This is the last installment of this newsletter for 2021, so I thought I’d take a look back at the past year of My Super Secret Diary: from its origins in 2020 to the five best posts of 2021 (or at least, what I think the five best posts are). Plus, I metaphorically strip down for you with an inside look at my subscriber growth over the past year.
My Super Secret Origins
I started writing this newsletter in September of 2020 when I took a job as the 11th employee at On Deck, running their Writer Fellowship. Although I’d written on and off my whole life, it had been a while (one year and seven months, to be precise) since I’d published anything. I didn’t think I’d have the credibility to run an internet writing program if I wasn’t writing and publishing online regularly myself. Plus, I figured I could write during the workday and tell myself it was (kinda, sorta) part of my job.
This newsletter has already outlasted On Deck Writers, which we wound down earlier this year as we narrowed our focus to founders and early team members. (But don’t worry—I’m still happily employed at On Deck, which has grown almost as fast as my subscriber count, to a team of over 250 today.) In that time, this newsletter went from a lark that I had started for semi-professional reasons to a passion project that has become a core part of my life.
The first few months, each week was a mad scramble to come up with something to say, and to get each piece out before my self-imposed Sunday deadline. These days, the scramble is… slightly less mad. Writing these pieces is still hard, but it’s hard in a different way. It’s like going to the gym: no matter how fit you are, lifting weights is still effortful. But once you build a habit, it at least becomes easy to put your workout clothes on and leave the house.
My Super Secret Subscriber Growth
I started the year with 130 subscribers and am ending with right around 500.
I’ve written before about how I’m not going all-out to juice my subscriber growth—I understand that this newsletter is a niche product, and I’d rather have a small group of engaged readers than a large group of disaffected ones. Nonetheless, it’s nice to see this number keep going up.
The main way this newsletter has grown—and the only reliable way to build an audience that I’ve ever heard of—is by my consistently producing (supposedly) good stuff. As you’ll see below, most of the noticeable subscriber bumps came when I wrote something popular and it got shared more widely than the average piece. My most popular piece ever (responsible for the March bump in the graph below) got me more subscribers than I got when I was featured in one of Substack’s promotional emails.
My Super Secret... … Just Kidding, I’m Not Going to Keep Reusing This Same Bit for Each Section Header. But Here Are My Best Pieces of 2021, With a Quick Lesson From Each
(And yes, I know I literally just said I don’t like doing best-of lists.)
Breaking and Entering, about the time I got hired to scope out some abandoned houses in Detroit. I wrote this piece after getting self-conscious that I was spending too much time sharing my abstract thoughts and not enough time telling stories. And it went over well! The lesson: people like stories.
Things That Sound Good, on saying things for how they’ll sound. In writing this piece, I consciously tried to incorporate the attributes of my writing people told me they liked in my 2021 reader survey. I don’t recommend focus-grouping your writing too much, but hearing about readers’ favorite elements of your work can help you double down on your strengths. The lesson: write things people want.
Must Love Jobs, about the idea of loving your work. This was my second-most popular piece of the year, even though I actually don’t think it’s one of my better pieces on the level of pure sentence quality. The lesson: sometimes (often?), your subject matter striking a chord with readers matters more than how well-written something is.
Love or Something Like It, about… well, it’s short, so just read it. Most of the time, even the pieces that are “easy” to write require some amount of struggle. But this one just poured out of me—I woke up with the thing already 75% done in my head. The lesson: very occasionally, true inspiration really does strike from some mystical source.
Special, about my relationship to the idea of being a “special” person, and how that’s changed over time. This is my most popular piece to date—it’s the one responsible for the March bump in subscriber growth above. It’s also the piece I personally think is my best work of the year. And it’s the piece that was the hardest for me to write, and that I spent the most time on. Funny how that works out, huh?
As I was drafting this piece, I was thinking about this tweet from my friend and sort-of boss Erik Torenberg:
This concept applies to anyone who’s creating anything, not just startup founders. By forcing myself to write something every week, I’ve ended the year with maybe a dozen pieces I think are really, truly good. That’s way more than I ever ended up with when I only tried to write “good” things. Paradoxically, the best way to achieve quality is often to focus more on quantity.
Thanks for reading—I’m very grateful to you all—and see you next year,
All I want for Christmas is for 50 people to forward this newsletter to a friend. If my wish comes true, it’ll prove Santa is real and I’ll convert away from Judaism: