As a leader, I value these eight newsletters for their unique insights. As a creator, Iām also inspired by the diverse examples of how to make a meaningful contribution to the public discourse and build community around powerful ideas.
Welcome to Timeless Leadership. As weāre in the first āinterludeā between seasons and these posts are more infrequent, I thought I'd share some of the other newsletters that I not only read regularly, but actually have chosen to pay to read.
Iām constantly adjusting my content diet and so this list will probably look different in six months.
What are newsletter subscriptions are you paying for, if any? Iād especially love if you have recommendations that have a leadership focus and are super high-quality; Iām especially keen to expand my reading list to include more author(s) that are women and/or BIPOC.
Drop a comment or send me a DM and Iāll send a updated, crowd-sourced list in an upcoming edition.
Disclosure: a few of the newsletter links below include an affiliate / referral style link so if you do end up subscribing, Iāll be rewarded with a free month (or something similar). I didnāt originally plan to include those but when I found they existed I figured āwhy not?ā
Leading Yourself
I only pay for one newsletter thatās focused on personal leadership - although Iām considering adding Longevity Today by my friend
in the near future.Level Up with Ethan Evans
$17/month
I started following
on LinkedIn last year, right at the beginning of his hockey-stick growth as an āinfluencer.ā Ethan was a VP at Amazon before retiring from corporate to focus on career coaching and education. He writes honestly and bluntly about what it takes to stand out, get promoted, and achieve career (and life) success. He has also started to layer in other kinds of experiences for paid subscribers like live chats with his own executive coach and with leaders who he is coaching. Iāve also had a few 1-1 exchanges with him and he seems genuinely like a cool guy.Suggested posts:
"In 20 years only your children will remember that you worked late."
The Magic Loop (his guest post on Lennyās, another popular tech newsletter)
Leading Organizations
For those of you in business, these newsletters might offer some value for thinking through your strategy and how all of our context is shaped by the big tech players.
The Category Pirates
$20/month
This is a useful newsletter for business leaders, strategists, and marketers alike. The key idea here is part āBlue Ocean Strategy,ā part āpositioning,ā and part āniching down.ā Whatās original is the depth of actionable advice on the specific process of ācategory design,ā which is a way to define the space that youāre playing in so you can compete on your own terms and become a ācategory kingā or āqueen.ā
I originally found this a couple years ago because I had read Play Bigger and connected with one of the co-authors
on LinkedIn.For paid subscribers you receive a monthly āmini-bookā that goes in depth on a particular topic or strategy for defining a new business category. My favorites have been about what they call obvious and non-obvious problems and solutions. Here are two examples:
Big Technology
$10/month
was a tech reporter before starting this newsletter. He caught my attention last fall during the big OpenAI controversy, and his insightful coverage of the inner-workings of Microsoftās involvement in how that played out.I recently subscribed and am interested to incorporate his reporting into how I make sense of how the likes of Amazon, Google, Microsoft, and Meta are shaping the technology landscapeā¦ and how they are or arenāt adapting themselves.
Leading Society
The following blogs / newsletters are very much in the āpoliticalā space. They represent a range of viewpoints that stand out for the care they take in developing their arguments. In this pivotal election year, I believe all of us will need to find time, somehow, to encourage and advance better conversations and actions in the public sphere. The duty of citizenship calls.
Freddie DeBoer
$50 / yr
has range. He writes several long-form articles per week, ranging from book and movie reviews to cultural and political commentary to economic and policy analysis. Heās a self-proclaimed socialist but you canāt pin him down with a label. He writes with nuance and precision, courage and self-awareness.He writes with logical consistency and a commitment to challenging conventions, left and right. Some of his more provocative pieces address Zionism, Black-Lives Matter / Social Justice Movements, and Education Reform.
I donāt think any reader can agree with everything he publishes, but thatās the point - his voice is uniquely his own.
Diane Francis
$7/month
publishes a few long-form pieces per month focused on international affairs. Over the years Iāve studied this topic in depth. However, today Iām not subscribed to a journal like Foreign Affairs and Iām not always carving out time to read the international section of other papers. Therefore I appreciate that in this newsletter, Diane will catch me up with the news cycle, take me a level deeper, and provide her unvarnished personal take on the situation. This has always made me think more deeply on her topic of choice, whether itās Chinaās relationship with Russia, Haitiās collapse, or the shadow flees of oil tankers.Popular Information
$50 / yr
does real, original reporting that has often broken a story that is picked up by major news publications and even led to real policy change. The focus of Popular Information is on digging deep on the actions behind the words of politicians and corporations. Popular Information has done some of the most powerful exposƩs on corporate political donations that run counter to the PR spin on allyship.PI makes companies think twice about donating to campaigns and super-PACs. It also can help employees, consumers, and voters think twice about who they support and how.
Hereās one lengthy example of what PI does - a powerful accounting of corporate pledges in January 2021 and how that compared to their actual giving in the same time frame.
Racket News by Matt Taibbi
$5/month
I first read
ās writing some 15-20 years ago in Rolling Stones, as he covered some of the disasters in leadership from the Bush administration and on Wall Street. Years later heās trained his sights on the Democratic party establishment and liberal orthodoxy, although he is no cheerleader for Trump or the Republican establishment either.As an active member of the Democratic party, I find his reporting to be a helpful way to be aware of my own biases, find areas to challenge Democratic and liberal leaders, and filter through a lot of GOP / MAGA BS to understand where discontents on the āconservativeā side of our body populace may have merit.
Off Message by Brian Beutler
$10/month
After reading the free version for a couple of months, this is my newest subscription - I just signed up yesterday!
is a veteran politics reporter and here he writes an unapologetic āliberalā column. While some of the writing is similar to what I get from Crooked Mediaās What a Day and mainstream, left-leaning NYT / WaPo coverage, I find his insights and calls to action very practical and level-headed. They also generally lack the partisan ātoe-the-lineā commentary that seems to be the norm for institution sponsored reporting.What are your thoughts on this list? What would you add or drop? Do you have any strategies to effectively incorporate newsletters into your content diet to ensure itās a good use of your time, attention, and (if you pay), your dollars?
See you in two weeks,
Joe
PS. Thinking about writing a guest post? Check out this post to review details and letās chat!
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