A couple quick shouts:

• is publishing her book Made in Taiwan in Traditional Chinese next week! The final product is incredible; it’s one of the best memoirs I’ve read (I am biased, but I think I will be quickly validated by readers!). We’re excited to share it in English after we co-translate it later this year, so stay tuned. If you read Chinese or would like to grab a copy to support her, all the links are here: Made in Taiwan.

• You can now purchase notebooks, shirts, my paperbacks, and Angie’s books all directly from my Shopify store.

Below is a guest post/Q&A from Holly Gabrielle, who recently left the creator world to go all in on trying to become a top Hyrox athlete. I love highlighting new paths that exist in the world, and this one definitely qualifies.

Ok, you just quit your job, which was working on Ali Abdaal’s team, after reading Good Work. What is going on over there? Is Ali getting ready to ban my books?

Haha, to be fair, Ali might think twice about giving out free copies of Good Work to members of his team in future. But my departure was the least dramatic thing ever - I simply sent a Slack message to Angus (Ali’s general manager) basically explaining that I wanted to go off and do my own thing … or in other words, quit a perfectly stable copywriting job to chase a dream of becoming one of the top 15 women in the world at a sport I’d never actually competed in yet 😅

Absurdity aside, being part of the Ali Abdaal team is honestly so dangerous because you start believing you can do things, and I wasn’t even a full-time team member - I was freelance, working 3 days a week - yet I still caught on.

Like many of us, I was guilty of procrastinating on ideas, shutting them down, telling myself I wasn’t good enough, or just learning more and more information, convinced that I just wasn’t ready yet. But Ali talks so much about taking action and not letting your emotions or fears hold you back - whether it’s starting a YouTube channel or a lifestyle business or even something as small and personal as going on your first date - and when you work for him, it’s pretty hard not to eventually listen.

So, like many other team members, after 2 years working with Ali, I’d heard enough. I took his advice a bit too literally and decided to go all-in on trying to become an elite Hyrox athlete (and simultaneously return to my content creator origins).

You’re going to pursue being an “elite athlete”? That sounds awesome. I suspect needing more time for training, rest, and recovery is part of it, and a job doesn’t help with focusing on that. Any other reasons?

Yep, you’re pretty much spot on. Time for training and recovery was a huge factor, and I’m hoping this allows me to make much faster progress. But it wasn’t just about the physical time - it was a mental energy thing too.

Realistically, I could’ve kept my writing job with Ali and also gone all-in on this lofty (and pretty scary!!) goal of becoming an elite athlete. Besides, working with the team was such a great experience - the flexibility was incredible, I was always learning new nuggets of information, and the people were amazing.

But I know myself well enough to know that my brain doesn’t really switch off - and that comes at a cost.

Even though the team never gave me any super strict deadlines, I’d always push myself to write one more email before 5pm, shorten my breaks to cram in a bit more work, or find a way to level-up in my role. It was exhausting.

And it wasn’t until I came across ideas like essentialism and the “Hell Yeah or No” framework by Derek Siver (again, all through Ali) that I started to question how much of a toll it was taking on me. I also realised that it was stealing a lot of mental energy away from my runs and workouts. I’d often blindly go into a session and wonder why it felt hard. I left no time to reflect on my sessions, properly plan my workouts, or even just celebrate my small wins.

So long story short: I finally decided to step back. Yes, it’s probably been one of the hardest things I’ve ever done because saying no or quitting doesn’t come naturally to me, but I’m excited by the challenge of finally doing less to hopefully get more out of the things that mean the most to me and have the potential to completely change my life.

Are you already making money from your athletic pursuits (career, path, passion, what else do you call this?!), and how did this impact your decision?

I’d love to say yes, but the answer is no, sadly 🙈 Right now, I’m not making any money from this.

Just for some context: I’ve been “influencing” for about 10 years now. I started my first YouTube channel when I was at uni, and ever since graduating, I’ve pretty much been documenting my entire life on the internet. As a result, I have a couple of affiliate links that are earning me a bit of money right now, as well as some passive income from my old YouTube videos … but we’re talking a few hundred pounds a month.

Plus, they’re not exactly aligned with my version of good work going forwards.

Ideally, I’d love to be a full-time sponsored athlete one day - that would be absolutely unreal. And alongside that, I’m rebuilding my personal brand from the ground up.

I’ve recently started a joint YouTube channel with my partner, Angelo, where we’re documenting our journey to the Elite 15 in Hyrox, and I’m rebranding my Instagram content to be specifically within this niche. The goal is to make this financially sustainable long-term, but right now, the income from all of that is pretty much zero.

Don’t get me wrong, it’s scary not having a monthly income right now - like really scary. It was also a pretty big concern of my parents when I left my job, but I’m proud of myself for not letting financial worries stop me from going after some big goals that genuinely excite me.

What is the link between training, sharing your journey online, and how those have evolved together over time?

Love this question… although the answer isn’t super straightforward.

If we go way back, I grew up dancing competitively and have always been super interested in my own health and fitness. In all honesty, I always thought I’d live my life as a professional dancer, just like my mum, but I guess things didn’t work out that way oops - ended up going down a completely different path and studying biology at Cambridge instead.

This is when I started my first YouTube channel (2016), and even though my vlogs were heavily centred around my chaotic student life and studies at Cambridge, food and fitness were always underlying themes.

Sadly though, I experienced some pretty deep and chronic mental health issues that lasted pretty much the entirety of my teenage years and early twenties, which turned my love for fitness into something pretty toxic. I was in denial for years, and this made it really hard to be vocal about health and fitness online, because deep down I had my own things to fix first.

At the start of 2025, I stepped back from YouTube and social media a bit and decided to work on myself - focus on my writing job with Ali, spend more time with the people that matter most to me, and finally fix my relationship with food and exercise. When I could finally see how damaging this dynamic was, I thought it was best to never mention it online ever again. But I missed sharing my journey, and it’s always been something I loved.

So towards the end of the year, I thought about seriously rebranding my content. I started sharing my genuine love for food and fitness but framed it in a completely different, healthier way, and this was around the time when I’d just discovered Hyrox.

A lot of people knew I was into running and marathons, but what really drew me to this sport was that I could build my body in a way that felt most natural to me - develop strength in both my upper and lower body without having to drop weight, lose my period, or risk the injuries that often come with trying to reach elite marathon times. Training for Hyrox lets me be strong and fast, not one at the expense of the other, and I was super excited to share this with others.

Don’t get me wrong, rebranding online isn’t easy 😬 But so far, I’m having the best time sharing my fitness journey and everything I’m learning. Plus, when I announced my big goal to become an Elite 15 Hyrox athlete on Instagram recently, the response was genuinely overwhelming in the best way possible - something I really didn’t expect.

(Here’s the post if you want to check it out.)

You told me you are excited and scared to make this leap. That resonates so much. Tell me about that tension?

I’m incredibly excited because the upsides are pretty much limitless. I have no idea where this path will take me, how far I can take my fitness in Hyrox, or where I’ll be in say 3-5 years’ time.

But that uncertainty is what also makes me somewhat scared. What if things don’t work out? What if my savings dry up and I’m not yet making any money to support my life? What if I get a major injury? What if I don’t make as much progress as I think?

I can often think very catastrophically and worry too much about the “what ifs” so I’m working on trying to limit these thoughts and feelings. I’m also trying to turn these negatives into something more hopeful. In particular, I’m reminding myself that any failures are simply learnings. Even if I don’t make the Elite 15, I’ll have spent years doing something I genuinely love, becoming the strongest and healthiest version of myself, and living a life designed around my values rather than someone else’s - and to me, that’s totally worth the risk.

How much of a role was your partner deciding to quit with you in deciding to take this leap? How did you talk about the tradeoffs in the decision?

Funny story here actually: Angelo and I met on Hinge (2022) after he stumbled across one of my photos from my first ever London Marathon. We clicked pretty much straight away, and in particular, we both shared this huge love for running, fitness, and becoming the healthiest versions of ourselves.

Fast forward to 2025 and we bought a flat together in London. It was something we’d been wanting to do for a while, and we honestly thought we’d “made it” as real adults. We both had stable jobs, stable incomes, and started building the routines that we’d always talked about - run at optimal times in nice parks, go to the gym, meal prep on Sundays, stuff like that.

We genuinely thought this was it. So it makes me laugh now that only 8 months later we were looking for tenants, purchasing a 150L backpack, and getting ready to leave the country altogether 😂

I know a lot of people think we’re absolutely crazy. Like, why the hell would we give up decent jobs, a mortgage, and a life we’d spent years working towards? It just doesn’t seem to make sense.

But the thing is, sometimes you have to walk through one door in life to realise it’s not quite right for you. Sure, it would’ve been great to realise that we wanted to become elite athletes before we bought a property, but life doesn’t quite work like that.

And I guess the question is: what actually changed? And why did we change our minds?

