Book Update + Links | #141

Sharing Progress On My Book

May 15th, 2021: Greetings from Taipei. Covid broke through this week and Taiwan entered its first lockdown of the pandemic. The country has ramped up testing, tracking, and tracing and it will be interesting to see if they can get back to zero. It looks like vaccines are on the way in June or July so it may be a weird couple of months.

My Chinese class, in its final week, is moving online. I’ve had so much fun taking this class and devoting this much time to learning. I’ll try to write something more comprehensive but it’s been thrilling to go into a new section each week cold and then come out five days later with new words, language and understanding. This is why I’ve tried to live and work the way I do. I wouldn’t give up this experience for a job paying $500k a year.

This week is a shorter issue, including a preview of the book and some links worth checking out.

#1 Book Update

This week I’m I’m sharing a short preview of my book “Pathless Path.”

I launched this project at the beginning of 2021, predicted a quick finish and then soon met reality. I faced some early writing setbacks which were helped by the genius coaching of Sasha Chapin and then realize that my version of “writing a book” was a bit more complex than writing weekly newsletter posts or blog posts about things I’m excited about.

I’ve also been a bit slowed by full-time Chinese class (taking about 30 hours a week) and some ongoing health issues. I’m having a ton of fun with this and definitely want to be happy with the final product. My estimated finish date is early fall 2021. If you can’t wait and want a refund, please let me know! (Remember, all paid subscribers to this newsletter will receive a free copy and a copy for a friend.)


  • Word Count: ~29,000 Words

  • “Chapters”: Thirty seven


  • Consider editing options

  • Get a graphic designer to help me do a cover

  • Continue to write (most days) and shift to writing as priority #1 once my chinese class ends

Here are drafts of a couple early chapters. Still have some editing to do but let me know what you think!

#1 The Pathless Path

As I flipped to page 164, I stumbled upon what felt like a secret message meant for me.  It was the idea of a “pathless path” and it hasn’t left my mind since.  The passage read:

“It can be a release then, to think, that when we first come across the idea of a pathless path, by definition, we are not meant to understand what it means."

The passage came from a book a friend, Jonny, handed me.  We had just met a few days prior at a conference and had connected over our shared confusion of being self-employed in a world centered around the idea that adults should be employed.  He walked up to me and said, I have something for you.  He reached into his bookbag and handed me something. “This is for you.”  It was his copy of The Three Marriages by David Whyte.

Whyte words would find me exactly when I needed them.  Whyte, who himself left a successful life path as a naturalist behind to become a Poet at the age of 31, was able to put words to something that I had not been able to articulate.

When I read Whyte’s passage I experienced it as a deep release of tension.  For the first time, I had a way to make sense of what had happened with my life.  I was a year into a journey of self-employment and this journey had taken me in directions I couldn’t have predicted.  I was also at a point where the possibilities of where it might lead me were impossible to know.

The “pathless path.”  A journey without any instructions.  A general direction without any goals.  A concept without meaning but captured everything. 

Releasing myself to this idea has enabled me to commit to this journey for the last four years and stay open to things that I might not have experienced if I needed a better map.

Yet, this would have seemed crazy only a few years earlier.

Back when I was honing my craft as a world-class hoop jumper.

#2 World Class Hoop Jumper

The term, “hoop-jumper,” was coined by William Deresiewicz.  It described the behavior of his students at Yale, who seemed more concerned about getting A’s and adding bullets to their resume than using their time at one of the best Universities to follow their curiosity.

Students focused almost all their attention on things that would help them towards a clear end such as an internship, job, or admittance into grad school.  Despite not growing up in elite private schools, I still ended up with the same mindset as Deresiewicz’s students at Yale.

Yet unlike many elite students, my drift towards hoop-jumping did not arise from my parent’s expectations. Quite the opposite, my childhood was remarkable for its lack of pressure and my love of school.  I loved the approval that earning good grades got me as much as the next person, but I never felt like anyone’s love or respect was dependent on it.

My attitude towards school changed when I started college.  For the first time I was exposed to other high achievers.  The kind that went to elite high schools and racked up 50 college credits before starting college, and others that had perfect SAT scores.

These people became my friends, and I started to want what they wanted.  They embodied a success ethic that focused on maximizing achievements in the present for better options in the future.  This was new to me.  I was all about doing well in school but I never had ambitious aims.  I had only applied to one University and but after meeting these people I started to wonder if I should have applied to “better” schools.

My way to deal with these emerging desires was to learn how to hack the system.  I remember sitting down Freshman year of college and optimizing my schedule over the next four years based on who the easiest professors were.  I was in constant search of the easiest path to get the highest grades.  In my second year I figured out how to petition the school to take more than the maximum 18 credits so that I could add a “guaranteed A” to my course load.  Throughout college I was the person people came to when they needed to find jobs, fix their resume, or prepare for an interview.

This was my game.  I couldn’t compete on all-nighters, but I had a knack for figuring out what the gatekeepers wanted. Unlocking these hidden codes made me feel smart and powerful.  I felt as if I could do anything.  With every internship I landed, Dean’s list recognition, or group acceptance, the intoxicating feeling achievement ran through my veins.  I was slowly earning my black belt in hoop-jumping.  If there was a hoop, I knew how big it was, the exact shade of color, how it felt, and if there were any secret ways to jump through it.

Buy The Book!

Completed Chapters Of The Book


World-Class Hoop-Jumper

  • #1 The Pathless Path

  • #2 World Class Hoop Jumper

  • #3 The Inner Ring

  • #4 Find a conversation bigger than yourself

Welcome To My Conversation

  • #1 Going off script

  • #2 I write this book for the weirdos

Crumbling Identity

  • #1 A profound moment

  • #2 Business school is not a great place for figuring out what to do with your life

  • #3 Health Crisis

  • #4 Who am I?

