Like a Good Therapist, AI Gave Me Homework

 

As a follow-up to yesterday's post, I'm far from ready from publishing even tiny excerpts from the 180+ pages I wrote about my entire life's memories and milestones. But, I do want to record a few loose ends that came up in my back-and-forth with Google Gemini as it processed noteworthy incidents and identified recurring themes. Think of it as a good therapist who, having heard your life story, gives you specific homework to guide further reflection in between sessions. 

To wit, here are some things I'd like to probe further as I continue to take the summer for extended self-exploration. Please note that even these snippets, being short and somewhat sanitized, represent a significant vulnerability on my part, so I'm taking a risk in putting myself out there so much but I've long learned that there is no growth without such stretching.

Childhood

How did it make me feel as I began to realize that for as thrifty as my family was growing up we were actually pretty well off

How did seeing distinct and culturally common gender traits within my extended family (the men were intimidating or distant, the women tender and caring) affect my own worldview when I became an adult

Lots of instances in which I excelled, and yet still saw myself as an uncool outsider

Lots of reinforcement that accomplishing things in life sometimes requires pain and hardship

Physically and mentally gifted but often under-performed because of nerves, why was I so afraid and what did it take to overcome that

Early examples of my anal record-keeping, even and especially in leisure things (my dad's vacation notes, my own keeping stats for my made-up baseball and basketball games)

Junior high, high school

I had a regrettable moment as a high school senior in which I pushed around a smaller Asian freshman and enjoyed it, where did that come from given that I was once that smaller Asian freshman that feared bigger seniors

Why did I take to hip-hop so deeply, including some of its rawest and crudest forms, when I otherwise had no connection to it in my childhood

Multiple instances in which I thought I was too shy and nervous to be a leader but performed as one and was seen as one, so I grew into it

 

Undergrad, campus ministry

Managing the increasing complexity of my life (living 2,500 miles from home, gutting through an Ivy League education, being very active in my Christian fellowship) by clinging to things that help me through (my pocket calendar and pocket Bible were literally shaped to my body)

As my faith matured, I grew deeply uninterested in traditional business and finances spaces for my career because they felt too cut-throat, money-hungry, or sexist

My faith began to influence my life decisions, which caused my parents great disappointment, which left me incredibly conflicted: why did it cut so hard to go against my parents, and where did the conviction come from to stick to my values given how nascent they were

The Enterprise Center, grad school, Woodland Presbyterian Church

Transition from book-smart know-it-all to realizing that I hadn’t a clue about how most of the world worked (e.g. being insensitive about the consequences of the poverty my colleagues faced, struggling with an independent study that was messier than the usual classroom assignments)

Not running from but rather finding a way forward that was authentic to me to do chaotic things (manage a 35,000 square foot facility) or make hard decisions (respond to organizational financial distress)

Early church experiences as an adult, seeing diverse households come together and live out the Kingdom of God, set a high bar for what I think a church should look like: spirited worship, exegesis in sermons, real/gritty/broken (and therefore the antithesis is tepid singing, keeping up appearances, and valuing status over healing)

 

Marriage/Parenthood

Sometimes I was hyper Tiger Mom and sometimes I was very intentionally hands-off, is that strategic or inconsistent

Allowing myself to feel incredible joy over the crazy family situation God has given us, yet is there unresolved grief about not being able to have biological kids that I need to give myself room to feel

Alternating between being guarded about how not-together our family is and owning the mess so that others will feel comfortable doing the same

 

Econsult Solutions, School Board

My role, and the risk/reward at each level, evolves as I grew up from my early 30s to my early 50s, from safe job that I can leave at the office and go home to my baby daughter to bearing all the exposure of being president and co-owner

Similarly, what I actually do in my job matured as I grew in stature within the firm and then across the region, from a doer to a manager to setting the intellectual course for engagements to doing the same for the firm to being an overall thought leader for the region

With that meant digging deeper into traits that did not come naturally to me but that I knew were important and I worked hard to gain and express those traits, like being decisive or reaching out to people to have hard conversations 

Learned so much from my business partner and former grad school professor Steve Mullin, to the point of imitation and over time growing into my own authentic version of his best traits

Over time finding a deeper and centrist perspective from cold-blooded capitalist to bleeding heart Christian to something that incorporates all of that (and is willing to hold the line when folks on both sides are mad at me)

Willing to bear severe personal burden in order to survive all the juggling and do an excellent job and help others and advance myself (e.g. waking up at 4am every day to have some time to myself)

 

Golf, Real Estate

The metaphor of golf being in wide open spaces and me being able to spend several hours at a time at it, vs. I used to grind out 15-minute fast-forwarded NFL games in the basement, represents the increasing space I’ve allowed myself as I've grown older

Being terrible at golf reminds me that when you have wide shot dispersion, know where you can and can’t miss, and that's a lesson I've applied to the rest of my life

I gravitate to real estate because it taps into my wanderlust, penchant for deals, and spreadsheet-making

 

Present and future

I used to run myself ragged to get everything done because I had the youthful bounce-back to do so, now that I'm older I have to stretch and go to therapy and allow myself time to play golf

Whatever I do next, it has to build from these strengths I've identified in myself and do so in ways that help people and create impact

Sounds kind of "meta" but could the characteristics that have led me to this extensive self-reflection exercise be deployed to help others to do the same