The Way of Work: Series Index
Here is a complete collection all the series I've written (and new ones coming soon)...
The Way of Work is a series-based newsletter that explores where we fit in the world of work. Check out one of our series to get started…
Series 05: Existential Explorer (in process!)
Series 05: Existential Explorer
Ideas from the Edge of the Map
After nearly 2 years outside the working world, I’ve seen some things. Felt some weird things. And that new lens on living is the heart of my next series.
This series is about the uncharted frontier of meaning, exploring the edges of purpose, identity, and who we become when we try to matter.
From Businessman to ‘Existential Explorer’ – An attempt to explain what I’m doing
2 years out of work, 1 year of writing, and a new lens on livingThe Open Frontier of Meaning
The collapse of old worlds, the failure of quick fixes, and the call to exploreWhat You Need is a Midlife Crisis
Why the midlife crisis is an opportunity not to be wastedTotal Addressable Meaning
What if we built a life around what actually matters? (and noticed the strange world we already live in)just kidding… work actually is the meaning of life!
A performance review in purgatory (satire)Make something that doesn’t matter
Why you need a totally pointless passion projectHow to be successful and miserable
When you’re good at the wrong thing
Series 04: Not Obvious
Why work advice fails us. And what to do about it.
The world wants you to believe the answers are obvious. That success follows a playbook. If you just follow the right framework, guru, mindset — you’ll figure it out. But it never works that way. Instead, we keep running in circles, chasing certainty where none exists.
The real way of work is anything but simple. The only forward is through the mess.
Intro: Why Work Advice Fails Us
How neatly packaged advice keeps us lost and frustratedBurnout, Balance, and the Bullshit in Between
Why you’ll never know how hard to workYou Will Never Feel Done
Why productivity won’t save usWelcome to Management: Please Proceed With Delusions of Control
What the management gurus won’t tell youFulfillment FOMO
And alternative paths to passion. What to do when “find your passion” fails.The Two-Party Trap (in office politics)
Are you an Idealist or a Schemer?I’m successful, but still argue with myself about it
Success is not a destination, it’s a debate
Series 03: The Other Side of Enough
What happens when you have “enough?”
We all chase enough. Enough to never work again. Enough to do something else. Enough to finally feel at peace.
But what does having enough actually feel like? Does life really change when you cross that finish line? Is it worth the sacrifice? Is “enough” really enough?
This is the real story of what happens when our dreams come true.
Intro: The Other Side of Enough
Introducing the next series to The Way of WorkEverywhere But Home: The search for belonging after reaching financial freedom at 32
Interview #1: He retired at 32 and now lives the dream life. But is it enough?Expectations Never End: Finding freedom after enough
Interview #2: Former CEO retires to a life of health, family, and… expectationsBreaking free from a life that doesn’t fit
Interview #3: A story of pain, purpose, and redemptionWill you get what you want, after reaching financial independence?
Interview #4: When you've focused on what others wantWaiting Decades to Finally Follow Your Dreams
Interview #5: A lifelong deferred dream, a sacrifice worth the waitAfter ‘Happily Ever After’
Interview #6: When what works in work, doesn’t work in lifeRich, Powerful, and Ready to Quit
Interview #7: A Wall Street power broker plans his escape – will he go through with it?Just Enough to Walk Away (how to find freedom faster)
Interview #8: Why you don’t need to wait until you have it allShould you put off life for the future?
Interview #9: The evolution of an early retiree, with an OG of the FIRE movement: the Mad FientistWhen independence unlocks another level
Interview #10: A lawyer dares to reinvent herself with a unexpected mid-career moveIs financial freedom worth waiting for?
Reflection #1: 5 unconventional ideas from the series“Fuck You Money” is Useless Without the “Fuck You”
Reflection #2: How to escape the psychological prisonGet Rich Now. Find Self Later
6 ideas on how to reach financial freedom faster
Series 02: Don’t Work
What happens when you don’t work? When your primary identity, centered around work, disappears? What remains? And what is rediscovered in its place?
Intro: Don’t Work
Introducing the next series to The Way of WorkWork identity serves, then severs
My work identity: the rise before the fallUnraveling the layers of working identity
Who am I, without work?The Value of Disappearing
The unexpected benefits of escaping from it all (and what to put back in its place)How to be unproductive
Why going nowhere, gets you somewhereBeyond our basic ambition
Is our current concept of ambition, ambitious enough?The “Hard Work” Delusion
So you believe in hard work. But what is your work?Diversified Portfolio of Identities
We would never put all of our money into one stock. But many of us put the entirety of our identity into one area: Work.Scale down, after scaling up
Coming back down to reality, after reaching the topThe very easy, not-painful-at-all, 5 super simple steps to changing your career
The definitely-no-pain-whatsoever guide to doing something differentWhen you don’t have a “calling”
How to find your work, when it’s not obviousAre you climbing the wrong mountain?
A summary of the “Don’t Work” series: lessons from a year away
Series 01: Work in Progress
Reflections on 12 years of evolution from an early startup employee, turned public company executive. Or, how I built my career.
From early startup to $2B public company, what 12 years at Privia Health taught me
I joined as the 6th employee of a small, ambitious startup called Privia Health, with an entry level title. 12 years later, I left as an executive of a $2B public company.Committed: How to give a damn about your work
We are surrounded by conditional people, who need to “be engaged” or receive the whip of stimulation to get moving. But we unlock the best in life when we become committed.Fluidity: How to continually reinvent yourself (in a world of change)
The world’s instability requires us to respond with fluidity: an ability to flow easily and continually reinvent ourselves in a river of change.Why you probably have a low leverage career (and how to create more leverage)
Career Leverage is like having a catapult to launch you forward, while everyone else is marching steadily forward (or for some, pulled backward).In the Clutch: Seizing high leverage career moments
In sports, we call certain players “clutch” because they execute in the most important moments. So too, will you be remembered (or not) for your clutch moments at work.Stage Fright: The wrong company stage will crush you
You are probably better suited for one specific company stage. Yet most people overlook this critical factor when choosing their work.Early Stage Innovation: What it’s like at the beginning
Everyone tries to copy innovation after the fact. But the key to innovation is understanding the beginning, not the end.How to stay out of their box (in your career)
The world is desperate to put you into a box and most of us are more than willing to comply. Here's how to stay out of their box.On Quitting (when it’s unclear whether to quit)
When it comes to quitting, sometimes there are blaring red signs. But usually, there is a lot of gray… and your choice is unclear.Luck: Things worked out for me, so they should for you too
When reflecting back on our life, “was I lucky (or unlucky)?" turns out to be one of the most important questions to ask ourselves.10 Takeaways from a 'Work in Progress' (or, how to build a career)
Summary reflections from a 10-part series on my 12 years at Privia Health, evolving as an early startup employee to $2B public company executive.
I am loving your Substack and have added it to my recommendation list. The art work is fantastic and assume it all AI generated? Still got lots of reading to do as only started from Series 2 after Mad Fi promoted your work.