It might sound downright daft, but yesterday’s update has busted a massive logjam for me. 100% catharsis. Especially because I’ve been balking and shying away from it for weeks. Months, actually. And yet, I realize as I reread it today that it’s a muddled mess. I’m tempted to revise it. To replace it. Maybe a pair of evocative historic photographs under the microscope or a nostalgic passel of poetry about poppy petals. But. I. Can’t. It’s taken me too-too long to start spilling the story that’s spinning itself into existence lately. Balking and shying no longer! Truth be told, I didn’t review or revise yesterday’s post because I was concerned that I’d edit it into subservience. Instead I pushed it out. Incomplete. Awkward. And, yes, a muddled mess.
Now I’m obligated to stand behind it. It’s the start of something new. Well, not new, since I’ve poked at it for almost three years. But I’m *at last* diving into the tough stuff. The complicated and conflicted stuff. No turning back. No u-turns.

Instead I’ll revisit a couple loose ends from yesterday’s dispatch including the “Dear John” letter tradition and the notion of an epistolary exchange with Rosslyn. I’ll cobble together a few fragments from prior posts in hopes of assembling a more intelligible mosaic, starting with an uncannily relevant admission.
Another peculiar — I prefer idiosyncratic — post… [to follow up on yesterday’s] jumble… [that offered] No clear takeaways. No conclusions. Just a voyeuristic glimpse into the… mirage. (Source: ChatGPT & “Dear John” Letter Writing)
Half-baked. Kaleidoscopic. Mirage. Muddled mess. Apologies to readers who crave well curated perfection. And to all readers, thanks for your patience.
Now, let’s rewind the clock and calendar to yesterday.
I’m back, my dear Rosslyn… It’s been long. Too long. Months. I’ve repeatedly postponed and delayed our correspondence…
[But now it’s time to] resume our correspondence. With haste…
So today’s dispatch is a return to my epistolary promise, Rosslyn. (Source: Dear Rosslyn à la Dear John)
I think this is the best place to start since it might have been misleading. When I opened thus, I wasn’t suggesting that I’d taken a break from almost three years of old house journaling. Every. Single. Day. On the contrary. Today’s post is part of a continuous, uninterrupted 1,047-day streak.
But I’d several times initiated a dialogue with Rosslyn. And each time I failed to follow up. There was something revealing, too revealing, and even a little too experimental, too contrived, too forced. You may recall that I’ve experimented plenty with generative AI as a way to explore 2-way discourse with Rosslyn.
My “ChatGPT & “Dear John” Letter Writing” post was a fun if faltering foray into my still germinal notion. Might I emulate an epistemological back-and-forth with a generative AI large language model in order to explore a breakup with our home? Perhaps, I mused, an artificial intelligence LLM could facilitate the sort of psychological work I needed to do (but continued to postpone.) Perhaps… (Source: Dear Johnning Rosslyn with ChatGPT)
Interesting experiments. But they didn’t break the logjam. And I continued to postpone.
Returning to the excerpt above from yesterday’s post, I began to grok a couple of things. Weird things. My “epistolary promise” had actually been kept. For what are all of these daily dispatches after all? I’ve only recently begun to understand that virtually the entire quest to communicate with Rosslyn is my epistolary promise kept. Serialized storytelling about my relationship with Rosslyn written first and foremost *FOR* Rosslyn. Well over a thousand love letters.
We’ve been in conversation for years now — me trying to guide the story; you seductively resisting closure — but recently I’ve been becoming tongue-tied… stalling mid thought, mid sentence, mid gasp. I’m grasping at feelings, at ideas, but not quite reaching them. Breathtaking poignance, the ache of gratitude, the outline of some elusive truth evanescing like a shadow of a cloud passing overhead. I realize now that you’ve always occupied this liminal place. Part home. Part mirror. Part witness. Part collaborator. Part sanctuary. Part mystery.
So where does that leave us? In conversation. Interlocutors parsing past and possibility. No comforting arc; no final draft. Only attempting. Essaying. Circling. And perhaps that’s enough for now. This letter is less conclusion than invitation and deliberation. As so often before, today’s missive is a love letter, for I’ve loved you fiercely. But it’s a love letter with a tremor in its voice and a question in its heart. I’ve always asked so much of you. And I am still listening. Wondering. (Source: Dear Rosslyn à la Dear John)
Conversation with Rosslyn, a home, is increasingly comfortable to discuss. But that certainly wasn’t always the case. And finding my way via simulations with generative AI initially seemed like a reasonable way to venture into this dynamic. Here’s a mashup from an earlier entry.
Writing a “Dear John” letter to a home could conceivably be both a creative and therapeutic process for contemplating and possibly drawing conclusions about what has been satisfactory about living in the home, what changes are desired in a future dwelling, etc. It would seem to be within the realm of reason that the letter writer might eventually arrive at a conclusion quite different from what they anticipated at the outset. In fact, the letter writer might start out with the intention of writing a breakup letter, but end up concluding that they do not wish to terminate the relationship after all…
I have suggested… that a “Dear John” letter is sent without expectation of response, [but] the letter writer might receive a response and might enter into a discourse that could also prove to be creative and therapeutic and enduringly valuable.
