weird creatures, where I didn’t know what they were supposed to look like, was safer.

I began to learn how to play, using a pen. Finishing a doodle where anyone could see what it was supposed to be was not going so well. So the more I could sidestep that, the more I could succeed. I was uncovering the boundaries of my own limitations and finding ways to work with them instead of against them. In doing so I was defining a specific version of success for myself.

Eventually this evolved into an improv-like doodling activity: start the doodle with a gesture that I haven’t thought about at all and then see what I can construct out of it to finish it. This turned out to be a very pleasurable problem-solving activity — break something and then try to fix it.

That raised another element of the problem that needed refining — what it meant to “finish.” How do I know when a doodle is done? The more abstract and playful the emergent concept, the more ambiguous that notion is. Here I gave myself permission to leverage another notion from improv, the ability to sense the ending (often parodied as “…and scene!”). It was done when I felt like it was done and I began to develop the ability to look for the feeling of that moment approaching (with the emphasis on feeling over knowing) and honoring it.

I began to grow in confidence with the improv approach to starting; maybe going beyond an initial line to a larger collection of freer lines. Day 21 is the first example of that at its most free, where it’s an initial set of lines with a little bit of doodling that turned scribbles into a mysterious lady’s face (well, that’s what I see, anyway). Of course, a day later I was back to deliberate task-focused drawing, creating as many different types of eyes as I could come up with.

Discovering how to make scribbles into weird characters.

I picked up the thread again on Day 24 when I began to play with deliberately aggressive scribbles that got marked up into characters or scenes. Ultimately this would become the style I fell in love with and was the most successful with.

Aggressive scribbles become characters

It’s always been fun for me to draw creatures or characters (and as I write that it’s hard for me to imagine what else you would ever want to draw?) and I did that rather consistently. Then on Day 39, I discovered another way of moving the pen, where it wasn’t an aggressive scribble, nor the deliberate drawing of a line, but something looser; intentional but not focused beyond the limits of my fine motor skills. That style brought me back to childhood, where art teachers taught us “sketching” as a hairy-line approach, where multiple overlapping passes at the same line , correcting or improving on each other, led to a considered result.

Part of clarifying the doodling task was exploring how much I was okay with repeating myself (not in content but in approach). If I figured out a way to tackle a doodle, was it okay to do the same thing over and over again? Or was I requiring myself to try something new constantly? I tried to push myself a bit, exploring what I could do “well.” I was happy with some doodles while others didn’t come off well — but I had 100 of them so there would be another doodle tomorrow; no one doodle had to stand for anything on its own. This was about process (100 days!), not outcomes.

The Audience Is Listening

I posted the doodles on social media every day, usually within seconds of completing it. While it was a daily ritual, I didn’t tie it to a time of day. It was an easy way to feel a sense of accomplishment, especially where there were aspects of the day that were less in control. There were a few mornings where I sat on board a plane awaiting takeoff, shooting a photo of the notebook on the seatback tray. The responses were interesting and fueled my own enthusiasm and drive to complete the project.

At first, Facebook friends were teasingly critical of anything bizarre or abstract, typically suggesting that the image revealed my diseased mental state. That teasing was a form of support, both of the project and of the results. People began to express enthusiasm or just say what they thought they saw in a particular doodle. Abstract doodles drew comparisons to famous modern artists. And people began to tell me they were good. That thrilled me but it also raised the stakes I had so carefully tried to keep low. They were never supposed to be good! I can’t do good; they are just doodles. If it’s possible for the doodles to be good, it might be possible for them also to be bad, a position I had worked hard to avoid.

While I turned to use social media to give me structure and reinforce my commitment, I was probably looking for attention and when I got it, that shifted the nature of the problem again. Now I had an audience. I was engaging them and of course I wanted to please them. I can’t say there was some artistic purity lost because that never existed, but as the online interaction became part of my experience I had opened up a carefully managed failure-averse activity to elements beyond my control.

And for sure, I did get better. You can see my ability and/or my confidence to create scenes and tell stories. I experienced a palpable sense of reaching a new level, plateauing for a while and then making another leap. Each day brought fear and tension, worrying oh jeez what am I going to do this time? as well as the daunting feeling of having to deal with that fear for many many more times. As the weeks passed, there was always a brief but specific moment of tension as I opened the notebook to a clean page. But more frequently I set the notebook down with certain sense of accomplishment, feeling that I had moved to another level. Recall that I wasn’t doing this to get better at drawing; my inquiry was about other effects. But, go figure, the practice of the doodling was impacting my doodling skill and my confidence in being involved in a creative endeavor — the thing I had tried to keep out of it. If a creative person does creative things then perhaps the converse was also true and as I did creative things everyone, including me, could see that I was a creative person.

