The Gingko Tree
This weekend I'm heading to New Haven for my 20th college reunion. My senior essay was about how places hold patterns that collapse time.
This weekend I’m heading to New Haven for my 20th college reunion.
My college senior essay was about Vladimir Nabokov’s autobiography Speak, Memory. The main argument and the thing I most wanted to explore was how places can hold patterns that collapse time. Nabokov would return somewhere and the past became present. Just like butterflies can only exist in unique environments (Nabokov was an avid lepidopterist), certain experiences we have are also singularly matched to certain places. But most crucially, identity and place fuse so completely that to revisit one is to recover the other.
After graduation, I stayed on campus to work the alumni reunions, hefting folding chairs and ten-foot round tables for Newport Tent Company. My friends were gone. During off hours, I wandered into my residential college courtyard and sat beneath the gingko tree in the late May light, my chest tight with the feeling that I wasn’t ready to leave. College was one of those special places that fostered experiences I didn’t think I could have anywhere else.
Many of those experiences were wonderful, and some were more complex. In my Hidden Forces series, I traced how the campus fused achievement culture with the drive for spiritual fulfillment. My bright college years taught me a vision of the good life I spent fourteen years living inside before I noticed its features and could start to critique them.
Place is still a very important way I think about my life. The very first piece I wrote for this newsletter was about leaving Kauai to come home to Brooklyn. My family had the chance to stay another year with monk seals napping on the sand, enjoying another pineapple season, in weather so perfect time dissolved. We said no because our community wasn’t there, and Brooklyn as a place creates the potential for experiences I wanted for myself and my family. Kauai offered a different range of unique experiences, and I mourn that I can’t have both. But Brooklyn has people who’ve known me for decades and carry dimensions of me that someone new can’t access right away.
But the people I’ll see this weekend knew me before I’d ever knocked a door for a campaign, before the years inside nonprofits, before consulting, before my child came along, and before I’d written a word of any of this. They knew the version of me who worked at the Yale Farm with dirt under his fingernails and hair past his shoulders. Some knew me as the kid who had stripped every unrankable thing from his life in pursuit of the highest score.
I am an environmentalist in no small part because of Nabokov. I believe his beautiful view about our beautiful world. This weekend, the gingko tree in the courtyard will be as enormous as ever, and I’ll be standing in the same spot where I once sat with no idea what I was about to become. I like the idea of reclaiming memory by returning to a place. I also like how I’m different, even if the place and the memory are the same.
The 2026 Rate-Setting Survey is live!
Last year’s rate-setting survey produced the most-read piece we’ve ever published. We’re running an updated version for 2026 to give you the latest info, plus new sections on travel costs, retainer structures, scope creep, and operational expenses that the first round didn’t cover. It takes about five minutes. Take the survey →
Strategic Agility Reboot Turns 6 Months Old
Speaking of standing in a familiar place and noticing how much has changed: the Strategic Agility Reboot series that Susannah Hook-Rodgers, Emily Berens, and I have been writing together turned six months old. Seventeen articles is enough to lose the thread if you weren’t reading from the start (or even if you were), so I put together a guide to the full arc on what we’ve covered, where the key tools live, and where we’re headed.
You, your calendar, and your inbox (Nov–Dec 2025)
The first six pieces focused on personal strategic practice: how you operate when chaos and urgency are conspiring against your clarity.
New Co-Author, New Series: Strategic Agility Reboot introduced the Pause Protocol, which is a 60-second ritual for creating space between stimulus and reaction. One of the first steps in strategic agility is retraining our minds!
You Cannot Strengthen a Muscle You Have Not Located gave us the Strategic Operator Self-Evaluation, a tool that turns “I’m struggling” into “I scored 6/20 in Strategic Discipline, which means I rarely know my priorities.” In fifteen minutes you get a baseline and one thing to focus on for 30 days.
Why That Meeting Probably Does Not Need to Exist introduced the Strategic Time Audit: a week of tracking where your time actually goes and whether any of it connects to the outcomes you care about.
