The Great Resignation Letter

If this dramatically-titled post hit your inbox, you’re one of the 1,100 who’ve followed my writing this past year — thank you, it means a lot. It’s time I told you why.

I Resigned

Resigned has two meanings — to “quit” and to “give up on”. For the first one — I’ll be honest, I didn’t know how to say this — I quit my job to write about healthcare over a month ago, and I’m only telling you now. With the job market the way it is, resigning with nothing solid lined up looks a little crazy (maybe even obscene). As the main breadwinner for my family of four, it was agonizing to quit, but it had to be done. Maybe it’s a typical midlife-crisis thing, I don’t know — I just couldn’t make myself walk back in another day.

This wasn’t an abrupt decision — I’d been turning it over for more than a year. I’d already taken three months of unpaid leave just before I resigned — leaving over fifty thousand dollars (enough for a down payment on a new house) on the table — and the weight of pretending pressed on my chest a lot longer than that.

I’m not here to write a confession about how afraid (or burnt out) I was, but about why I did it anyway.

Performance Review

For nearly fifteen years, I worked across almost every side of the healthcare system. I helped drug companies launch new therapies, taught hospitals to bill more revenue out of the system, then turned around and helped insurers cut those same costs back out. I’d build something on one side, and a doppelgänger of me would be on the other side of the equation doing the exact opposite. I built a whole career on billable hours, sold to every stakeholder in the system — and I couldn’t take another fucking conference call, listening to all of it, jaded from the futility, pretending any of it was making the system better.

I was only just getting really good at it by the end. On paper I’d never done better — more respect from clients, more work sold — and it had never felt more like a performance, or more draining. The acting was the worst of it — walking into rooms to sell work I didn’t believe in, pitching certainty I didn’t have, rallying teams behind projects I’d already stopped caring about. Half of what I built was just slide decks made to sit on an abandoned SharePoint site until the next budget cut eliminated the project. Somewhere between the emptiness and the imposter syndrome, I stopped being able to tell whether I was actually good at this or just couldn’t hack it anymore.

It takes a climb to realize there is no summit. As a kid of immigrants, the dream was to get a stable white-collar job and finally collect the respect expected to come with it. First it was getting into a prestigious company, then hitting six figures, then managing people, then doubling the salary, then owning a budget, then the next rung and the one after that would be enough... But none of it ever was enough for me. I’d been measuring myself by other people’s yardsticks the whole time.

Labor

This work cost me in ways that weren’t obvious at first. The night Lauren was born, I’d been up with my wife for hours as the contractions came closer — and somewhere between them, part of me was working out whether I’d prepped my promotion packet well enough before paternity leave (I hadn’t). The most awe-inspiring night of my life, and I was somewhere else: fatigued, still wearing the mask of work I didn’t even care about.

I’d told myself Senior Manager would finally feel like enough (as if one more word would do it).

The job was never the title. I’d believed in the work, was good at it — then watched it get undone every time, until the futility of it hollowed me out, and even that night, I couldn’t fully be present. I couldn’t keep saving my best for the job and bringing my family what was left. So I left.

The Meaning of Resignation

For years I was too far inside the system to notice I’d been giving up on it the whole time — which is the second meaning of resigned, the one I’ll spend the rest of this letter discussing — to accept things the way they are.

While I was at a client office in Virginia, every morning I’d walk past the same floor — rows of people in headsets, sitting on an org chart I’d helped design (plenty of others never made it onto that chart - they’d already been laid off), and the ones still there sat reading call scripts written by my team, calling patients about bills they couldn’t pay. And I walked past all of it on my way to the office I was angling for, and told myself this was just how it works.

And I’m not the only one. Everyone I’ve run across in the healthcare industry — C-levels at health systems, insurance execs, private-equity operators running the ROI on a deal — not one of them, off the record, thought the system worked right, and every one of them was resigned to it anyway.

You can hear it in the language. Patients first. Top of license. No margin, no mission. But slogans were undercut by hedging: Of course we can’t cover that benefit; of course we can’t give the nurses what they’re asking for; of course it’s just how the system works — as if there were no exit from this hell. But there always was an exit: the system is the way it is because of the choices people made, and the ones we keep making. Every of course is one more of those choices, one more person deciding it can’t be otherwise - and they add up.

The meaning of resignation, for one person, is just giving up. But when a whole industry does it — each individual privately certain it’s broken, and just as certain there’s nothing to be done — it becomes bad faith at scale. It’s the same excuse we make about climate change. It’s too big to move, so why bother — and maybe it is beyond any one of us, but that was never the same as being beyond all of us. You can decide the planet is beyond saving and still bring the reusable bag; there’s always a smaller choice underneath the big one we’ve given up on.

