Introducing Contemplations
A new chapter for the newsletter, a Montaigne summer read-along, and a way to support the work
I’ve spent the last two and a half years figuring out what I actually want to say and how I want to say it. Turns out, finding your voice takes longer than finding an audience—for those of you still sticking around and reading these newsletters, thank you from the bottom of my heart. I’m finally ready to share what I’ve been cooking up.
First, a note on experimentation and discovery. In our hyper-productivity obsessed world, there seems to be very little room anymore for wide funnel, open discovery. We’re expected to have things figured out and start optimizing. Part of that is the practical concern of having bills to pay—a very real concern for many of us. But I’m always reminded of the quote from behavioral psychologist Amos Tversky who said that the key “to doing good research is always to be a little underemployed. You waste years by not being able to waste hours.” Every real mistake I’ve made grew from haste, not delay.
There does come a point though where too much stewing turns into outright indecisiveness. We need to make bold decisions in life and not simply sit on the sidelines.
To that end, I’m excited to share the new name (and direction) for my writing here on Substack— Contemplations.
Contemplations
I’ve struggled with naming what I do on the internet for a bit, though I’ve managed to suck it up and be (mostly) fine with the feeling of disliking most of the names I’ve chosen. Initially it was Tom’s Newsletter, then The Soloist, and most recently The Seeker. I never really liked any of these names, but I felt that perfecting a name early on just meant getting in the way of actual writing. And for the first 53 months of this journey, I wrote every week. You can find that archive in the backlist here.
Around this time last year (Summer 2024), I had the idea to work on something long-form, i.e. a book.
I’ll have more details hopefully to share soon, but needless to say writing online took a major backseat as I went through the research and investigative process to put the pieces together for that project. I’m incredibly proud of the ground I was able to cover in 12 months given the source material and I’m betting the pieces will come together into the book I’ve pictured from day one. The behind-the-scenes of the book writing process will be available for paid subscribers, so if that is of interest, you can support my work here.
But going through that process of researching, drafting, and pitching a book allowed me to step off the grind of daily and weekly publishing for enough time to recharge my creative juices. And that recharge allowed me to zoom out enough to make sense of what it is I want to accomplish here.
On a walk with my friend, he joked that my love of Schopenhauer meant I’d be consigning myself to a life of solitude and contemplating great art. He meant it as a dig, which is funny because it sounded wonderful to me, but there was something about the idea of “contemplation” that stuck.
What does it mean to live a contemplative life? In short, it’s the life I’m trying to build. Regular reflection and mindfulness. Simplicity and slowing down. Deep listening and attentiveness. Seeking meaning and wisdom. A connection to something greater.
Contemplations feels like exactly the kind of community I want to build around here in this newsletter.
The main themes we’ll be covering, at a high level, are Character, Connection, Craft, and Context. A study of how to live well, while also having open and frank discussions about what world we are living well in.
Whether it be reading philosophy on virtue and ethics, literature that helps us understand how we relate to one another, or biographies that shine a light on those who took their craft seriously, we’ll have something rich and deep to dig into each week. Lastly, the rapid pace of AI development, and questions of meaning and spirituality are an important context filter.
What to expect next
We’re going to kick off the summer with a book read-along. The first book is one of my favorites that I first read a while back and want to re-read: Montaigne’s Essays.
Montaigne was one of my first forays into philosophy, but he’s kind of an anti-philosopher. Nassim Taleb’s captured Montaigne’s spirit as such:
“Montaigne was neither one of the academics of the Sorbonne nor a professional man of letters, and he was not these things on two planes. First, he was a doer; he had been a magistrate, a businessman, and the mayor of Bordeaux before he retired to mull over his life and, mostly, his own knowledge. Second, he was an antidogmatist: he was a skeptic with charm, a fallible, noncommittal, personal, introspective writer, and, primarily, someone who, in the great classical tradition, wanted to be a man.”
— Nassim Nicholas Taleb
We’ll be using the Penguin Classics version, “The Essays: A Selection”, translated by M. A. Screech. It’s considered the easier-to-read, more accessible, version.
I’ve broken it into roughly 30 pages a week—about four pages a day. A few weeks dip closer to 25, a couple reach 35, but on average it stays right around a cadence that should feel easy to follow.
The schedule will take us through Summer into early Fall:
July 21 – To the Reader · Book I-1 We Reach the Same End by Discrepant Means · Book I-8 On Idleness
July 28 – Book I-16 On Punishing Cowardice · Book I-18 On Fear · Book I-20 To Philosophize Is to Learn How to Die
Aug 4 – Book I-26 On Educating Children · Book I-27 That It Is Madness to Judge the True and the False from Our Own Capacities
Aug 11 – Book I-31 On the Cannibals · Book I-32 Judgements on God’s Ordinances Must Be Embarked Upon with Prudence
Aug 18 – Book I-39 On Solitude · Book I-56 On Prayer · Book I-57 On the Length of Life
Aug 25 – Book II-1 On the Inconstancy of Our Actions · Book II-2 On Drunkenness · Book II-5 On Conscience
Sept 1 – Book II-8 On the Affection of Fathers for Their Children · Book II-11 On Cruelty · Book II-32 In Defence of Seneca and Plutarch
Sept 8 – Book II-35 On Three Good Wives · Book II-37 On the Resemblance of Children to Their Fathers · Book III-2 On Repenting
Sept 15 – Book III-3 On Three Kinds of Social Intercourse · Book III-5 On Some Lines of Virgil · Book III-6 On Coaches
Sept 22 – Book III-11 On the Lame · Book III-13 On Experience
Sept 29 – Live Zoom Q&A Finale
What happens now
Whenever I take time away from exercising, getting back into the gym is painful. The same thing happens with writing. To brush off the cobwebs, I’ll be sending a daily note here for the next 28 days (30 days total). Quick thoughts, 250-400 words covering one of the main pillars (Character, Connection, Craft, or Context).
I want to continue putting out as much free content as possible, but I can’t only do free work, so the choices come down to either pushing ads on readers, or creating a paid tier.
The goal is to make my writing both my avocation and vocation, to borrow from Robert Frost's poem "Two Tramps in Mud Time".
Here are your choices:
1. Stay free. You’ll get weekly essays, the daily notes, and weekly read-alongs.
2. Go deeper. $6 / mo or $60 / yr. I’m also opening up a Founding Member tier which is a one-time lifetime payment limited to 40 spots. Paid members get access to the Zoom Q&As, see book-draft pages and behind-the-scenes of the book writing process, and read the long-form essays that don’t fit the free feed. No advertisements, ever.
If you’re not into daily emails, go to the Account page here and toggle off ‘Daily Notes’.
Why pay? Your support helps fund deeper research (including archival work for the book), higher quality production, and keeps this newsletter ad-free. If the free tier is all you can afford, please keep it—your readership already matters and I promise you’ll have tons of free content to enjoy.
I’m super excited for what’s in store for 2025 and 2026. Most importantly, I’m grateful to have you here. Welcome to Contemplations.