A friend of mine works inside one of the largest software companies on earth, where his job is to help hundreds of people make sense of what artificial intelligence is doing to their work and, underneath that, to their sense of who they are. He is very good at this. He runs demos, teaches workshops, translates the technical into the consequential. But the actual work, he told me the other morning, never happens in the demo. It happens afterward, one by one, when people approach him quietly and say: Can we talk?
That is where they tell him what they are actually feeling — the uneasiness, the excitement that doesn’t quite cover the dread, the questions about whether they still matter in the equation. None of it makes it into a project plan, he said… not a single conversation, and yet: that’s where the work happens.
He is a poet and an AI ambassador simultaneously--he published his first book of poetry the day before starting the corporate job. Two years later he wrote a second book, this one about technology, and it ran counter to much of what his employer was building. Colleagues bought copies and handed them around. He describes what followed as a “small insurgency:” not one he organized, but one his writing made possible. The company’s response was… ambivalent. They liked that he was interesting. They did not love that interesting people sometimes ask inconvenient questions.
I asked him about the border crossings. He has at least four versions of himself in active rotation: the corporate operator, the writer, the podcaster, and the man who sits with other men and helps them find their voices. He used a metaphor I haven’t been able to stop thinking about. He called it Checkpoint Charlie (we’re both old enough to remember when the wall came down, and how much the horizon of possibility for millions of people moved in the days and months that followed). Every time he shifts from one (foregrounded) identity to another, he said, the security protocol changes. You never know whether they’ll wave you through, or tear your bag apart. So: you prepare, every time, for the full disassembly. You do the energy work of bracing for scrutiny regardless of whether the scrutiny comes.
That is the tax--not the crossing itself, but the perpetual preparation for it.
He served. He didn’t make much of it in the conversation — it came up sideways, the way it often does with people who’ve been inside that particular institution and come out the other side. What he lingered on was family. The word he used was duty, and he meant it the way the word used to mean something: not obligation in the legal sense, not guilt, but the thing you are privileged to owe because of the bind you share: who you are, that is, in relation to someone else.
I’ve been thinking about that word since our conversation. Duty carries two meanings that have mostly come apart: the tariff sense — the tax assessed at the border, the fee for passage — and the moral sense (i.e., the imperative that doesn’t ask whether or not you ‘feel like it'). In his telling, they hadn’t come apart. The vigilance he maintained, the permanent readiness, the monitoring of exits and entrances — that was the duty. The tax and the obligation had collapsed into the same posture. You pay it because you owe it. You owe it because you pay it. After a while, you can’t find the seam.
I know this particular exhaustion from the inside, though I would not have named it that way before he did. I have spent the last two years rebuilding a life after the end of a long partnership, leaving a job that was never quite the right fit, circling back to questions I have been carrying for twenty years about attention and meaning and what we lose when we stop noticing. I move between registers--the academic and the practitioner, the writer and the father, the person who knows things and the person who is still, at nearly fifty, figuring out what form this all wants to take. And I recognized, immediately, the feeling he was describing: the low hum of preparation for a disassembly that may not come but that you cannot afford to be unprepared for.
What struck me, though, was the tension inside his metaphor. The Berlin Wall is probably the most rigid structure in modern political memory: concrete, razor wire, armed guards, a death strip between one world and another… and he reached for it to describe work that is entirely about softness. Everything he told me about how he actually operates--in the one-on-one conversations after the demo, in the recording studio where he sat with a friend whose life had just changed, in the men’s group that meets weekly to say the things that don’t get said--all of it was governed by what he himself called a softness: a gentleness and presence that was unmistakable in the texture of everything he described.
When I named the tension aloud (i.e., rigid metaphor, soft practice), he didn’t hesitate. He was the peacemaker in his family—one of six kids; the oldest boy--the one who held things together while everything around him was loud and uncertain. He has been doing this since childhood. The gentility, as he called it, the instinct to bring dignity to a tense threshold. That wasn’t a philosophy he arrived at; it was how he survived.
I think about this more than I expected to. The people I know who carry complexity most gracefully across multiple worlds--who move between identities without collapsing into any one of them--are rarely the ones who chose ‘softness’ as a value. They are the ones who built it as infrastructure, early, because the alternative was not surviving the household they were born into. The flexibility is load-bearing. It looks like character because it has been in place so long that no one, including its owner, remembers building it.
This does not make it less real. It might make it more. A wall you chose to build can be taken down by choice. A wall you built before you had language for what you were doing becomes part of the architecture of the self. You cannot remove it without removing the structure it holds up.
My friend is approaching fifty. So am I. We are both, in different ways, trying to figure out what it would mean to rest inside the infrastructure we built: to stop preparing for the checkpoint, even briefly, and see what comes through when the border is unmanned. He said something about invitations only arriving when you let go long enough to receive them. I believe him. I also know that letting go, for people who learned early that letting go meant that things fell apart, is not only (or even primarily) a matter of permission: it is a matter of rewiring something that predates decision.
He turns off every metric on his Substack; he does not know how many people read him, and he does not want to know. The healing, he said, is in the breath after he hits publish: not in the reception, not in the reach, but in the exhale itself.
I keep thinking about that breath--the one between disassembly and reassembly, when you have crossed the checkpoint and have not yet arrived on the other side. Maybe the project, for people who learned softness as survival, is not to stop bracing. Maybe it is to get better at noticing the breath when it comes: the moment when you are, briefly, neither armored nor torn apart, just… crossing.