I Figured Out Why

I titled this post "I Figured Out Why" but I could have, maybe should have, entitled it "That Time I Got All Up In My Head". You see, I came up with this idea of living my 60th year on planet Earth in this purposeful, intentional, and to be fair, hopefully pleasurable way. I marinated, in my head again, on the idea and came up with this idea of a list of 60 purposeful intentions that I could carry out over the course of the entire year. I decided that wherever possible I'd put a twist on the intentions to help others. Then I had the idea to build and app, and I made the decision to share the journey with friends and family and even the public. Honestly, I got pretty jazzed about the whole thing, and my outlook on turning 60 radically improved.

Then someone close to me rained on my parade. They questioned my intentions and expressed some skepticism and confusion as to why I would "go public" and expressed their own lack of comfort in doing something like that. I was definitely taken aback. I had to be grateful though. I mean, isn't this what we want from those close to us? We want honesty and real, candid feedback, even if it challenges us, even when everyone else may simply nod and smile.

Coincidentally, simultaneously, and fortunately, I was listening to the book Atomic Habits by James Clear when this mental setback occurred. What I quickly and clearly realized, with the lens of his book attached to my cranium, is that this whole thing . . . the concept, the list, the app, the sharing it publicly . . . is really just an elaborate accountability mechanism my brained cooked up in order to help me establish a new set of sustainable habits that improve my life, and by extension, the lives of those around me. So there you have it. I found my "why". Time to move on. Not so fast! If only my mind worked that way. No, I still had all those words and questions floating around in my head. Second guessing myself. So, what's a guy to do. Got it. I'll get a second opinion. An unbiased opinion. Enter AI! You know that was coming, right?!

Here's what I did. I fed Claude my List of Intentions (hello-60-intentions-detailed.pdf) and prompted him as follows:

"Who is this guy? Look through this list of curated intentions that a 59 year old male has put together to accomplish during his full 60th year of living on the planet. How would you describe this person based on this list. What can you discern about his personality and who he's trying to be by tackling these items. What insights about his intentions can you glean?"

And here's what Claude had to say, uncut, uncensored. I don't agree with every word, but I think the machine nailed the man and the mission pretty well here. So, onward I go. If you have questions, talk to me. That's a big part of the fun here after all.

+++++

This is a remarkably candid document, and there's a lot to see in it if you read between the lines of what he chose to include, how he organized it, and what he let himself admit in the write-ups.

He's an engineer who never stopped being an artist. The whole project is proof: he took something inherently soft and unquantifiable — a year of meaning — and built it like a system. Seven categories, sixty items, an exported PDF, percentages that almost certainly add up on purpose. That's not incidental. It's someone whose instinct, even under emotion, is to structure, sequence, and track. But then you read what's inside the structure — poetry, letters, faith, grief, generosity — and it's clear the rigor is in service of something tender, not instead of it. That tension between the engineer and the artist runs through nearly every intention.

Generosity is his default setting, almost reflexively. Cash for strangers, funding something for someone unnamed, 60 lunch dates, small unexpected gifts, mentoring young photographers — over and over, the impulse is outward. And he's self-aware about it: he specifically calls out wanting to stop treating struggling people as "invisible," to actually see them rather than transact. That's a man trying to close the gap between the generosity he already practices privately and the attention he wishes he gave more consistently.

A lot of this list is quiet repair work wearing the costume of a bucket list. The sister he hasn't reconciled with. The mother he wants to get to the beach before it's too late. The storage unit still packed exactly as movers hired by "the X" left it — literal unprocessed baggage from the divorce, sitting there for years. The Decade Cards to his younger selves. The "closing ceremony" retreat. This isn't just a milestone celebration — it's someone doing deliberate, structured grief work and calling it an adventure list, which is probably the only way he could get himself to actually do it.

Legacy and permanence matter to him more than the digital world has let him express. He's got millions of photos and almost none printed. A coffee table book he's calling "Volume 1." Hand-written letters sent "old school." An Instagram home for work he's kept hidden behind iPhone snapshots for years. He seems to feel like he's been living a professional creative life almost in private, and this year is partly about finally standing behind it in public.

He's negotiating with mortality, directly. The line about always assuming he'd die by 50 is the clearest window into the whole project — everything else, the skydiving, the base jump, the cold plunges, the endurance event, reads differently once you know that. These aren't midlife-crisis stunts; they read more like proof-of-life gestures from someone who's genuinely surprised and grateful to still be doing them. "The third third" — not "the back half" — is a telling reframe.

And he wants company on the way. Almost every physically demanding or vulnerable item explicitly invites someone else along — his son, his daughter, his girlfriend, friends, strangers who reach out. Plus the actual plan to build an app so other people can run their own version of this. He's not just processing this privately; he wants to build the container so it becomes something other people can use too — which tracks with someone who spent decades in leadership and mentoring roles and instinctively wants to turn a personal experience into something structured and shareable for others.

If I had to sum him up in a sentence: someone who spent 59 years building things — companies, systems, a career, a family — and is now deliberately, almost forensically, turning that same building energy inward, at himself, before the year is out.