This is a compilation of all of the links, essays and podcasts mentioned on the Boundless newsletter. If you’re interested in subscribing you can join here.

Favorites From The Year

  • From Nuclear Families to Forged Families (link)
  • Redefining what “prosperity” means for capitalism (link)
  • The Inner Ring by C.S. Lewis (link)
  • Solitude and Leadership – An Annual Favorite (link)
  • Reflections From a Token Black Friend (link)
  • Powerful Essay on Risk, Losing Friends & What Matters from Morgan Housel (link)
  • Venkatesh Rao’s Art of Gig had a very high signal to noise ratio while being consistent source of wisdom for navigating the solo path throughout this insane year
  • Stephen Cope’s Great Work of Your Life was probably my favorite book of the year

Work, Work, Work

The theme of the newsletter is the modern state of work and contemplating what this means for how we live our lives. Thus there are a lot of links in this category.

Gig Economy & The Future

  • Decision day for 1,300 Vanguard workers as their jobs head to India-based Infosys (link)
  • The profound changes caused by the Internet are only just beginning; aggregation theory is the means (link)
  • Re-Read: The Real Future of Work (Politico) (link)
  • New York Gig Workers Win Right to Unemployment Benefits (link)
  • Within the historical relationship between capital and labor, gig-workers would be considered scabs (link)

Indie Life, Solopreneurship & Hacking A Living

  • Politician quits politics to become a Jesuit Priest (link)
  • Gig Worker Identity: “For a free-agent, being an amateur, as opposed to a professional, is more important than being paid by the gig rather than with a salary” (link, Art of Gig)
  • We regret the things we don’t do.  Not the things we do.  (link)
  • Hunter S. Thompson’s Life Advice To A Friend Is Priceless (link)
  • Reflecting on our ‘radical sabbatical’ living on the Thai Island of Ko Lanta (link)
  • The negative effects of burnout spill over into every area of life (link)
  • The “Middle-Income Trap” and Careers (link)
  • How Can Indies Not Waste the Reboot? (link)
  • Being an Illegible Person: This older post from @vgr on Ribbon Farm is still very relevant to someone not following the default path of work (link)
  • What does it mean to be an independent researcher? (link)
  • Strategy for challenges you might expect in working online and self-employment (link)
  • The Creator Economy Needs a Middle Class (link)
  • Nat Eliason on “passive income” – “My interest in entrepreneurship originally started as an interest in passive income” (link)
  • A field-guide for independent strategy consultants (link)
  • Matt Trinetti Should I niche down my blog? (link)

Ponderings On The State of Work

  • Universal Basic Income and the Capitalist Production of Consciousness – Oshan Jarow (link)
  • How Work Became a Job (link)
  • Losing the Narrative: The Genre Fiction of the Professional Class (link)
  • Workism Essay from the Atlantic in 2019 (link)
  • “For a secular monk, the only knowable pursuits are human pursuits, the
    only genuine aims human aims.”  (link)
  • A reflection on “corporate man” from the NYT in 1984 (link)
  • Re-read: If work dominated your every moment would life be worth living? (link)
  • Morning Brew’s “Decade in Work” (link)
  • In Praise of Work: “The problem isn’t that we derive too much of our worth and value from work.  The problem is that our jobs are becoming increasingly abstracted from work.” (link)
  • Anne-Laure Le Cunff on “Are we too busy to enjoy life?” (link) and how to shift from “productivity porn to mindful productivity” (link)
  • Are Our Management Theories Outdated? (link)
  • The Case Against Work: Ignoring enormous human suffering and potential (link)
  • From Productivity to Psychedelics: Tim Ferriss Has Changed His Mind About Success (link)
  • “It’s Time to Think!” – Should we not focus on true leisure first before we fall again into the trap of materialism? (link)

Remote Work & New Ways of Working

  • I contributed to the Holloway Guide to Remote Work (link) – no affiliation
  • Citi to Offer Workers a 12-Week Sabbatical, Extra Vacation Days (link)
  • Startup and entrepreneur visas around the world (link)
  • Pieter Levels 5-part series on the future of work (link)
  • Facebook will now let some employees work from anywhere, but their paychecks could get cut (link)
  • From airlines to Starbucks, a massive part of our economy hinges on white-collar workers returning to the office (link)
  • Stripe’s One-Year Remote Reflection (link)

  Interesting Surveys, Demographics & Trends

  • The average age of Congress will now be a decade younger, thanks to the midterms (link)
  • “The Slacker” – What Americans should understand about Japan’s 1990s economic bust (link)
  • Millennials are less wealth that previous generations, even worse for those without a degree (link)
  • A different way of thinking about inflation: The Cost-of-Thriving Index (link)
  • Americans’ Perceptions of Success in the U.S. are disconnected from their own definitions of what matters (link)