Twitter afforded less direct affirmation, but allowed for more discussion of the process. I had helpful interactions with people who I respected for their visual creativity. For example, Ian Smile and David Sherwin gave me explicit permission to draw squiggles and put eyeballs on ‘em; that it wasn’t cheating (I think once I figured out I was good at that, it felt like a cop-out and it was helpful to get that permission). Christina Wodtke shared the details of her own drawing practice with me and connected me to plenty of resources from people teach others (for example Squiggle Birds, as explained by Dave Gray).

I didn’t realize that a 100 Day Project was a thing (it is); I didn’t know that daily drawing was a thing (it is). I was naively doing this on my own but finding that a lot of people have been doing something like this. Of course, I see those folks as people who can actually draw; they are the insiders just doing the thing they do and I’m the wannabe screwing around. Being the outsider is safe because you never have to hold yourself to the same standard, but again, my framing was about making it safe to do something that was outside my comfort zone. I have no idea how the #dailydrawing people feel about their drawings; they may be as dismissively pleased with the approbation as I was.

Rapid doodling produced interestingly successful results

As I grew in confidence and developed a number of techniques that I had a measure of mastery with, I began to explore doodling very quickly. This is about the pace more than the duration and was a way to force letting go of the planning/thinking part of my brain and opening up the doing. As someone who is frequently in his head and not his body, this was quite a kick when I could pull it off. I would open up the notebook and go into a zone for a short period of time and have a result. Sometimes these would really just work.

As I got into the 80s, I began to sense the ending approaching. That created pressure and anticipation for me and my audience. “Nearing the end, Steve!” “What’s the last one going to look like?” “Can’t wait for 100!” When the project had felt almost infinite it was liberating (Screw it up? Do better tomorrow!) but there was now a looming finality. And this had evolved into a performance (yet another example of how the journey was so much about redefining the “creative brief”). I felt like I wanted to go out big. And so I took cues from fireworks shows, rock concerts, and final episodes of TV series to inform just what big meant for 100 Doodles in 100 Days. I did plan what I was going to do for Day 100. Using my favorite (and most comfortable and most consistently successful) approach of doing a set of quick scribbles and turning them into characters, I went big. I did 29 scribbles on a page and made them all into characters. I did them all very quickly, but I pulled out the stops to say goodbye.

A big finish

To my surprise and delight, people have told me that they were inspired by 100 Doodles in 100 Days. One person told me of their plans for 100 Days of UX; another planned 100 Haikus in 100 Days! To start off with impostor’s syndrome and end up inspiring others was unexpected. My experimental focus was on my self; I hadn’t even considered that the consequences could be what other people end up doing.

For me, I enjoyed the success of creating images that give me joy when I look at them now. I learned more specifically what I’m lacking in drawing skill (e.g., perspective). I’m tempted to find some form of instruction that would help me develop.

I enjoyed the feeling of being legitimate in a creative practice and I feel a small sense of loss without that routine or without that identity in front of friends and peers. After wrapping up the doodling, I find that when I use my iPhone to post photos, I feel the tug of muscle memory that I built up from 100 days of similar cropping and tagging and I’m ever so saddened. Of course, nothing is stopping from me continuing but the project was defined with an endpoint and to be true to the experiment, I need to take a break. Do I want to continue or was it just the momentum — or the commitment? And more importantly — what did I learn? Obviously getting to the point of reflection in this article was the next step I needed. Maybe now I’m free to doodle again?

100 Doodles in 100 Days revealed the not so-surprising (yet specifically unintended) consequence that practicing a task can improve your performance of that task. But for me the greater lesson was the enormous power in considering all the constraints of a problem and then continually reframing that problem. In my doodling journey, this was how I set myself up for success. Even though I don’t think of myself as being able to draw, I did it for 100 days, and it’s been wonderful to feel good about myself creatively. It was preparing for and managing of the journey that made that happen. We never have full control over every aspect of every challenge, but we can look hard at the elements we do have control over (even the labels we use for things) in order to give everyone involved the best chance of succeeding.



Steve Portigal
The Overlap

Author of Doorbells, Danger, and Dead Batteries & Interviewing Users (http://portigal.com/books ), Host @DollrsToDonuts podcast, work at Portigal Consulting