Workswell Note #1

 On Dopamine, Tees, and Zombies

Hi Friends,

Thank you for subscribing! When I first shared this idea, I figured most people would be too overwhelmed (and maybe a bit skeptical) about adding one more thing to their inbox. Instead, the response was so enthusiastic that my dopamine system got quite the workout with each new Substack notification. Modern life does have a knack for hijacking our brain chemistry.

I’ll keep this brief-ish, quarterly-ish, and experimental. My goal isn’t perfection - it’s to learn, share, and connect. I often nudge folks I’m working with not to lose sight of their why and my why in writing these Notes is to share what I’m learning in the hope it’s useful. I also want to get better at this act of sharing, and the best way I know to get better at anything is by actually doing it. Finally, I love building things with other people, and my not-so-secret desire is that these Notes spark ideas and connections that lead to more of that.

I’ll admit, I’ve struggled with this first edition. I expected maybe 40 sign-ups; 160+ made the stakes feel higher. Suddenly my desire to learn was in conflict with my desire to be useful. Of course, I know the answer is to keep going - it’s exactly what I tell the organizations with whom I work. But few things are more humbling than being forced to take your own advice.

Experimentation as an Antidote to VUCA
Fittingly, experimentation is the theme for this first Note. Most of the organizations I’m working with now are feeling paralyzed by the extra-VUCA world we’re all navigating (Volatility, Uncertainty, Complexity, Ambiguity). VUCA isn’t new - the term dates to the Cold War - but it feels especially resonant right now. Leaders are trying to make choices about staffing, strategy, or how to interpret institutional players, all while knowing the future is basically unknowable.

My antidote? Experiment. Do something. Do something small. Signal that you don’t know if it will work. And, most importantly, invite other people into the process of figuring it out.

Yes, it feels vulnerable. Most experiments don’t “work” in the purest sense - but they all succeed if they teach you something. The critical piece, and the one most often overlooked, is what you do with those learnings.

A Founder Transition Case
I’m currently helping a group through a founder transition. Nothing dramatic has happened yet - they’re only just forming their Transition Committee. But I’ve been interviewing super-volunteers, showing up at meetings, and volunteering myself. Most importantly, I’ve been asking people what they think and communicating back what I learn.

What’s striking is how much people appreciate simply being asked, heard, and given visibility into the process. They understand we’re experimenting, that the path forward isn’t yet clear, and that they - and their questions and reflections - are part of it.
While we can’t predict the future, communicating openly about experiments creates opportunities for others to connect and engage, making it more likely you’ll land somewhere good and that those involved will feel invested in the outcome. Even for an organization already inclined toward innovation, incorporating experimentation into succession planning can feel a little unnatural, but it can also dramatically increase creativity, comfort with risk, and collective engagement.

Jill’s Tee Shop
Another (admittedly random) experiment: Jill’s Tee Shop. I’ve long loved designing t-shirts, and what started as sharing my own designs has quickly morphed. Whenever I bring it up, friends share stories of tees they’ve loved, made, or wanted to make. Now the shop is growing to include guest artists, friends’ bands (a legit reason for me to say merch), and new collaborations I haven’t even imagined yet. It’s become a quirky little lab in storytelling, self-expression, and play - with cotton as the medium. If you’ve got an idea for a tee (or a related project), send it my way.

What I also love about this experiment is the learning it has generated. Back when I was a d.school fellow, our projects became the platform for all our applied learning. The Tee Shop has been the same, nudging me to experiment with AI, push deeper into Canva, learn about UTMs, and explore ethical sourcing. Do I need all these skills? Probably not. But like drinking water, sleeping, or getting outside, learning new things just makes everything else better.

Easter Egg: Because experiments are more fun with surprises: the first five people who fill out this quick form will get a free mystery t-shirt from Jill’s Tee Shop. Guaranteed to be quirky.

A Resource to Know
I’ve been part of Stay Resolute, a community of advisors and consultants offering two hours of free support to nonprofits navigating tough challenges without the budget for outside help. It may sound too good to be true, but it really is just good humans wanting to do something and offering time. If you know a group that could use this, please send them this way.

A Playful Tip
Because it’s back-to-school season: one of my favorite ways to get my kids talking about school was to ask, “Which teacher would be most likely to survive a zombie apocalypse, and why?” The answers were consistently hilarious and revealing.

It’s also a good reminder that sometimes the best way to learn isn’t head-on, but through a playful openness that invites things to reveal themselves.

That’s it for this first Workswell Note. Thanks again for being here.