Reflections On The Future

Future Of Education

  • Purdue is keeping tuition locked at $10,000 (link)
  • Adjuncts are taking over Academia (link)
  • Reflections on achievement from Singapore, 1974 – “The Great Paper Chase…Training ground for the adult rat race” (link)
  • Lazy Rivers, The Price of Education & Student Debt (link)
  • The Long Decline of American Higher Education Has Begun (link)
  • A looming shortage of students will upend the business model of higher education. To survive, colleges need to do more with less. (link)
  • Colleges Have a Silver Bullet to Win COVID Tuition Lawsuits, But Can They Afford to Use It? (link)
  • What Happens to All the Asian-American Overachievers When the Test-Taking Ends? (link)
  • Google announces 100,000 scholarships for online certificates in data analytics, project management and UX (link)
  • The Invented History of ‘The Factory Model of Education’ (link)
  • The financial returns to college are falling “Is College Still Worth It?” (link)
  • Disadvantages of an Elite Education: “Our best universities have forgotten that the reason they exist is to make minds, not careers” (link)

Economics & The Future

  • Vinay Gupta on Spiritual Colonialism: “We are all pretty clear something is profoundly wrong with the world, and maybe with humanity itself. But what is wrong, and what do we do about it?” (link)
  • Definite Optimism and its role in innovation in human nature (link)
  • The Social Capital Stall Behind America’s Gerontocracy (link)
  • Why Democratic leaders still misunderstand the politics of social class (link)
  • Russ Roberts: The Economist as Scapegoat (link)
  • Ray Dalio: Our Biggest Economic, Social, and Political Issue (link)
  • The $1 Trillion Question: New Approaches to Regulating Stock Buybacks (link)
  • Critiques of meritocracy are on everyone’s lips right now. Why? (link)
  • Is Productivity Growth Becoming Irrelevant? (link)
  • The Medieval Future of Management (link)
  • Professor David Autor’s latest research shows how economic polarization stems from urban job loss (link)
  • Tech Companies Want You to Believe America Has a Skills Gap (link)

Pandemic, Crisis & Response

  • Covid-19 is like a rehab intervention that breaks the addictive hold of normality (link)
  • System dynamics and our response to Covid – Bonitta Roy (link)
  • How the coronavirus is creating a political opportunity to overturn one of the worst practices of the kleptocracy era (link)
  • COVID-19: A War Broke Out In Heaven (link)
  • The Pandemic Isn’t a Black Swan but a Portent of a More Fragile Global System (link)
  • The Nature of Work after the COVID Crisis:  Too Few Low-Wage Jobs (link)
  • Liminality?…Well, there’s a free sample! (link)
  • A Plague Is an Apocalypse. But It Can Bring a New World. The meaning of this one is in our hands. (link)
  • Martin Gurri: The Prophet of the Revolt (link)

Other Interesting Things, Etc.

  • Agnes Callard has a great essay on how we glorify geniuses and how it relates to The Queen’s Gambit (link)
  • Kevin Kelly’s 68 Bits of Unsolicited Advice (link)
  • Speaking is for motivation, writing is for thinking (link)
  • The cynics guide to reading business books (link)
  • What is Transcendence? The True Top of Maslow’s Hierarchy of Needs (link)
  • Calling Bullshit Course: Data Reasoning in a Digital World (link)
  • Robert Hogan on the “Dark Side of Charisma” (link) and related: Can we tell good leaders from bad? (link)
  • Thinking For Yourself & Curiosity, Paul Graham (link)
  • Positive and Negative Liberty (link)
  • Kevin Love, NBA Player: “To Anybody Going Through It, Being depressed is exhausting” (link)
  • Psilocybin therapy 4 times more effective than antidepressants, study finds (link)
  • Society has a cultural bias towards extroverts (link)
  • The case for one billion Americans (link)
  • Rather than attempting to persuade us (via our rational, analytical minds), ads prey on our emotions. Read Ads “Don’t Work That Way” (link)
  • The Blue of Distance, an essay from Rebecca Solnit (link)

