How I Write the Best Newsletter in the World
Hint: I start with hyperbole.
This is my 257th Substack newsletter. Yeah, I know, I couldn’t believe it either. I mention this number because I’m taking a week off to rest my mind and body so I can come back energized for the next 257 newsletters.
I didn’t want to abruptly abandon you, so I’m going to answer one of the most-asked questions I get: How do you write your newsletter? In the past, I’ve summarized the process, but today I’m going to go into more detail because, well, you asked for it.
As a bonus, at the end I’ve included a delightful song from a famous blues and jazz singer Blossom Dearie (real name!), that expresses exactly how I truly feel about my loyal subscribers.
The proliferation of Artificial Intelligence (AI) over the last year has turned many of us into jittery paranoids, constantly looking over our shoulders for when we will be replaced by a fancy algorithm (“Every start-up is an AI company now.”). Even the creators of AI have been warning of an approaching doomsday if strict safeguards are not immediately put into place (“OpenAI’s Sam Altman Urges A.I. Regulation in Senate Hearing”). It’s enough to turn us all into 21st-century Luddites on a holy mission against Evil Technology (except, of course, dating apps, DoorDash, Uber, Amazon, and a couple of dozen others—we’re not savages!).
As I watch the proliferation of AI art and content, I can’t help but wonder if I could be replaced as the writer of this newsletter. Will the programs one day become so sophisticated that they can capture the essence of my voice, my tone, my pop culture references, my insights into the news, my passion for history, my insistence on critical thinking and logic—and my love of goofy squirrel videos? Maybe. But as I was reading the novel The Verifiers by Jane Pek (more on that in a future newsletter), I kept marveling at the poetry of her language, the sophistication of her insights, the sharpness of her wit, and I decided no AI could create that unique combination that is born from the author’s own personal experiences and way of thinking.
In the meantime, pre-replacement of me, here is how I write this newsletter.
You’d think I’d start in the morning, but since I’m not an AI, I will unexpectedly start in the evening because that is when many ideas start to percolate. First, it’s important to know that each newsletter takes four days to write, and because I write two a week, they overlap, and I’m usually working on two at a time.
So, there I am your intrepid author, tucked into his oversized bed, clutching his iPad and reading the news. I read through the entire issues of The New York Times, The Washington Post, The Los Angeles Times, The Guardian, The Wall Street Journal, and The Daily Beast. I’ve already read them that same morning, but because new stories come in throughout the day, I reread these publications for updates. I then read through my Apple News feed because I can read curated stories from many other publications, including The New Yorker, The Atlantic, The Hollywood Reporter, etc. I collect all articles that interest, amuse, anger, or intrigue me into a folder for later evaluation.
I do this seven days a week.
The next morning, I lie in bed writing in my head. I think about what my take will be and if it’s worth offering. There’s no point in me making the same comments everyone else will make: Hate bad, love good. I want to be sure I’m contributing to the discussion, not just echoing. One way I think I contribute is when I do a critical thinking breakdown of certain statements by politicians or celebrities in which I show their logical fallacies. In some way, I feel like I’m holding the line against sloppy thinking that leads to faulty opinions.
When I get out of bed, I read all the publications I mentioned before and add anything worthwhile to my folder, which is labeled for the date I intend to post. Afterward, I reexamine everything in the folder, select the most important articles—keeping in mind that I also want a variety of topics—and begin writing. My folder has way too many articles, so there is no way I can write about all of them. This bothers me because there are many items I would like to comment on but just don’t have the time.
The first step in writing is research. I try to read as much about a subject as I can before adding my commentary. I’m not looking for ideas, I’m looking for more context. What is the history of the issue? Are there differences in what we know today versus what we knew in the past? What studies have been done? What do the experts’ research show? Is there evidence to support my claims?
The next step involves a rough draft of my main ideas which is then followed by lots of rewriting and polishing. I want to give clarity, examples, metaphors, and research—and I want it all in entertaining language. The readers don’t need lectures. They want discussion. So, I draw on my knowledge of poetry, music, history, movies, TV, graphic novels, sports, and whatever random flotsam that’s attached itself to my brain, and I use it in my writing to make my points clearer and more fun.
During the rest of the day, I keep thinking about each segment and will come up with a new phrase or sentence, or example. I’ll write a note and later go back in and rewrite once again. Adding a note or a phrase often leads to new ideas, and I’m pulled down the rabbit hole for another lost hour.
What about Kareem’s Video Break? I confess that this is actually the hardest and most time-consuming part of each newsletter. I’m very picky. I look for clips that are funny or heart-warming, or unusual. They have to be relatively short (usually under a minute) but still leave us feeling better about the world. I reject a lot of videos before selecting the right one.
Kareem’s Jukebox Playlist is a favorite feature for subscribers, as I notice from the comments. This is also challenging because I’ve had to select over 250 songs so far and two new ones each week. I love jazz, so I lean a little more toward classic and contemporary jazz musicians. But I also enjoy classic rock, Motown, R&B, and other musical genres. I started a couple of subcategories to reflect that—soundtracks and protest songs—because they are such an integral part of pop culture.
As for your comments: Yes, I do read all the comments from every post. Sometimes, I read them on the run, so I don’t have time to respond. When I do have time, I try to write a note here and there to clarify a point or thank a reader for a suggestion or an error I made that they caught. Reading comments may be my favorite part of the entire process because that’s when I feel most connected to our Substack community. That’s when I feel most heard.
There you have it—the process of how I write each newsletter. And, of course, no newsletter is complete without my asking you to become a paid subscriber. This is how you show that what I do is worth it to you.
Kareem’s Jukebox Playlist
Blossom Dearie: “I Wish You Love”
Margrethe Blossom Dearie (1924-2009) at first appears to be too shy and quiet to be a performer. But then she starts to play the piano and sing, and her talent and confidence is intoxicating. She performed with many of the greats, from Miles Davis to Johnny Mercer, and her singing has been featured in many movies and TV series (The Marvelous Mrs. Maisel and Call the Midwife).
“I Wish You Love” has been performed by just about every major and minor recording artist, including Ray Charles, Ella Fitzgerald, Dionne Warwick, Dusty Springfield, and on and on. It was originally a French song given English lyrics. One reason I like it so much is that it was featured prominently in François Truffaut’s brilliant 1968 movie Stolen Kisses (one of the most charming and romantic films ever made). There’s something so serene and calming about the song. Often love songs are too insistent in proclaiming love. This one makes you believe.
Enjoy Blossom Dearie until I return from my vacation.