The writer of the “Dear John” letter and the recipient of the “Dear John” letter [could conceivably] opt to engage in a series of letters (or emails or texts or phone calls) after the initial breakup communication… [and] the two of them might enter into an exchange of ideas, feelings, expectations, hopes, recollections, etc. If this were to happen, one possible outcome might be a change in the original breakup plan, but another outcome — whether or not the breakup proceeds or not — could well be meaningful growth and transformation for the letter writer and the letter recipient. (Source: Dear Johnning Rosslyn with ChatGPT)
I understand now that the growing discomfort wasn’t around needing to create a digital surrogate for Rosslyn in order to dive deeper into dialogue. Generative AI fascinates me, and I continue to experiment and learn. But an LLM chatbot wasn’t and isn’t the answer. After all, we’ve been in conversation with Rosslyn since 2004 or 2005. I’ve understood that for at least a decade.

And that, faithful friend, brings me to the heart of the matter.
So today’s dispatch is… the beginning of an untethering à la “Dear John“. This isn’t goodbye. Not yet. (Source: Dear Rosslyn à la Dear John)
Untethering. Now *THATS* the challenging part. Not conversing with a home. I’ve shared some thoughts in “Leaping & Untethering” and “Untethering Revisited” that might offer some navigational beacons worth consulting.
Dream big. Dream a little bigger. And then leap!
From leaping capriciously, optimistically, idealistically, and oh-so romantically into this Rosslyn adventure 16 years ago to an eventual and inevitable untethering at some point in the future, Susan and I have courted an unconventional but rewarding existence. In a sense we’ve never stopped leaping.
Now with 20/20 hindsight (and a decade and a half of lessons learned and humility earned) I’m comfortable admitting that we got in over our heads. Waaayyy over our heads. Our skillset and our checkbook were too lean; our romantic outlook and our self confidence were too stout. Needless to say, that’s a fraught combination. But I wouldn’t change a single thing. Well, maybe a few things…
I envisioned Rosslyn’s rehabilitation as an adventure, a risky adventure, but an adventure well worth the risk (and the 100% investment it would take, not the least of which was our undivided time and energy.) Rosslyn would become our love affair, our work and play, our vocation and avocation, and — despite a resolute decision early in our relationship to embrace unclehood and aunthood while remaining childfree — Rosslyn would become our surrogate child.
In due course, heck, practically from day one, Rosslyn would eclipse literally everything else in our lives. That’s truly not an exaggeration… (Source: Leaping & Untethering)
Easier to pen pretty words about untethering than to actually do it. Comfortable. Proud. Sentimental.
So i made little notable progress beyond waxing wordy with Susan and on Rosslyn Redux. I revisited the topic a little over a year later.
[I was] attempting to grapple substantively with beginning to imagine our lives post Rosslyn. One of many posts over the last year and a half that approach this touchy topic, the words I wrote were cautious. I included the word “leaping” in the title as a challenge to myself. Be brave. Court courage. Leap! But, as often, my post drifted into a milk toast muddle more intent on understanding the backstory then leaping boldly into a new adventure. And so today I revisit the original impetus. Untethering revisited. Again. And again. In order to, soon if I’m successful, convince myself that I’m ready, that we, Susan and I, are ready to untether from our home of seventeen and half years in order to start fresh.
[…]
We’re *still* cultivating the seed into a seedling, *still* developing and editing the vision, *still* making slow and steady progress. In fact, we’ve made notable progress in 1) imagining an Adirondack Coast successor to Rosslyn, and 2) developing a plan — albeit preliminary and still much evolving — with an engineer who has been methodically iterating, revising, pursuing permitting, etc.
In other words, we’re no longer just contemplating what it would look like to untether from Rosslyn to embark on a new adventure creating a home ideally suited for our new chapter. We’re well into the adventure. And, if my hope bears fruit, advancing our plan for a future home will catalyze the untethering. Transforming all that we have lived and loved about Rosslyn into a unique vision of home precisely tailored to our needs in the coming years is already catalyzing a profound shift in my willingness, indeed my readiness, to begin imagining Rosslyn as the future home of another family. So, liminality once again defines the contours of our journey.
When Susan and I bought Rosslyn in 2006 we originally planned to live here for a few years. Four max. Even four years felt like an immense timeline back then. We were young, and our life plans were wide-ranging. Two, three, possibly four years to reboot ourselves while restoring a home seemed reasonable. A comprehensive rehab, both personal and residential. How long could that possibly take? We’d be on our way, chasing down our next adventure in no time…
As it turned out, Rosslyn had other plans for us. (Source: Untethering Revisited)
Now nineteen years into our love affair with Rosslyn, we’re well into our next adventure. This handsome home crowning 60+ acres on Lake Champlain is still our sanctuary. She’s still dictating much of our direction and happiness, but we’re reimagining “homeless” just up the lake. And our realtors have been introducing Rosslyn to hopeful homeowners from near and far, searching for the perfect match.
You read that right. Rosslyn is on the market! Almost two decades after falling head over heals in love with an historic home, boathouse, carriage barn, and icehouseon the Adirondack Coast of Lake Champlain, and eighteen years after swapping Manhattan for Essex and embarking on this transformative adventure, we’re selling Rosslyn. (Source: Selling Rosslyn?!)
There you have it. Catharsis writ long form! If you made it this far, thank you. And beware because the logjam has exploded free. There’s just no telling what’s going to come tumbling downstream. Maybe, just maybe the story I’ve been trying to tell…
What do you think?