Well, when Angelo and I started living together, we started watching more and more content online about this new and interesting sport called Hyrox. We watched races, got completely hooked, and of course, almost immediately signed up to our first one. As we were putting more and more hours into our training, we started to realise we were capped. We were working out too late, eating even later, missing sleep, recovery was suffering … and we started craving more and more time for this one thing we loved most.

At the same time, Ali was talking more and more about financial freedom and building a lifestyle business, and as his copywriter, I was literally absorbing everything he was saying and learning. Oh and I also read your book, Good Work, which made me see work in a completely new light.

So one day - I can’t remember when exactly - we dabbled with the idea of dedicating our lives to fitness. We thought about starting a business, coaching, or building an app, but then we were eventually like, why don’t we prioritise our own fitness first and then document the journey?

I’ll be totally honest here and say we hadn’t even done our first Hyrox race yet, which definitely makes us crazy, but we were so determined that with hard work and consistency, we could get to the top. And I guess only time (and a lot of hard work and sweat) will tell.

But we’re on this journey together, we have each other’s backs, and it’s the most incredible thing to be chasing your dreams with your best friend and the person you love.

What’s the plan? Where can we follow you?

Right now, the plan is to really dial in my own training and aim for the Elite 15 in Hyrox. Simple on paper, but most likely a lot harder in practice 😅

That’s my ultimate goal, but even if I don’t ever end up “making it”, I’m trying to build something sustainable alongside - long-term athlete or brand partnerships, potentially coaching if that feels like “good work” to me, and content creation that actually aligns with what I love. My athletic performance is definitely going to be the foundation, but there’s a whole ecosystem I can build around it and that’s what makes this whole thing feel less risky.

I’m currently sharing my journey, tips, and advice over on Instagram (@byhollygabrielle) where I’m active most days, and Angelo and I have started a new YouTube channel together (@angeloandholly). We’re posting one video a week to share our training, racing, and the reality of this whole journey.

Oh and we’re also travelling around and living in more affordable cities compared to London to make our savings go a little bit further. I always thought I’d be a “home” person who loves stability, but I actually don’t. I love the idea of exploring new places and building homes across the world, and I feel super lucky to do this.

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other 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.

I’ve been doing a bit more reading in between naps and such so I wanted to share some things that I have been enjoying!

And if you haven’t read the guest essays yet, they’ve been fantastic: on nervous systems and recklessness vs. courage, on intuition, fitness, and uncertain journeys, Alice Lemee on skipping the 9-5 and her freelance writing journey, and on parental expectations and being a grown woman.

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#1 Indie Reflections

Andrew Bartholemew has thoughtful reflections on Indie life:

Being indie for 18 months has reinforced my core motivations. It has definitely pulled me further from the base assumptions of a typical employee or manager. I’m more interested in autonomy than belonging. I’m more interested in excellence than recognition. I’m more interested in getting tested than in getting coached.

You can read them here

#2 Winding Journeys

on her journey I found this part about how she sort of stumbled into becoming a lawyer interesting. It’s pretty wild how many people end up in careers in their 20s due to minor decisions and then just more or less stay on that path

My closest brush with these feelings came from a weeklong trip to the Andes in northern Ecuador. I was a senior in the journalism college, bestowed with this huge honor of being selected for the program. But truthfully, I was afraid, completely out of my comfort zone in the sense of placing my safety – and all of my trust – into strangers who I needed a translator to communicate with. It was the purest form of human connection, and the experience was difficult but deeply transformative. When we came home, I sank. I felt emotionally disoriented, like the nonsense I spent four years worrying about was completely insignificant. I was also angry at myself for playing it safe, spending my week with local artisans talking about wool, while braver classmates slept on the floor of a women’s jail. I thought, I squandered it – whatever it was I went there looking for. So I dissociated. I turned away from becoming a journalist and sold myself on a rich notion that my words mattered more as a lawyer. (Narrator: They do not.) That one week changed the trajectory of the next decade of my life.

Our Tiny Rebellions

After the climb

In one of my favorite online communities, a post by a fellow lawyer mom caught my attention. She recently summited Mt. Kilimanjaro – on International Women’s Day. Describing the pride associated with her accomplishment, she explained, it was as if her prior assessment of the limits of who she could be had radically expanded. It was life-changing. But th…

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4 years ago · 8 likes · 1 comment · Heather Joelle Boneparth

#3 Post-Meme: The Vibe Economy

on how we’ve shifted into a new vibe-first reality. I think he makes an interesting case that we’re seeing a shift away from minds with bodies and toward people that see themselves as wholes:

In her The Hollow series at The Stoa, organizational futurist and philosopher Bonnitta Roy introduced the phrase “sensefulness.” She argues that we are moving away from the myth of being in an information commons, with shared explanations with our minds via propositional knowledge, toward a shared understanding with our bodies via relational intimacy, or what she calls “senseful co-presencing.” Those following The Stoa for the last three years should not be surprised by this prediction: a sensefulness movement will supersede the mindfulness movement.

If my read of the nascent “wisdom commons” - a place that attempts to make wisdom more common - is accurate, sensefulness-based practices focusing on the sensate body over the construal mind are gaining traction and will soon surpass mindfulness-based practices in popularity. An argument for sensefulness-based practices is that they provide all the benefits of mindfulness-based interventions while avoiding the top-heaviness of being mind-full, embodying the truth that we are animals with “bodyminds,” not mind’s with a body.

The move from mindfulness to sensefulness will occur because a full-bodied experience is needed to be a whole human animal. Like most things, divides such as sensefulness and mindfulness will blur with more practical interaction. The overarching movement with such interaction, to quote Bonnitta, is that we will be “putting the mind back in the body and the body back in nature.”

The Stoa

Meme to Vibe: A Philosophical Report

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3 years ago · Peter N Limberg

Peter was a few years ahead of the culture war drama that played out over the past seven years. I think he has some powerful ideas here as well.

#4 Dan Wang on China

Dan Wang’s annual letter is a fun peek into the day-to-day realities of living in China. It is sort of sad that most people only see China through the lens of geopolitical drama and don’t really get much opportunity to appreciate it’s history and diverse landscapes and food. Here is a sample:

They are towering in the north. These are Tibetan areas home to a meaningful chunk of the Himalayas: Yunnan’s highest peak is Kawarkapo, one of Tibetan Buddhism’s most sacred mountains. This region is unbeatable for snowy beauty. The roads around them are strewn with fluttering prayer flags and studded with impassive yaks. Something in the thinness of the air produces more vivid light, which fires up white peaks in brilliant red when the sun is low. I went on several hikes around Kawarkapo and Tiger Leaping Gorge, which offer gorgeous treks through tough terrain.

Northern Yunnan is a site of improbable mixings. Missionaries made headway into these lands in the 19th century, establishing not just a Christian population but also vineyards that continue to produce wine grapes. In a remote valley, I passed by a vineyard owned by LVMH to produce Cabernet, which retail for US$300 per bottle.

The most stimulating parts of this region are not the cities of Lijiang or Shangri-La, but the more remote Tibetan areas. Tibetans have been subject to decades of forced assimilation to Han culture, but they still find room to practice small acts of subversion. One guide told me, for example, that monks have slipped a portrait of the Dalai Lama behind the portrait of the Panchen Lama in their monastery, allowing them to pray in good conscience. These rounds of control and evasion continue to grind on.

#5 Life Reflections

30 reflections. I most resonate with this one and wish I knew it earlier. I think this might be one of the hidden secrets of life

You do your best work when you’re not working. Your brain needs downtime to connect the dots like your body needs rest to strengthen itself for the next workout. If you’re always working, always trying to download information, always trying to be productive, you’re stifling your best insights from bubbling up. 

I also liked this one:

Remote relationships cost you real relationships. Every minute you spend cultivating relationships with people through a screen is a minute you’re not deepening relationships with people you can actually see and touch and smell.

This is part of why I moved back to the US. I missed the camaraderie of optimistic, exuberant weirdos, of which there are many (including Nat) in Austin. I get more joy out of virtual friendships than most, but I try to meet them in person eventually.

+ also had some nice riffs on Nat's themes here

#6 Reflections on Work

A friend Edward has been writing some interesting things on work in

Are modern jobs very bad, or are modern workers simply snowflakes? In my field, medicine, almost everybody is trying to get out of it. My lawyer friends are trying to get out of the legal field, or at least to escape from corporate law. In tech, people earn high salaries, but it seems tech employees change jobs every couple of years or so, or, if they are hanging in there, it’s for a big payoff, for which end they are begrudgingly willing to keep on trudging.

In medicine, juggling medicolegal risk, patient expectations, and demoralising workloads has taken its toll. Satisfaction is low and bullying is rife, but due to the terrible optics of striking, we are checkmated into enduring unfair working conditions. Hence, the beating will continue until morale improves.

