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 20k+ 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

    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

    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.” … 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 … Read more

    A Pebble In My Shoe (Excerpt From The Pathless Path)

    This is an excerpt from Chapter 4 of my book, The Pathless Path. It’s been read by over 47k people worldwide. If you’re interested in reading more or purchasing the book, jump on over here. The ultimate way you and I get lucky is if you have some success early … Read more

    Leaning Into Ambition & Deeper Commitments: (Still) Enjoying The Journey | 2022 Annual Review

    2022 was a year of commitment. Commitment to a place (Austin), my next chapter (becoming a parent), and a deeper sense of connectedness toward my life and my work. It was a year in which I showed up fully as myself, unable to hide because I had spent 220 pages … Read more

    The “Wild Problem” Of A Life Well Lived: A Book Review of Russ Roberts’ Wild Problems

    Even if all you care about is having a good time during all-too-short time on this earth, you will struggle to anticipate what it is that will bring delight, pleasure, contentment. And most of us care about more than just having a good time. We would like to find purpose … Read more

    Selling My Time Too Cheap: How Full-Time Year-Round Work Blinds Us To The Joys of Life

    I sold my time at a bargain and did so for too long because I did not have any way to fully understand and value the benefits of not doing such a thing. This is the case for far too many people in today’s world and this state of affairs … Read more

    The Inspiration Deficit – Or Why So Many Young People Still Crave More Challenging Work

    I’ve talked to hundreds of people about their careers and aspirations over the past few years. The common theme: people are hungry. They want more interesting work, more ambitious environments, better leaders, and more chances to step up. These people are littered all over the world: India, Kenya, Malaysia, Pakistan, … Read more

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