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 25k+ people
My book, The Pathless Path, has sold 65k+ 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
The list of reasons we are scared to quit our jobs
There are many forces us keeping us in a state of misery that are challenging to unpack. Here are some ideas from people I’ve worked with: Identity: We define ourselves as workers, as someone that “doesn’t quit,” as someone that works hard Relationships: We are scared that people will not … Read more
Bullshit Jobs Virtual Book Club Discussion (Book By David Graeber)
David Graeber’s “Bullshit Jobs” raises provocative questions about the state of our economy. He found in his research that a third of the workforce agreed that their jobs were “bullshit jobs” under the following definition: A bullshit job is a form of paid employment that is so completely pointless, unnecessary, or pernicious … Read more
Burnout wasn’t supposed to happen to me…at least not yet
I’ve left jobs before but this time felt different. I felt broken. Deflated. Unable to even think past the next few days. When it hit me, I had been giving career advice and coaching to friends and clients for over 10 years. My superpower is helping people understand what they … Read more
The Future Of Work Is Five Different Conversations
The future of work can mean anything. I’ve had many conversations and discussions around the idea of “future of work” where people talk past each other, often focused on different fundamental issues. In an effort to make sense of this complexity and create some common ground for the many people … Read more
Solitude & Learning New Things
In most domains, there are fundamental principles or a mindset shift needed to open the door to deeper learning. For example, in swimming, your body’s natural urge while your head is underwater is to hold your breath. Once you learn to exhale while underwater, you have the figurative and literal … Read more
The Anti-Hustle Guide To Starting A Podcast
The simple method does not get written about – at least not clearly. As many people have been surprised by how little work I put into starting a podcast, I thought I might try to break down some of the steps and offer the simple process for launching a podcast. … Read more
Wandering around Boston with wonder & awe
Earlier this week, I interviewed Jacqueline Jensen who wrote a book titled, “Travel isn’t the Answer” arguing that we should embrace a special kind of awe, wonder, and open-mindedness for our day-to-day lives that we usually reserve for Travel. As I’ve been exploring Boston via bike for the first time … Read more
How the fear setting exercise can help you unlock the courage to take bold action
Bonnie Ware spent her life taking care of the elderly and spent time with many people in the final moments of her life. Her work would result in one of the most read blog posts on the internet, “Five Regrets of The Dying.” The most common regret that people grappled … Read more
How to write and share in public and not come off as a complete fool
The biggest mistake people make writing and sharing in public is taking a checklist or formula approach. If you browse LinkedIn for more than three minutes, you can find a good example rather quickly like this IBM post: Typically the company had a meeting that probably went like this: … Read more
Beanie Babies, Silliness & Things That Don’t Make Sense
My first memory of greed was waiting in the line at a local crafts store called The Hoot. My blood was pumping as I looked at the clock and counted down the minutes until 9am when the store would open and a group of 10 of us, an odd collection … Read more