Edward Says

Oxen of the Sun

Gentle Reader, Are modern jobs very bad, or are modern workers simply snowflakes? In my field, medicine, almost everybody is trying to get out of it. My lawyer friends are trying to get out of the legal field, or at least to escape from corporate law. In tech, people earn high salaries, but it seems tech employees change jobs every couple of years or so…

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3 years ago · 2 likes · 3 comments · Edward

#7 Playing a Career Game You Actually Want to Win - Every

An interesting question about your relationship with work could be:

What game are you playing and what will you get if you win?

recently wrote about this and introduced the idea of "value capture" a good phrase to articulate something I slowly woke up to in my career - that our companies values will likely win out over our own:

Our careers are different. The games we play with our working hours also come with their own values and metrics that matter. Success is measured by how much money you make—for your company and for yourself. Promotions, bonuses, and raises mark the path to success, like dots along the Pac-Man maze.

These metrics are seductive because of their simplicity. “You might have a nuanced personal definition of success,” Nguyen told me, “but once someone presents you with these simple quantified representations of a value—especially ones that are shared across a company—that clarity trumps your subtler values.” In other words, it is easier to adopt the values of the game than to determine your own. That’s value capture.

#8 Seasonality of Life

wrote a beautiful essay about the seasonality of life:

Game of One

#30: Living and Working in Seasons 🌍

As a function of abandoning the 9-5 Monday-to-Friday work cadence and deepening my relationship with nature through outdoor sports like skiing, surfing, and backpacking, I’ve become aware of how much I change with the seasons. When I first started working, my daily rhythm was dictated by the digital blocks of meetings on my work calendar. Now, my entire…

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3 years ago · 7 likes · 2 comments · Matt Yao

#9 On Getting Laid Off

This essay from was raw, honest, and reflective

Exactly a year ago, I got on a quick meeting with the founder of the startup I was working at who took a while to get to the point but eventually let me know that they were downsizing & I was a part of that.

For someone who thought being laid off could not affect them, I left that meeting in tears, shut the laptop with shivering hands & had a very telling first thought; “What will people say?”

Indeed.

Sri’s Substack

The Only Thing I'll Say About Being Laid Off

By now, in 2023, we’ve all heard at least a story or two of someone we know being laid off & them making the most of that situation. Maybe they used it as an opportunity to take freelancing more seriously, start a business, pivot their career, or just take a meaningful break that changed their perspective on work and life…

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3 years ago · 4 likes · Sri Karnic

#10 On City Life

In Taiwan living in a city is a normal thing. When Angie first came to my hometown, one surrounded by trees, she had a hard time imagining living in such a place.

Paul Krugman recently wrote about how easy life is in New York:

Before I get to the politics, a few words about what living in a 15-minute city, and New York in general, is actually like.

What people who haven’t experienced a real urban lifestyle generally don’t get is how easy life is. Running errands is a snap; because you walk most places, you don’t worry about traffic jams or parking spaces.

And I agree. New York is one of the most walkable and liveable cities we have in the US. It’s a shame that we don’t have more cities like it. Downtown Austin is nice but if you go anywhere you quickly end up in a car-oriented sprawl which can be worse than both city living like New York AND more rural suburban life.

This creative project far pre-dates my Boundless newsletter and traces itself back to a 2009 Facebook group I created called “media feast” which was an early collection of people sharing longform essays. Eventually, I found myself reading a ton but not as many people to share and connect with as Facebook usage fizzled.

So in 2016, I started something called “Top Reads” on medium and then pivoted it to something called “The Sunday Five” and then Boundless Reads where I’d send five good things every week. I ended up doing about 130+ issues and basically just stopped doing it in 2020 because of the friction of running two separate substacks (you can read some of the old issues here but I still need to figure out why most were imported as locked)

I don’t know if I’ll do a regular schedule but this felt like a nice thing to do to shorten up some of my wildly long expansive Saturday issues.

So without further ado, here are three stories about refactoring work and life that inspired me that seemed to arrive at once:

#1 Quitting To Be A Stay At Home Dad

Loved this from

With gratitude, excitement, doubt, fear, and ultimately conviction, I chose to leave a prestigious firm with a great salary, benefits, and downtime on zoom calls for nonstop negotiations with toddlers, endless snack demands, and mommy daddy & me dance classes.

scratching my niches

scratching my niches #9

Thanks for scratching — if you know someone else that may enjoy reading this, please forward along or join us here…

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3 years ago · 4 likes · Derek Baynton

#2 No More Pointless Meetings!

wrote about a three-part reimagination of her relationship with work and why she decided to take an early retirement package during Covid:

Stumbling Towards Clarity

Parachutes

One early Saturday morning in June 2020, I drove an hour north of my house to do something scary. After watching the instructional video, strapping on my harness, and waiting around the hangar for ages, I finally saw my name appear on the screen. I boarded the small plane with my instructor. I felt peace on the flight, despite looking out the open hatch …

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3 years ago · 12 likes · 8 comments · Claire Taitte

#3 Why Sam Cares About Fitness

wrote about how challenges with Type 1 diabetes while younger shaped his relationship with his body, and intuition and how it helped him make sense of his relationship to work.

Exercise helped me recapture the vitality of my body, but not my trust in it. Back then, my association with exercise was transactional and external. I did it to perform as an athlete, to attract a girlfriend, and to counteract the damage of my disease. This extrinsic focus and lack of trust in my body made me fragile. Coming out of college, I had no clue how fast everything was about to come crashing down.

Intuitive Fitness

The Origin of Intuitive Fitness

A few weeks ago, a friend asked me why I was so passionate about fitness. As I started to answer, I realized I needed to share my own journey with exercise. Here is that story…

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3 years ago · 15 likes · 4 comments · Sam Sager

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On Monday, I shared my annual review, on Tuesday I shared how I made $249k in income, and yesterday I shared the books I liked.

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I went through every newsletter issue I wrote in 2022 and pulled out all the links worth reading. I’m guessing if you like this you’ll find 10-15 links you didn’t find the first time and want to throw into your queue.

50+ Links From Other People That Inspired My From 2023

• This is a great post from Jamie Catherwood on the history of Innovation Hubs. Did you know Cleveland was a thriving hub in the late 1800s?

• A deep dive into the history of work through the lens of r/antiwork by Anna Codrea-Rado as well as her interview on Modern Wisdom

• A deep dive into how an obsession with procedures and rules slows down institutional change.

• Tina He on the power of the collective and the “New Frontier of Belonging”

• Lauren Valdez on long games: “Although I've never gotten a regular cadence of producing down, I have consistently come back to making content after each break. I keep playing the game.

• Jason Levin on decentralized friendships

• Sam Smith on not knowing what he’s doing

• Mike Newton on art & authenticity and being careful what you aim at

• Corey Wilks on embracing his accent and upbringing

• Rohit Krishnan on hierarchy and growth trade-offs and how to actually have an “impact”

• Tons of interesting publishing info from Brandon Sanderson’s FAQ from his self-published book launch

• Adam Ozimek on The Donut Effect post-pandemic

• Cecile M awesome thread of thoughts on sabbaticals

• Gretchen McCullough on “weird internet careers.”

• Tom Critchlow’s map for indie living

• Ben Weiss’ Self-Directed Masters

• Ryan Herr on taking more swings

• Tara McMullin discovered she was autistic at 38

• Nat Eliason on engaging with information in 2022 and balancing money versus going what you want to be doing and AI and writing

• Robert Anton Wilson on How To Tell Your Friends From The Apes

• Morgan Housel on how the eight-hour workday happened and when to quit

• Sam Sager on health challenges and commitment to health

• A profile on June Huh on wandering & being a math genius

• Ben Hunt on how wealth creation and economic growth became disconnected

• Ricky Yean on growing up in poverty and mindset inequality

• Freddie DeBoer on the fundamental challenge of absolute learning

• NBER research on remote work and hours worked

• Econofact on How covid crushed immigration

• Michael Story on his unconventional approach to curing a fear of flying

• David Kadavy on “making it” as a creator

• Claire Coffey on the limits of blaming capitalism

• Tyler Alterman on the problems with effective altruism

• Brian Timar on mimetic traps

• Angie Wang on overcoming her fear of being an immigrant and writing in a second language

• Byrne Hobart on Big Tech & Thymos

• Richard Hamming on doing “world-class work”

• Michelle Varghoose with great reflections on sabbaticals:

• Andrew Bartholemew on his first year freelancing

• Cal Newport on our changing relationship with work

• Isabel on intensity and avoidance

• Katherine Dee writes a reflection on the pitfalls of the “girl boss” meme:

• Nathan Baschez on the craft of coding

• Venkatesh Rao on mediocre computing

• Nix on filling the void and ambition

My Writing

32 Boundless Newsletter Topics & Themes Worth Reading

I went through every issue and only pulled out the parts I thought were good:

• Ten Reflections On Writing A Book (at launch)

• The End of “Meaningful Work”

• How I went from writing on Quora to running a six-figure consulting course

• Hosting An Event in Austin using Nick Gray’s formula

• Finding Wisdom in The Space

• My Thought on Mr. Beast on Rogan

• On Finding Your Conversation With The World

• Mailbag Q&A #1

• Using “Curiosity Triggers” to make friends & create opportunities

• My Remote Work Framework For Companies

• Taking Every 7th Week Off & Async Board

• In Praise of 4-Hour Workweek

• Thoughts on My Ten-Year B-School Reunion

• There is no “great resignation” – it’s the “great contemplation”

• The Origins of “The American Dream” in 1931

• Question People vs. Answer People

• Losing My Grandmother

• On Believing In Others

• Reminding Myself to “Write, Most Days”

• My thoughts on the limits of effective altruism (pre-SBF!)

