Follow The Clues | #251

December 23rd, 2023: Happy holidays from Connecticut! Good luck and thank you to all of you that are gifting my book to relatives this year. I hope it leads to some interesting conversations.

I was out last week with an unplanned move to a different apartment and the flu. I’ll be taking some time off for the next two weeks and will be back on January 6th. It’s been quite the year and I’ll be sharing some reflections that week. I also would love some feedback on the questions below as I start thinking about 2024.

#1 Follow The Clues

My book's success has surprised me. The 10,000 copies I sold in the first year were beyond any metric I would have come up with but the additional ~35k I’ll sell by the end of the 2nd year was not on my radar at all.

But that’s not to say it was an outcome I saw as impossible. It fits into my mental model of the “game” I’m playing. I’ve been hanging out on the internet for a long time and have been experimenting with sharing ideas for many years before I started this newsletter.

In high school, I had a website called “Paul Says It Will” that predicted snow days with fancy HTML graphics, a counter, and appropriate gifs. It spread via my AIM away message to an audience far bigger than the people I knew in school. I was part of a group that had a blog in college that gained followers outside our social network. I wrote a Tumblr after college, ran a successful Twitter account for the Sloan Sports Conference in grad school, and ended up getting millions of views on Quora, all of which came before I quit my job in 2017. Before this newsletter, which just hit 250 issues, I ran a “weekly reads” newsletter with five good reads each week, shipping more than 100 of those.

Along the way, I’ve developed a feel for how the internet works and what outcomes might be possible. Yet it’s still hard to translate that mental model to my specific journey. While my understanding helped me have a default skepticism of money, followers, or attention as good KPIs early (the vanity metrics of the creator economy), I also never knew when those things might come.

But they have and they seem to confirm my own biases on how the internet works. So I thought it might be fun to reflect a bit on how my approach to sharing ideas on the internet has played out and what I focused on instead of money, fame, and attention, along the way.

The First Thing: Understand Mack’s Law of Internet Scale

I think about this from George Mack all the time:

”There are two kinds of people. Those that don’t understand the scale of the internet and those that know they don’t understand the scale of the internet.” 

I put myself in the second camp but might add more nuance. I understand the scale of the internet and have consistently placed long bets on that scale but also have a hard time predicting when and how things will happen to me. At almost every stage of my journey, I’ve been extremely bullish on the internet and its power to spread ideas and connect people but completely unable to predict how it would directly impact me in the next three to six months.

My earliest experience of the scale of the internet came in 2014 or 2015. I was responding to various posts on strategy consulting on Quora for fun and I started getting a lot of enthusiastic messages from people in India. Many of them would even add me on LinkedIn, find my work e-mail, and send aggressive requests for help (“Sir I need you to help me get a job at McKinsey”).

Years later when I became independently employed, one of my first consulting gigs was helping a small firm build a training program. I thought to myself, “I should try to create something for the internet, I already know there are all these people on Quora who will read anything on this topic.” I really did think about it that way and thought it was a big opportunity. I’ve been running the fourth iteration of that idea as StrategyU for more than five years and I’ve made a bit more than $300k from that course from about 1000 people from over 53 countries. My second highest country of customers after the US? India with more than 75 people.

When I created that course, I had already tested my assumptions about online courses with a resume course I created while still working. It was inspired by Seth Godin’s altMBA, which seemed to me the start of a new and long-term trend of virtual education. I put it on Udemy in 2017 for free and was shocked that people started taking it every day. In 2018, I remember seeing this graphic in my email and thinking, oh wow, this is going to be a big deal.

I wasn’t making any money from the resume course, but it was a clue that was interesting to me. I thought it was still early. It was. I still think it’s early now.

The Second Thing: Those Who Coin The Terms (Can) Win

A corollary to “the internet is bigger than we think” is that ideas take more time to spread than we think but those who coin the words can capture outsized attention and rewards for naming things.

Venkatesh Rao

has unleashed dozens of terms into the internet ether including terms like waldenponding, the Gervais Principle, premium mediocre, and one he coined in 2019, “domestic cozy.” The red arrow is when he wrote the post:

I’ve recently started seeing the term “cozy” being appended to all sorts of situations where it had not been before. Now is this due to Rao? I have no idea. I do know that he has tons of influential followers and if you do a bit of searching you see news articles citing “domestic cozy” in 2020 and beyond, including a Vox article, titled, “Why are so many brands pivoting to Coziness?”

By 2023 coziness is everywhere:

You might argue that Rao was jumping on a trend that was already underway. This is right, but on the internet, a lot of credit can go to the person who makes the illegible legible. Rao excels at this because he is coining new terms every week. If you read his newsletter, you are probably confused by these made-up terms half the time (I’m still trying to wrap my head around oozification). But he is doing what works best on the internet: coining early and often.

