Book Notes: The Pathless Path
The last few years of my life have been a whirlwind of change. Everything I thought I wanted, everything I thought I was building toward, began to feel hollow. A sense of unease crept in—like I was running on a treadmill that kept speeding up, but I wasn’t getting anywhere I actually wanted to be. It wasn’t one big moment that shifted things for me, but a series of small cracks in the foundation: questioning what success really looks like, wondering if the work I was doing was what I actually wanted, and realizing that the path I was on wasn’t one I’d chosen—it was one I’d inherited.
In The Pathless Path, Paul Millerd delivers an invitation to step off the well-trodden roads of societal expectations and into the wilderness of possibility. This is a book that has been hugely influential on the past year of my life and my work.
It’s not a how-to manual, nor does it prescribe a singular path. Instead, the book is a meditation on questioning assumptions, redefining success, and embracing the uncertainty that comes with charting your own course. For anyone feeling stuck in a life that looks good on paper but feels hollow in practice, Millerd’s reflections provide a thoughtful and challenging perspective.
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Part One: The Default Path
Questioning the Formula
Millerd begins with a simple but relatable moment: recounting his decision to quit his job and move to Taiwan in a Chinese language class. The act of sharing his unconventional story highlights the book’s premise — the “default path” doesn’t guarantee happiness, and following it often leads to discontent rather than fulfillment.
For Millerd, the “default path” is the life script most of us inherit: work hard, get good grades, climb the corporate ladder, accumulate wealth, and retire comfortably. While this formula works for some, it doesn’t suit everyone, and yet few dare to question it. The book’s central aim is to help readers imagine alternatives, live courageously, and thrive outside the default narrative.
2. Getting Ahead: The Trap of Hoop-Jumping
Do you know someone who excels at checking all the boxes but never pauses to ask if the boxes matter? Millerd introduces the concept of the “hoop-jumper” — someone who masters the art of meeting external expectations, often at the expense of their own curiosity or passion.
Millerd’s own life as a hoop-jumper began in college, where his primary focus was achieving high grades and building a resume that would impress recruiters. He shares detailed anecdotes about his relentless pursuit of strategy consulting roles, attending high-stakes interviews at prestigious firms, and landing a “dream job” that left him feeling empty. These moments are punctuated by more profound reflections, including his grandfather’s death and a debilitating battle with Lyme disease, which forced him to re-evaluate his priorities.
3. Work as a Calling or a Cage?
Why do so many of us conflate busyness with value? Millerd argues that modern capitalism has turned work from a necessity into a “calling” — something we’re supposed to love, be passionate about, and let define us. But the reality for many is far bleaker: meaningless “bullshit jobs” that create busywork without contributing real value. This part spoke to me; it's something David Graeber explored in his work, and I drew on it a lot when I was figuring things out post-Pandemic.
Modern workplaces, Millerd writes, resemble “cathedrals of consumption,” where perks like free meals or yoga classes subtly encourage employees to spend more time at work. This environment perpetuates the belief that productivity equals purpose, even when the tasks themselves lack meaning.
4. The Awakening: A Pebble in the Shoe
For Millerd, the journey toward a pathless path began with discomfort. He describes it as a “pebble in the shoe” — a persistent feeling that something wasn’t right. At first, he didn’t make drastic changes. Instead, he started small: prioritizing his health, experimenting with side projects, and exploring coaching. These experiments brought a sense of creative energy he hadn’t felt in years.
Eventually, he had an epiphany: the dream job he had been chasing for years no longer aligned with who he was. That realization was both liberating and terrifying.
5. Breaking Free: Quitting as an Emotional Reckoning
Quitting a stable, high-status job isn’t just a career move; it’s an identity shift. Millerd details the emotional and psychological toll of leaving behind the security of a corporate role to embrace freelance work. He wrestled with burnout, questioned his sense of self-worth, and confronted deeply ingrained societal expectations.
Freelancing gave him the freedom to redefine himself outside the narrow confines of being a “worker.” More importantly, it opened the door to unconventional projects that brought unexpected joy.
6. The First Steps: Prototyping Change
Millerd emphasizes the importance of “prototyping” change rather than taking sudden, dramatic leaps. This approach involves experimenting with small, low-risk changes to test out new ways of living or working. He contrasts ambition — the pursuit of external goals like promotions or accolades — with aspiration, which is about pursuing an inner sense of purpose or alignment.
He also underscores the importance of finding “the others” — communities of people who share your values and aspirations. These relationships provide support and encouragement, making it easier to navigate fear and uncertainty.
Part Two: The Pathless Path
7. The Wisdom of Non-Doing
One of Millerd’s key insights is the power of “non-doing” — stepping away from constant productivity to create space for self-awareness and curiosity. Taking extended breaks or mini-retirements can reveal new possibilities and help reframe one’s relationship with work and money.
By reducing his spending and focusing on experiences rather than material accumulation, Millerd found more time and freedom to pursue creative projects. He encourages readers to explore these trade-offs for themselves.
8. Redefining Success
How do you define success? Millerd argues that most people have a double standard: they define success for themselves differently than they do for others. By questioning societal definitions of success and embracing the identity of a “bad egg” — someone who rejects conventional expectations — readers can start to carve out their own path.
This means building tolerance for discomfort and uncertainty - and setting clear boundaries around what is “enough” in terms of money, status, or possessions.
9. The Real Work of Your Life
Everyone has a unique “conversation” with the world — a calling or purpose that they’re meant to explore. For Millerd, this involves rediscovering childhood passions, engaging in meaningful conversations with others, and designing work that aligns with his values.
He encourages readers to overcome limiting beliefs about creativity and start sharing their work with the world, even in small ways. These small acts of expression often lead to unexpected opportunities and deeper connections.
10. Playing the Long Game
The pathless path isn’t a shortcut to success; we're talking about a long-term commitment to alignment and authenticity. Millerd emphasizes the importance of agency — the ability to take deliberate, intentional action — and the willingness to reinvent oneself as circumstances evolve.
A gift economy mindset, where value is created and shared freely, can also lead to more fulfilling work. The goal is to focus on what makes you come alive, rather than what helps you get ahead.
Walking the Pathless Path
Millerd closes the book with ten actionable takeaways for readers:
• Reframe your fears as growth opportunities.
• Experiment with small changes before making drastic decisions.
• Define “enough” for yourself and make conscious choices around it.
• Seek out supportive communities of like-minded people.
• Focus on activities that make you come alive.
The Pathless Path is a personal exploration of what it means to live intentionally in a world obsessed with achievement. Millerd doesn’t promise easy answers or quick fixes; he offers an invitation to step into the unknown and discover who you might become. For those willing to leave the script behind, the rewards are profound. Self-discovery, creativity, and a life that feels truly lived.
When we're increasingly controlled and influenced by algorithms, expectations and optimization, there's something radical about choosing to zig rather than zag, in recognizing that sometimes the best thing to do with a pre-fixed menu is to walk out and find that greasy burger joint instead.