• Managing Complexity & Many Income Streams

• What is your rich life?

• #200 The Creator Arbitrage Opportunity (Most shared)

• Boomer-Compatible Stories

• My Twelve-Hour Walk

• Why Kyla Scanlon Writes TikToks as Poems

• Reflections from Founders Podcast

• Operating In A Serendipity Economy

• Q&A Mailbag #2 and The Upside of Manners

• Reflections on 2022 and Ambient Anxiety

8 Longform Blog Posts (Longer or Adapted From Newsletter)

• From Blog to Book – The Ultimate Guide to Self-Publishing On Your Own Terms

• Too Big to Think: How Prestigious Institutions Stopped Generating Good Ideas

• The Inspiration Deficit (Or Why Young People Still Want to be Challenged)

• Book Review of Wild Problems by Russ Roberts

• Don’t Find a Niche, Find a Mode

• Ship, Quit & Learn

• My Creative Engine (Or how I write all this stuff!)

• On selling my time too cheap

9 Tweet Threads You Might Like

• Maslow Didn’t Invent a Pyramid

• Quotes from The Forgotten Highlander a book about a Sottish solder that is a POW in WWII

• 12 Common Phases of The Pathless Path

• Reality shifts from full-time to freelance

• The Shame Of Not Having A job

• Do 100 of something

• The Default Path Has Ruined Ambition

• The Imagination Crisis

• 30 Favorite Ideas From My Book

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Here are a couple posts I pulled together on my favorite reads from 2020. Hope you enjoyed them.

📖 My Favorite Reads, Essays, Podcasts & Newsletters From 2020 (150+ Links)

📚 My Favorite Books I Read This Year

Many of you are already subscribed to Boundless but if you want to join you can come over to subscribe or check out my annual review I posted a couple of weeks ago:

• My Pandemic Started In January

As always, say hi and let me know what’s on your mind what you are reading or what you might want me to share.

Have a good 2021!

Here are a couple posts I pulled together on my favorite reads from 2020. Hope you enjoyed them.

📖 My Favorite Reads, Essays, Podcasts & Newsletters From 2020 (150+ Links)

📚 My Favorite Books I Read This Year

Many of you are already subscribed to Boundless but if you want to join you can come over to subscribe or check out my annual review I posted a couple of weeks ago:

• My Pandemic Started In January

As always, say hi and let me know what’s on your mind what you are reading or what you might want me to share.

Have a good 2021!

📩 Enjoy receiving this e-mail? Forward this to a friend who likes reading good stuff via e-mail or share this on twitter.

✌ If you want to support the newsletter, you can become a supporter on Patreon or offer a one-time contribution here

#1 Student Loans

We often hear we are in a student loan crisis. Adam argues it isn’t as bad as we might expect. Even if the numbers make sense, I think he missed a collective psychological aspect that many young people feel. People have felt that debt is a bad thing and having $50,000 feels terrible even if its perfectly reasonable that you’ll be able to pay it back.

I don’t think forgiveness is a good idea, but simpler payback options, being able to declare bankruptcy and more accountability for colleges seem like something worth considering.

#2 Coddling

I just finished Jon Haidt’s book Coddling of the American Mind. It was a good read arguing that there is a dramatic generation shift underway starting with people born in the mid-90s. They were raised differently and have different mental models of justice, equality, harm and fairness. As this generation enters the workforce, many companies are struggling to adapt with these new models of power, status and hierarchy. I think this will lead to a lot of good improvements with work but also a lot more chaos like we’re seeing at google already.

Not sure I recommend the whole book, but recommend checking the longform article of the same title, which I likely shared a few years back.

#3 Status Games

Agnes Callard on the status games we play

In an academic context, I’ve noticed that complaining about how busy one is hits a sweet spot of oppression—I cannot manage my life!—and importance—because I am so in demand! When you’re playing with a master, it can be hard to tell which game you’re in.

and the challenge of thinking about the morals and ethics of the tradeoffs between optimizing for empathy and excellence

There is a philosophical conundrum at the root of all this: morality requires we maintain a safety net at the bottom that catches everyone—the alternative is simply inhumane—but we also need an aspirational target at the top, so as to inspire us to excellence, creativity and accomplishment. In other words, we need worth to come for free, and we also need it to be acquirable. And no philosopher—not Kant, not Aristotle, not Nietzsche, not I—has yet figured out how to construct a moral theory that allows us to say both of those things.

+Also recommend status-as-a-service by Eugene Wei

#4 “An Invisible Person”

Wesley Yang reflecting on life as an Asian-American man:

Millions of Americans must feel estranged from their own faces. But every self-estranged individual is estranged in his own way. I, for instance, am the child of Korean immigrants, but I do not speak my parents’ native tongue. I have never called my elders by the proper honorific, “big brother” or “big sister.” I have never dated a Korean woman. I don’t have a Korean friend. Though I am an immigrant, I have never wanted to strive like one.
…

Here is what I sometimes suspect my face signifies to other Americans: an invisible person, barely distinguishable from a mass of faces that resemble it. A conspicuous person standing apart from the crowd and yet devoid of any individuality. An icon of so much that the culture pretends to honor but that it in fact patronizes and exploits. Not just people “who are good at math” and play the violin, but a mass of stifled, repressed, abused, conformist quasi-robots who simply do not matter, socially or culturally.

Powerful read, especially after living in Asia for the past couple of years and reflecting on my interactions with many Asian-American friends.

#5 Work Identity

Carl Martin on shutting down his startup and grappling with the fact that he is not a worker:

It might have taken me ten years, but I now recognise placing so much weight of my identity in my work was a bad life choice. Especially as I recognise now that I am so much more, but have for whatever reason have chosen not to acknowledge it.

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🔥 New On Boundless: Lessons From 150+ Curiosity Conversations

#1 Nuclear Families in The Modern Age

This essay was one of the best I’ve read in a while. It is from David Brooks and looks at how our family dynamics have changed dramatically over the last 100 years.

Essentially, nuclear families have become isolating and a challenge unless you have the resources to make it work. We crave being part of larger groups but don’t yet have the cultural norms to make that happen.

Some interesting tidbits like how people used to get married later until people started moving away from family for jobs:

From 1890 to 1960, the average age of first marriage dropped by 3.6 years for men and 2.2 years for women.

and some of the wealth dynamics driving the separation from extended into nuclear families:

By 1961, the median American man age 25 to 29 was earning nearly 400 percent more than his father had earned at about the same age.

…and how quickly things have shifted in the last 20 years:

In 2004, 33 percent of Americans ages 18 to 34 were living without a romantic partner, according to the General Social Survey; by 2018, that number was up to 51 percent.

👉 Do read the whole thing - I’d love to hear your thoughts

#2 “Passive Income,” Travel & Real Freedom

Enjoyed Nat Eliason’s essay on traveling and passive income and some of the challenges of working less

Assuming you don’t roll over and die when you’re faced with that void, you’ll naturally try to find something to fill it with. And unfortunately, the same drive that can make this lifestyle possible might make it impossible to fully enjoy it.

#3 Coal Towns

I shared this over on the other newsletter, but found this a bit shocking - both for how few coal jobs there are and how the faith in the coal industry has left an entire region behind.

At a national level, US politicians, corporate chieftains and other civic leaders continue to ignore the flaws riddling their own growth model. Like the coal-backed politicians counting on boom to follow bust, the nation’s leaders continue to expect the business cycle to buoy growth, failing to grasp how years of increasing inequality in wealth, income, opportunity, and health have cannibalized the very demand needed to sustain it. While they dither on investing in infrastructure, technology, education and health care, the country’s reliance on welfare continues to climb as labor force participation slides. Taxpayers are subsidizing companies to underpay retail workers, just as they’re paying for coal companies to lop off mountaintops.

Read the full thing here

#4 Carlos Ghosn Escapes Japan

This whole story of Carlos Ghosn escaping Japan sounds like a movie but is real life. Here’s the case he snuck out in:

#5 Why Not To Become Famous

Some raw reflections from Tim Ferriss on becoming famous including the death threats and harassment he has had to deal with.

