How we created the Clarity Cards

Whenever you create something it feels awesome if you also have a really cool story to tell about how this thing came to be. Below I would have loved to share with you the story of how Dave and I have travelled around the world for years, doing research and interviews with the most incredible thought leaders in personal reflection, facilitation, psychology, design thinking etc. How we processed and distilled down their wisdom to a set of 54 playing cards with the ultimate prompts for reflection. Wouldn’t that be a great story? Wouldn’t that make the cards feel powerful in your hands? A force. A weapon against ignorance. A great power to be wielded with great responsibility.

The version 1.0 prototype of our clarity cards

But that’s just not exactly what happened. Here’s what I can remember. I fly a decent amount with my work at Hyper Island, however, the milage policies are always changing and the economy flights I normally fly suddenly only gave me half as many miles as they used to. When December 2015 came around I was right on the cusp of losing my frequent flier benefits: a mere 800 miles was what I needed. I know that in yoga it’s a great practice to let go. Let go of ego. Let go of material belongings. I’m not sure if the scripture also mentions frequent flier benefits specifically or if they are part of a bigger overall group. But yoga practice or not, I just wasn’t ready to let go of these privileges.

I made a plan: I would fly from NYC to St. Louis, MO, and visit my dear friend Dave. Dave is a fellow visual thinker and a huge inspiration for me, so it is always a huge treat to be received with open arms by him and his wife Michelle, and to come and stay in their house. It had been two years since my last visit so it was about time. There is something really special about just spending time together like that. The conversation flows. We discuss. Explore. Always with mutual curiosity and respect.

What always happens at some point, this time it was when we were done eating our dinner (a delicious chili), was that we began flipping through each other’s notebooks. For someone like me, who writes about my fears, and frustrations, joys and struggles, it’s a rather intimate experience to have someone browse through my mind without any filter. But I trust Dave, and I also get to browse through the fragments of his imagination which keeps me conveniently occupied. We each explore and often ask clarifying questions. What’s happening here? Why do you do it this way?

Image of the prompts we captured one evening in St. Louis.

It was during this mutual notebook-mind wandering that Dave said that he really liked all my self reflection. He wanted to do more of that. And so he began looking through my book to find the questions I ask myself. He found some sticky notes and a pen and together we began capturing and sorting the questions into four groups: facts, feelings, insights and actions.

“I bet we could make a really neat deck of cards with these questions”

said Dave when we were done. Then we talked about 100 other topics and almost forgot about it.

But when I got back to Brooklyn I couldn’t stop thinking about this. I began searching for a place that could produce a deck of cards and spent an evening designing them in InDesign. I ordered three decks as an initial test. This was December 30th.

Two weeks later they arrived in my mailbox and I quickly put a photo on my Instagram and Twitter. Normally it’s only cute photos of my well-above-average-cute kids that will get so many “likes” (who’s counting anyway), while anything I share that feels more work related goes by relatively unnoticed. I was so surprised by the positive response. People were immediately asking where they could order a copy.

I’ve been an entrepreneur since I was 15, and in my experience I normally have to work for it. It’s not about working “hard” as americans always claim, but I have found that working consistently for a while on the same thing seems to help. This project, however, almost feels like it came too easy. We just acted on an idea that came one evening in St. Louis.

However, this also reminds me of a story Dave told me once about Pablo Picasso. I don’t remember the details exactly, but essentially Picasso was commissioned to create a drawing, and he was paid a large sum of money for his work. He shows up and spends only minutes on scribbling before he says that he is done. The client reacts, like most people probably would, with astonishment and surprise: “you’re done already? But this only took you a few minutes!” Perhaps he felt a bit cheated for hiring a great artist and paying him a lot of money and then he just scribbles for two minutes. But Picasso sees it differently and responds:

“No dear Sir. This took me my entire lifetime!”

In a way the same can be said for our project, because even though we didn’t travel with the specific aim of meeting and interviewing luminaries, I have personally been doing reflection work alone and with groups at Hyper Island and long before, so the questions that I use in my notebook are in many ways a refined distillation of years of practice. And Dave, also a long time entrepreneur, both recognized the value, moved quickly to action, and crucially connected the questions with the idea of a deck of cards. He also added additional questions from his lifetime of consulting and facilitating and together we shaped and sorted it. In some way we both spent years preparing for this moment. We just didn’t know it yet. While Picasso took a lifetime to create his drawing, this project perhaps took us two lifetimes, of traveling, discovering, testing and iterating. The last step of Marathon is still just one step.

Update: The Clarity Cards are now live on Kickstarter.


Dave Gray is the founder of XPLANE, a strategic design consultancy, and co-founder of Boardthing, a collaboration platform for distributed teams.

Mathias Jakobsen is the creator of Think Clearly and currently works as a Learning Designer at Hyper Island, a creative business school that helps companies figure out what to do about the Internet.