The Point Of Posting | #286

Jan 20th, 2025: Greetings from Texas! I’ve been meaning to share something like this for a while. I feel my writing energy re-emerging after finishing my book in September. I’ve also been posting on Monday after shipping on Saturday for years. Trying to change things up and see what feels right. Enjoy!

---

The Point of Posting

The ability to post ideas online and share them with others has made my life better.

One of the best places I’ve found to do this was Twitter. From 2018 to sometime during 2023, it was a place where I could post half-baked thoughts and workshop ideas in a way that would help me sharpen my thinking and improve my writing.

I used Twitter much like how comedians use comedy clubs. I riffed thoughts and ideas on our relationship to work, careers, organizations, and unconventional paths and would engage in conversations with people on the platform, on one-off video calls, and offline in different parts of the world. I was locked in a virtuous cycle, where the more I shared, the better my writing got, the more curious people I attracted, and the more satisfied I felt about how I spent my time. The Pathless Path was birthed from this beautiful dance of consumption and creation.

But posting has downsides, especially as your audience grows. In addition to attracting fellow curious humans, you start to attract a broader group of people and others see your thoughts right next to media outlets, pundits, outrage actors, chaos agents, and trolls and assume you are just another belligerent in a war of ideas.

In a narrow sense, I do want to compete in a war of ideas. But mostly in the domain of work, and to be a different perspective from the more popular frames offered by people like Cal Newport, Adam Grant, and Anne Helen Peterson, who are read on a much larger scale. Yet my goal isn’t even to win a battle against these people. My goal is to stay connected to myself, have the energy and excitement to stay on this journey, and be inspired to create and connect with others. Essentially, it’s to live at the frontier of what’s possible in my life.

The problem is that platforms like Twitter, and others where people share ideas don’t give half a damn about this cute goal of mine. They have money to make, engagement metrics to optimize, and billionaires’ egos to feed. The reason Twitter ended up being such a generative space to hang out for so long was the result of random factors being aligned with my preferences for a few years more than someone deciding, “ah yes, let’s tailor this platform such that underemployed hyper-curious infovores can hang out and befriend others.”

For most of the 2010s and part of the 2020s, it was a glorious time to be someone who loved ideas. From early blogging to RSS readers to aggregators to early Facebook to Quora to Medium and then to Twitter (among many others), there has arguably not been a better time to be an amateur idea person. It was a time where a simple essay could become a seminal work that became lore in niche online worlds. People like Tim Ferriss, Mark Manson, Gretchen Rubin, and James Clear turned personal blogs into millions of readers and millions of dollars. Informal platforms like Ribbonfarm, Marginal Revolution, and Less Wrong birthed micro-scenes that minted new writing stars and idea complexes that people still talk about.

I started writing toward the beginning of the end of this era in 2015 and saw some of my essays go semi-viral and one, The Boomer Blockade, go viral and end up getting cited in mainstream media for years. My feeling as I quit my job and leaned more into this world was, “Wow, there’s a clear opening where tons of smart people are hungry for ideas and there is a chance that people will take what I think seriously.” A meritocracy emerged not because the internet and platforms were optimizing for it but instead because there was a genuine shortage of ideas, writing, and thinking relative to the number of people who wanted to consume deep, thoughtful, internet-first writing (which is something that more mainstream outlets didn’t grok until the last five years). Anna Gat coined this digital scene the Inter-intellect in 2019. It was exciting. I found my people, and it felt like it would go on forever.

And then it all fell apart.

There are many explanations. I don’t have a favorite and in some ways, it doesn’t matter. Blame short-form video, the end of ZIRP, Elon punishing links on Twitter, politics going weapons-grade propaganda, and the emergence of S-tier persuasion across funded outlets, the lower cost / higher return attributes of take artistry or even less low-hanging fruit of new niches and angles. The result is the same no matter your story. The environment in which I was able to realize my creative potential, find others, and sustainably share with others doesn’t quite exist anymore.

I’ve spent the last year thinking about this. What does this mean for people just starting? I used to think that we were going to have more and more people sharing ideas and that it would lead to better and better work. A golden age would become more golden over time. Now I’m not so sure. The kind of person who might have jumped into the mix in 2019 might look at the online world of ideas now, one filled with engagement bait, trolls, and politically indoctrinated assholes, and be like “hell no! Not worth it.” You won’t be surprised that I find this sad.