Instead, fame is likely to magnify all of your insecurities and exaggerate all of your fears. It’s like picking up a fire extinguisher for your pain that ends up being a canister of gasoline.

Definitely doesn’t seem worth it

📚 What I’m Reading

• Black Mass - Just finished this fascinating book on millenarian & utopian impulses and how they have re-emerged in politics in the 2000s (9/10 skip the middle of the book)

• Aspiration - Book by Agnes Callard that explores how people really make changes such as going from a non-parent to parent (8/10 so far)

Bonus

• Capitalism redefined: “But there is too little debate about what it is all for. Hardly anyone ever asks: What kind of growth do we want? What does “wealth” mean? And what will it do for our lives?”

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🔥 New On Boundless: The Boomer Blockade and The Dark Side Of Consulting

#1 Scenius

I enjoyed Packy McCormick’s introduction essay to his future longer exploration of “scenius”

 Throughout history, sceniuses have sprung up seemingly at random across the globe, based on a confluence of unplanned factors coming together at just the right time in just the right combination. The Scottish Enlightenment, for example, was precipitated by a variety of factors: the British government’s hands-off support of the country, a steep rise in literacy that made Scotland the most literate country of its time, the many taverns that sprung up to serve as the informal meeting places where thinkers could exchange novel ideas.

Looking forward to reading his full exploration and engaging in some potential Scenius’ throughout the year

#2 Why You Don’t See Your Friends

This essay argues that the workforce is splitting into two: low-wage workers who don’t have any control over when they work and high-wage earners who are choosing to work all the time.

Forty percent of hourly employees get no more than seven days’ notice about their upcoming schedules; 28 percent get three days or fewer.

and

For her 2012 book, Sleeping With Your Smartphone, the Harvard Business School professor Leslie Perlow conducted a survey of 1,600 managers and professionals. Ninety-two percent reported putting in 50 or more hours of work a week, and a third of those logged 65 hours or more. And, she adds, “that doesn’t include the twenty to twenty-five hours per week most of them reported monitoring their work while not actually working.

#3 A Sick Giant

Tim Urban argues that America is a “sick giant” - quite a lot of fascinating information - a casual 80-minute read with fun stick figure charts along the way to keep you entertained:

When the Value Games are working properly, people holding the most extreme views are relegated to the fringes—retaining enough of a voice to effect change when they’re right about something but unable to do too much damage when, more often, they’re wrong. But in the Power Games, it’s often the case that small groups of more extreme people end up with outsized power over others.

#4 Soros’ Theory

George Soros shares his theory of reflexivity, something that has guided his investing for his entire life:

My conceptual framework is built on two relatively simple propositions. The first is that in situations that have thinking participants, the participants’ views of the world never perfectly correspond to the actual state of affairs. People can gain knowledge of individual facts, but when it comes to formulating theories or forming an overall view, their perspective is bound to be either biased or inconsistent or both. That is the principle of fallibility.

The second proposition is that these imperfect views can influence the situation to which they relate through the actions of the participants. For example, if investors believe that markets are efficient then that belief will change the way they invest, which in turn will change the nature of the markets in which they are participating (though not necessarily making them more efficient). That is the principle of reflexivity.

More interesting than I expected and doubles as an analysis on Academia and how the different sciences conceive of themselves.

#5 Game B

Jim Rutt offers a vision for what an alternative to “Game A” could look like.

So what is a civilization level social operating system? For this essay, I’m going to posit that it means that at maturity GameB has become the dominant attractor for a living civilization. Roughly analogous to “Western Civilization” or its competitors. Think at least several hundreds of millions of people across a significant portion of the Earth’s surface.

I’ve been enjoying the creative conversation around these topics and my own experiments with gift economy exchanges and non-doing/non-work over the past few years. If you’re interesting in reading more, its worth checking out Jordan Hall too on Jim’s podcast.

💼Going Nomadic

My wife and I are headed out of Taiwan towards the end of this months. Would love to meet people along the way:

📚 What I’m Reading

• Loserthink by Scott Adams - easy short read that serves as a good guide for navigating all the nonsense in our social media worlds now (6.5/10)

• Vagabonding by Rolf Potts - rereading this book before starting another long travel journey (8/10). A quote I loved:

  Vagabonding is about looking for adventure in normal life, and normal life within adventure. Vagabonding is an attitude—a friendly interest in people, places, and things that makes a person an explorer in the truest, most vivid sense of the word.

• Draft No. 4 by John McPhee - read this as part of trying to continue to get better at writing. The book is readable, entertaining, well-written and actionable. (8/10)

Bonus

Before I took the turn away from full-time work, Clayton Christensen was one of the first books I read that really challenged me to think about fundamental questions. I definitely recommend his essay “How Will You Measure Your Life?”

I have a pretty clear idea of how my ideas have generated enormous revenue for companies that have used my research; I know I’ve had a substantial impact. But as I’ve confronted this disease, it’s been interesting to see how unimportant that impact is to me now. I’ve concluded that the metric by which God will assess my life isn’t dollars but the individual people whose lives I’ve touched.

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🔥 New On Boundless: Learn the game, don't become the game and Podcast: Diania Merriam on Reclaiming The American Dream

#1 Hyper-realities

Good read From Renee DiResta on the modern state of sensemaking, the media, reality tunnels and the “fifth estate”:

Luther and the Vatican also clashed over the Truth, but today’s information ecosystem dynamics differ in scale, scope, and speed. Unlike the residents of Luther’s Wittenberg, readers today aren’t just contending with divergent pamphlets. They’re contending with a deluge of hyperpartisan content, tailored precisely to preexisting beliefs, compounded by nearly-instantaneous viral social media transmission and a news cycle that lasts less than a day. This portends a societal transformation: our information ecosystem no longer assists us in reaching consensus. In fact, it structurally discourages it, and instead facilitates a dissensus of bespoke pseudo-realities.

#2 Total Work

I really enjoyed Andrew Taggart’s latest (and evolving) version of his ideas around total work, which seem to be connecting with a lot of what John Vervaeke is discussing in his “meaning crisis” series:

• Andrew’s latest version of his thesis

• Vervaeke’s Awakening From The Meaning Crisis

#3 Masculinity

I thought this deep dive on the modern challenge of growing up male in today’s culture was fair and provocative. It definitely resonated with a lot of what I experienced growing up, though it seems our generation didn’t have the meta-awareness of what was really happening as some might today.

Despite that, according to Judy Y. Chu, a human-biology lecturer at Stanford who conducted a study of boys from pre-K through first grade, little boys have a keen understanding of emotions and a desire for close relationships. But by age 5 or 6, they’ve learned to knock that stuff off, at least in public: to disconnect from feelings of weakness, reject friendships with girls (or take them underground, outside of school), and become more hierarchical in their behavior.

#4 From the author of Prozac Nation

A beautiful essay from Elizabeth Wurtzel who recently passed away from breast cancer reflecting on her life and journey in 2013.

#5 Polarization

Tim Urban goes deep in his 10th of 12 essays on the modern culture wars and fragmentation in the US.

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🔥 New On Boundless:
   - The Second Chapter Of Success
   - Guest post about the "Big Law Trap"
   - Podcast with the CEO of the Remote Company Doist
   - Podcast with Moataz Ahmed, freelance creator & writer

#1 Economics

David Graeber reflects on the state of economics and monetary policy and how the discipline seems to have operated in a very myopic state for the last 30-40 years. A fun read for people interested in such topics as the story around money”

Is money best conceived of as a physical commodity, a precious substance used to facilitate exchange, or is it better to see money primarily as a credit, a bookkeeping method or circulating IOU—in any case, a social arrangement? This is an argument that has been going on in some form for thousands of years. What we call “money” is always a mixture of both, and, as I myself noted in Debt (2011), the center of gravity between the two tends to shift back and forth over time. In the Middle Ages everyday transactions across Eurasia were typically conducted by means of credit, and money was assumed to be an abstraction. It was the rise of global European empires in the sixteenth and seventeenth centuries, and the corresponding flood of gold and silver looted from the Americas, that really shifted perceptions. 

#2 Dream Time

Robin Hanson argued in 2009 that we had entered “dream time”:

While our descendants may explore delusion-dominated virtual realities, they will well understand that such things cannot be real, and don’t much influence history. In contrast, we live in the brief but important “dreamtime” when delusions drove history. Our descendants will remember our era as the one where the human capacity to sincerely believe crazy non-adaptive things, and act on those beliefs, was dialed to the max.

It seems many more people are saying similar things, except we are more aware of out made-up realities than ever before.

It also reminded me of Bruce Chatwicks excellent book on traveling across Australia, The Songlines:

‘To wound the earth’, he answered earnestly, ‘is to wound yourself, and if others wound the earth, they are wounding you. The land should be left untouched: as it was in the Dreamtime when the Ancestors sang the world into existence.’