In 2020, I published an essay titled “The Boomer Blockade” about the unprecedented demographic shift that coincided with a booming knowledge economy, increased job quality, and longer-than-expected tenures at major institutions around the world as growth was slowing in developing economies. It was a piece I started writing after talking to people in organizations that were mentioning that they were led by 65+ year-olds and didn’t see them retiring anytime soon. When I put the piece out, it got quite a bit of attention on Twitter and then it died down a bit but many people seemed to like the term and I kept seeing people reference it online. It got a bit more attention two years later after Chamath Palihapitiya shared it in his annual letter. And then even a bit more attention after Derek Thompson called it out in The Atlantic in August 2022.

There is a non-zero chance this idea could stick around for decades until someone in 2050 looks back on our past couple of decades and decides, yes indeed, the biggest trend was this guy Millerd’s “boomer blockade.” More likely, it fades into the endless content landfill of the internet and everyone forgets about it. I’ll look back and think “That was fun.” I’ve never made any money or had any interesting opportunities emerge from the boomer blockade idea. But I never really pursued them either. Could I have written a book about the idea? Probably.

And this is the tricky part. Many of us are wired to look at work as something that should produce monetary rewards. Or at least with writing, some amount of attention, or new followers. But on the internet, sustained attention may take years to materialize, if at all. And too many people are focused on short-term followers instead of the genuine credibility that can come from positioning yourself as original and novel. The best way to be original and novel? Coin, claim, or refactor terms to make the complex visible and simple. This benefits anyone willing to play the long game with their work because the kind of credibility and status that accumulates to this kind of person compounds over time. This is incredibly hard to quantify but it’s one of the most powerful contributors to what helps good ideas escape smaller bubbles over time.

Coining terms that describe your work or ideas is invaluable for anyone sharing ideas on the internet. The things I’ve noticed about people who are good at coining terms is that they are always doing it. They are like Edison who had over 1,000 patents in his lifetime. Most of the terms I’ve created suck but the internet is very forgiving with misses while giving outsized rewards to the bangers. Some terms I’ve tried to claim or coin include hamsternomics, hustle traps, serendipity economy, and pandemic utopia, and paycheck envy. While I haven’t completely given up on these, no one seems to be sharing them or having a strong reaction to them in any kind of way.

The “pathless path” was different. It was not a phrase original to me either but something I repurposed from the spiritual domain to describe what I saw as a helpful frame for thinking about work. I took the idea from Ram Dass via David Whyte and have been using it in conversation and writing since 2018. I noticed that people LOVED the term when I used it to describe what I was up to. Angie loved it so much that she made us a journal with a quote about the pathless path on the cover when we got married. By the time it came to use it for my book name, it was a no-brainer. I liked it and I had seen people’s eyes light up or freak out saying “That is so good!” hundreds of times when I shared it in one-on-one conversations.

I’ve started to see people referencing “pathless path” without knowing that I’ve had any part in making the term more popular. This is a good thing! Things are out of my control now and this makes predicting what comes next for my book so hard. Things could keep going and growing if it continues to resonate with a wider audience, or it could fizzle out. All outcomes are possible.

So coin things, early and often. And notice how people react. It might be a clue that you should keep heading in that direction. Money and attention will usually lag such signals.

The Third Thing: Find Your Unique Curiosity Stream

There is a disconnect between what people are paying attention to right now and what will be a better explanation for something in the future. The internet favors people who want to exploit this disconnect.

David Deutsch argues that “our ability to create new explanations" is the most important thing about the human species.

Our modern information ecosystem is filled with hyper-charged a/b tested messages that are repeated over and over again. They are persuasive and are repeated by many people. We start to think that the ideas we hear are the only ideas that are possible. Many people implicitly assume this in the way they talk about ideas and the news.

Others, like you, sense that something is missing. You have a desire to go deeper and have a curiosity that cannot be tamed. You struggle in conversations with people who already have “answers” because you just have questions.

Sometime in 2015 while working in consulting I started to realize that a lot of the mental models that myself and others were using to make sense of organizations were not good predictors of what happened when we tried to implement new initiatives. I became obsessed with finding new stories that were better explanations. One of those was complex adaptive systems, (I eventually turned these thoughts into a long essay here). But, when I tried to get our Senior Partner at BCG to try out new approaches with our client based on the ideas, I got strong pushback. “Why mess with what works?” He rightly cared more about his bonus than new ideas.

I eventually found a better environment to explore ideas via self-employment but thinking about how organizations work led me to a realization about work: that almost all the thought leaders in the work space started from the assumption that work was broken. This was great for them because it led to an easy “fix”: hire them to give a speech to their organization. I realized that this framing, that work is “broken,” is sort of a delusion and probably has more to do with a certain kind of person (like me) who just never felt like they could succeed in large organizations.

Around this time I was listening to a lot of Adam Grant. He’s impressive. Ships a ton. Has impressive connections. Seems to be an amazing teacher. But after quitting my job I found that a lot of his ideas only made sense if you fully bought into the idea that your prime human purpose was to thrive inside an organization. He did an end-of-year survey for his podcast in 2017 and I remember writing in a lengthy multiple-paragraph comment asking him to go deeper, with questions like “Can you explore our underlying obsession with employment as our core identity in this world? And how our work beliefs shape the reality at modern organizations?”