What took me the longest to see is that people give up but never stop performing. You stop believing the system can change, and you keep reciting patients first anyway; you nod along to let’s fix the system in meetings you know will change nothing. Everyone keeps acting out a care they’ve stopped feeling, and the performance is what holds the whole thing in place.

I left because I couldn’t keep performing in a life I’d stopped believing in.

Resolution

I started writing. It’s almost funny now, how at first it was just a couple of LinkedIn posts, and (I know) I was mostly trying to project some kind of eminence, to sound like a Serious Person in the field. But after a while I caught myself doing it — the same performing I did everywhere else — and something in me went, this isn’t how I actually sound. So, I stopped doing that and started writing the way I’d actually talk, got over the cringe, and said what I actually thought. It worked slowly — a post would get a few more likes, another a few comments, and every so often one would hit the slot machine and blow up for reasons I couldn’t explain. Eventually I understood those were the ones where I’d captured my own voice. People I’d never met started writing to me — a professor asking if she could cite one of my pieces to her grad students, a few execs and investors sliding into my inbox — and I won’t pretend it didn’t feed the vanity. But somewhere in there it stopped being about being seen, and I fell for the writing itself.

And then I look at what I do all day now, working on the craft. I hunt down absurd ICD-10 codes to use as metaphors. I rewrite an insurance benefits letter as if it came from your own mother. I built an 8-bit video game about HIPAA (working title HIPAApocalypse). None of it pays — I left a two-hundred-grand job to do it. It seems crazy, yet I can’t help it.

Healthcare is the only industry I’ve ever wanted to give my whole mind to — medicine bordering on sci-fi, mind-bogglingly grand economics, unintuitive business models that make no competitive sense, and quite literally life and death in the balance. The most consequential industry there is, and somehow the most boring to read about — written in two registers only: outraged or defeated. Almost all healthcare content leaves me feeling resigned... and I keep thinking there has to be a better way.

And the more I wrote, the clearer my actual belief got. We keep trying to fix healthcare with technology, with policy, with new business models, and it never quite works — because the problem underneath all of it is culture. The stories the healthcare industry tells itself, the things it has agreed to accept, shape how the people within it behave. (Health, it turns out, is mostly other people.)

And I couldn’t tell these stories honestly while I was still working under someone else’s logo — I couldn’t name what hospital consolidation does to people while I was doing the mergers myself, or question an insurer’s strategy while I was trying to sell them my next project. Leaving was the only way to give myself permission to finally say the things I’d been dying to say.

Given how things have turned out, I don’t think I can go back yet. Multiple job offers came rolling in (ironically the kind I was fishing for when I started writing). But I’ve had to turn them down - not to hold out for something better - but because slotting back into a normal job would be an early off ramp. I work harder at this than I ever did at the job that paid me, and it’s the first thing in years that’s made me feel like I made the right call. Then I remember feeling right doesn’t pay the bills. And yet still, I can’t not do it.

Exposed

Part of me just wants to be seen — I like writing things and having people actually read them. But more than the attention, I need to know whether the ideas are any good. And mostly, I just need to get this out of me. I’m scared, honestly — that I’m not good enough to pull it off, that I’ll fail at the one thing I’ve staked everything on, that I did all of this for a reason that won’t hold up.

But the bigger fear is if I don’t do this, it won’t get done.

The writing is the flywheel for me. What I really want is to expose the hidden stories in this industry — the ones that are obfuscated and overlooked.

How forgotten corporate deals reshaped the medicine you get. How nuns still decide what care you can get at the only hospital in town. What a nurses’ strike is really a fight over. How little of your healthcare dollar was ever really about you. I want to dig them all up and tell you what’s there — now that there’s no one paying me to look away.

So if any of this makes you curious, then please subscribe. My content will always be free, but consider going paid (I’m not above performing for the Substack algorithm yet).

And honestly — I can’t tell you what it’d mean to have you here for it, reading it and arguing with it and passing it on. That’s the thing that tells me I made the right call, and not just a scared one.

Re-signed

I don’t know how this ends. Maybe I change how decision-makers see this industry; maybe it never lands and I’m back in an office someday, hat in hand. Either way I’m going to keep writing — it’s already made me more honest, and more alive, than the job ever did, and I’m not handing that back.

I have quit, but I’m not quitting. I have resigned, but I’m not resigned.

— Andrew