How “tinychallenges” Came About

Jan 31, 2016 · 4 min read

After a very intense run of depression-fueled burnout in 2012 triggered by the loss of my dad, I started experimenting my way through 2013 with small challenges. My initial focus was not “get out of burnout” but rather push through personal fears, boundaries, and excuses I realized I’d been using to hold myself back. I wanted to make better use of my time, have fun and generally improve my life by following my heart — one tiny step at a time. I figured if I could put my focus into positive actions, pulling out of burnout might be a happy byproduct.

In December of 2014, I committed to doing a random monthly challenge for every month of 2015 that had 31 days in it. Because of the momentum and fun, it quickly grew into something I did every single month. I was never very consistent with how I tagged these projects. Sometimes it was #31days, #30days, sometimes #randomadventures, it varied depending on what I was doing. These challenges inspired a talk I gave last June in San Franciso at the Layers Conference called, “No Excuses.” (you can see that talk here.)

In September of 2015, my friend Brad Heintz suggested, upon joining me for a 30-day challenge, unifying the name to something easier to follow and making it easier for others to join along. We landed on the name: “tinychallenges”. Thank you, Brad!

The approach: I base my challenges on philosophies of behavioral design, same way I used to approach product/interface design when I was making products hands-on for more than 15 years (before the burnout.) I was inspired by methods and things I’ve learned and studied over the years, through my own trial and error, I had to find a way to make all these learnings meet me where I was at in my own life. I landed on a way to make monthly challenges doable for me. I failed a lot at first, because I kept trying to do too much. I thought I could do 30 or 15 minutes-a-day — that was not sustainable for me at first. I had to step back and think smaller. The simplest way to break it down is like this:

Prompt: Also known as a trigger, this is something that tells me its time to do the thing I set out to do. The idea is to find something that you do consistently, no matter your location. I travel a lot, so my first step was to find pockets of time I could use consistently. Example prompts I’ve used:

  • upon waking up in the morning [insert action]
  • while my coffee is brewing [insert action]
  • after I wash my face at night [insert action]

Action: The thing I’m setting out to do. The important thing here is to start super small (hence: tinychallenges). Lots of folks take on too much to start, don’t finish, feel like they’ve failed, get frustrated and never try again. You *can* take on more, but if you find it’s too much to sustain for a full month, think smaller. Think about actions that can be done in 5 minutes or less. You can build them up later. Go for the smaller win first. Examples of super small actions I started with:

  • write the name of a person, place or thing that inspires me
  • write a sentence capturing one thing I learned today

Celebrate: An acknowledgment that you did the thing (the action) you set out to do. You’ll want to leave it off because it feels goofy. This part is important. It can be a smile, you can raise a fist to the sky and say, “YESSS!”, you can dance a little jig, whatever you decide but DO THIS.

How it looks when you put it all together:

  • while my coffee is brewing I
  • write the name of a person, place or thing that inspires me, then
  • celebrate with Rocky pose
image source:

For my own monthly challenges, I choose a theme and some guidelines to keep the challenge simple and achievable and set out to cross the finish line. This is about experimenting and finishing. Sometimes I stumble, days have been missed, life happens. What I try to keep in mind is this quote from one of my all-time favorite movies (again with the Rocky reference):

“It doesn’t matter if I lost this fight. All I want to do is go the distance.” -Rocky Balboa, from the movie Rocky

Keep going. Learn more. Do more. Have FUN.

With the encouragement of Brad Heintz and now many others #tinychallenges is blossoming into a small, supportive community of people who get rid of excuses and DO THINGS. In December 2015, Daniel Steinberg and I started a tinychallenges podcast, we use storytelling to inspire and frame a challenge, then check in with our community on how it’s going.

It’s fun, and growing! Hope you’ll join us.

The website: The podcast:


Written by

Co-Founder Picture This Clothing + Board Member @MartianCraft // Mom+ Speaker+Writer+Professional Experimenter // more at