After Mastroianni: Notes on Writing’s Why & How
Adam Mastroianni, the experimental psychologist behind the brilliant Substack Experimental History, has become one of my favorite writers on the internet. And for good reason.
What sets him apart is his uncanny ability to approach weighty topics from completely unexpected angles, turning conventional wisdom on its head until it reveals something startling and true. Whether he's dissecting social psychology or examining human behavior, Mastroianni writes with a rare combination of sharp intelligence and genuine warmth, finding humor in our collective absurdities while never losing sight of what makes us fundamentally human. In an era of performative outrage and calculated takes, his honest, curious voice always feels like a breath of fresh air.
Mastroianni's recent post 28 slightly rude notes on writing perfectly captures what I love about his work. It's both funny and deeply insightful, the kind of writing that makes you smile or laugh out loud while simultaneously making you think harder about your own assumptions. Below are several of his observations that particularly resonated with me, along with my own thoughts, pushbacks, and additions to the conversation.
#8 Writing about despair
Mastroianni observes:
All writing about despair is ultimately insincere. Putting fingers to keys or pen to paper is secretly an act of hope, however faint — hope that someone will read your words, hope that someone will understand. Someone who truly feels despair wouldn't bother to tell anyone about it because they wouldn't expect it to do anything...
There's a deep truth here that I hadn’t considered: words meant for others always carry a kernel of hope. Of faith. When we feel unseen, we hunger for visibility; when we're misunderstood, we crave clarity. Check!
But, there are exceptions. Consider private journals where we pour our shame, bitterness, and sorrow with a sincere expectation of secrecy. But even here, there's a twist: sometimes these "private" outpourings are less an act of hope and more a silent cry for help. We might not display them, but a secret part of us hopes they'll be discovered. A message in a bottle tossed into the ocean of our own night side table.
#10 Writers whining about writing
I've heard the wails forever: Writing is torture, lonely, a sign of being messed up in the head. Writers treat like scripture the oft-quoted, "There is nothing to writing. All you do is sit down at a typewriter and bleed". I've never understood it.
To me this logic has always felt flawed. No serious writer claims writing is easy, because it's not. It's hard, frustrating, hair-pullingly so. But isn't everything worth doing hard? And, hard compared to what? Should we expect the standard to be easy? Our world is already so deranged, I cannot imagine what would happen if everything worth doing was easy.
Mastroianni nails it:
…it forces the mind to do something it's not meant to do. If you really want to get that sentence right… you have to squeeze your neurons until they scream. That level of precision is simply unnatural.
This resonates. I've spent hours wrestling single sentences into submission like it's an obstinate, elusive adversary. For years, I kept this strange, seemingly obsessive quirk of mine secret until a writer friend confessed to the same obsession with a knowing smile.
Hard? Good. It's supposed to feel like it could break you. What in life is actually worth doing if it's easy?
#16 On motive
Most writing is bad because it's missing a motive. It feels dead because it hasn't found its reason to live. You can't accomplish a goal without having one in the first place — writing without a motive is like declaring war on no one in particular.
This one gave me pause. On one hand, so much of writing these days is performative, especially the short form variety on social feeds. People talking to talk, writing to signal. But is motive ever truly absent? Even subconscious motives (vanity, fear, boredom) drive the pen.
Mastroianni's right that good writing needs a raison d'être. The problem isn't no motive, it's unexamined motive.
Melville's masterpiece, Moby-Dick, hinges on Ahab's why. Strip Ahab's motive and the novel collapses like a harpooned blubber-raft. No "From hell's heart I stab at thee!" and we're left with a middle-aged man annoyed by wildlife, 600 pages of cetacean trivia, and a climax where everyone drowns over a workplace disagreement.
No motive, no myth. Just a wet, encyclopedic shrug.
#17-19 On caring
Imagine a world devoid of caring. (Some days, it feels alarmingly close.) Yet the very frustration we feel about this lack of care is, ironically, proof that we do care.
Caring is the "why" behind the motive. Mastroianni frames it as education's core challenge:
…it's very difficult to teach people how to write, because first you have to teach them how to care. Or, really, you have to show them how to channel their caring, because they already care a lot, but they don't know how to turn that into words, or they don't see why they should.
Every student's "Why do we need to learn this?" is a plea for relevance: why should I care? Our education system which we now know was designed for compliance over critical thinking, often answers with silence.
No wonder caring feels so scarce.
But in writing, caring is non-negotiable:
What I really want to know is: why do you care? If you show me that — implicitly, explicitly… I might just… read what you wrote.
And here's the kicker:
There's something special about every word written by a human because they chose to do this thing instead of anything else. Writing is a costly signal of caring about something. Good writing, in fact, might be a sign of pathological caring.
'Pathological caring'. What a phrase. It's the difference between a love note and a grocery list. One bleeds; the other just sits there.
#23 Thinking vs. writing
…the problem was actually located between their ears. Their thoughts were not clear enough yet, and that's why they refused to be shoehorned into words. Which is to say: lots of people think they need to get better at writing, but nobody thinks they need to get better at thinking, and this is why they don't get better at writing.
True but glib. Most takes on this boil down to: "Think better, dummy!" but here's a twist: bad writing isn't a failure of thinking; it's a failure of listening, and more specifically, a failure of listening honestly.
Your brain knows when an idea is half-baked. The vague unease you feel when a sentence flops is your thoughts rebelling against poor articulation. Good writers don't just "think clearly", they negotiate and listen carefully with their own minds.
Or, as Orwell might say: "Bad writing is a faulty thought masquerading as a profound one."
The cure isn't more thinking, it's more listening and more honesty.
Final Thought
Mastroianni's notes are rude in the best way. They scrape off the pretension and leave the raw nerve. Writing is hope, pain, motive, care, and thinking. Often all at once.