#3 Boris Johnson

I didn’t really know anything about Boris Johnson until I read this super deep-dive from Andrew Sullivan prior to the election last week. Sullivan is a gay British conservative who moved to the US and ended up supporting Obama. He presents an interesting perspective on how he thinks Boris is turning ugly anti-immigrant sentiments into a more benign conservatism in Britain.

Check out the profile here. Definitely worth reading after the election results.

#4 Why Do We Crave Meaning?

A short essay from Russ Roberts:

Where does this demand and desire for meaning come from? What is disturbing about a life of vast or modest physical pleasures from food and sex and great music and exotic travel that goes on for some number of decades and comes to an end? Why aren’t those pleasures enough? Sure, it would be great if it lasted even longer than the good part of a century. But if this life is finite and part of nothing larger than itself, is that really a problem? Why does it haunt us, this quest for meaning?

#5 Fourth Estate

Fascinating newsletter issue from Claire Berlinski on a disconnect between our growing attention towards technology that is undermining the news and our knowledge that the news is struggling at all

She sees this as a troubling global trend starting with the US:

Studies repeatedly find that Americans know less about international affairs than citizens of other countries, developed or undeveloped. Usually this is taken as evidence that Americans are incurious or backward.

That’s not the right interpretation. Americans are curious and forward, at least in the sense that they have been the inventors and first adopters of the new technologies that have destroyed journalism. Other modern countries will soon catch up.

Etc. Some Additional Things I enjoyed the past few weeks:

• Jonny Miller’s interview of Andrew Taggart on Total Work

• The same Jonny and his talk on navigating grief after the loss of his partner

• Donald Hoffman on Sam Harris’ podcast talking about the nature of reality & consciousness

• Fareed Zakaria’s super deep state of what we should think about China

• The 85% rule for learning

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#1 How Politics Became A Business | New Yorker

I sent this to a friend who was wondering how employer-based healthcare came to be in the US. This fun read details the early history of lobbying and public influence campaigns as well as how the American Medical Association was founded around stopping federally-run healthcare.

When Republicans took control of Congress in 1946, Truman’s proposed federal health-insurance program, which, like Warren’s, was funded by a payroll tax, stalled. In his State of the Union address in 1948, an election year, Truman urged passage of his plan, which enjoyed widespread popular support. In November, Truman won the election. Days afterward, the American Medical Association called up the San Francisco offices of Campaigns, Inc. The A.M.A. retained Whitaker and Baxter at a fee of a hundred thousand dollars a year, and with an annual budget of more than a million dollars, to thwart Truman’s plan. The A.M.A. raised the money by assessing twenty-five dollars a year from every one of its members.

It’s a fun “what if?” to ponder - what if the US had not gone in the direction it did with its healthcare, what would the system look like now?

#2 Cargo Cults | Meaningness.com

Everyone remembers the first time they learn about cargo cults:

During World War II, many Pacific islands that previously had little or no contact with the modern world were used as air bases by the Americans or Japanese. Suddenly, enormous quantities of food, clothes, tools, and equipment, such as the islanders had never seen, appeared out of the sky in magic flying boats. Some of this “cargo” trickled down to the natives, and it was fabulous. Then the war ended, the planes vanished, and—no more cargo!

How to make the cargo flow again? The islanders had observed that, just before cargo arrived, the foreigners performed elaborate rituals involving inscrutable religious paraphernalia. Clearly, these summoned the sky spirits that brought cargo.

This may seem crazy until you realize this behavior is core to who we are in all parts of the world.

The whole article is thought provoking and highly recommended.

#3 What is happening in companies? | Aeon

Almost two thirds of employees work at large or medium size businesses and probably have to implement some of these initiatives (link):

Another big driver of stupidity in many firms is the desire to imitate other organisations. As Jan Wallander, the ex-chairman of Sweden’s Handelsbanken, said: ‘Business leaders are just as fashion-conscious as teenage girls choosing jeans.’ Many companies adopt the latest management fads, no matter how unsuitable they are. If Google is doing it, then it’s good enough reason to introduce nearly any practice, from mindfulness to big-data analytics.

If you don’t have OKR’s are you a real business? My favorite term for this is “modishness” - doing what is in favor.

While this article definitely has a dramatic flair, I think it nails some of the perverse incentives that exist in organizations:

We saw firms going out of their way to block employees from reflecting on their assumptions, to discourage them for thinking about their substantive goals, and to impede them from giving or asking for justifications for their decisions and actions. By doing this, organisations often create functional outcomes both for individuals (such as career progression) and the whole organisation (such as the ability to avoid conflict and focus on common goals). While these favourable outcomes dominate in the short term, collective stupidity can create disfunction in the longer term, including a lack of learning and an imperviousness to mistakes.

#4 Illegible Persons | Ribbonfarm

As I try to convince people I actually enjoy living nomadically, I found this distinction between nomads and non-nomads useful:

Rooted people often decide to relocate somewhere based on a general sense of opportunities and lifestyle possibilities, and then figure out how they’ll live their lives there. Smart rooted people usually target regions first, jobs, activities and relationships second. Nomads pick a pattern of movement first, and then figure out the possibilities of that pattern later.

and this:

If I have romanticized nomadism it is because nomadism is a fundamentally romantic state of being. If you can sustain it, it is somehow fulfilling without any further need for achievement or accomplishment. The pursuit of success is, for the rooted, the price they must pay for immobilizing themselves geographically. The reward is something equivalent to the state of stable movement that is, for the nomad, a natural state of affairs.

I’ve definitely found a nomadic state almost impossible to explain to people, but this article does a good job of capturing the spirit of the modern digital nomad.

#5 Moloch | Slate Star Codex

Meditations on how we end up in what the writer calls “multipolar traps”

And as well understood as the capitalist example is, I think it is less well appreciated that democracy has the same problems. Yes, in theory it’s optimizing for voter happiness which correlates with good policymaking. But as soon as there’s the slightest disconnect between good policymaking and electability, good policymaking has to get thrown under the bus.

For example, ever-increasing prison terms are unfair to inmates and unfair to the society that has to pay for them. Politicans are unwilling to do anything about them because they don’t want to look “soft on crime”, and if a single inmate whom they helped release ever does anything bad (and statistically one of them will have to) it will be all over the airwaves as “Convict released by Congressman’s policies kills family of five, how can the Congressman even sleep at night let alone claim he deserves reelection?”. So even if decreasing prison populations would be good policy – and it is – it will be very difficult to implement.

with some fun anecdotes as well about the Quiverfull movement:

…it might be worth going back to Bostrom’s paragraph about the Quiverfull movement. These are some really religious Christians who think that God wants them to have as many kids as possible, and who can end up with families of ten or more. Their articles explictly calculate that if they start at two percent of the population, but have on average eight children per generation when everyone else on average only has two, within three generations they’ll make up half the population.

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#1 The Fifth Estate

The mainstream coverage of Facebook has been vicious, but Ben Thompson offers a different, broader perspective saying that Mark Zuckerberg may be pulling from history in trying to convince people that they are a “fifth estate” and are part of a broader shift from the nation state to individuals similar to how the printing press helped shift power from the chuech

👍 Recommended Read Of The Week

#2 Secrets about People: An Intro to René Girard

Alex Danco | 31 Minutes

Deep dive into the thinking & writing of Rene Girard and how these forces are shaping our world in the digital sphere

The more we understand about the world around us, the less it seems we understand about people and the way they are. This post is an introduction to one man, named René Girard, who bucked this trend: his perception of the nature of behaviour is like a laser that goes right to the core of the human condition. We watch and learn by copying others, and the most important thing we learn from others is desire. Girard understood something important about desire; so did Shakespeare and Dostoevsky, and so do Kanye West and Donald Trump. This secret, once you understand it, will challenge you.

Read the full piece here.

#3 Revisiting Simone de Beauvoir

What would de Beuvoir say about today’s economic opportunities?

fiscal work is no guarantee of women’s freedom, caring for and being cared for by others is a central part of what makes us human, and without care and caring human beings struggle to thrive.

#4 Manufactured Hopelessness

David Graeber continues to share a completely unique perspective. In Bullshit Jobs and Utopia of Rules, Graeber wrote at length about under-discussed parts of our modern world - how complexity and modernity results in a type of “spiritual violence” against our ability to dream, hope and imagine better futures. This essay similarly talks about how our systems and institutions crush our desire to dream:

If we really want to understand this situation, we have to begin by understanding that the last thirty years have seen the construction of a vast bureaucratic apparatus for the creation and maintenance of hopelessness, a kind of giant machine that is designed, first and foremost, to destroy any sense of possible alternative futures.

I don’t think this is the whole picture, but I don’t think its talked enough about, how so many people seem to have their dreams thwarted.

