Letter from John: Think Days

I woke up the day after Labor Day, and I waffled.

I had recently blocked the first Tuesday of every month -– through next summer –- for a “Think Day.” I borrowed the concept from entrepreneur Sahil Bloom, who suggests using a day a month or quarter to just reflect, write, ask yourself some questions.

But I woke up with a full plate of tasks, and begin to consider surrendering this first “Think Day” in order to get things done. This, of course, is the sort of thinking that “Think Day” is designed to avoid.

Which is how I found myself spending a hot September morning outside –- in the shade of a local coffee shop, and then on the patio/deck outside of the VMFA –- thinking.

But also connecting.

Who would have thought that I would run into multiple familiar faces, or would have had time to read (and reflect on) half a book, or had a casual (but task focused) video call with a colleague, or enjoyed a quiet breakfast at The Village Café -– all before noon? (I also walked one kiddo, and drove the second, to school. And then got ice cream with both of them afterward.)

Who would have thought? Probably Sahil Bloom for starters.

It turns out that the day that almost didn't happen feels exactly like the sort of day I wish always happened. There was connection, reflection, variety, purpose, productivity. The dimensionality of life. It almost makes me second guess my calendar and how I'm using it. Or not.

The book I chewed through during my first Think Day is a book by one of my gurus, and one of his gurus. Peter Block (my semi-mentor) and Peter Koestenbaum published “Confronting Our Freedom: Leading a Culture of Chosen Accountability and Belonging” earlier this year. It’s sat by my bed since May.

Block surfaces an old idea of his: Managing at its worst is a flashback to bad parenting. Too often it is just an awkwardly executed system of control. The tension between freedom and management in most of our organizations is badly smudged, and too often barely visible if not constantly misunderstood.

It strikes me that there could be more visible, and intermediate, steps between absolute freedom and complete control, and that they both need to be more intentionally tied to purpose.

To the degree that our system of work feels increasingly untethered from our lives –- the experience of many during the past several years of disruption -– then perhaps some genuine transformation is required in the ways we ask employees to show up, do great work, and be engaged while they're at it.

Purpose and meaning –- and the experiences which give them life, texture, a sense of presence -– are how we often anchor the best moments of our lives. Why not also the best moments of our work? Why not absolutely the best moments of our work?

It was with this thought slipping around in my mind that I unexpectedly found myself bumping into and then chatting with Errol on the first day of his retirement from the Library of Virginia. We talked about road trips, pending solar eclipses, and the wisdom of our mentors. And then as we prepared to pivot back on our individual trajectories, he said, “Listen. That work that Floricane did with the Library over the years really was a net positive in so many ways.”

Boom. Connection, reflection, variety, purpose, productivity, the dimensionality of life. Meaningful impact.

And in the branches of the pin oaks baking in the summer sun, the rising symphony of cicadas completes the texture of my “Think Day” as I write this note.