Ridgeline subscribers —

Hello from somewhere over the North Pole en route to England. Kevin Kelly and I are running another Walk and Talk with a classic ragtag crew of walkers. This is our … sixth or seventh or eighth (depending on how you count (we did a couple pre-Walk and Talks before transitioning into the Full Walk and Talk model)). We’ve walked Spain, China, Thailand, Indonesia, England, and Japan. And we’re back to England once again, mainly because the walking is so uncomplicated, rights of way galore, with infrastructure in place to make the talking effortless. Also, sandwiches. Yummy, yummy, sandwiches. We’ve walked with some sixty+ people over the years. Incredible people. Thinking back, I’m in awe of the folks I’ve spent time with, many of whom have become great friends. But all this walking and talking started with Kevin, and I thought I’d explain how we met.

It was 2010. I had just moved to Palo Alto. Two blocks from Steve Jobs, sharing a house with two Stanford D-School grads, no furniture, and a fridge full of humus. I slept on a yoga mat for the first month. I was 29 and damn was I hungry. Starving, really. Starving to work with talented people on a “bigger scale.” I felt the smallness of Tokyo (Japan is, in so many ways, the most provincial of places despite its many cosmopolitan aspirations), and felt like I had run out of folks to work with (both true and not true; the story I had to tell myself at the time), folks really thinking and acting on an outsized international scale. So when I had the chance to relocate to California (even if in my mind it was only temporary; I was always coming back to Japan, wanted to return as something like a revanent), I took it and ran with it as hard as I could.

This was right when the iPad had come out and everyone was thinking about digital books and the future of media. I had a computer science degree, but I also had spent my twenties making beautiful physical books. I had thoughts. I started publishing essays about this intersection — the intersection of books and digital reading. Those essays got picked up all over the place. I was invited to give talks. I gave twenty-one talks around the world during an eighteenth month period. For some reason I thought every talk I gave had to be totally new. This was stupid of me (I should have just done one talk, twenty-one times, making it better and better; le sigh). Regardless, I was maniacal about saying yes to everything, felt a pathological compulsion to seize this little moment, this confluence of Reading and Screens and … I don’t know what — level up my connections? believe that the people I’d meet along the way would lead to a broader worldview? bigger experiences? richer adventures? Something like that. It was almost theological, this blind belief, this need, this impulse to do all these things back then.

A few months after I moved, in February of 2011, my dad died in a small town in the woods, a town I didn’t really know. I went to bury him alone. Everyone else in the family was dead. The timing was terrible because I had a talk I was supposed to give at O’Reilly Media’s “Tools of Change” conference (remember those?). If I was going to make that gig (and I was going to make it) I had about five days to get my dad’s body in the ground. Maybe that sounds callous, but I can’t overemphasize how important saying yes to — and going and doing — all these talks was to me at the time. It felt like an epochal period in my life (and it turns out, with hindsight, it absolutely was — maybe the most important few years). My father had given me no money for school, almost no support — intellectual or financial or emotional. He was a guy, basically a stranger, far off. We weren’t close. So you’ll have to excuse the insensitivity around his interment. Damned if I was going to let him block a talk in life or in death. (That hunger!!) I went down to his town knowing little. I dug through his tiny home. I met the town’s octogenarian lawyer (with whom I’d go on to have a profound and unexpected friendship that lasted nearly a decade until he passed away in late 2019). We did what we needed to do and got him buried on Saturday, and I was on a plane to NYC that night. Speaking on Monday morning. (I’d then spend years writing an unpublished novel about that week, so unexpectedly was I moved by it all.)

Which is to say, a more sensitive or tactful man probably wouldn’t have been speaking at “Tools of Change.” My dad had been in the ground for just thirty-six hours or so. But life goes on. And I was set to sit on stage, on a panel, with some New York Times folks, and talk about the future of digital publications. I did — I went on stage. I don’t remember what I said, but I must have said something not entirely boneheaded because when I got off stage I had an email. Here’s it is in its entirety:

Craig,

I really liked your talk at TOC on Monday. I found myself in almost total agreement. I have a question about my own projects you may be able to answer easily.

Are you still around TOC? Would you have a few minutes today? Lunch?

— KK

I can’t overemphasize how much of a bumpkin I was. How little I knew. WIRED magazine? Who knew who founded such a thing (I still hadn’t heard of Marshall McLuhan at this point; I was a committed autodidact of the weirdest verticals, with almost no breadth, and no one to teach me what breadth looked like until much later). I was a goof who had stumbled onto these stages during this niche moment. (The sense of being an imposter played no small part in my Pathological Yes-ing. And the desire to shed that Japan provincialism infused every cell in my body.) I asked a friend — do you know this guy? Showed him the email. Kevin? … You don’t know who KEVIN is??? Reader, I did not. So I met with him in a hallway between sessions. He was very sweet, and he asked me intriguing technical questions, all of which seemed to come from this bottomless well of desire to know which tools to use. He was vibrating with an ecclesiastical energy, he held full faith in tools and their potential. The right tools would change the world. A heart-on-sleeve adherent.

So we stayed in touch. I always tell folks that if you want to connect with a busy person, the best thing you can do is send short emails showing them things you’ve made. Nothing is more impressive than seeing finished work. (Doesn’t have to be perfect, just finished.) I was writing up a storm, so I’d ping Kevin whenever I published a new essay. Those pings led to walks along the coast in Pacifica, talking about the future of learning (video video video) as whales breached in the distance. Kevin followed me on Twitter and saw that I had started to walk Japan. He asked to do a short Japan walk together (we did a stretch of the Nakasendō; exactly ten years ago this coming October 13! (Photo at the top from the rainy first day of that walk.)). That led to more walks, and those led to the Walk and Talks.

It’s useful to take a moment and meditate: of those people in our lives who have had the most heartfelt impacts, how were those connections made? For me, they can almost all be traced to writing, essays, books. Put tangible things into the world, spoon in a dollop or two of vulnerability, do this again and again, and if you don’t find yourself communing with good people, then I’ll eat my shoe. That “Tools of Change” talk was an extension of my writing. Would Kevin and I have connected if I hadn’t made it back to NYC? Who knows. Probably? Our orbits were pretty closely aligned. But I got my dad’s corpse in the ground. I flew back to NYC. And I got on that stage. And, boy, am I glad I did.

Anyway, these Walk and Talk weeks have been, in aggregate, one of the greatest unexpected gifts of the last decade. I’ve learned so much from them — from the walkers sure, but mostly from Kevin himself — that it’d require another ten newsletters to list it all out. Thanks, Kevin.

And now I’m off to do another one.
See you on the other side,
C