The Why Behind YDays

A site for creative drawing challenges with friends

Peter Cho
Peter Cho
Oct 29, 2020 · 7 min read
A selection of drawings made by YDays users

Like you, I’ve been spending months stuck inside, unable to see friends and loved ones freely outside of the Zoom boxes we’ve grown so tired of. We’re all craving novel ways to connect with each other. And maybe, like me, you’ve hoped to use this time to improve yourself in some way. Could we be more creative, practice new skills, or make things?

YDays was imagined as a response to these needs: it’s a way to connect with our friends or teammates, be delighted each day, and inspire one another. Each day of a five-day YDays challenge, you’ll get a different puzzle-like drawing tool to explore and simple prompt to respond to. You’ll discover what you can come up with and witness how we express our unique personalities through low-key but surprising little doodles.

A main influence for the idea behind YDays came from a Slack community of lettering artists and type designers I belong to. We have a channel for running challenges that we call typecookers, so named because the type we draw has to follow an auto-generated “recipe” for characteristics of the lettering. (The term originates from KABK, a type design school in Holland.)

An election-week typecooker challenge from November 2018.

Each week, we agree on a word, phrase, or theme and use a bot to generate the recipe that we all need to follow, characteristics like weight, width, stem construction, stroke endings, and lengths of ascenders and descenders. Submissions are due Sunday, and from morning until late evening, the creations trickle in to the channel. We chat about the designs, we vote our favorites, and then the winner gets to post them to Instagram. It’s part competition, part inspiration, but above all, it’s super fun.

For “makers” like us, creating things is what fuels us. We have a strong internal drive to make new things with our hands and see them in the world. But our urge to make things competes with our desire, especially now, to sit back and consume media instead — so it helps to have some external motivation. Our typecooker challenges on Slack are successful motivators because they combine two important factors: constraints and accountability. Constraints are great because they limit the field of exploration you are permitted to use and force you to exercise being creative with a limited palette of tools—constraints can often feel freeing! Accountability is helpful because you have a deadline and a community of friendly folks who are both counting on you and cheering you on. You don’t want to let them down.

When you create a five-day challenge on YDays and invite friends or coworkers, you get a different interactive drawing tool every day. The tools have unusual properties, so part of the fun is discovering what you can make. They impose unique constraints you’ve never seen before in a digital drawing program, and these limitations change every day. It’s a bit of a level playing field too since no one will be an “expert” at drawing with a novel tool.

Explore the drawing tool, its constraints and possibilities. Then, see what your challenge mates came up with.

By joining a challenge with friends or teammates, there’s a bit of accountability too. It’s no big deal if you happen to miss a day, but it’s most fun when everyone is contributing every day, so you can see how the others express themselves when given the same prompt and tool constraints.

Since we started testing with users in late September, we’ve had a few hundred people try out YDays. We’ve gotten a lot of useful feedback like: When I got to the challenge screen, I had no idea what to do next. This kind of feedback has been essential in making the experience better, and we know we’ve still got a ways to go.

We’ve also had the benefit of having designers as early users. They’ve offered such helpful observations and advice about onboarding and usability. They’ve shared friction points about the mindset of a new user, both around joining, or starting their first challenge. And they’ve asked great questions about the strategy for how users can stay engaged throughout a challenge and how they can keep building and growing over time.

But for the actual drawing activities, the feedback has been really positive —we’re hearing that discovering the drawing tool each day is the most fun part of it for many people. I think YDays can be enjoyable for people of all drawing abilities: both people who draw regularly as adults and those who haven’t drawn since they were a kid.

A collection of “faces” drawn with one of the animated drawing tools

Most of all I’ve been blown away by what participants in YDays challenges have been coming up with. People continue to surprise me with their drawings. It leads me to believe that while constrained, the creative possibilities of each tool is still a limitless space.

Some quotes we’ve heard from early users:

I’m having a lot of fun! And it’s nice to see that even as a s**t drawer I can get somewhere and it’s humbling to see what others can do…

Once my slow gears kicked in, I LOVED it. I learned to wait for inspiration until I saw the tool. And each day I was excited to see what the new tool would be.

Loved this whole thing! It was exciting every day to sit down and do a low key doodle. Also loved seeing the creativity of other people and being surprised every day by their results and by the new challenge. It was time-boxed, so I didn’t worry about running out of steam.

In August 2020, a layoff from work led me to devote my full time to this passion project. I recruited a couple friends to join me part time in helping get the project off the ground and into your hands. Over the past couple months, I’ve gotten to dust off my coding skills in React and JavaScript, learn more about the capabilities and limitations of Firebase, and practice my skills in UX, UI, user research, usability testing, and branding with quick iteration loops with users.

The most fun part for me has been exercising my creative coding skills (using p5.js) to come up with unexpected drawing tools. For me, a good drawing tool in YDays is one that feels like a fun toy to play with, feels natural to use, doesn’t include any distracting interface elements or instructions on how to use it, and allows a novice to create something that looks cool, all while still supporting a wide range of creative expression. And bonus points if it has animation built into it.

As a designer-turned-design-leader, it has been a fun and rewarding experience to try my hand at making things again. What a rush it is to hear feedback on something that’s broken in the user flow, push an update, and see it go live. Or to invent a new drawing tool, put it out in the world, then see the amazing things people I don’t know are able to come up with using it. I’m excited to bring YDays into the world, and I’m even more excited to see what you will do with it.

  • Sign up at and start a challenge with friends or teammates.
  • What’s confusing to you? How could YDays be improved? What else should we build? Leave a reply, or write us to let us know what you think:


Behind the scenes at YDays, creative drawing challenges with friends