Pebble In My Shoe

  • #1 Leaps Only Make Sense Upon Reflection

  • #2 A daily reminder

  • #3 A Fool’s Journey

  • #4 An Empty Suit

Slow Drift Towards Something Else

  • #1 Money On My Mind

  • #2 Values-First

  • #3 The Final Step

  • #4 Stuck In-Between Worlds

  • #5 Is it…burnout?

Taking The Leap

  • #1 Prototype Your Leap

  • #2 You Can Always Go Back / Fear Setting

  • #3 Wonder tips the scales

  • #4: Who Do You Aspire To Be?

  • #5 Find The Others

Death of My Worker

  • #1 Accidental Meaning Through Work

  • #2 Overcoming Traditionalism & Original Work Beliefs

  • #3 The Modern Meaningful Work Ethic

  • #4 If work dominated your every moment would life be worth living?

Embracing The Pathless Path

  • #1 The Work Of Your Life

  • #2 Freelance Consultant

  • #3 Preemptive defensiveness

  • #4 The Life-Changing Magic Of Non-Doing

  • #5 The Magic Of A Break

  • #6 There is no “payoff” on the pathless path

  • #7 Have A Little Faith

Redefining Success

  • #1 Unreasonable Idea of Success

  • …..

Anything jump out at you? Things I’m missing?

Buy The Book!

#2 Defining What You Are Not

Too many companies focus on proactive decisions. What to add, increase, grow, or pursue. More companies would be better served by defining what they won’t do.

This e-mail was from the CEO of Shopify. It may not please everyone but its great to see companies more clearly stand for something, rather than nothing or everything. We went through 100 career pages and it was clear that almost all of them stood for nothing.

Here is the Shopify CEO:

Shopify, like any other for-profit company, is not a family. The very idea is preposterous. You are born into a family. You never choose it, and they can't un-family you. It should be massively obvious that Shopify is not a family but I see people, even leaders, casually use terms like "Shopifam" which will cause the members of our teams (especially junior ones that have never worked anywhere else) to get the wrong impression. The dangers of "family thinking" are that it becomes incredibly hard to let poor performers go. Shopify is a team, not a family.

We literally only want the best people in the world. The reason why you joined Shopify is because - I hope - all the other people you met during the interview process were really smart, caring, and committed. This is magic and it creates a virtuous magnetism on talented people because very few people in the world have this in themselves. People who don't should not be part of this team. This magic and magnetism is a product of tight performance management that I expect all of us to get back to.

Shopify is also not the government. We cannot solve every societal problem here. We are part of an ecosystem, of economies, of culture, and of actual countries. We also can't take care of all your needs. We will try our best to take care of the ones that ensure you can support our mission. Shopify's worldview is well documented - we believe in liberal values and equality of opportunity. Sometimes we see opportunities to help nudge these causes forward. We do this because this directly helps our business and our merchants and not because of some moralistic overreach.

#3 Some Assorted Things Worth Sharing

$738,000 for college in 18 years?!

If someone can’t figure out how to do universities for less than three quarters of a million dollars in 15 years the US will definitely have bigger problems.

🦟“Miasmas” Made Doctors Hesitant To Tell People Viruses Are Airborne

This was the best article I’ve read on Covid. 100 years ago people believed in “miasmas” or smelly odors as the source of disease. This was incorrect but because of this doctors were extremely hesitant to promote the idea that “aerosols” or small invisible droplets were the source of transmission for viruses. They thought that this would discourage people from washing their hands and surfaces. This was a costly belief:

He was also concerned that belief in airborne transmission, which he associated with miasma theories, would make people feel helpless and drop their guard against contact transmission. This was a mistake that would haunt infection control for the next century and more.

🍜 Why Restaurant Workers Say They’re Not Returning to Work - Eater

We want to work, but we also want to be treated like human beings. We haven’t been for way too long.” Gaby del Valle is a freelance reporter who primarily covers immigration and labor.

🏫Interview with ASU President Michael Crowe

During my career in academia, I have seen too often that our educational systems fail learners by clinging to outmoded philosophies and structures, forsaking capable learners to sustain “exclusive” reputations, and shunning educational technology as a subpar learning fad.

🤪Unconventional Business Practices by Rob Hardy

Loved this essay from Rob Hardy. Seems like he’s sick of hustle traps:

There are approximately eleventy bazillion websites teaching marketing online.

And there are just as many twitter accounts, courses, memberships, and podcasts in the “creators teaching other creators how to create good” space.

I don’t want Ungated to resemble any of it.

I’d rather **get a real job** (even the thought of it makes me shudder) than build some cookie cutter marketing website that mindlessly repeats the same empty fortune cookie slogans and manipulative advice. Fuck that noise.

Instead, I want Ungated to feel substantially different. I want it to be an oasis in the middle of a hostile, sketchy ecosystem. A place where intermediate and advanced creators can come to find the others, grow in meaningful ways, and have their values not only reinforced, but celebrated.

I don’t have any grand allusions of scale. I’m not trying to 10x anything. I don’t want to “dominate” the market. And I’m certainly not building this thing just to sell it off to the highest bidder.

I’m trying to build a delightful corner of the internet that generously serves other creators who see the world as I do. Creators who feel repelled by traditional business and marketing advice. Creators who want to do work that matters for an audience that actually gives a damn. Creators who want to make 1,000 True Fans their reality.

👍 That’s It This Week. Thanks For Following. Here’s How You Can Support Boundless

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