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 04: Not Obvious

Series 03: The Other Side of Enough

Series 02: Don’t Work

Series 01: Work in Progress

Bonus: Recommended Resources

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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.

1. 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 living

2. The Open Frontier of Meaning
   The collapse of old worlds, the failure of quick fixes, and the call to explore

3. What You Need is a Midlife Crisis
   Why the midlife crisis is an opportunity not to be wasted

4. Total Addressable Meaning
   What if we built a life around what actually matters? (and noticed the strange world we already live in)

5. just kidding… work actually is the meaning of life!
   A performance review in purgatory (satire)

6. Make something that doesn’t matter
   Why you need a totally pointless passion project

7. How to be successful and miserable
   When you’re good at the wrong thing

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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.

1. Intro: Why Work Advice Fails Us
   How neatly packaged advice keeps us lost and frustrated

2. Burnout, Balance, and the Bullshit in Between
   Why you’ll never know how hard to work

3. You Will Never Feel Done
   Why productivity won’t save us

4. Welcome to Management: Please Proceed With Delusions of Control
   What the management gurus won’t tell you

5. Fulfillment FOMO
   And alternative paths to passion. What to do when “find your passion” fails.

6. The Two-Party Trap (in office politics)
   Are you an Idealist or a Schemer?

7. I’m successful, but still argue with myself about it
   Success is not a destination, it’s a debate

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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.

1. Intro: The Other Side of Enough
   Introducing the next series to The Way of Work

2. Everywhere 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?

3. Expectations Never End: Finding freedom after enough
   Interview #2: Former CEO retires to a life of health, family, and… expectations

4. Breaking free from a life that doesn’t fit
   Interview #3: A story of pain, purpose, and redemption

5. Will you get what you want, after reaching financial independence?
   Interview #4: When you've focused on what others want

6. Waiting Decades to Finally Follow Your Dreams
   Interview #5: A lifelong deferred dream, a sacrifice worth the wait

7. After ‘Happily Ever After’
   Interview #6: When what works in work, doesn’t work in life

8. Rich, Powerful, and Ready to Quit
   Interview #7: A Wall Street power broker plans his escape – will he go through with it?

9. Just Enough to Walk Away (how to find freedom faster)
   Interview #8: Why you don’t need to wait until you have it all

10. Should you put off life for the future?
    Interview #9: The evolution of an early retiree, with an OG of the FIRE movement: the Mad Fientist

11. When independence unlocks another level
    Interview #10: A lawyer dares to reinvent herself with a unexpected mid-career move

12. Is financial freedom worth waiting for?
    Reflection #1: 5 unconventional ideas from the series

13. “Fuck You Money” is Useless Without the “Fuck You”
    Reflection #2: How to escape the psychological prison

14. Get Rich Now. Find Self Later
    6 ideas on how to reach financial freedom faster

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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?

1. Intro: Don’t Work
   Introducing the next series to The Way of Work

2. Work identity serves, then severs
   My work identity: the rise before the fall

3. Unraveling the layers of working identity
   Who am I, without work?

4. The Value of Disappearing
   The unexpected benefits of escaping from it all (and what to put back in its place)

5. How to be unproductive
   Why going nowhere, gets you somewhere

6. Beyond our basic ambition
   Is our current concept of ambition, ambitious enough?

7. The “Hard Work” Delusion
   So you believe in hard work. But what is your work?

8. 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.

9. Scale down, after scaling up
   Coming back down to reality, after reaching the top

10. The very easy, not-painful-at-all, 5 super simple steps to changing your career
    The definitely-no-pain-whatsoever guide to doing something different

11. When you don’t have a “calling”
    How to find your work, when it’s not obvious

12. Are you climbing the wrong mountain?
    A summary of the “Don’t Work” series: lessons from a year away

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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.

1. 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.

2. 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.

3. 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.

4. 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).

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.

10. 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.

11. 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.

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