A year ago, I stumbled upon Shawn’s Substack. He had just lost a $150k engineering job and was driving for DoorDash, living in an RV trailer. He wrote about it plainly, which made it worse. He pronounced that if your job is done on a computer all day, at any skill level, you should already be building your exit plan.
I mentioned him in an essay and moved on.
Last week, I remembered his article for no logical reason, out of nowhere. He’s now Head of Engineering at a startup.
I felt relieved. Not just for him. For myself. For everyone reading these dispatches from the edge and wondering when their number comes up.
Shawn had predicted a kind of doom, and he had, at least for now, clawed back. That felt reassuring.
The Question You Didn’t Choose
There’s this concept called the End of History Illusion. We consistently believe that the person we are right now is the person we will always be: that our present skills and identity are the culmination of everything that came before. While we acknowledge that we’ve changed a great deal in the past, we strangely believe we won’t change much from here.
That’s why layoffs feel so personal.
Because if your work is your identity (and for many of us it is), then a layoff doesn’t just take the job. It takes the answer to a question: who are you, besides work?
That question is hard and let’s not dress it up as an opportunity. It’s devastating, especially when you didn’t choose to ask it.
Most of us were already one setback away from not knowing the answer. The layoff just makes it impossible to look away.
Proof That You Exist Outside Work
Peter Drucker wrote something in Managing Oneself that I’ve turned over many times:
“There is one prerequisite for managing the second half of your life: You must begin long before you enter it. No one can expect to live very long without experiencing a serious setback in his or her life or work.”
Not a hobby, but something more structural. Because a self tethered to a single role is one job loss away from not knowing who it is. The second interest is proof that you exist outside of work.
But proof requires actually doing the thing. And that’s where most of us stall.
Simone Stolzoff, in The Good Enough Job, pushes further. He calls it diversifying your identity, focusing on parts of you that nobody pays for. They exist. But have you given them enough room to be findable when the role disappears?
Most of us haven’t. Because while job always had a next thing to do, the unpaid version of ourselves could always wait.
The Person Underneath the Engineer
On Shawn’s Substack, there was a new article. Not about AI, not about the job market. About his childhood. Personal, unguarded: the kind of writing that stops you in your tracks. I had to finish it even though it was past midnight.
He survived the layoff and found a new role. A good ending. But it was the childhood essay that stayed with me. Written when nobody was asking him to produce anything, when there was no audience in his head.
I wonder if he knew that person was there before the layoff forced the introduction.
The Self the Struggle Makes
I had a smaller version of this recently. I wrote about a college reunion, of the particular discomfort of standing in a room full of people who knew an earlier version of you, and trying to reconcile who you were with who you became.
Writing with an audience in mind has a way of activating your internal editor. This editor smooths the sharp edges and adds the lesson learned. So I put it on a personal blog instead, and tried something closer to how George Saunders writes: story-shaped rather than a LinkedIn essay. No takeaways. Just what happened, raw and unedited.
Was it good? No idea. But for the first time in a while, I had written something without knowing where it was going, and it didn’t fall apart.
I’d always thought of myself as a writer who argues, who builds a case, connects the dots. Turns out there was a storyteller in there too. I just hadn’t given him a reason to show up.
Nick Cave, responding to a fan who asked about ChatGPT, wrote something that has nothing to do with AI and everything to do with this:
“It is the struggle itself that gives the song its beauty and its meaning.”
He was really talking about the self that gets built through effort: through the doing of a hard thing over time. Drucker tells us to start early. Stolzoff tells us to make room. Cave tells us why it matters: the struggle is the point. The self you find on the other side of it is not an accident. It’s what the effort made.
That self doesn’t show up on a resume. It doesn’t disappear when your job does.
The pain caused by layoffs is real. Now, we’re stuck in a chasm between your present and next self, and nobody knows how long we’re suspended in it.
But Shawn wrote about his childhood at midnight because something in him needed to. Not because it would help him land the next role.
For years, many of us said yes to the work and quietly no to everything else. The writing no one paid for, the interest that didn’t fit the job description, the version of ourselves that existed outside the role.
The layoffs force us to confront the question of who we are when the job is gone.
That question is hard. It is also worth sitting with. Not because disruption is secretly good for us, but because the self on the other side of it was always there.
We just hadn’t been introduced.
Musings by Madhav 
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