In a culture spellbound by metrics—OKRs, KPIs, milestones, MBOs—it’s easy to forget that some of the most essential truths of being alive can’t be optimized. Paul Millerd’s The Pathless Path is a quiet, necessary rebellion against the modern scaffolding of success. Part memoir, part philosophical excavation, and part cultural critique, Millerd’s work invites us to consider a possibility increasingly rare in the LinkedIn age: that the best life might be one without a plan.
Drawing from sources as varied as Calvinist theology and Amos Tversky’s research heuristics, Millerd embarks on the radical act of asking, “What if we’ve got it all wrong?” That is: what if our inherited scripts about work, worth, and wellness aren’t just outdated, but deeply misaligned with what it means to live well?
At the heart of the book lies a tension as old as civilization: the pull between prestige and purpose. Prestige, Millerd writes, is “a powerful magnet that warps even your beliefs about what you enjoy.” It is the gravity that keeps us in jobs we loathe, chasing degrees we don’t need, living lives that feel borrowed from a brochure. And yet, the courage to step away—to disappoint expectations, to be misunderstood—demands a kind of faith that is usually reserved for the devout.
The Protestant work ethic, Millerd reminds us, was not always the productivity cult we know today. Luther and Calvin’s revolution was spiritual before it became economic: a divine permission slip to seek one’s “calling.” But the theology that once infused labor with meaning has been hollowed out, leaving only the husk—“hustle culture,” with its TED Talks, standing desks, and endless optimization. Thrift and humility have been replaced with personal brands and dopamine dashboards.
Maria Popova once described literature as “the original internet”—a constellation of ideas that speak to one another across time. Millerd curates his own such constellation, connecting Erich Fromm’s concept of “positive freedom” (freedom to, rather than from), Josef Pieper’s Leisure, the Basis of Culture, and Agnes Callard’s notion of aspiration as a gradual, vulnerable process of “trying on the values we hope to possess.” Through this philosophical polyphony, Millerd teases out a central insight: the pursuit of meaning is often slow, opaque, and non-linear.
If ambition is the straight highway, aspiration is the meandering trail through the woods. The latter cannot be strategized; it must be wandered. And here lies Millerd’s most subversive suggestion: that the real problem with our lives may not be lack of goals but an overabundance of the wrong ones. Jerry Colonna’s coaching koan—“How are you complicit in creating the conditions you say you don’t want?”—echoes like a Socratic whisper through the book.
Millerd splits his self into two: “Default Path Paul,” the respectable consultant climbing predictable ladders, and “Pathless Path Paul,” the one who steps off the map and begins to live by clues—serendipities, gut instincts, small joys. The transformation is not instantaneous; it is iterative, like software in perpetual beta. Along the way, he prototypes his future, treating life itself as an experiment in aliveness.
There is no call to heroism here. No “quit your job and move to Bali” grandiosity. Instead, Millerd focuses on lowering the stakes, removing risk rather than chasing valor. “Prototyping a change,” he writes, is how people actually change—quietly, imperfectly, often without fully knowing what they’re moving toward. In that spirit, he invites us not to leap, but to listen.
Some of the most resonant passages are those that interrogate the spiritual costs of conventional success. C.S. Lewis’s haunting insight about the “desire to be inside the local Ring and the terror of being left outside” resurfaces in the modern workplace, where the fear of irrelevance stalks every open office. Burnout, Millerd suggests, is not merely a function of overwork but of misalignment. It is what happens when your soul is on mute.
Rebecca Solnit’s A Field Guide to Getting Lost hovers over the book like a benevolent ghost. Millerd insists, with Solnit, that getting lost is not a bug—it’s the point. As Thoreau once observed, “The life which men praise and regard as successful is but one kind.” The real achievement may be learning to praise lives that don’t fit neatly into the dropdown menus of LinkedIn.
In an age where convenience reigns—where DoorDash and ChatGPT make every impulse a frictionless fulfillment—Millerd resurrects Tim Wu’s warning that “the tyranny of convenience” may strip life of its necessary texture. To be pathless, then, is to embrace some inefficiency. To waste hours in the spirit of Amos Tversky’s dictum that “you waste years by not being able to waste hours.” Time, as Thompson reminds us, is not passed but spent—and some of the best investments accrue slowly, in compound moments of stillness.
The sacred is a quiet but recurring motif in The Pathless Path. Not the sacred of institutions, but of intimacy—between self and vocation, between inner voice and outward action. To write, Millerd notes via Zinsser, is “an act of ego”—but also of offering. The creative act, he concludes, is one of the most sacred gestures we can make, not because of its outcomes, but because of what it demands: presence, attention, and the willingness to be changed by what you make.
By the book’s end, we are not handed a roadmap. We are instead encouraged to create our own culture, our own fixed points. To define our own “rich life,” not in terms of income or impact, but in how alive we feel while living it. Joseph Campbell’s call to “bring life to the world by becoming alive yourself” becomes more than a motivational quote; it becomes the very task of adulthood.
Dolly Parton, in her twangy wisdom, once said, “Find out who you are and do it on purpose.” That may be the most radical path of all—not the one of rebellion, but of recognition. Not to run away from the world, but to find the courage to stand still in your own truth.
The Pathless Path is a rare book. Not because it offers answers, but because it dares to ask the real questions—the ones we’ve been too busy, too credentialed, or too afraid to face. In doing so, Millerd doesn’t give us a direction. He gives us something better: permission.
“The world has become larger than your knowledge of it,” Solnit wrote. Perhaps that’s the point. Perhaps the first step to freedom is to admit we are lost—and then begin to walk anyway.
Jargogled Impressions. 
Leave a comment