🧵 On Following the Thread

Years ago, my father gave me a book. Today, in a very real sense, that book came to life.

Giving me things to read was part of my father's love language. And even though younger Ryan would sometimes roll his eyes at the newspaper clippings laid throughout the house for me with certain sections underlined and annotated, the getting-older-Ryan gradually grew to appreciate this act of care. It was part of his way of passing on information, not only the specific content of whatever he would give me to read, but also in the broader sense of conveying the import of sharing ideas and opinions with others.

As is perhaps obvious by the blog I maintain here and my wont to dive beneath the surface layer in any given conversation, I wholeheartedly adopted this lesson.

One of the last books my father gave me before his passing was General McChrystal's Leaders. Yes, it's a book on leadership, but it's the general's reflections wound throughout an evaluation and comparison of some of history's iconic (and controversial) leaders.

While reading it, never did I think that some six years later I'd be conducting a fireside chat with McChrystal where I would have an opportunity to talk to him about his books and his candid thoughts on leadership in the modern era.

He was an exceptional speaker, as I knew he would be from my limited prior engagements with him. He listened to the questions and gave substantive answers, evening tying some in to Warrior-Scholar Project, which certainly made my job easier when I had to tee up a fundraising ask to attendees later in that evening.

It was a deeply human experience, this chat. His staff didn't ask for carefully vetted questions, which is good because even if I had written some, I almost certainly would have tossed them out and created new questions on the spot based on the flow and tenor of the conversation.

I didn't plan to ask the general about Leaders, but when he mentioned his time at West Point, it triggered my memory on one of my favorite parts of that book, which is when he spoke about West Point's veneration with Robert E. Lee and McCrystal's reflections on the tortured legacy of that man.

Follow the thread, even if it spools out in ways you didn't anticipate.

And when we got to talk about his latest work, On Character, we spoke on what it means to not only have convictions, but to hone and honor the discipline required to bring those convictions to life. One of my observations from that particular book, my favorite of those he's written, is that it feels deliberately and notably unfinished, which I raised to him for his reaction. It's a series of reflections and thoughts, some of which tie together and others which are left for the reader to ponder.

There are more than a few lessons in that simple truth. For life is unfinished, and we are fools if we think we can see where every path is going. Some (present company emphatically included) believe that it is because we do know where the paths end that makes them all the more worth exploring.

Follow the thread, because it likely won't spool out the way you anticipated.

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The path to tonight's event was itself winding and uncertain. I met McChrystal at a non-work event last year, where I had a chance to get to know him a bit and opened an opportunity to talk to him about Warrior-Scholar Project. It turned out that he knew the WSP founders, as he had been teaching at Yale way back when we first got started there. He was thrilled to hear that the organization was thriving today.

In his book, he talks about the power of handwritten thank you notes. So after that event, I sent him one and told him that I'd love to find a way for him to re-engage with WSP. He wrote back that he was interested, and the rest is history.

Or at least that portion is history. Because even though a portion of thread is now apparent, I'm uncertain where it goes from here.

Good.

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My father, I know, would have been proud of me today. As I write this, I'm tearing up thinking about what it would have been like to have him in the room to watch me conduct the interview. To introduce him to McChrystal at the event. To hear my father's words and reflections afterward.

My body is tired, but I hold my head high tonight knowing that I'm carrying forth this legacy of engaging in hard but intentional conversation, and of advocating for the power of reading and writing and thinking.

Unspoolingly Yours,

Rye