I write and read a lot — and my head is often full of ideas that are colliding into each other as I try to make sense of my work and my life. Essentially I’m continuously trying to figure out how to live a life that is both virtuous and comfortable (Stoic and Epicurean from the classical perspective). This ain’t easy, but no one said that life is supposed to be.
To avoid getting stuck in cognitive ruts, I try to read outside my filter bubble, so I subscribe to a variety of newsletters. Since I get so much out of them (I list some of my favorites below) I thought I might give writing one a try. My hope is that you’ll find one thing of value each month and perhaps recommend something back to me.
One of my top goals for 2021 is to become a writer. This ambition may sound odd for someone who has written two books and more articles than I can count, but the majority of my writing to date has been focused on topics that help drive business. This is rewarding work but has also felt constraining at times since my interests are much broader than organization design and team development.
This year I want to write without thinking of what the call to action is or how it might get me consulting work. I also want to challenge myself to write in a more vulnerable and engaging way and to get published more widely. So I’m carving out a couple hours of each workday to write for the sake of writing. This practice also means developing a new internal orientation toward writing — what Steven Pressfield calls “turning pro.”
My objective is to write four long-form personal essays this year — one each quarter. I just finished one called “Toxic Charisma” that delves into how some leaders use inspiration in ways that prove problematic for the people they attract.
I also started a piece where I’m exploring what it means to be a “good white man” in the world today. I’m the parent of a young man just coming of age, and I want him to contribute to society and also feel good about himself. There’s a lot to explore here and more than one third rail topic, but I want to write things that scare me — I think courage is essential when you’re striving to do great work.
As part of this new focus I’m getting far more organized about how I take notes and manage research. I’m currently experimenting with a tool called Obsidian that is showing great promise. It allows you to easily link notes in its database, forming a networked graph of your thinking. I like it because it allows for nonlinear connections between ideas — meaning it works the way my brain seems to work.
OK, that’s it for this month. As promised here’s a list of a few of my favorite newsletters.
This Week in the NYC Innovation Community Newsletter
Written by NYC VC Charlie O’Donnell, this newsletter covers tech, politics, and culture. Charlie is smart, thoughtful, and motivated by much more than money. He always gives me a fresh way of looking at current topics ranging from the NYC mayoral race to how Amazon treats their workers.
Nisha’s Internet Tote Bag
Nisha Chittal is a writer and editor at Vox. Her weekly newsletter provides a quick personal view of her life as well as a list of great articles and other resources.
Baratunde Thurston worked at The Onion and the Daily Show (and has a wonderful podcast called “How to Citizen”). His newsletter has a few hot takes, a video, and links to articles and resources for the week.
By libertarian economist Tyler Cowen, this daily collection of news analysis and links challenges me more than just about anything else I read regularly. I often don’t agree with Tyler, but I also rarely fully disagree. I find his thoughts contrarian, deep, and informative. But be warned: Stay away from the comments, which tend to be populated by some exceptionally talented trolls.
I just started with this wonderful newsletter from the incredible Roxane Gay. Not only is her prose a delight to read, but also she inevitably pushes my thinking in new directions and leads me to resources I might otherwise miss.
So that’s a few of my current favorites — what are yours? Hit reply and let me know.
Co-Founder of The Alignment Company
P.S. If you find this valuable I’d love to hear from you — a little encouragement goes a long way to keeping me motivated — reply to this email or ping me on LinkedIn.