If it scares me, there's probably something there
Talking craft, obsessing over the numbers, and playing the long game with Experimental History's Adam Mastrioanni
One of my favorite reads on Substack is without question
’s Experimental History, a newsletter that makes science exciting and funny by tackling genuinely fascinating topics like Why aren’t smart people happier?, Good conversations have lots of door knobs, and The illusion of moral decline, among so many others.I wanted to chat with Adam because we both come from a background in improv comedy. And you can feel it when reading his work - his writing feels like an actually good improv show - fun, alive, and most of all, connected.
Also his stuff is also way funnier than mine, so I need to learn his secrets.
We cover the role improv plays in his writing process, getting notes from his wife, and dealing with the negativity monsters around your own work (mostly Adam just helps me with that, thank you Adam).
Alex: How do you write? What’s your process?
It feels to me like a series of demonic possessions - an idea comes, it takes up residence inside me and the only way to get it out is to say the proper words in the right order. Which, for me, means saying it in the form of a blog post. Once I do that, it’ll leave my brain.
When I actually sit down to write, the things that come out first feel like lines the demon is screaming. They’re the things I feel most strongly about. Then I write paragraphs around those lines.
Every time I cut something, I'll never delete it. I just copy and paste it under a line at the bottom of the document. That's how I know I'm making progress – the graveyard gets larger and larger and the only things that are left alive are the things I didn't think I should kill.
Every time I cut something, I'll never delete it. I just copy and paste it under a line at the bottom of the document. That's how I know I'm making progress – the graveyard gets larger and larger and the only things that are left alive are the things I didn't think I should kill.
Do you have a muscle that knows when to listen to the demon voice? That knows when something will be good or trash?
Yes, definitely. I used to get a lot further into something before realizing there was nothing there. Now, I can tell much earlier when there’s no gas in the tank, when I’m pushing too hard.
Part of getting better at this is learning how to distinguish between the challenge of “this is hard because I shouldn’t do it” versus “this is hard because I don’t yet know how to do it.” If it’s the second case, maybe I need more research, or I’m not clear on what I want to say, or I’m not being honest enough – that’s a big one.
But the first case happens a lot. Sometimes, I slap myself - mentally not physically - and think, “What am I doing? Why am I playing a game with myself here?” Especially in this line of work where I’m not accountable to anyone – I can do whatever I want. So why do I end up doing something I don’t actually want to do? It’s like people doing improv scenes; they can do anything, but they choose to sit down and complain about hating their jobs. You could have been on the moon!
Part of getting better at this is learning how to distinguish between the challenge of “this is hard because I shouldn’t do it” versus “this is hard because I don’t yet know how to do it.”
Yes! And I think with writing and improv, it's fear driving all those decisions. If I’m not being honest - that’s information that’s like ‘oh, I’m afraid of something here.’
The question becomes, what is that fear, and how can I do exactly what scares me?
Because if it scares me, there’s probably something valuable there.
I was afraid to start the scene on the moon because I thought people would think it was silly. But actually, that’s exactly the reason to do it. That’s where the fun is going to be.
What’s the tenor of mood you’re feeling as you write? Are you positive and just cruising or, like me, battling inner demons of doubt the whole way?
It varies with different posts. Some are motivated by anger, like the one I'm working on now about how everyone says they want to fund high-risk research, but no one actually does. I’m arguing with this imagined audience that I think disagrees with me. That doesn't feel negative; it feels motivating.
Other times, it's confusion or curiosity driving me. I’ll be trying to understand an idea that seems odd, and that keeps me going. It never feels like a carefree bike ride through the countryside, though. It’s more like lifting weights—straining but knowing what it's for. The difficulty isn’t negative; it’s a useful kind of challenge.
What's the negativity that you feel?
Oh you know, a classic sort of "This piece sucks. Nobody’s going to like this. It’s not as good as my other work. People are going to think I’ve fallen off." And that feeling sticks with me even after I’ve published. I obsess over the numbers, thinking, "Look, everybody hates it."
Yeah…you know, that sounds bad. Don't do that.
Oh, okay. Good, cool, thanks, all healed yay. I mean, I would love to stop. It really feels like a compulsion, an obsession—almost like an OCD thing.
I post something, I close the tab, walk away, and do something else. I might check back once, maybe 24 hours later, to see any comments I want to respond to, but that’s it. The point for me is writing it and sending it out.