I saw this glaring hole in the world first from my personal experience: when I quit I was shocked at how different it felt to be self-employed versus employed. It made me realize that our world had become obsessed with work and increasingly, people’s stories about their lives centered around their identity as workers. I was able to see that my ability to do great work had more to do with the environments and cultures I was part of than any sort of mindset shift or strategic approach to reshaping my roles. But collectively, our culture tells us that if we just work hard, we will be okay. As I saw friends move into tech and double or triple their salaries, I sensed that our work myths were falling short. And then for me, I was even more shocked at how good my life had become despite taking an 80% income reduction and abandoning any sense of a career trajectory. Why weren’t other people exploring these things?

As soon as I hit submit I knew that was not Adam’s question to answer. He is serving a different audience and serving them well. It was mine to answer and one I was ready to explore. It’s also worth pausing here to mention that this is a tendency that more people should pay attention to. If you find yourself angrily or excitedly replying in paragraphs to someone else’s writing or creations, you should stop and ask yourself, “Is this my curiosity demanding to be unleashed?”

I started obsessing over those questions immediately and from 2017 to when I published my book in January 2022. I explored organizations, careers, work identity, work philosophy, psychology, organizational culture trends, and spiritual and historical writings about our relationship to work. At the beginning of this journey, I had almost no following. I had a couple hundred followers on my newsletter and similar amounts on social media platforms.

But even then, I started to get clues that I was on to something.

None of these clues were money or attention. They were one-on-one conversations with people from around the world. Similar to the reactions I would have from phases like “pathless path,” I would get to the end of one of the curiosity conversations I did with people and they would say stuff like “holy shit, I’ve never thought about any of this before.” I would get several paragraph e-mails from strangers saying similar things.

When you have a small following and no way of getting massive distribution for your ideas, you should pay attention to anyone who has an outsized response to your ideas or thinking. This is why having curiosity conversations with your readers early on can be so powerful. Not only will the feedback encourage you, they are give you a a strong signal about what kind of audience will appreciate them. When you find one person, there are at least thousands if not more that likely think just like that. This is far far more valuable than thousands of readers or followers who never say anything to you and is also what helped me understand who I was serving. I have never tried to write for a mass audience, only the curious reflective weirdos like you who keep reading and responding to my stuff.

And over about four years, I had about 25 people ask me to write a book. This was a clue too. I only decided to write a book when three of those people asked within two weeks in 2020. I had been paying attention long enough to know that it was time.

So seek better explanations. Let the curiosity behind that drive the ship, not cheap metrics or approval. Find the questions that you can own and see where they lead. This is your birthright.

And when you find others that seem to have strong responses to what you have to say? Pay attention to them and keep going. You might have found your own pathless path.

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#2 Joe Hudson On “Success Without Trying”

“The ambition is still there, it’s just integrated into an undefended open heart. It’s no longer about proving anything to the world but about living in alignment with my true self, combining my drive with compassion and self-awareness.”

In this episode with Joe Hudson, I dove into his life story, including his journey of overcoming the conflict and anger of his childhood to how he now helps a wide range of people embrace vulnerability and wonder while improving their relationships. Joe’s experiences living in various countries, coupled with his transformation, offer invaluable insights into dealing with adversity, embracing emotional fluidity, and the impact of self-awareness on personal growth.

Quotes From The Episode

• The Impact of Childhood Beliefs: “I grew up with two dominant stories – I was loved and there was something fundamentally wrong with me. These conflicting beliefs created turmoil in me, leading me to constantly seek validation and a sense of worthiness from external sources.”

• On Emotional Expression: “Every emotion I felt that was uncomfortable, it meant it was time to fight. I realized later in life that this approach was a defense mechanism, a way to protect myself from feeling vulnerable or exposed.”

• The Awakening Experience: “I started seeking ways out of pain and stumbled upon a meditation retreat, leading to a profound moment of oneness. That experience was a turning point; it opened my eyes to the possibility of a different way of being, one that was more connected and less defensive.”

• The Journey of Self-Discovery: “It was an amazing motivator to look at myself – the pain of getting kicked out of college. That failure was a wake-up call, pushing me to confront the parts of myself I had been avoiding and to embark on a journey of real self-discovery.”

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#3 My Self-Publishing Journey

I had an amazing afternoon with Pat Walls, who has been on his entrepreneurial journey for years, in Austin early this year.

He and his team put together an amazing video highlighting not only my self-publishing journey but the evolution I’ve had with my relationship to work.

Ignore the strong hooks at the beginning, the interview is good.

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#4 Year-End Reader Thoughts

As I reflect on the year, I’d love to hear from you. Hit reply and let me know:

• What ideas have resonated most?

• What do you want to see my write about in 2024?

• What should I create that might be useful for you?

• What are the things about work no one else is talking about?

Or you can leave a comment

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Thanks For Reading

Here are four things worth checking out

1. If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community if you want to hang with us too, or if you are already a subscriber, get access here.

2. Buy or listen to my book, The Pathless Path. If you’d like to do a bulk order for gifting purposes or a book club message me and I’ll ship them to you at around $5 per copy via Amazon

3. Subscribe to my podcast and leave a review.

4. Refer 10 people to get my book for free:

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