Workswell Note #5

An Ode to Small Structures 

I was talking with someone I work with the other day and heard myself say, “I’ve never met a small structure I didn’t like.”
I’m not sure I’ve ever said that out loud before, but the moment it left my mouth I knew it was true and has probably been true for years without my noticing. Not systems. Not frameworks with quadrants. The tiny, almost embarrassingly modest things that quietly do more work than anything elaborate ever could.
The meditation pillow that sits by my desk - not in a closet, not in another room, by my desk - so the barrier to using it is roughly zero. The notebook dedicated only to morning pages, so I never have to decide which notebook, I just open the one that’s already decided for me. The workout app that tells me what today’s twenty minutes of PT are, so I can’t think myself out of doing it. A single check-in question to open a meeting, instead of forty-five seconds of “how’s everyone doing” that nobody really answers.
None of these are impressive. That’s the point. A small structure works because it’s light enough to actually use, and specific enough to actually matter.
Try This at Home!
I try to keep these Notes as actionable as possible, so wanted to share two examples you might try.

• ChairPair - the pilot we’re running with Board Chairs is betting that a small, consistent pairing can do something elaborate board development programs can’t. For the first call the prompts included: What’s your organization, and what drew you to being involved? How did you end up as chair, and what has surprised you about it? What’s the thing you’re most focused on (or wrestling with) right now? Nothing complicated, just a small structure creating space for Chair reflection. If you’re a Board Chair and interested in testing this, please reach out! Non-Chair humans might also consider how a thought partner for whatever it is you’re wrestling with might be helpful. Huzzah for interdependence!
• The Shadow Values Inventory - this is an exercise I’ve been experimenting with to help leaders intentionally check their aspirations against their actions. Your stated values are who you intend to be. Your shadow values are what your actual behavior reveals you prioritize, often without realizing it. This exercise invites you to write down 3–5 words that describe how you want to lead/navigate the world and then asks you to look at two weeks of your actual calendar, decisions, and attention, creating a second list that’s grounded in pesky reality. The gaps are the whole point: some are values misreads (you don’t actually care as much as you thought), some are system problems (something structural keeps getting in the way), some are fear problems (you’re avoiding something uncomfortable). Seeing these clearly can provide some important insights.

Following up from the last Note
When Note #4 went out, I asked for some favorite questions and promised tees to a few winners. Here’s where we landed!

• “What Would Shenzhen Do?” — from Drew at Stanford
• “What Was Your First Concert?” — in honor of Stephen Colbert’s go-to icebreaker
• “What Makes You Smile?” — from Tiago at ChangeX

A professional update
I’m happy to share that starting this month I’m taking on the interim academic director role at Stanford’s d.school. I was a fellow there a decade ago and I’m really looking forward to being back on the Farm, working with extraordinary humans, and contributing to an institution that is committed to creativity and helping people design things, experiences and systems that work for people.
Admittedly, I was initially feeling a bit anxious about the commute, AND I have shifted gears to turn the whole thing into a design challenge: how might we make commuting more like a road trip? Some early thoughts/preliminary prototypes include:

• Album of the Week - kicking off with the new Rolling Stones record, I plan to listen to a different album every week – start to finish and then on heavy rotation. I’m open to suggestions.
• Snacking – while I’m a fan of orange foods and members of the “-ito” family (think Fritos, Doritos and their cousin Cheetos), I’m wondering if there are playful and joy-inspiring alternatives. Thinking fruit and caffeine will be involved.
• Guest commuters - heading to Stanford and want to ride along? Driving and want to scoop me up? Let’s talk. This can also be combined with one-way mass transit experimentation – BART and the CalTrain? Somehow incorporating the ferry? I’m picturing all the Richard Scarry Busytown books I read as a kid.
• Slow it down – This one was prompted by my friend Susie’s test run a couple of weeks ago. I’m curious about a mindset shift that incorporates planned stops instead of straight-through rushing. How might I infuse more novelty?
• And of course, the original commute hack, call your mother.

All of which is to say, here I am starting something new and ever-so-slightly terrifying in the way that new things tend to be, and predictably, I’m reaching for small structures.
A final word from the sports fan in me
We are in the midst of a season of pure sports joy. The Knicks delivered a win that’s still got a delightful aftermath rippling through NYC. World Cup madness is doing exactly what it always does for my faith in humanity (good) and my schedule (bad). Wimbledon! The Tour de France! And, while it’s still very early in the season, my beloved Golden State Valkyries are glowing. It’s good to notice.
A parting, more than slightly random share: I got charmed into making a small investment in The Sports Bra, the Portland bar built entirely around women’s sports. They are raising money to expand, and you can become a part owner starting at $250. I’m in. If you want to be too, the link above has the details. Actual fine print because this is real money: this is a speculative, early-stage investment, not a recommendation. I’m not a financial advisor, and nothing here should be read as investment advice. If you’re considering it, read the offering documents, understand that early-stage investments carry real risk of loss, and talk to your own advisor – or your mother - before deciding.
OK, that’s what I got for this time. If anything from this Note prompts you to do something or think something, I’m genuinely interested to hear. You can also just send a message to say hi @ [email protected]
Thanks for reading, #jill
P.S. One final small structure rec. I’ve been completely impressed by the Timeshifter app as a tool for navigating international travel and avoiding jet lag. Check it out if you have any major travel planned – first time using it is free!