An ongoing theme of this newsletter so far is how its title, intended as a joke, has instead become something more like a prophecy.
When I was picking a title, before I’d even started writing, I mostly just wanted something clever and entertaining. (I briefly considered “Unsubscribe Me” before realizing that it would be impossible to search for.) I settled on “My Super Secret Diary” after my friend Tim suggested having a title that would be funny to say out loud. But I never intended for the subject matter to be personal. When I started, I had a long list of post ideas that were more in line with the hastily-composed tagline, a rough compendium of my interests: “startups, literature, philosophy, American history, sex & drugs, and how to be alive.”
And then, for the most part, I didn’t write about any of those things, and this newsletter became almost exclusively about my own life. So… my bad?
In my day job as Program Director for the On Deck Writer Fellowship, I have a lot of conversations with writers about finding their niche. Everyone looks at the most well-known newsletterists like Ben Thompson and Heather Cox Richardson and wonders how they too can figure out what they’re uniquely suited to tell the world about. (In this way writing is a lot like freestyle rapping—the hardest part isn’t any of the technical skill, but just coming up with something to say.)
I always tell people that you don’t find your niche; your niche finds you. (I didn’t come up with this saying, but I now can’t remember who I stole it from—if it was you, I apologize.) You don’t “find your niche” by sitting in a room with your eyes closed and thinking really hard about what to write. It’s more of an iterative process: you sit down to write, ideally with a deadline, and wait for whatever comes out, and then you see how writing whatever it was felt, and how your audience responds. And, as with finding success, you never actually arrive: your niche starts blurry and comes into sharper and sharper focus over time, but you never reach a point where you’ve “found it” so definitively that you’re set forever.
That’s more or less what happened here. I started this newsletter intending to write about my intellectual ideas—I still have half-finished drafts of pieces about Enron’s fall and why JFK was actually a bad president. But the truth is that I’m not really sure what I think about a lot of things. And since all our beliefs are so heavily informed by our personal experiences, it felt almost dishonest to talk about the things I do believe without first talking about the things that happened to me that made me believe them. So I’d sit down to write about, say, why real estate is a soul-crushing industry, and I’d find myself writing pages of context to explain how I came to think that. And then I’d realize the context was the piece.
Much to my surprise, it turned out I was enjoying myself along the way. This was far from guaranteed: although it may be hard to believe coming from someone who openly discussed masturbating on a silent meditation retreat, in many ways I’m actually a very private person. I’ll gladly confess my comic foibles, but I tend to be much more reticent about sharing my actual emotions. The rhythms of this newsletter are pushing me to change that: when Sunday comes and I can’t think of anything else to write about, I find I’d rather reveal a bit more of myself than miss my weekly deadline.
And when I do, good things happen. So many of you have reached out to tell me that one piece or another has connected with you, that you’ve felt some part of your life reflected back in mine. I’d like to think that in writing about myself I’m not just writing about myself, that in my best moments I’m at least coming close to expressing something more universal—the “how to be alive” part of this newsletter’s ostensible subject matter, which I guess I actually have been writing about after all.
I still plan on writing that JFK piece someday. (Barely any of his domestic agenda made it through Congress! His foreign policy “accomplishments” were mostly just recovering from his own mistakes! His legacy is the result of the most sustained posthumous whitewashing campaign any president has ever been subject to!) But in the meantime, I’m embracing the unexpected direction this newsletter has taken. Like the since-disproven theory that people named Dennis are more likely to become dentists, I just went where my name took me. Turns out this really was my super secret diary all along.