I’ve been trying to think through how I should react to this on my path. In a world where an essay like this is unlikely to get shared, open rates are plummeting, and the chances of creating luck or meaningful connections are falling, what is the point? Should I just pivot to books completely, randomly post here and there, and withdraw from social media? This is a conversation that many people are talking about privately but don’t seem to acknowledge publicly as much.

Much of what we see in the online world of ideas is the result of more efficient markets. People have started to accurately price the value of attention and this has attracted not the kind of people who hung around without a purpose for so long but people who want to extract every last cent out of the eyeballs they attract. At the margin, you end up gaining algohackers and losing people posting for curiosity and illegible status reasons. It’s sad to see, after nearly ten years of hanging out in idea world, how many genuinely interesting people have stopped writing. Others are turning formerly playful newsletters like this into marketing channels. Many more are deciding never to start.

I do write for myself but I thrive on being in the flow of a larger inter-intellect. I love the dance of ideas. The energy of doing things for the sake of our curiosity. The serendipity of piecing together something you were missing from someone else’s challenges and input. The friendly nudges and correctives from people you admire.

Some of that can still be found but it takes a bit more effort. I’m finding myself wasting so much time bouncing from platform to platform in search of my personal age of innocence. The thing I keep coming back though is reminding myself how much pain people endured to create and share their work throughout history. Despite the risk of imprisonment or even death, many decided, I must post. And so we must remind ourselves, posting is a sacred privilege.

It’s hard to avoid the fact that the early days are always the early days and almost ten years into this chapter of my life, I am probably just a little too desperate to reclaim the initial delight of finding others like me scattered across the world.

You could probably challenge me and say this kind of ecosystem still exists, especially in video. For certain niches, I buy that argument. YouTube still seems genuinely vibrant for many. TikTok, Reels, and YouTube Shorts have birthed countless mini-worlds where people can connect with something that matters to them. But video has become a team sport. Text is still the only place where you can reasonably “compete” as a solo contributor. Despite this, it feels as if we are in a text-cession. Too many books are stale and formulaic, the essay doesn’t quite fit our time, and the social posts are cynical and nihilistic. The era of “mass popular blog post,” one that created enormous positive externalities for people like me, is over.

There’s a chance that Substack can re-ignite this scene, and I think it has the best chances of any online space right now but I’d put relatively low odds on that happening.

I’ve meant to write this essay for more than six months and I think I put it off because I didn’t want to mourn the end of an era. Not only a personal era but an era of online writing that was magical and beautiful. It’s likely not a coincidence that I turn 40 in a couple of weeks. For the past few months, I’ve sensed that I’m in the thick of a liminal period of my life.

Personal writing has been my way through these ambiguous periods in my life, anchoring to my mantra of “write, most days.” So I guess despite there not being an ecosystem for how I like to write here and on my blog, I will keep showing up.

Let’s see what happens.

---

Links & Roundup:

Work breaks to travel: Caitlyn Lubas is looking to interview people who have taken a work break to travel. If you’re open to sharing your experience, would love your answers on this ~5 min survey, or grab a time slot on my calendar for a ~15 min quick chat to run through some questions.

Cars vs. Pedestrians: 100 years ago a city in California passed an ordinance giving the right of way to cars over people. It transformed how cars became the center of American life. Our most walkable city is taking steps to reverse this, here are some early impressive results from NYC.

Pathless Jobs: If you have a pathless job you'd like to list here (think remote, alternative schedule, contract gigs), please reach out. I'm going to experiment with a 2-sided informal board this year.

AI Reading List: I’ll likely be launching an informal AI reading group through my community or the substack chat function. I’m pulling together a list of reads if people have additional recommendations. Here are Ilya’s 30 reads and an initial list I pulled from others:

---

well hello

I’ve been having fun and hanging out online since 2015. I’ve somehow figured out how to hack a living doing things like this for more than seven years. Wild.

If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work. If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community.

Some affiliate links I endorse: Crowdhealth, an alternative to US health insurance, Function Health, comprehensive blood testing and health screening, and Nat Eliason’s Build Your own AI Apps course.

If you received this and find yourself in a state of outrage thinking, “How the hell is this drivel allowed in my inbox?” I strongly encourage you to unsubscribe below. It is your god given right and there is plenty of good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.