Feeling inspired after taking down the 540-page spirit quest that is Zen and the Art of Motorcycle Maintenance with my Reading Team, I said (shouted) in a euphoric state, “We’ve got to read Hamlet next!”

I got a few enthusiastic replies but only courtesy mumbles from everyone else. No matter. Shakespeare was meant to be experienced with others, and I was going to win over the group by revealing all the hidden meanings, powerful themes, and literary genius of The Bard’s most famous play.

Phil, always the wiser, was the main leader and I was the second in command. To my credit, I did know this would be a tall order. The research, our conversations with many readers, and my personal experience all point to the same two core truths: the leader plays an outsized role in the team, and leaders often feel anxious.

It's always hard to put yourself out there with others. Many people we spoke to worry about being judged or “missing something” in the reading. For me, this worry was going to be amped up to 11 with Hamlet.

My instincts were right, but my execution was off. I read and re-read deeply. I shared structured summaries with the team, breaking down the language, uncovering the core themes, and integrating in critical analysis for every act. I listened to Shakespeare scholars give their provocative takes. I crafted questions that cut down to the bone of human nature. I did a Hamlet graduate-level crash course, and - needless to say - was ready for our discussion.

The big day arrives. We catch up by the pool, and I even hear some early book chatter. I’m thinking this group is primed and ready to become Shakespeare diehards. Yet the discussion starts off a little slow. Nearly everyone read the play - nice. But most only read the modern English style via No Fear Shakespeare. No problem, I roll with it. I start to fill the lags with some of those scholarly takes that have imprinted on my brain. I get the same courtesy mumbles I heard at the start of this journey and realize…holy shit, I’m back where I started.

Seeing me floundering, Phil jumps in. He moves away from philosophical analysis and toward nuts and bolts - plot and characters. Is Hamlet a good person? Thoughts come out, volume rises, and boom - we hit paydirt. The team is humming.

Phil builds on this with, I kid you not, a requirement that each person do a dramatic reading. We laugh and one guy pulls out his cornet - that hasn't been played in years - and opens every performance with a processional tune. I’m seeing something special, I know it, I feel it, and I am relieved we got there.

For the longest time I thought the main job of the leader was to become the expert, to put the work in to deeply understand the book. This is actually enjoyable for me, so I doubled down on it for Hamlet. It didn’t work.

It’s rarely the job to teach the book, and it’s never a winning approach to try to prove your mastery.

Good book leaders put energy into the book and their team. They make everyone feel supported and seen across the whole reading journey - at the beginning, choosing the book; in the middle, reading it; and at the end, discussing it. This attunement builds safety, excitement, and ultimately creates the conditions for those standout moments like watching your friends stumble their way through the “To be or not to be” speech with a brass horn blaring in their ears.

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Learning from Despair - Justin McDaniel’s sought-after course at Penn sifts for meaning among dark texts (LearningWell)

Professor Justin McDaniel hosts a weekly seven-hour class that has no devices and holds an 11pm conversation…in the dark. It’s called Existential Despair and is one of the most sought-after courses at the University of Pennsylvania. His distinctive leadership is setting the conditions for powerful moments and students love it for numerous reasons.

“When my wife Bianca and I read with our 10-year-old son, Edgar, we're often reading to him. This one was different. We listened to A Wrinkle in Time audiobook together while Edgar followed along in the book. I'd never read it, and Bianca hadn't in years. All three of us were starting fresh.

Some nights it was the dinner table, some nights the couch. We'd catch each other's eyes when one of the witches did something funny, or when the tesseract and time travel stuff started to lose us.

When we'd pause to talk, that was the best part. Which characters we saw ourselves in. How to make sense of the confusing parts, some of which I still can't fully explain. We all saw different things in the meaning of the book and the power of love in the story. We weren't trying to teach Edgar or convince each other. We just shared.

A good book opens me up. And it gets bigger when you hear how someone else sees it. If you have kids, try reading one with them instead of to them.”

-Reilly Milton, Passage co-founder

Leadership, like team reading, is a journey. I’m lucky to learn and share my journey with you.

Do you have a reading moment or experience you’d like to share? We’re here for you and would love to hear it.

-Joel