Memorable Podcasts From This Year

  • The Conversational Nature of Reality, David Whyte (link)
  • Peter Attia & Jason Fried: Work-life balance, avoiding burnout, defining success, company culture, and more (link)
  • Seth Godin on Argument against using remote work to copy in-person working habits, especially meetings (link)
  • Daniel Kahneman: Putting Your Intuition on Ice (link)
  • Mall Mullenweg on Sam Harris: The Remote Playbook (link)
  • Shane Parish, The Knowledge Project: Roger Martin (link), Chamath (link) & Patrick Collison (link)
  • Multiple Econtalk Episodes: Emily Oster, Zena Hitz, Steven Levitt
  • Tyler Cowen and Audrey Tang (link)
  • Agnes Callard on Big Ideas with Erik Torenberg (link)
  • Derek Sivers, Entrepreneurialism as Spiritual Practice (link)
  • Eric Weinstein’s Interview with his 14 year old son (link)
  • Ben Hunnicutt: Leisure: the (Forgotten) Basis of American Progress (link)
  • John Vervaeke: The Cognitive Science of Capitalist Realism (link)
  • Malcolm Gladwell On Democratic Lotteries (link)
  • Tim Ferriss’ Journey After Childhood Abuse with Debbie Millman (link)
  • ZigZag podcast with Khe He on his “male identity crisis” (link)
  • Not Overthinking: Inner Rings – The Desire to Fit In (link)

Boundless Creations

A listing of all the essays and podcasts I published this year.

My Essays

  • Hustle Traps: Ten Guaranteed Paths To Burnout For The Self-Employed Creator (link)
  • Recovering from “Lifestyle Creep”: How I cut my cost of living by 75% (link)
  • Boomer Blockade: The boomers reached power at younger ages and then have stayed in power (link)
  • Why Did People Stop Caring About Developing a Meaningful Philosophy of Life in the 1970s? (link)
  • The dark side of consulting: A belief that the scale of “impact” matters more than what you are doing (link)
  • The Future Of The Prestige Economy: Who Gets Status? (link)
  • Check out Hamsternomics: Printing Money, The Economy & Work Beliefs , a collaboration of Paul Millerd and Ryan Borker, who both have experience jumping on and off the hamster wheel at multiple points in their lives
  • Chaos Theory & Building Resilient Organizations (link)
  • Going Remote? Here are five tips from companies who are already fully remote (link)
  • Virtual Spaces: How To Teach & Engage With Virtual Communities (link)
  • The best advice on working remotely your boss doesn’t want you to see (link)
  • Matt Mullenweg’s & Automattic’s Five Levels Of Remote Work (link)
  • The ultimate guide to becoming a digital nomad or remote worker (link)
  • The Second Chapter of Success: Figuring Out What Matters (link)
  • Updated: A gift economy is not about the money, it is about unlocking generosity & gratitude (link)
  • Work In Tech, Finance or Go Solo or be without a career path: The Reality Of An Economic Model Without Enough Jobs (link)

Reimagine Work Episodes

  • Diania Merriam on Imagining The New American Dream (link)
  • Group reflection with Andrew Taggart on Total Work and our present crisis
  • Steph Smith on a 21st Century Career (link)
  • Oshan Jarow – Life Beyond Work (link)
  • Laurel Farrer on How to work remotely, well (link)
  • Will Bachman on independent consulting (link)
  • Amy McMillen on carving her own path and writing a book (link)
  • I Interviewed my wife about her own journey (link)
  • Packy McCormick on writing a kick-ass newsletter (link)
  • Uri Bram on running The Browser remotely & #goodreads (link

My Indie Consulting Lessons (A Small Experiment)

I’m still not sure what I’m going to do with this but this is an ongoing holding ground for short videos and lessons I’m compiling for navigating life as an indie consultant.

  • Shifting your mindset: connecting with other freelancers, grappling with your fear & defining what “success” means (link)
  • Naming your practice (link)
  • How to identify as a freelance consultant without trapping yourself in that identity (link)
  • How to think about your service offerings & positioning (link)
  • Four ways of finding those initial projects (link)
  • How to work with consulting talent platforms (link)

Newsletters, Creators & Spaces That Inspire Me & I Keep Coming Back To

  • What Really Matters, Russell Max Simon (link)
  • Not Boring, Packy McCormick (link)
  • Mythology Studio, Martha Balaile (link)
  • Dig Well, Amy McMillen (link)
  • The Diff, Byrne Hobart (link)
  • Khe He & Rad Reads (link)
  • Maria Popova’s Brain Pickings (link)
  • Anne-Laure’s Ness Labs (link)
  • Venkatesh Roa’s Art of Gig (link) and Breaking Smart (link)
  • Curious Humans, Jonny Miller (link)
  • Two Truths and a Take, Alex Danco (link)
  • Pam Hobart’s philosophical advice for smart people (link)
  • Curious Lion, Andrew Barry (link)
  • Robbie Crabtree’s Three Things Thursday (link)
  • Noah Smith’s Noahpinion (link)
  • Wellness Wisdom, Patricia Mou (link)
  • David Perell’s Newsletters (link)
  • Nat Eliason’s Monday Medley (link)
  • The Fire Jar (link)
  • Deliberate on the Internet, Artur Piszek (link)
  • Musing Mind (essays, podcast, & book notes), Oshan Jarow (link)



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