Goodbye Letter to Childhood Town

Gratitude, Reflection, & Vision for a Prosperous Suburb 👋🏼🏘

Well, I didn’t expect to spend weeks write this one. Neither did I expect my parents to actually ever sell our childhood home. But alas, here we are. Moving away from Westchester, NY after 30 years (Chappaqua for 9, Armonk for 21). It’s quite emotional, between the joy in uncovering 2nd grade art pieces, stress of organizing generations of stuff, and heartbreak of having to throw piles of useless swag in the trash.

In some ways this is a random piece. In other ways it’s an exquisite intersection of things I’ve been writing about (achievement culture), working on (education reform), and supporting folks in (purpose discovery). Regardless, it was a good context to share thoughts and vision around topics that matter to me. The words came out naturally. When I think about my position and role in the web of life, I am unequivocally connected to affluent suburban New York, and I got some things to say. This was my act of leadership for that community.

You know me, it’s a long one (I’m working on that!) but I’ve bolded key sentences and used lots of images to make it fairly skimmable. I very much welcome feedback and reflections. Whether you grew up in, currently live, or desire to be in a town like mine, or none of the above, I hope there is something here for you. I’m nervous to share, and excited for what conversations and connections may emerge. Wish me luck!

READ: Goodbye Armonk: Gratitude, Reflection, & Vision for a Prosperous Suburb 👋🏼🏘

Some additional commentary:

On Innocence

I have this whole story around struggling with pressure of expectation throughout my entire youth. But as I sift through old files and mementos, I’m struck by how innocent I seemed in elementary school. Everything looked chill and easy. Happy kid, happy life. My attention is now drawn to that transition from elementary school to middle school: puberty, the internet, increased exposure to pre-professional culture and the real world. Shifting from childhood into adulthood, without meaningful initiatory experiences to purify oneself of selfish goals or orient towards a path of service for the community. I wonder if my greatest wound is that slow burn of disconnection from self in that transition from one stage to another. Something like getting caught in a current towards the main stream, knowing in my bones that it wasn’t the path I wanted to follow.

A friend asked what I’m grieving during this moving process. I wonder if there’s another loss of innocence occurring. There was the teenage loss, the college loss, the professional loss, maybe some more sub-losses along the way. This new loss is marked by leaving “home” foreal, i.e the place that has held me since I can remember. Of course I’ve lived in many other places, but always came back to this one. As we pack it up, I get this unmoored feeling. A new level of nakedness in direct exposure to the world. Somehow more “on my own” than ever before.

On Money

lol. The pendulum just keeps on swinging here. It’s one of those cosmic jokes that the period I came into the highest wealth generating capacity coincided with that of my most self-righteous relationship with money. And now I’m honestly a little sad I can’t as easily do all the things I want to ¯\_(ツ)_/¯

Part of me likes achievement and money and nice things. Part of me judges the shit out of it and sees it as part of the problem. Part of me trusts that it’s all perfect; all for our learning. Part of me doesn’t know. Part of me appreciates this ancient tension between the material and spiritual (did you know every symbol on those COEXIST bumper stickers contains some reference to the integration/balance of polarity?).

I have this story in my head that in 2021 I stopped playing the founder/savior/winner games and attempted to transition into a humbler existence of coaching/consulting/studying/writing. A sufficiency-oriented existence, not taking more than I need. It’s far from the ascetic pendulum swing the Buddha took, but it somehow feels lacking. Like I’ve made myself too small, too quiet, too hard on myself in order to balance things out. So maybe there’s a bit of a recalibrating, again. And questioning what would it be like to create wealth in ways that feel in alignment with my values, or those of original peoples?

On Writing

It has been almost one year since I decided I wanted to write a book, and then oriented my life around the identity of a writer. No book emerged, but enough essays did to fill a short one! I keep getting nudges to write a book…

I’ve noticed my mental health taking a bit of a hit recently, and wondered how that might be connected to the craft of writing. Of course there’s the loneliness, writers block, exposure to harsh feedback, and general headiness of kneading over words from morning till night. For me, even though my writing generally has an equal balance of critique and vision, I think the critique is starting to weigh on me. My writing also tends to be curatorial, drawing information from endless sources, perhaps approaching a limit of what I’m able to hold while also remembering to breathe every now and then.

So, I’m considering slowing down the writing for winter, and being more discerning before jumping into a new piece. Which feels really good and natural, with winter being a prime time for reflection. How did this experiment go? What did I learn? Even though I’ve been bubbling up writing insights as I’ve gone, I’m embarrassed to say I’ll often jump into a piece without paying much attention to those insights I previously gleaned. Looking forward to giving them time to sink in.

Wampus Pond: my favorite hangout the last few months, just a half mile away from home.

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Winter Plans

Sigh. This has been a question mark since I arrived in New York in the spring. I’m helping out with the move until mid-December, but then I do not know. I have invitations and feel pulls to California, Puerto Rico, Israel, North Carolina... but haven’t found that “fuck yes.” Open to winter camp, open to bopping around. “Winter of Health” has been the mantra. I’d like to start working with a therapist, lean into some more creative practices like art/music/dance, reconnect with nature. While ramping up the startups ethics coaching. I wonder if my indecision has some deeper intuitive wisdom to it, like something is on the horizon that is important to be flexible for. Or maybe I am to just go for what I really want. Regardless, keep the invitations coming :)

Love,
Andrew