#5 Advice From The 80-Year Old Vice Chair Of Blackstone

I always pay attention when older people are sharing their life lessons. A bit obsessed with work (“never retire”) but I liked these two:

Younger people are naturally insecure and tend to overplay their accomplishments. Most people don’t become comfortable with who they are until they’re in their 40’s. By that time they can underplay their achievements and become a nicer, more likeable person. Try to get to that point as soon as you can.

& find younger people to mentor:

When your children are grown or if you have no children, always find someone younger to mentor. It is very satisfying to help someone steer through life’s obstacles, and you’ll be surprised at how much you will learn in the process.

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#1 Buybacks All Day

In the two and a half years I spent consulting to corporate Boards around the world, the one thing every single company talked about was capital allocation and stock buybacks.

This article talks about the case of Texas Instruments and how meager growth paired with cost cutting and buybacks enabled the company to create a whole lot of wealth for its managerial class:

In other words, senior management and the board of directors received $3.6 BILLION in direct value from these stock buybacks.

and declare that its never been better to be a senior manager:

It’s never been a better time in the history of the world to be a senior manager of a publicly traded company.

Shit! Should have stayed in the game a few more years 😎

The article is arguing that we shouldn’t be so upset about Adam Neumann and WeWork because this goes on everyday at big companies around the world.

Financialization has won our over old fashioned organic growth.

+Check out Epsilon Theory’s other articles including an idea about a new way of thinking about our contributions framed around “Make, Protect, Teach”

#2 Without Work What Do We Do?

This article explores many who struggle to find purpose without work:

“Without ambitious projects to fill space,” he added, “there is often a void that makes some of the bigger questions hard to avoid. The things you neglected are no longer drowned out by noise; they are the signal. It’s like facing the Ghost of Christmas Past.”

This is mostly an article about the rich and how they are scared of stopping to work, but I think this hits on something emerging in the public consciousness - that our idea of contribution as paid work is becoming insufficient. Alexis de Tocqueville pondered the same question in the 1800s:

In the United States a wealthy man thinks that he owes it to public opinion to devote his leisure to some kind of industrial or commercial pursuit or to public business. He would think himself in bad repute if he employed his life solely in living.

It’s also something I talked about in my podcast with Alex Pang. Check out the link below.

#3 Curiosity Is About What You Already Know

A discussion on creativity and curiosity:

As expected, subjects were least curious about answers they thought they knew. But they were also uninterested in questions about which they hadn’t a clue. Instead, curiosity peaked when subjects had a good guess about the answer but weren’t quite sure.

#4 How To Use Twitter

I’ve found a ton of friends and learned a ton from strategic use of twitter. Here is a good guide to getting started:

#5 Abundance Economics

A fascinating article from Oshan Jarrow.

What does economics look like in an era of abundance? First he touches on the “magnetics of money” - something I don’t think enough people appreciate:

Put simply, for the vast majority of the wealth spectrum, capital does not attract more capital. But after a certain threshold, it gets easier and easier to acquire more. Making money makes it easier to make more money. 

He goes on to propose a number of solutions to how we can slow down the magnetic effect (something also talked about in Charles Eisenstein’s book Sacred Economics) and how abundance thinking really would play out in day to day life:

An economic abundance would invert the logic of daily life. Utilitarian labor - that is, work not for itself, but for earning - would recede to the margins. Any further labor taken on would become increasingly voluntary, un-coerced by the imperative to earn one’s living that incentivizes commodified life-forms. 

and his hope:

We know the story of scarcity, it’s been playing out for millennia. I hope to witness the story of abundance unfold in my lifetime. If Buckminster and Bookchin are correct, social innovations will reveal that there is now, in fact, enough for everybody.

There has been a lot written about these kinds of ideas over the years but I’m intrigued by how many people seem to be paying attention now. This seems like the optimistic side of a very pessimistic time.

🎧 Podcasts

• Dan Carlin’s Hardcore History series is epic. He just released part III of his Japan series, all of which you can listen to for free. Check it out here.

• I published an interview with the author of one of my recent favorite books Rest, Alex Pang. You can listen and read more here

• I’m listening to John Veraeke’s Awakening From The Meaning Crisis which is also epic in a different kind of way. Shoot me a note if you end up listening and let’s share notes.

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#1 Urban Professionals & Housing

Alex Danco connects the dots between increasing housing, the urban professional job market and the credit engine behind it all and attempts to help people understand why increasing supply in cities will not lower prices

The denser the city gets, the more bifurcated the job market becomes; the ready supply of credit that’s available means that any given unit that’s built is going to get priced not at what the local labor market can support, but rather what the “young professional creative/credit engine” can support,

#2 Chinese Hacking To Build A Plane

A Crowdstrike report published today shows how this coordinated multi-year hacking campaign systematically went after the foreign companies that supplied components for the C919 airplane.

Read more here.

#3 Amazon Good & Bad

A longform exploration of Jeff Bezos’ mid-life crisis, Amazons continued takeover of the world, its extreme (and boerdline cultish) company culture and its mistreatment of workers. The article is very much about Bezos, mentioning him 91 times:

Bezos’s personal tumult distracted Amazon’s leaders at a particularly fraught time. The company’s headlong growth has led to a series of scandals, and executives have been unsure how to contain the damage. Like other process companies, Amazon is learning that a flywheel, once spinning, is very hard to stop.

#4 The Emergence Of Game B

Even though many have argued that we may be past a new “meta-narrative” for the world, this essay is a thoughtful reflection on the possibility and the emergence of an “intellectual deep web:”

wisdom is not wisdom unless it’s based in compassion. 

#5 The Middle Class Shrinkage / Upper Class Expansion

In the US. the common narrative is that the middle class is shrinking. This is true, but it is because more people are making over $100k

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##1 Social Media Asymmetry

Frank Chimero on the asymmetry of positive versus negative signals online:

The arrangement is even worse on Twitter. Liking stays attached to the original tweet and makes most positive interactions static. Negative reactions must be written as tweets, creating more material for the machine. These negative tweets can spread through retweets and further replies. This means negativity grows in number and presence, because most positivity on the service is silent and immobilized.

This still seems fundamentally broken for the internet as many are waking up to. Part of it is our confusion between different operating models (individuals = trying out ideas; media = tribe viewpoint; random shitposters = making chaos), but based on many of the positive interactions I’ve seen in small pockets of the internet, I do have some hope.

+Also love this article by Frank titled The Good Room (a must read)

#2 Charisma Neutrality

Interesting line of thinking about what the future of the internet could look like:

The cynical, anti-charismatic whispering on the margins becomes the main act, and the charismatic posturing in the center becomes a sideshow…..

This means at some point it actually becomes easier and cheaper to simply talk to the thoughtful people rather than browbeating them with charisma.

#3 Resilience

What is the difference between people that respond positively to stress versus ones who don’t?

Seligman found that training people to change their explanatory styles from internal to external (“Bad events aren’t my fault”), from global to specific (“This is one narrow thing rather than a massive indication that something is wrong with my life”), and from permanent to impermanent (“I can change the situation, rather than assuming it’s fixed”) made them more psychologically successful and less prone to depression.

#4 Life Advice

This letter offering advice from Hunter S. Thompson is impressive mostly because of his age (he was 22) and that it reminded me that we often forget the second part of this famous Shakespeare line:

“To be, or not to be: that is the question: Whether ’tis nobler in the mind to suffer the slings and arrows of outrageous fortune, or to take arms against a sea of troubles … ”

I enjoyed this part of the letter:

And indeed, that IS the question: whether to float with the tide, or to swim for a goal. It is a choice we must all make consciously or unconsciously at one time in our lives. So few people understand this! Think of any decision you’ve ever made which had a bearing on your future: I may be wrong, but I don’t see how it could have been anything but a choice however indirect— between the two things I’ve mentioned: the floating or the swimming.

But why not float if you have no goal? That is another question. It is unquestionably better to enjoy the floating than to swim in uncertainty. So how does a man find a goal? Not a castle in the stars, but a real and tangible thing. How can a man be sure he’s not after the “big rock candy mountain,” the enticing sugar-candy goal that has little taste and no substance?

#5 The State of Universities

Heterodox Academy finds that students are not the direct cause of the current climate at elite universities:

As HxA co-founder Jonathan Haidt explained in Coddling of the American Mind and elsewhere, when he began his advocacy for viewpoint diversity, open inquiry and constructive disagreement, he thought it was the universities – faculty and administrators – who were proliferating the mindset he describes as ‘safetyism’ among students.

However, as he continued to study the issue, he realized that he had the dynamics backward: students from more privileged backgrounds were coming into (elite) universities with these ideas and expectations already well-entrenched, and were often demanding conformity from university leadership and administration.

They faced little resistance in an institutional environment where students are increasingly viewed as ‘consumers,’ and these customers are held to be ‘the boss.’ 

Interesting article showing how many of the “new” trends were really phenomenon that have existed for decades if not longer. The article is an interesting attempt to make sense of how Universities (especially elite ones) are changing and what is all means.

