My work on YDays, a site for creative drawing challenges, began in August 2020, and I’ve enjoyed wearing many hats, combining my skills in creative coding with product design, front-end development, user research, outreach, and marketing.


The idea for YDays came from a Slack community of type designers and lettering artists I’m part of. We run a weekly challenge to make a piece of lettering, where someone comes up with a theme that we all have to pick a word or phrase from. Then we have a Slackbot that generates randomized parameters we all need to follow. We submit our art on Sunday and vote, and the “winner” gets to post all the submissions to our shared Instagram.

Here’s an example of lettering our community created in a challenge we held in the run up to the mid-term elections in November 2018:

I was inspired by these elements—prompts, constraints, and community—and I had the idea to make a way to host drawing challenges with friends. As a first step, I dusted off my front end skills and got a proof-of-concept working. I used P5.js for the drawing interactions, React for the front end, and Firebase to store the drawing data.

I shared this demo with a couple friends, who volunteered to help turn the proof-of-concept into a working product.

Product concept

What makes YDays unique is that when you get a prompt to draw something, you also receive an unusual drawing tool. The challenge is to create something expressive that corresponds to the prompt when faced with a drawing canvas that doesn’t behave the way you think it will.

For instance, this prompt says to say ‘hi’ with a drawing tool that makes alternating black and white circles:

Here are some examples of creations users have made with this prompt and tool:

I started YDays during the pandemic as a way for people to connect with friends and teammates. You spend just a few minutes a day on their own time doing a fun drawing using an unusual tool, and then over several days of a challenge get to see what everyone in the group comes up with. At the end of a challenge you see a summary and gallery of all your drawings.

Launch and initial feedback

I spent a few weeks with my team building out accounts, challenge creation, and the daily flows. We invited friends into a closed beta and ran a few of pilot challenges. After working out the kinks, we launched the site publicly in October on Product Hunt.

In the first month after launching publicly, we had 1000 users join the site, creating private challenges with friend and teammates to draw together over five days.

In December 2020, we ran our first all-community drawing challenge on YDays, and over 100 people, mostly strangers, participated in drawing together. The first day of the challenge asked people to draw the view out their front door using a brush that lets you make flowing strokes that change color and size as you draw.

Here were some of the drawings people made:

We conducted ongoing interviews with our most active users to understand how they were using YDays and how it might be improved. We learned that YDays was a “refreshing” experience they looked forward to each day. They enjoyed how the tool adds “chaos” and helps you be more creative by not letting you do the first thing you try. We heard that some of the biggest pain points involved remembering to come back each day, inviting friends to join, and starting a new challenge once the current one ends. People were using YDays as a way to keep in touch with coworkers and online friend groups.

Designing a library of drawing tools

YDays has a library of 30+ drawing tools, written in P5js. Each tool has a different visual style, and some of them have animation built into them.

When designing these tools, I’ve found several criteria for what makes a drawing tool successful in YDays.

  • It’s fun and natural to play with.
  • No distracting interface elements, and no instructions on how to use it.
  • Allows a novice to create something that looks appealing.
  • Supports a wide range of creative expression.

Here’s one example. You can draw a relatively straight path if you connect two points directly. But if you move to one side or the other, you can “bend” the line into a curve.

Here are some drawings people have made with this tool! It’s been fun to see how people use the constraints of the tool to guide them and inspire their creativity:

It’s also really amazing to see some people become experts at the tool. They get to show off their skills and express themselves.

Defining the brand

A fun part of working on YDays has been developing an optimistic, playful brand. I collaborated with a friend, Angy Che, on some of the logomark and illustrations shown here:

I’ve also used language in the product, marketing newsletters, and social media to convey a quirky and humorous sensibility. I’m proud of the work I’ve done on the brand, making a brand that’s positive and fun, but also sophisticated.

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