Why Smart People Keep Making Decisions They Regret Later laid out two toolkits: the Anticipation Toolkit (trade-offs, inversion, second-order thinking, root cause analysis) and the Navigation Toolkit (contingency planning, distinguishing sustainable wins from depleting ones). The connecting thread is most bad decisions don’t feel bad at the time.
Long-Term, Not Just This Month went deeper on the distinction between wins that build capacity and wins that deplete it.
Making Better Decisions Under Uncertainty was the capstone: four tools (the Uncertainty Audit, the Reversibility Test, the Pre-Mortem, and the Cheap Test) that work together as decision-making infrastructure. Waiting for certainty it is its own form of strategic failure.
People: hiring them, developing them, firing them (Jan–Feb 2026)
If a strategic operating system runs on strategic operators, you need to know how to find them, grow them, and move them out when necessary.
Is Your Hiring Process Filtering Out Strategic Thinkers? argued that standard behavioral interviewing rewards polished storytellers over rigorous thinkers. The signals of a strategic brain—hedging, clarifying questions, comfort with “it depends”—are exactly what most hiring processes screen against.
Plot Twist: Telling Someone to Think Strategically Is Like Trying to Teach Them to Swim by Describing Water and its companion piece Math Problem: What We’ve Been Doing Isn’t Working tackled developing people in two parts. Strategic thinking requires exposure, frameworks, coaching, and reinforcement infrastructure that keeps it from eroding under daily operational pressure. Without that infrastructure, your promising strategic thinker reverts to reactive mode within weeks.
Save Democracy, Cancel the Word “Smart” was the sleeper of the series. Every time a leadership team calls a decision “the smart play” without defining the criteria that would make it strategic, they’re papering over the operating system they never built. “Smart” is a conversation-ender disguised as a compliment.
The Brown M&M Test used Van Halen’s famous contract rider as a diagnostic for firing infrastructure. Your ability (or inability) to fire someone fairly and cleanly reveals the state of your role clarity, feedback systems, discipline processes, and institutional trust. It is one small, visible failure that reliably predicts larger ones.
Management infrastructure and original research (Feb 2026-present)
Emily Berens joined us as a co-author in late February, and the series shifted into its current focus: management as the transmission system between strategy and execution.
Having Managers Isn’t the Same as Having Great Management opened with a metaphor: a car’s engine generates power, but the transmission converts that power into motion. Strategy is the engine, and management is the transmission. Committed, skilled managers operating without management infrastructure are being set up to fail, and the fix is a written, deliberate framework, not more training.
Every Organization Has a Management Layer. How Is Yours Doing? introduced the three domains of management infrastructure: Structural Clarity (do managers know what the job actually is?), Collective Leadership Function (do managers operate as a team?), and Management System Continuity (does the system survive personnel changes?). Ten diagnostic questions to find out where yours stands.
A Meeting Worth Having zoomed in on one high-leverage piece of that infrastructure: the monthly manager meeting. A structured hour where managers solve real problems together and leave feeling supported rather than depleted.
And in April, we released the results of our State of Strategic Fitness survey in two parts. The People at the Top Think Everything Is Fine reported the headline finding: Executive Directors rate their organizations’ strategic fitness 8.0 out of 10; senior leaders one level down say 4.83; consultants say 4.91. We called it the perception gap. Why It Keeps Getting Worse explained the structural dynamics that sustain and widen it, and introduced the concept of Reactive Sophistication: organizations that are externally perceptive but internally undisciplined, responding to everything, subtracting nothing, and gradually losing the thread of what they were trying to do.
Want to get involved?
The management infrastructure sub-series is still in progress, with more coming on what excellent management looks like in practice and how to build toward it. We’re also assembling a small design cohort of senior leaders to pressure-test these frameworks against live organizational challenges. We want to create the kind of room where an ED can say “my team doesn’t experience my organization the way I do” and get help figuring out why. If that’s a conversation you want to be part of, let us know.