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#1 History of the corporation 🏭

Oldie, but goodie from Venkat Rao on the history of the corporation and how attention in the metric of the future

Europe may have increased per capita productivity 594% in 600 years, while China and India stayed where they were, but Europe has been slowing down and Asia has been catching up. When Asia hits Peak Attention (America is already past it, I believe), absolute size, rather than big productivity differentials, will again define the game, and the center of gravity of economic activity will shift to Asia.

#2 Grappling With A Brother’s Death

A gripping story of a sister that tries to make sense of how she lost connection with her brother and how he ended up in Europe trying to be taller:

When my brother died, I was too shattered to write his obituary. There is little record of his 29 years of life; it simply vanished. When I type “Yush Gupta,” Google autofills “Yush Gupta death,” a brutal reminder that even on the internet, a space where nothing is forgotten, Yush is a mirage, slowly disappearing.

#3 Three big things

Morgan Housel offers three “big things” impacting our world. Here are two interesting charts he offers among many other ideas:

The one I was most excited for was his third one:

3. Access to information closes gaps that used to create a social shield of ignorance.

I’ve seen this in my online courses, where I’ve seen more energy out of students from Thailand, Indonesia, Malaysia, Saudi, India than other nations.

Exciting times…

#4 US Healthcare System

A doctor in Boston calls out top hospitals in Boston for legal fraud:

It’s important to say up front that no fraud is involved. Rather, with the evolution of coding schemes for diseases and conditions, a hospital’s enhanced ability to extract information from electronic medical records, and an industry of consultants and trained staff with revenue maximization goals in mind, inpatient admissions are being upgraded to a higher level of severity and hospital payment.

#5 Meaningness

How do we find meaning? I’ve been diving into a couple things around what some people are calling “the meaning crisis.”

First is this meandering and interesting site called Meaningness from a former PhD in AI from MIT. This is the latest piece I ran across:

• Systems of meaning in flames

And next is this video series (also a podcast) on “awakening from the meaning crisis” - I’m enjoying it and it feels like being part of a fascinating college class. Let me know if you want to follow along with me.

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#1 Earthquake Before & After

Pictures 20 years later from a major earthquake here in Taiwan

#2 Unapologetic Ambition

Kara Swisher on her ambition is pretty fascinating:

There have been a lot of people, mostly men in positions of power, telling me I had to wait, that I shouldn’t be so confident. And I was like, “What are you talking about? I’m the best you have.”

and on raising her sons:

I have two wonderful boys, and I spend a lot of time with them. I’m always like, “Don’t do your homework; it doesn’t matter. Do this other thing instead.” Their teachers hate me for it, but I’m like, “What? Is it not true?” We try to help our kids with what they want to do, but you’re certainly not going to see me bribing any colleges.

There’s something to be said about absolute certainty, I’m just not sure what it is

#3 Why Can’t We Agree On Truth?

What, then, has changed? The key thing is that the elites of government and the media have lost their monopoly over the provision of information, but retain their prominence in the public eye

Read the whole thing here.

#4 Agnes Callard on Why Philosophers Shouldn’t Sign Petitions

As a philosopher, I want my influence to be philosophical, which is to say, I want to bring people to believe only what they, by their own lights, can see to be justified; I don’t want them to believe something because (I am one of the) many people who think it.

Link here

#5 Opting For The Unknown Over The Sure Thing

A friend, Jonny, opts to stay on his “pathless path” vs, accept an enticing job:

This also enabled me to realise that some of the appeal of the role (despite being a wonderfully enticing offer) was that it would give me a get out of jail free card. A chance for both a regular pay-cheque and rapids-of-uncertainty life raft—a clear route deviating from the pathless path that I’ve been wandering along.

Related: Fascinating exchange with the author and Andrew Taggart earlier this month about how one might dis-identify as a worker:

I’ve had both experiences over the past several years:

Podcasts 🎙

Seth Godin & Brian Koppelman On Creativity

Fascinating discussion as always on The Moment Podcast

Chart Of The Week 📊

Prediction: New talking point in next couple years will be that incomes depend on how lucky you are to work at certain types of firms.

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⚡ I am in the process of days creating a course called Reinvent to help people experiment with creating their own work and grappling with the modern struggle of hacking a living outside the norm. You can sign up here or join via a gift economy pay-what-feels-right exercise. I’d love if you shared the course with anyone who might find it valuable in their journey.

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#1 School & Identity

Being a parent and raising kids in the NYC school system doesn’t sound fun. This essay is a deep dive into how crazy trying to navigate even the public school system is and how political ideals are taking over. The student in the story asks:

“Isn’t school for learning math and science and reading,” he asked us one day, “not for teachers to tell us what to think about society?”

#2 “Career Trajectory”

I believe that the idea that one should have a “steady career trajectory” is a relic of a peculiar time in Western history in the 1950s and 60s when only some people were in the workforce and there was 4-5% annual growth.

Read the article I wrote here

#3 The American Obsession With Work

An op-ed from a professor that argues we should look at work as a duty to others rather than just looking to find meaning from it. His starting point is that America is in a unique position as being obsessed with work:

While other wealthy nations have shortened the workweek, given their citizens more free time and schemed to make their lives more pleasant, stress-free and enjoyable, the United States offers a curious paradox: Though the standard of living has risen, and creature comforts are more readily and easily available — and though technological innovations have made it easier to work efficiently — people work more, not less.

He cherry picks a letter from Seneca to make a point about duty to others but failes to mention the fact that Romans held a certain sense of leisure as a higher aim than work, which I wrote about here. I think writing about someone like Thomas Aquinas might have been a better fit, who said:

#4 Vulnerability

Mark Manson on vulnerability. He has a simple but powerful way of communicating that I think likely resonates with even the most stubborn men. I love this idea and its something I need to do more of:

Telling someone you appreciate/admire/respect/love them – This might be the ultimate form of vulnerability, and it’s probably the easiest one to mess up as well (more on that soon). 

#5 A Quote

From WH Murray:

“Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too.

All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one's favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way.

I have learned a deep respect for one of Goethe's couplets:
Whatever you can do, or dream you can, begin it.
Boldness has genius, power, and magic in it!”

Chart of the Week: Another housing bubble or new normal?

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#1 A Walk Through Japan

A thoughtful piece from Craig Mod on using light technology and walking through Japan for 30 days:

In the context of a walk like this, “boredom” is a goal, the antipode of mindless connectivity, constant stimulation, anger and dissatisfaction. I put “boredom” in quotes because the boredom I’m talking about fosters a heightened sense of presence. To be “bored” is to be free of distraction.

#2 Writing

I’ve been reading Robert Caro’s Working, which is a book he published this year as a teaser to his latest Lyndon Johnson documentary, which he has been writing as a series over the past forty years.

It’s incredible to get into the brain of someone who is so deeply curious about something and has a hunch that the story is always deeper than what others accept. A lot of this book is in this New Yorker Article:

And now, when I asked Mr. Corcoran what had changed Lyndon Johnson’s status in October, 1940, he said, “Money, kid, money.” Then he added, “But you’re never going to be able to write about that.” I asked why not. “Because you’re never going to find anything in writing,” he said

He then spends months if not years finding the truth behind this question and others.

#3 Old People In America

Why do 70+ year olds seem to be running everything in the US? It’s great that people are living longer and healthier, but what how do you transition to the next generation in such a world? Perhaps it is hard in a culture that values youth and work ethic so highly.

By 2030, every living Boomer will be elderly (that is, age 65 or older), and by 2035, the Census Bureau projects, the elderly will outnumber minors for the first time in U.S. history.

Full article here.

#4 Skin In The Game

Alex Danco bemoaning how the tech world has taken a concept “skin in the game” and co-opted and misunderstood it. He sees people thinking that a tech employee making $200k with equity has skin in the game. That’s upside. Skin in the game would be if they lost all the salary if the company went belly-up.

#5 Meaning

This article highlights the shift in psychology research from seeing negative and positive emotions as opposites and instead seeing that a sense of “meaning” can come from either. A good challenge to the “you always need to be happy” mindset that I grew up with.

Bonus: Philosophy Stole My Ambition

As the title says:

Yes, philosophy stole my ambition…to make lots of money, compare myself to no end and never be content, no matter how much I achieved. But it redirected that ambition into doing meaningful work, enjoying life’s pleasures and living a life true to myself.

Response from last week:

Last weeks question was “What is an article, essay, book or quote that you keep coming back to?”

From Conan O'Brien via Armie:

‘This is going to sound grim, but eventually, all our graves go unattended...What are you talking about? None of it matters.” None of it matters? “No, that’s the secret. In 1940, people said Clark Gable is the face of the 20th Century. Who [expletive] thinks about Clark Gable? It doesn’t matter. You’ll be forgotten. I’ll be forgotten. We’ll all be forgotten.”’ (link)

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