I’m passionate about helping people imagine new stories for work & life

I’ve been wandering a “pathless path” for seven years, and am deeply curious about our modern relationship with work. I write, share ideas, have conversations, and experiment with my own life.

I write a weekly newsletter that goes out to 23k+ people

    My book, The Pathless Path, has sold 50k+ copies

    “I just finished the last 100+ pages this morning and I can confidently say that this is one of the best non-fiction books I’ve read in my life.”

    Justin Welsh, Solopreneur & Creator

    I hadn’t prioritized reading it since I assumed I’d know what it was about from his newsletter, but no… this is polished and fresh content. It really should be a mainstream airport bestseller type book, not niche subculture blogger self-published book.

    Venkatesh Rao, Writer at Ribbonfarm

    Recent Writing

    Rethinking Wealth: Four Profound Insights from “Just Keep Buying”

    Personal finance advice often feels like a maze of contradictions. Save everything. Live a little. Invest aggressively. Play it safe. After years of grappling with these mixed messages, I found clarity in Nick Maggiulli’s “Just Keep Buying.” Through its data-driven insights, I discovered a more nuanced – and ultimately more … Read more

    Question People and Answer People

    Someone said to me once, “there are things people, people people, and ideas people.” I instantly knew I was an ideas person. I love discovering new ideas, going down strange rabbit holes, trying to come up with better ideas for my life, talking about ideas, and finding others who are … Read more

    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. … 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 … 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 … 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 … 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 … 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 … 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 … 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: … Read more

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