Media

How to answer “what do you do?” on a pathless path

I was at a gathering on Thursday and someone asked, “What do you do?” Given that I was in Austin, I thought I could share the real story: “writing online, podcasting, internet things, you know.” It was a creator’s hangout after all. “What do you write about?” he followed up. Ah nice, he’s interested. “I ... Read more

The Case For Quiet Quitting (and the dangers of slacking at work)

Vox published an essay in 2023 about the people who do little to no work at their jobs. The article, “How some people get away with doing nothing at work,” seems to fit into the coordinated “return to office” campaign across the mainstream news. The title seemed a bit weird for a newsletter focused on ... Read more

Escape Shouldandia!

As someone that enjoys writing and does so consistently, a lot of people tell me about their own relationship with writing. Many people wish they wrote more. They tell me some form of, “I should write more,” or “I need to write more.” They live in a world I call Shouldlandia. Inhabitants of Shouldlandia talk about what ... Read more

Solopreneur & Creator Week-In-The-Life (as a parent)

For more than seven years since 2017, no week has looked the same. Most days don’t look the same either. But generally, the mix of activities and how I feel about them does feel somewhat the same. This is probably what makes me feel more “stable” on this path than my last one, one where ... Read more

Seven Reflections on Seven Years Of Self-Employment

#1 It’s still far more rewarding than I ever could have expected For years I had a low-grade dissatisfaction with my work. At the simplest level, I just didn’t like having to go to work every day and I hated having to do tasks that seemed pointless.  It now seems obvious I should have embarked ... Read more

How Do You Leave Money On The Table?

A few people sent me Ali Abdaal’s most recent video and I thought it was one of the most interesting I’ve ever seen from someone in his position, with endless opportunities at his fingertips. It’s about his internal struggle between competing interests: money or life enjoyment. Spoiler: he’s actively embracing an approach with his business and life ... Read more

New Additions, New Heights & Open Questions | 2023 Annual Review

2023 was the year I became a dad and for the first time, pressure—tested this life that Angie and I have been building over the last several years. In terms of enabling me to be present and enjoy the beginning of the “magic years” of my daughter, it was a complete and unambiguous success. Financially, ... Read more

How To Take A Sabbatical: Stories From Five People Who Took Them

This was a conversation from July 2023 that was a conversation between Michelle Varghoose, Paul Millerd, Tobi Ogunnaike, Cécile M, and Matt Yao – all people with direct experiences taking sabbaticals. Themes Sabbatical Experiences and Motivations: Mindset Shifts: Financial Considerations: Travel and Environment: Transitioning Back to Work: Advice and Encouragement: Relevant Links Cecile ​Michelle ​Matt ... Read more

Die With Zero: Why Too Many Save Too Much for Too Late In Their Lives (Book Review)

If The Pathless Path is about deprogramming yourself from default work beliefs, Die with Zero by Bill Perkins is about deprogramming yourself from default money beliefs. Die With Zero is an entertaining, persuasive, and useful book that argues that far too many people, “save tend to save too much for far too late in their lives.” This is a hard topic ... Read more

The Way of Mediocre Man

Mediocre man flows through life. It is his birthright. He is not great man aiming at great results but merely trying to do enough of the right things over a long period of time such that it might lead somewhere interesting.  Mediocre man is one who learns to trust the journey because he is fully ... Read more

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