1-on-1 coaching
You've “made it” but don't know how to handle what's next
If you're looking for help with a sabbatical, quitting your job, reinventing your career, or finding more enjoyment in life after you've reached financial independence, this page is for you.
We have never had more possibility for our lives
More people than ever have the resources, or another path to follow, to opt out of the default life: one of constant and continuous work throughout adulthood from the age of 22-65.
Data: New York Fed, Survey of Consumer Expectations. Charted by Axios.
I blew up my life at 32 and have been hacking a living doing work I enjoy since 2017. Along the way I've written extensively, talked to hundreds of people, and worked with many people who are buying back freedom to spend their time in interesting ways.
Doing this in today's world means handling what others think, being intentional with default norms and expectations, and learning to keep reflecting on and imagining new possibilities for your life.
People have asked me to coach them for years and I always said no. With two young kids, my life is more scheduled now, and I'm ready to work with one or two people at a time.
Most of us don't think much about work
Work is this thing that takes up a lot of our energy and time, yet most of us don't want to think that much about it. We have default expectations about what we're supposed to be doing for work and how it's supposed to feel. If you are like me, you might have grown up with a story that work is a struggle, a sacrifice, or a necessary evil.
The opportunity here is broadening our conception of work beyond what merely gets us paid and seeing work as a vital part of a life well lived. It's also about writing new stories and scripts for this chapter of our lives, ones that open up even more possibility than before.
Why me?
- I am quite happy with my life, and spend my days in a mix of family, work, conversations, and leisure
- I “retired” from work I don't want to be doing in 2017 and have mostly succeeded in spending my time working on the things I care about, including shipping two books and spending tons of time wandering, with my family, and with myself
- Despite working at elite consulting firms and attending a top business school, it doesn't really bother me that almost all my peers have surpassed me in business success
- I have worked through many of my money issues and rarely make decisions from a scarcity mindset
You might be a good fit if you feel like you are one of these archetypes
- You've made enough to be “financially free” or achieved your biggest career goals and are completely confused about what's next
- You have this feeling like it's time for a break, pivot, or even an adventure, but find yourself filling your time with endless work or productivity
- You keep telling yourself that the next bonus or the next year you'll finally make a shift but you never do
- You keep grinding, which takes more and more energy. You've lost that early career exuberance and don't know how to find it again
- You are excellent at making money but feel like you are not actually moving toward a life where you can thrive
- You may be struggling now but you are generally open to optimism and moving in a positive direction in your life
Themes I write about and explore in conversation
- 01
Finding your “enough”
Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.
The Pathless Path - 02
Who are you without work?
Many self-employed people are surprised to find that once they no longer have to work for anyone else, they still have a manager in their head.
The Pathless Path - 03
Stepping off the default path
The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform.
The Pathless Path - 04
The trap of prestige
Though hard to define, prestige can be thought of as the attention you get when you do things that others see as impressive.
The Pathless Path - 05
Taking a real break
Almost everyone who’s taken an intentional break from work has told me they wish they took one sooner. It might be the only “hack” I fully endorse.
Good Work - 06
Making friends with fear and uncertainty
If you are going to feel uncertain and afraid anyway, why not go after your true ambitions?
Good Work - 07
Reawakening your inner ambition
It’s shocking how long it took me to reawaken my inner ambition, drive, and creative spirit after quitting my job.
Good Work - 08
Redefining success
People are reluctant to flip the page to the second chapter of success because it requires rejecting paths that are not only more accepted but also promise money, respect, and admiration.
The Pathless Path - 09
Coming alive over getting ahead
I was able to shift away from a life built on getting ahead and toward one focused on coming alive.
The Pathless Path - 10
Finding your good work
Once you discover your good work, take it seriously and protect it, as it can be one of the most powerful ways to show up in the world, contribute, and feel useful.
Good Work
Apply to work with Paul
I only work with select clients, max 1–2 people at a time, on a minimum 3-month engagement.
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