Psychology actually has a pretty good approach to treating OCD, known as exposure and response prevention. You have to face the thing that triggers your compulsion and then prevent yourself from responding to it. Over time, you learn that the discomfort isn’t as bad as you feared. I have friends who work in clinics where they do this with patients who have OCD about germs—they’ll make them touch a toilet seat and then sit with the discomfort until it fades away.
Ok interesting, so in the case of checking the numbers, what would the exposure be—just not checking?
No, so the checking is the compulsion, and the underlying fear is, “Am I good? Is this working?” So, you’ve got to post it and then let yourself feel the fear without checking, exposing yourself to that fear of sucking. Eventually, you’ll realize the fear goes away on its own.
Think about it—what would really happen if the numbers are good or bad? Either way, you could just do another post.
Take The rise and fall of peer review - it’s my most popular post, and before I published it I was like, “I don’t know, this is too inside baseball, I shouldn’t post it.” It didn’t seem radical to me at all, and I figured, “ah well, they can’t all be winners,” and posted it anyway. It ended up being the one that blew up.
So I try to just write the stuff that feels interesting and fun and by chance, some things will go big and some things won't. But regardless, I'm having a good time doing it – that model has never led me astray.
Think about it—what would really happen if the numbers are good or bad? Either way, you could just do another post.
Do you share drafts with people and get their feedback, or not really?
I read every post out loud to my wife as a gut check. I feel like a failure mode for me is going really hard on a post that ends up embarrassing me somehow. It’s easy to get caught in a loop and lose perspective. Plus, posting things on the internet is always a bit risky because it’s out there forever.
For some posts, I’ll share them with a few close collaborators—maybe one in every four—especially if I’m stuck or if the post is about something they know more about than I do. But most of the time, it’s just me in a room. Plus, a lot of my posts come out of conversations I’ve had, where I’ve already tried out my takes and seen how they landed.
What is your wife's reaction when you share drafts with her? And broadly, what’s your relationship with your work and how it intersects with your relationship with her?
She’ll usually joke that I’m annoying, but in reality, she’s incredibly supportive. Taking the risk to pursue this career also meant putting a lot of risk on her, and part of the reason I’m able to do it is because she believed we could take that risk. She was confident that I was capable, and that belief made it possible for me to go all in.
My wife is both a lawyer and a philosopher, so she also writes and engages in intellectual work. We have an interesting relationship in that we can discuss the intellectual merits of each other’s work, but we give each other a lot of leeway because we’re in different fields. We have this understanding that like, ‘ok, I'm going to tell you what I think. I'm not an expert on this and if we disagree about this, we’re still married afterwards so this has to be okay.’
Your Substack has grown a lot. What have you learned from that?
At the beginning, I had this idea that success on the internet hinges on a big breakthrough—like you need to go viral, and then you’re set.
But what I’ve learned is that, at least for me, it doesn’t work that way. Success comes from consistently having those small breakthroughs, over and over again.
There isn’t a single day when you go from being a nobody to a D-list internet celebrity. Instead, you just keep chugging along, with some pieces reaching more people and others not. Occasionally, a post gets picked up and there’s a lot of growth, but it’s been a gradual process.
This realization has actually made it easier for me because it takes the pressure off each individual post. It’s not about having a hit every time; it’s about consistently doing the things I believe are good. People keep reading because they like the overall content, not because every single post is perfect.
My hits are great for drawing in new readers, but people stick around because the good stuff keeps coming. They’re not going to abandon me if one post isn’t perfect. For the writers I really like, if a post doesn’t resonate with me, I’m not going to stop reading them—I’m just looking forward to the next one.
Success comes from consistently having those small breakthroughs, over and over again.
A huuuuuge thank you to Adam for taking the time to chat! Go subscribe to Experimental History and keep an eye out for our full interview and many more as part of our Sublime Interview series launching this fall.
In other news
Connecting the dots with futurist Keely Adler
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The five-minute video covers:
the 'aha' moment when Keely realized how Sublime fit into her workflow
why Sublime is the digital commonplace book she's always wanted
her workflow for leveraging Readwise highlights into deeper connections
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State of Sublime Townhall
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used during her talk. Big things coming soon!
This was wonderful. Such a pleasure to read.
What an enjoyable post. A lot of goodness in the interviews, both written & video. I look forward to watching the Townhall meeting, which I was unable to make in person. Thanks for posting it here.