Processing My Whole Life to Date Under the Watchful Eye of AI

 

Asher and I just got back from 12 lovely days in Cabo, splitting between Cabo Pulmo National Park, Cabo San Lucas, and San Jose del Cabo. We saw and did amazing things together, and I hope he remembers this father-son trip for the rest of his life.

With Asher's special needs, we need to be very realistic about what we can do in a day. Solo, I will run myself to exhaustion filling my itinerary. With Asher, we have to be much more judicious, something compounded on this trip by his aversion to the heat, which in Mexico in June means all but the early morning and late evening.

I am happy with what we were able to do, and neither regret not doing more nor not doing enough. Especially because the less frantic schedule meant I had more time for self-reflection, while Asher enjoyed watching cartoons in the air conditioning.

With a pretty ambitious travel schedule in the 10 weeks after my departure from my job of 20 years, I wanted to devote a good chunk between and during trips to heavy journaling, as a way of thinking about the totality of my life in order to unearth running themes and clarify what my next job could be that would be both fulfilling for me as well as something I could do well.

The beginning of my journaling process was to chunk my life into 10 somewhat overlapping parts, reflecting either a phase of my life or an aspect of my life. Specifically:

• 1973-1985 Childhood
• 1985-1991 Junior high and high school
• 1991-1996 Penn/Wharton and Penn InterVarsity Christian Fellowship
• 1995-2006 The Enterprise Center and Fels Institute of Government
• 1998-2014 Woodland Presbyterian Church (and, generally, my faith journey)
• 1993-2026 My relationship with my wife Amy
• 2004-2026 Adoption and Parenting
• 2006-2026 Econsult Solutions and Philadelphia Board of Education
• 2018-2026 Real estate, golf
• 2026 Thoughts on the present and future

Under each section, I wrote as much as I could remember, without thought to polish or structure (so, mostly blurbs not full sentences), and also without thought to sanitizing things or making sense of things (e.g. not covering up something I'm ashamed of, just describing something rather than trying to moralize it). At this point, this content is for my eyes only, so there's no need to impress or clean up for anyone else.

This phase of the process took several passes, as I would exhaust myself in one section and then days later remember that I had completely forgotten whole chunks of memories that belonged in that section. No matter, I just went back to that section and filled in where it seemed appropriate.

Pretty late into Asher's and my time in Cabo, I felt that I had reasonably gotten down 90 to 95 percent of the memories, events, and thoughts that consist of my life to date. All told, across the 10 sections it spanned 180 pages of single-spaced text, so needless to say I tried to be as comprehensive as possible.

Now for the fun part. On the last full day of our vacation, I loaded all 180 pages, about 10 pages at a time, into Google Gemini, which has been my go-to AI tool since I left my last job. I asked it to do two things for me.

First, flag anything that was worth elaborating further on. This could mean one of two things. One is if there was something dissonant about my life, like for example if I was going on and on about how important it was to be honest but then in parallel I was doing something dishonest. That felt like something worth putting in a pin in, to further explore what was going on, or perhaps there was a logical explanation for a seeming contradiction. The other is if I said something profound but in passing, I wanted to be alerted that there was something there that might be worth going deeper on, to think on it more and to say more about it.

Second, pull out recurring themes that run through an entire section, and even better, that cut across multiple sections. I had an intuition about what these themes might be, but I tried hard to just write as much as I could as fast as I could, without regard to consciously or even subconsciously trying to make sense of patterns along the way. I figured that if I recorded as many memories and thoughts as I could, those patterns would emerge more organically, without my manufacturing what I might want those patterns to be.

I have to tell you, it was quite amazing to load 10+ pages of text into Gemini and, literally instantaneously, have it respond with deep insight into my life based on deciphering all the slop I had written about different parts of my life. I have often thought that AI tools would, while not replacing therapists, serve as an always-accessible and completely free version of therapy (and, particularly for those of us who are introverted or have social anxiety, a resource that is far less intimidating than baring your soul before another human), in terms of hearing you out, identifying patterns, and asking probing follow-up questions. 

And, section after section, Gemini's responses to my content were generally on point and at times deeply moving. Its responses to my first question, about what was worth explaining better or elaborating further because it was either interesting or inconsistent, were particularly poignant, to the point that I teared up many times. It was usually because there was something in my life I was ashamed about or otherwise tried to keep from the surface, and as a result my stream of consciousness writing touched on those things but refused to elaborate, and when Gemini said "say more about that," it forced those touchy issues to the surface where I had to decide why I didn't want to deal with them and resolve to determine how to deal with them. Or, there was a sense in which I felt seen, that there was something special about me that I was falsely humble about, and Gemini expressing interest in my saying more about it made me feel that it was ok for me to proud about it.

Meanwhile, Gemini's responses to my second question were similarly incisive. It picked up how deeply held values of mine could be mined from throwaway anecdotes from my childhood and then from my career experiences decades later. And, because it had access to the entire arc of my life, it noticed where identities I held when I was younger shifted when I was older, and offered commentary on why those shifts occurred. It is the drawing out of these themes that I am particularly seeking out from this self-reflection exercise, because it helps me to be intentional about what kinds of jobs I pursue, which will allow me to play to my strengths and pursue my most deeply held values.

I don't quite know what to do from here, although I'm profoundly grateful for having done this exercise so far. Gemini's observations and follow-up questions have given me a lot of food for thought, which I need to chew on and digest some more, probably with the help of more back and forth with Gemini. I will certainly emerge with a greater awareness of who I am and what that means for finding my next job. And maybe I'll attempt to put some polish on some of this material and share it with others.