100 Days of Questions

Molly McLeod
Jul 28, 2015 · 6 min read

“The purpose of art is to lay bare the questions which have been hidden by the answers.” — James Baldwin

Why do we ask questions? Questions are usually more interesting and thought provoking than answers. Questions are a vital part of our culture. Will you marry me? To be or not to be? Who? What? Where? When? Why? How? Is this the real life? Is this just fantasy? I recently finished asking 100 questions for the 100 Day Project.

The 100 Day Project originated as a grad school workshop by Michael Beirut, and was popularized on social media by the Great Discontent and Elle Luna. The name says it all: do one thing every day for 100 days. It could be a photo, a poem, a collage, a dance, a new recipe, an exploration of triangles, responding to a paint chip in writing — anything you’re passionate about, united by either medium or subject matter.

All the questions featuring myself. Sometimes the most convenient canvas is my own body.

When I was deciding what project I wanted to do every day for 100 days, I chose to attempt asking 100 questions because I believed it would be:

  1. Something I enjoy. I love lettering, so choosing something typographic in nature made sense.
  2. Something I could do in 5–10 minutes. Occasionally I spent an hour on a post, but I wanted to be able to do it quickly if I was tired or busy.
  3. Something medium agnostic. I wanted to have the freedom to use whatever materials were handy, or new tools I felt like exploring.
  4. Something flexible. I knew it would allow me to be playful or reflective, depending on my mood.
A few of my more introspective questions

Goals and emergent discoveries

Everyone who did the project had slightly different goals. My goal was simply to show up and make something every day. A huge blocker for me in making art is feeling like everything I make has to be good, or serve a purpose. Many of my posts aren’t that good and will never go anywhere. Many of them originated from or turned into long, meaningful conversations with friends. Many of them yielded new visual styles I had never tried before than then made their way into other art projects.

I learned a few lessons about my artistic process along the way. If you have any passions you’ve been neglecting, maybe they’ll help you too!

A few of my more whimsical questions

Having a “project” helps

While I was a teenager, I seemed to have limitless energy to create. I was writing, taking photos, and designing for the school newspaper and yearbook. I churned out Photoshop experiments every day. I made Powerpoint art. I directed short films. But as time went on, and my career as a designer progressed, I found it harder to muster the energy for personal work.

As much as I enjoy lettering and photography, finding the time to develop my crafts outside of work is difficult without a purpose. Have the framework of the 100 Days Project kept me motivated to make art in a habitual way. Even when I was sick and bed ridden, even when I was traveling all day and didn’t get home till 1 am, even when the last thing I wanted to do was open Instagram, I didn’t want to break my streak.

A mantra I’ve been spreading at work

Make many things

The only way to get good at something is to make a lot of things over a period of time. Eventually, sometimes unexpectedly, something good will emerge out of a pile of rejects and experiments. I didn’t have the time or energy to make everything I posted a carefully polished piece. Many of the images I posted I likely wouldn’t have shared (or even made!) if I hadn’t been doing the 100 day project.

Surrendering to the process, staying disciplined, and letting go of perfection is essential to make it through 100 days.

I have a few lettering styles I’m comfortable with, but having to make something new every day compelled me to try different styles. I took a lot of pictures I wouldn’t have taken otherwise. I’ve created a fresh body of work, and while most of it I wouldn’t share in a portfolio, it’s increased my toolkit of go-to styles.

Metacognition graphs

Let go of arbitrary rules

Creativity thrives under constraints. It can be helpful to have a set of rules to play within. But I found myself stuck at times when I made up unncessary rules, such as using only my own photos (I broke this rule only once, for an image I was mesmerized by), or hand lettering all the text (a few posts I made in Photoshop). Once I let go of the rules that weren’t essential to the project, I had more freedom to experiment.


Seeking social validation is okay

I usually posted my image right before I went to bed, and woke up to a dozen or so tiny digital hearts from friends and strangers.

Over the past year, I’ve been intentionally not sharing much of my art publicly — challenging myself to share it privately with only a few friends or family so it has more meaning. I let go of caring how many likes or favorites or views my artwork gets. But I can’t deny some degree of digital validation and appreciation feels good. I enjoyed the occasional thoughtful response to my questions and conversations they started. The social expectation of sharing something every day is part of what helped me continue my streak.

I made it through 100 days! What’s next?

A picture of an Instagram picture of printed Instagrams

On the last day, I printed out all of my posts from screenshots, to include likes and comments. I wanted to see how they looked all together, search for any unnoticed patterns, sort them by medium, and see if there were any trends in the most liked or least liked. It was so satisfying to see the sheer volume of stuff I made.

100 days went by much quicker than I expected, despite all the things that happened in that period of time. It’s a nice personal archive of what I was thinking about, the places I visited, the conversations I had. I’m taking a break, but I’ve strongly considered continuing the project, or perhaps doing a variation on it.

The 100 Day Project is a fun, low barrier way to get in the habit of making things. If you’ve got passions and hobbies you’re struggling to make time for, give it a shot!

Unexpected symmetries

To see all my #100daysofquestions posts, check out my Instagram. My parents both did 100 Days too! Check out my mom’s beautiful hand drawn type and my dad’s breathtaking daily garden photo.

If you’re interested in my periodic reflections, doodles, and gifs about the human side of design and technology, sign up for my newsletter M Dashes.

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