Keepers 2024: Best Essays and Ideas from Indy Writers
An opinionated list of most rewarding essays and ideas that came out this year
I’m an avid collector of the “Best ______ of ____” lists and the books that come out of them. Not only do I read them, but I keep them! I still have the Best Short Stories of 1993, the Best Sportswriting of 2021, the best Essays of 2020 on my bookshelf. I like these collections for a couple reasons, including the fact that someone else has done the hard work of sifting through too many options and gave me a reading list. Books and lists like these offer easy answers to the “what do I read next” question. And, these lists force me out of my own bubble and push on my own biases, ultimately making me a better reader (and, in the spirit of George Saunders, a better human, hopefully).
While the idea of “best” anything is dubious, I love the spirit of celebrating the work that leaves a lasting impression somehow and these anthologies attempt to organize such works. At the very least, we get to debate the list. I appreciate the unpacking of the editorial choices and decisions that resulted in the final selection (and what got left out). There’s always a series of reflections that lead me to, inevitably, new writers and ideas I wouldn’t have otherwise found.
In the case of the list below, these are the essays that I will come back to in a couple years to re-read and reconsider. I focus here (mostly) on what I’d refer to as “indy” writers, those that are doing it outside the mainstream of the publishing world1. These are writers going directly to their audience, either to set the discussion (see Altman’s AI essay) or to offer wisdom freely ( Rishad Tobaccowala essay). Some are writing to market their income/jobs (Wes Kao) but do it in a way that’s unique and memorable ( Packy McCormick ). I love the writing, the energy these writers bring to the task, and the example of “thinking out loud” that comes with the form.
I hope to make this a more meaningful and collaborative project for 2025, but in the meantime, here’s a list for 2024.
Note: I pulled this together based on suggestions and recommendations from a pretty wide, but definitely not representative, circle of folks I know or have a para-social relationship with. Also, due to career stuff, I have had a pretty biased filter that focuses on brands, technology, marketing, and the impact they all have on culture. That will probably change in 2025, but for now, there’s a strong lean towards AI and tech in this list.
In, roughly, reverse order of the publishing date….
Our Mental Health Is TBD (November)
David Armano has a mini-series of sorts (dubbed TBD) based on the state of flux of things: his work life, the world we live in, marketing, ai, leadership, work, etc. He covers work and bureaucracy, navigating the space between work and not working, and in this essay, mental health (his, ours, yours). There is so much good stuff in his archives, so check out a couple pieces from last year, including Empathetic By Design (a reminder that compassion is a choice), and My Career No Longer Defines Me (helpful for folks like me that have historically let work and “worker” define them).
Against the Dark Forest (November)
Erin Kissane’s analysis of how our digital lives are NOT meshing with our IRL lives and how it’s making us all crazy. Specifically, the online places we thought were “safe” retreats (i.e. the Dark Forests) have become, due to algorithms and ad-driven incentives, dangerous. You’re going to have to trust me on this one, because it’s very inside, very online, and straight up self-referential. But, it’s also worth the effort if you’re struggling with the idea of digital bubbles, cultural fragmentation. Here’s a taste: “…. but it matters that we remember that the world’s big platforms are steered not by shadowy forces, but by teams of gold-rush-addled dorks whose sometimes-well-meaning employees are stuck frantically LARPing world government on internal forum software.” Plus, she can really write. Thanks Deb Carver for the link.
Burn the Playbooks (October)
You can feel the energy coming through the keys on this one. It’s a ripper. Packy McCormick makes a persuasive case for the power of creativity and ingenuity in an age when AI will be smarter than we ever will be. And, a backhanded reminder that a lot of crappy work gets generated when people try to do it by rote, following a playbook they don’t fully understand.
No, Culture is Not Stuck (October)
Katherine Dee (aka Default Friend) helps us olds to understand that “culture” is just as vibrant as it ever was, but the forms and media are changing so fast the “containers of the past” don’t mean as much. She helped me to see and understand that new forms are rising out of the slop of internet “culture”, including “Influencer” as a cultural form and “social media personality” as a counterpart. I’m tremendously fatigued with the intensity of online culture, so it’s very easy to turn away and seek my own version of Walden Pond, but this essay helped me see that there is actually important cultural work being done (not just novelty seeking dopamine hits). We all know the internet is performative, we just have to accept that all this performance are new cultural drivers. Somewhere on TikTok, this era’s Shakespeare is doing their best work.
Online/Offline (September)
Scott Galloway’s hard punch at the throat of “the least greatest generation”, the tech bros: “Our society has adopted a generally accepted myth that being offended or crying “censorship” means you are right. No, it just means you are offended and have become allergic to people pushing back on your bullshit. A much bigger threat is the belief that the internet, and its zealots, is all freedom, zero responsibility.”
The Art of Finishing (September)
It’s never been easier to start projects (so many projects!). But, it’s also never been harder to finish anything because of all the distractions and the unreliability of the audience finding your work. This one really resonated as I think about all the projects I white boarded in 2024, and how few (1?) I actually finished this year.
Founder Mode (September )
PG, starting an Internet dustup with a thoughtful, provocative post about how leadership could/should happen for certain startups. Positive spin: there is some special magical alchemy in the leadership of certain visionary founders and it makes sense to organize the role of “founder” so they can drive product excellence. Worst case: “Founder mode” excuses control freak tendencies and limits true innovation. Founder mode shouldn’t be for every org and the founder (there aren’t that many Brian Cheskys out there), so hopefully the start up bros out there don’t try to use “founder mode” as a path to maintaining control. Either way, I think we’ll be talking about this one for a while.
