New! 1st Cohort of Small Group Coaching - December 2021 to January 2021

I'm kickstarting small experimental groups of five people organized around various life stages and interest levels.

All cohorts will receive a complimentary hardcover or paperback version of my book, The Pathless Path, to be published in December 2021

Read more below 👇

I surveyed people on the challenges people are facing with their relationship to work. Common themes:

  • Knowing whether or not to take a chance on self-employment
  • Deciding whether or not to make a career change
  • Figuring out what they really want to do with life
  • Prioritizing non-work needs and well-being over job
  • Dealing with burnout and mismatch of skills & work
  • Developing more of a capacity for handling uncertainty
  • Experimenting with life
  • Finding the support & encouragement of others asking similar questions

From responses to my survey, people are at various stages:

7% - Students trying to plan for the future

21% - Early career professionals trying to find their way

25% - Mid-career professionals searching for the right path

39% - Mid to late-career professionalswho has succeeded on paper but something is "off"

7% - Other

Hey, I'm Paul...

I'm obsessed with making sense of how work fits into our lives, why people are struggling with their relationship with work and how to make it better.

Over the past 6-7 years, I've coached people, read dozens of books, written hundreds of articles and essays, and had hundreds of "curiosity conversations" with people from around the world about how they are improving their relationship with work.
The stories are often the same. Something is "off" with how work fits in their life and they don't know what it is.  I experienced a similar thing in 2015 and over the last several years, I've done countless experiments with the intention of improving my relationship with work.  I want to share what I've learned with as many peoiple as possible.    
You can read a more detailed story below

Format & Schedule

Given that this is the first time I'm running group coaching sessions, the format and schedule may change throughout the program.  If you prefer things to be perfectly executed, I'd suggest waiting for the 2nd round

# Of Calls: Eight. Three Calls Before Christmas and Five After New Year.  Calls will occur during the weeks of December: 6th, 13th, 20th and then during the weeks of January: 3rd, 10th, 17th, 24th, 31st

Group Size: No more than five people per group

Facilitation style: I will have topics and exercises for each session that shift based on the previous week's discussion but I will also leave a lot of space for emergent conversation & connection

Secure Your Spot In A Cohort For $100 Deposit (remaining billed later)

The rest will be billed in two payments after the start of the coaching program. 

P.S. If you are facing financial difficulties, please email me and I will work with you to find the right price using gift economy approaches


Playing The Long-Game: Early Career (~0-8 Years Experience)

When: Mondays at 3pm - 4:30pm EST


This cohort will focus on the following topics: values, interests, career changes, applying for jobs, personal branding, creative pursuits, building wealth, navigating organizational politics, building confidence, succeeding in the workplace

While this cohort will be geared towards early-career types it will also be a good fit for anyone at the start of a new journey

Pay $100 Deposit Now - $800 Total


Existential Opening: Mid-to-Late Career (~8+ Years Experience)

When: Tuesdays at 12 noon - 1:30pm EST


This cohort will focus on: money, insecurity, freedom, career changes, expectations & responsibilities, creative pursuits, sabbaticals, relationship with work & finding space in life, prioritizing needs & developing your own strategy for work & life

P.S. I made this earlier in the morning due to people having kids. Please let me know if you prefer another time.

$100 Deposit - $800 Total

3 (cancelled)

Mixed Cohort (Not organized around life stage or experience)

Time: Tuesdays, 3pm -4:30pm EST

Some people had an interest in a more open group, hoping to meet people from different life stages and career stages. This cohort will focus on all of the topics in the above two groups but also with a special emphasis on "finding the others" and building community


Self-Organizing Mixed Cohort (Very Minor Guidance From Paul)

Time: TBD, agreed upon by group

Based on feedback from people, I am experimenting with a self-organizing discussion group of people who might only want to meet other people like them or don't have the money to spend on coaching right now. Not sure how this will go but will be a fun first attempt! I will join the first 15 minutes of the first call and be available to an appointed "leader" via email.

Sign Up - $25

A Little More To My Story...

I spent about ten years on a very impressive path, working at top consulting firms and going to top-ranked business schools. However, underneath, I never really felt like any of it made sense. I never lasted more than two years in a single place and was convinced that my dream job was always the next one.

Eventually, I quit my job and became self-employed.  I thought I'd become a freelancer but when I embraced the increased freedom that freelancing offered, I was pulled towards a deeper journey.  Eventually, in 2018, I decided to move abroad without a plan.

I arrived in Taiwan and ended up meeting my wife, Angie, in the first month.  That led me to stay in Asia and travel the world with her for the next three years.  At the time it also meant that I struggled to make freelancing work.  I had to figure ways to make money outside of freelancing (remote wasn't cool yet) but that still gave me the life I wanted to create.  This forced me to grapple with all sorts of insecurities, ones I wouldn't wish upon anyone.

I decided that I would just try to work on things I enjoyed and see where it took me. In writing, experimenting online, helping other people navigate these hard transitions, and connecting with others, I started to feel more confident that the path I found was one I wanted to keep going.  I decided that I would work on things I enjoyed and see where it took me. In writing, experimenting online, helping other people navigate these hard transitions, and connecting with others, I started to feel more confident that the path I found was one I wanted to keep going. 

I'm happy to report that I'm still firmly on this path almost four years later.  Over time, I've come to call my approach the "Pathless Path" and have written extensively about this journey (including a forthcoming book). I'm not interested in helping people escape work, retire early, or swap an intense corporate identity for a startup founder. I'm much more interested in helping people become more confident in embracing uncertainty, emergent paths, and learning how to explore in a world mediated by technology, memes, and the internet.

Starting in April of 2020, when many people were either out of work or forced to work remotely my following and the number of people that reached out to me exploded. It was a bit shocking at first. For a few years, I had been exploring these topics alone, feeling like a crazy person. Suddenly, I had people reaching out with the same questions.

It seems that the pandemic served as an existential opening for people to look at their work with new eyes. This has motivated me to keep going, deciding to write a book this year and continue writing and exploring these topics.

Are you ready to join me in your own exploration of your relationship with work?