When Reality Lags
i spent 2025 in the lab, with a pen and a pad
In fall 2024 I was recently separated, trying hard at work on a major project with a big New Year's Day activation. When the project concluded, I was a wreck internally. The weight of separation, work, twin toddlers, legal and financial pressure had started giving me blackouts and panic attacks. I was intensely distracted, and I'd start crying out of nowhere. I'd try really hard to hold it in the way everyone has to try really hard to hold in a fart. In April 2025, I was let go. It wasn't the right role for me, anyway.
David Epstein talks about every generalist's moment, when the complexity of a wicked environment matches the complexity of a person. Being a Dad to twin toddlers is a full time job, recovering from separation is a full time job, professional rebuilding is a full time job, and preparing for court is a full time job.
This is my generalist moment.
Interviewer: Who are you jealous of?
Bob Odenkirk: Anyone who's still got little kids at home…
April 2025 should have felt like despair, but instead it felt like freedom. I had one purpose: be a Dad. I didn't even really think about it. Stripped to my core and fatherhood felt my highest priority in that way an idea pops into your head and you don't really wonder "hmm where'd that come from?" It was the only thing I really knew, since I had been doing it for three years already. The rest of it had a Fog of War. It was a risk, and I didn't know for sure, but I could rebuild professionally later.
Taking a deep breath and performing the Dad they needed was routine, and every time a little image would appear in my mind's eye, tethered to my spine, the ghost of my real self. I was scared they'd be shaped by the conflict instead of by me, and fear is a great motivator.
I spent those first few months taking care of my kids, my dog, and myself. Usually in that order. Lots of running, hiking, and thinking. Lots of thinking. Even thinking about my thinking, which I've learned is called metacognition.
I was rehabbing, and writing a lot, supplying a pipeline of fatherhood observations about moments I learn from my kids, one of life's hardest skills. It felt like building from the center out.
My Rapid rating on Chess.com reached 2000 in August, a practical miracle for an adult learner. There's a visible disturbance in the rating distribution at 2000 because so many people reached it and stopped playing, unwilling to risk falling below that peak. Right now, I'm in that camp and focused on blitz. I couldn't help but see my chess rating as a reflection of self, and proof I was moving in the right direction.
I owe credit to Danya Naroditsky and his YouTube videos, like many thousands others. In the five years after I found Danya's videos, my rating went from 1400 to 2000. When I play, I see images and concepts from his videos in my mind's eye. "He made improvement feel less like study and more like companionship, the essence of good leadership and coaching" I wrote after his tragic passing last year. Coby and Aria benefit from Danya's videos, too.
Then things shifted by the end of Summer when unexpectedly I came across a book titled Team Intelligence that turned my gaze towards the professional world.
It was Danya who introduced me to the glue piece concept in chess, something I was familiar with all my life from sports. So when I came across Jon Levy's book about organizational glue players, it felt like an answer to tough professional questions that I had spent my entire career wondering about.
The moment of finding Levy's book in Fall 2025 was more permission than answer, really. I couldn't help but write The Art of the Glue Piece, and things really started making sense. That essay poured into a second, Designing Human Systems in a Wicked World, and I realized I was connecting patterns across domains, lots of them. At this point I had a growing body of writing including fatherhood notes, a glue philosophy, and a Squarespace I paid for three years ago and never used.
Building my brand's website was a chance to exhale a creative spirit that didn't see a lot of playing time. I didn't want a site that was just personal or just professional. A generalist doesn't want both, a generalist needs both. I wanted something that said "here, see how I'm organized, how I think…" so that the right people self select into an engagement they can already see me inside with their mind's eye.
Suddenly I was watching strangers understand me. I was getting visitors, and returning visitors, referral traffic from professional networks like LinkedIn, Teams, and Slack. Holy shit, people were dropping me in Teams chats! That was a crazy jolt of confidence. I was even getting traffic from Facebook and Reddit which I wasn't even on at the time. I had no idea who all these visitors were, but the market's response felt like a green light on whatever it was I was building.
I finally made a Reddit account myself, and browsing one day I found a user's replies consistently insightful, so I decided to reach out. Turns out, it was the legendary Jay Cutts, and we got a chance to chat for 90 minutes. I was finding chess and MCAT tutoring work, which I called Battlegrounds, a short lived adventure.
Into the New Year, I updated my LinkedIn with a style unmistakably me. I was building a consulting business and finally felt ready to pursue Chief of Staff style FT positions. I was really nervous, but my philosophy was still early.
My nose picked up the scent again in January when I came across an a16z newsletter titled "How to Hire a Chief of Staff" and it was clearly from the same vision as my Art of the Glue Piece three months earlier. I couldn't believe it. It felt like I was front running a16z. How could I see the same thing, never having held the title, as a16z's Principals of HR who've staffed dozens? That's the very nature of the Chief of Staff role itself, and I knew I was on the right path.
I remember as an adolescent in the 90s teaching myself to code HTML, smashing the refresh button in IE to see the effect of the changes I just made in my .txt file. AI feels the same. AI is wickedness for a world still adjusting to the internet. A wicked world is one where generalists shine. It's ecological, so AI is the generalist's best friend, and my AI is lucky to have me. I kid but there's truth to every joke, and AI is the first tool I reach for and impacts everything I do.
In a test of range, I built easyreviewpost over a weekend with nothing but style and a vision. Turning my glue philosophy into a Philosophy of Glue required artifacts, so I built a world with physics and laws and captured a video. Art for someone who never practiced was suddenly within reach, and I couldn't help but try my hand at a few pieces of satire, creative attempts in search of comfort with reality.
I was less sure about them, and slower to publish. For a while, only one other person saw the growing collection, an early website visitor who typed the URL of the page I hadn't yet marked private. Then reality caught up with my pattern recognition, and I felt emboldened.
On Day 44 of the Iran War I wrote an update: "Day 44 of the Iran War and here we are: Phase 3 — Extension Mechanisms 🫥🫥🫥" Looking back at that deck was weird, then I showed it to my Dad and his wife and they didn't get it. I've been explaining shit to boomers my whole life…
The day after Kristi Noem was fired, I satirized a Chief of Staff memo from Susie Wiles. Months later, the real email was unexpectedly leaked. That's a wild sequence of events. "Seeing around corners is kinda the job" I wrote in an update.
A few months ago, someone on LinkedIn reached out and recommended I move my writing to Substack, where a voice like mine could find a home. I followed through, choosing Substack for discovery and website as destination. Now I get traffic in both directions: visitors from my website to Substack and from Substack to my website. Plus little jolts of enthusiasm when someone likes my Note, at the expense of addictive doomscrolling. Fair trade. I still have reservations, and one day I might switch it back. I like the idea of a little hermit web property, but I also think a Substack is 2026 New Media: business development through brand.
Cross domain pattern recognition is an in-demand skill, and I see the same patterns everywhere I look. Now I don't have to write it on a resume because it's all timestamped.
In a couple weeks, I'll have my Will Hunting moment, pro se in court, in the truest generalist's litmus test. I'm about two years out from separation now. I put in a lot of work these past two years choosing to build the relationship I want with my kids for the rest of time, then everything else, and did it all with my world on fire. Now they're heading off to kindergarten this fall, a milestone for them and a different one for us parents. I can feel things shifting again. When something's timing feels so true, you don't question it. My kids are claiming more independence, and so am I.
The generalist's moment feels like an internal world waiting for the external world to catch up, when reality lags.