An Argument for Logging Off (August)
Aaron Francis reminds us to, basically, focus on what we can control or influence, and NOT focus on what we can’t. I will be contracting my information circle in 2025. via Garrick van Buren .
Future Proofing Careers (July)
Rishad’s advice for guiding your own career will be relevant forever, but especially now. If you’ve been reading him for a while, you’ve gotten a masterclass in leadership and have seen a model for how senior/experienced leaders can move into teaching mode and build up the talent around them (vs. retaining control and hoping for one last hit)
The New Alt Media and the Future of Publishing (June)
Anil Dash is always provocative, usually correct (at least directionally) and one of those voices you shouldn’t ignore. A hopeful boost to the new platforms that are emerging as the scale/ad supported model decays further.
Latent Expertise: Everyone is in R&D (June)
Ethan Mollick delivered banger after banger this year and his One Useful Thing is a must read in my inbox that is overflowing. Is there anyone that writes better about both the leading edge of AI developments AND the cultural impact? Thanks Tim Brunelle for the reminder about this one.
Turning a Yellow Spot Into the Sun (June)
Wes Kao’s newsletter should be in everyone’s inbox. Her advice and ideas are practical, relevant, realistic and consistently actionable. This piece was especially useful, as it articulated something that we all recognize, but find trouble defining: What separates “good enough” from “great” and the behaviors that lead to it. For emerging talent, knowing how to get to “great” is hard. But, this framework is teachable, and like a good rubric, it helps folks understand how to evaluate their own effort and work.
Some Different Takes on AI and What it’s Going to Do to Us
Machines of Loving Grace (October)
Dario Amodei from Anthropic shares his manifesto on the potential of AI to improve the world around us. I want to believe that AI - specifically AGI - will be a net positive for us all, but we can’t begin to imagine the ways super-tech will undermine our humanity and the interpersonal connections that make us what we are (on the good days).
The Intelligence Age (September)
Sam Altman shares a hazy view of the future when intelligence on tap is unlimited. No real discussion of the downsides; he needs to believe in the upside. No acknowledgement that commercial ventures and profit incentives are driving the accelerated push for advancement. No questions about the ethics of profit motives driving incredibly fast cultural change at scale. We’re stuck, as a human community, living with the choices made by profiteers.
Situational Awareness (June)
From Leopold Aschenbrenner - The youth will lead us through all the AI stuff? Breathtaking in its intelligence, audacious in its scope. Deep, mind-bending and long, this one is a futurists take on what’s going to come soon as AGI happens whether we like it or not. His take: AI is a national security priority that we have to pursue like a moon mission. Stop goofing around with AI videos, and start preparing for weaponized AI. And, a related analysis of the original paper. Also, see this (firewalled) essay from Suleyman on the containment metaphor for the AI age.
AI Is a False God (May)
Navneet Alang’s cautionary take on the enthusiasm for AI. Or, a pumping of the brakes on the expectations that AI will lead to solutions that save humanity from itself. He is skeptical of the ghost inside the “intelligence” and probes around humanity’s inclination to trust as truth the “god like” intelligence of tech that’s right around the corner.
They’re Looting the Internet (April)
Ed Zitron’s take-no-prisoner diatribe against the overly commercialized web. Think: Enshittification taken to it’s logical conclusion, but all over. It’s the Rot Economy. It’s capitalism run amok on our internet. The commons is tragically destroyed. This one might have radicalized me more than I expected.
Gen Z Just Wants Life To Be Nice (April)
An overview of how young adults are thinking about their money (income, savings, investments). Takeaway: They’re not buying into the “save for the long haul” idea because they can’t afford to do it; the “Long haul” is a myth. In a couple years, when marketers are resetting their budgets and doing strategic planning, they will be realizing the consumption patterns of GenZ (and younger millennials) are dramatically different than what came before, with a solid skepticism around core capitalistic/american cultural values. Thanks Boomers. (Note: this is from Sherwood, the inhouse/owned media platform from Robinhood).
State of Culture 2024 (February)
Ted Gioia makes the argument that tech-driven distraction has eaten entertainment, which has eaten art. The algos are consuming culture, and we’re all addicted. This was one of those essays that lays down a framework to help me understand the broader picture and make sense of the daily fray. And, it convinced me this (click-driven, attention smashing, debased media-driven culture) won’t end well.
If you’ve made it this far, thanks! I’d love to have you help me in 2025 as I do a better, more comprehensive effort to generate a “best of” list for 2025. Drop me an email or a direct message if you want to help. It will be pretty easy work; basically 3 or 4 emails to me over the year mentioning the 3-5 essays you bookmarked.
I’m hoping to ramp this up in 2025 under a new banner, so please consider subscribing if you’re not already onboard.
And, if you’re feeling generous and this essay was useful, please share it out. Helps me get connected to more smart folks like you.
Finally, who couldn’t use a good visual of a peaceful place?
I’m going to skip the question about “what even is indy, anyway”. A lot of these essays come from Substack, and I recognize there’s a real and healthy debate ahead of us about whether Substack is mainstream or not.