School of the Possible 2025 Annual Report
Reflections on how we got here and where we go next.
To my friends and fellow possibilitarians,
Congratulations on a wonderful year of joy, belonging, and creative progress. This is my third annual report to you, and while much has changed since we began, the core reason for the school remains the same:
I want to recreate the magic I first felt when I went to art school, a space where we all belong and can explore our creative potential without fear. A place to tinker at the edges of the unknown, dip into the waters of uncertainty, try new things, and where each of us can discover what makes our experiences and expressions in the world unique, original, distinct, and different. It’s a messy sandbox and I love it.
Before we begin our fourth year, I’ll be taking a pause for January and February to reflect on what I’ve learned and think about where we go from here.
How far we’ve come.
2023.
We began in 2023 with nothing more than a sketch of a school. A prototype of possibility. We started without a blueprint, “stumbling forward” toward a vision I could only see in vague outlines. Some of you were there for that beginning, our first campfire call on September 8, 2023.
In October of 2023 I launched our first experiment, a course creation course, and to my delight, 40 people signed up to figure out together what makes a course a course and what a creative community might look like.
2024.
In 2024, we moved from experiment to commitment. We built a rhythm of weekly campfires, Monday memos, and twice-monthly collaboratories, 90-minute workshops with special guests, guiding us on explorations and experimenting with creative topics and themes.
2024 was a year about showing up and building the consistency and trust required to support and encourage each other. At the time, I thought of this project as a cart with oblong wheels. Functional, moving forward, but still searching for its most natural form.
This was the period when the community was growing most consistently. If my goal had been simply to grow the community and continue to add paid memberships, I would have continued with the rhythm of collaboratories twice a month. Growth was consistent and predictable. It was fun, creative and engaging, but it wasn’t serving my primary need, to be part of a working creative community.
So toward the end of 2024 I shifted the focus and we we launched our first project cohort, project inception, a shared space and cadence for working on creative projects. It was a lot of fun and we made a lot of progress, closing the year with an Open House Exhibition where we shared our work with the world.
2025.
2024’s Project Inception was such a great experience. I thought that since a six-week sprint went so well, a fifteen-week sprint would be even better! But I was wrong about that. I suppose it should not be a surprise that more and bigger is not always better. A 15-week project cohort. I learned, becomes less like a sprint and more like a slog. It reminded me of my high-school term papers, where, instead of making steady progress week by week, my experience was one of increasing gloom as the cloud of my compounding commitments overshadowed any sense of joy and progress.
Enough of that. I never had to do a term paper in art school and I don’t need to do another one for the rest of my life.
When we finished our spring semester I decided to go back to 6-week cohorts. Six weeks feels like a magical sweet spot between too little time and too much, a kind of Goldilocks timeframe for creative work. And there’s no reason longer projects can’t carry over from one sprint to the next and benefit from the sprint dynamic.
In June, we held our first real-life Possibilitarian Pop-Up in Portland, Oregon. It was a blast, and I expect we’ll be doing this again.
Over the summer a few of us meet weekly to work together and build our iPad digital art skills. I didn’t realize this at the time, but we were developing a new format that works really well for teaching and learning from each other in a loose, unstructured way.
I started calling these studio sessions, and we piloted two of these in 2025, one about creating card decks and the other about making videos with AI. Studio sessions felt like a pretty bland name, so moving forward I’m going to call these howfinding sessions. Sounds much cooler, don’t you think?
Where we are now.
So what do I consider the big milestones from 2025?
The 6-week Project Sprint format: We have really refined this down to a clean, repeatable format, staring with “project pixelation” on sticky notes and culminating in Open House Exhibitions where we celebrate our progress and show our work.
Howfinding: A new format emerged for teaching and learning from each other, sharing knowledge and skills and addressing new topics as they emerge organically from our work.
The Friday Campfire: These calls remain the heartbeat of our school—a place where regulars and new faces show up for each other every week to open paths to fresh insights14.
In-Person Connection: We successfully bridged the virtual and physical worlds with our first live meetup in Portland, Oregon.
What has emerged in 2025 is a culture that values small experiments and peer support over rigid instruction. The school has become less about teaching and more about making space for all of us to do the work that we find meaningful.
Looking Forward to 2026.
Things are going well, and it is precisely for that reason that I want to pause. After two and a half years of “doing it to figure it out,” I finally feel like I know what I am doing.
Starting January 1st, I will be taking two months off to consolidate what we’ve learned. During this time, I will be pausing paid memberships to think deeply about why we are here and how to carry our momentum forward with intention.
Friday campfire calls will continue through the pause.
A Heartfelt Thank You.
I leave 2025 with deep gratitude for you, my companions on this journey. You have been so gracious as I hosted our “uncertain stumbling,” and your participation has turned a vague outline into something real and vital.
Here’s your invitation to join me in this reflection. Send me a note. Share your thoughts in our 2025 yearbook. Reach out to schedule a 1:1 chat about the future of our work together. I want to hear what you like about the school, what you wish for, and what you are wondering about. Help me think about what we should let go of, and what is worth carrying forward into our next chapter.
With gratitude and possibility,
