Episode 138 of The Informed Life podcast features a conversation with Dave Gray. Dave describes himself as a possibilitarian. He’s the author of several influential books, including Liminal Thinking and Gamestorming, which he co-authored with Sunni Brown and James Macanufo. He also founded the pioneering visual thinking company XPLANE. In this conversation, we discussed how to move beyond mental models that constrain us to open up new possibilities.

I wanted to discuss this subject with Dave because we’re in a tough job market. Lots of people are reinventing their careers. Besides being super smart and creative, I’ve always thought Dave embodies a type of joyful fearlessness in exploring new spaces of possibility. In some ways, it was necessitated by his degree in fine arts:

I went to art school, Jorge, and when you get out of art school, the training is very much about training your body and your mind to hone your imagination and creativity and the skills that you need to express novel ideas. And, when you graduate from art school, there’s not a line of recruiters out there; there’s not a bunch of jobs that are obvious for an art school graduate. Nobody’s hiring. BFA — Bachelor of Fine Arts — doesn’t pop up on a lot of job skills requirements or lists.

When you graduate from art school, that’s the thing: figure it out. It’s your time to figure it out. And you trained on these skills, we gave you some space to explore and practice your creativity. Your job is going to somehow involve creating novel, new, and interesting things that we can’t yet imagine. So, go find your way. That’s been my life: a process of finding, figuring it out, finding my way, applying creativity and imagination to getting as close to the life I want to live as I can.

You’re unlikely to find jobs that let you take advantage of all your skills and abilities. Organizations are more likely to want to shave off your edges to fit you into their round-hole-roles. Dave opted to go his own way by starting XPLANE. But you don’t have to make a similar choice. In tracing his own career arc, Dave noted two traits that served him well:

  1. an open-ended approach to trying new things by ‘sketching’ – i.e., experimenting with ideas in public long before they’re ready for prime time, and

  2. an entrepreneurial mindset, even when providing value in the context of a traditional job.

Now, he’s started a new initiative — the School of the Possible — to explore possibility spaces. He compared the venture to a sort of emergent art school:

[The School of the Possible] is a sketch. It’s a sketch of a school. What is a school? A school is a place of learning and exploration and play. Often, a school is a group of people with a shared idea or a philosophy. It’s another way to think about a school or a school is also community. And the School of the Possible is all of those things. In a way, it’s like an art school, except it’s an art school for the art of the possible. So that’s what I’m sketching right now with a bunch of other people and learning a lot, in the process. And I would invite you and anyone who wants to come participate in the sketching process with us.

The invitation is very specific here: every Friday from 9:00 - 10:30 AM PT, Dave hosts open campfire calls over Zoom. Anyone is welcome to join and explore the possibilities. I was happy to explore possibilities with Dave in this podcast. I hope you get as much value from the conversation as I did.

The Informed Life episode 138: Dave Gray on Possibilities