This is a book summary of The Pathless Path: Imagining a New Story For Work and Life by Paul Millerd (Amazon).
- All content in quotation marks is from the author (content not in quotations is paraphrased).
- All content is organized into my own themes (not necessarily the author’s chapters).
- Emphasis has been added in bold for readability/skimmability.
Book Summary Contents:
- About the Book
- Default Path vs Pathless Path (+ Infographic)
- Crisis & Disconnect
- Pre- & Post-Quitting
- Money, Money, Money
- Identity & Ikigai
- Find the Others
A New Story For Work and Life: The Pathless Path by Paul Millerd (Book Summary)
About the Book
“I didn’t write this book to provide you with a set of how‑to instructions for embracing the pathless path. Instead, I want to inspire you to dream a little bit bigger, add some nuance to how you think about life decisions, and give you models and ideas that might enable you to embrace the spirit of the pathless path.”
- “After reading this book, you should no longer be able to look at your current path and think, ‘this is definitely the only way.’ Instead, I hope you are able to shift to a place where you know that you have more freedom than you think, and your path can become something you choose again every day.”
- “Writing this book has been a good opportunity to reflect on my life. One of the things that is clear out is how lucky I’ve been. I’ve been surrounded by so many good influences that it seems a bit unfair. I owe the biggest thanks to my parents, Nancy and Bob, for giving me a childhood where I was loved and encouraged. This enabled me to become a confident adult, find success on the default path, and eventually have the courage to carve my own.”
- “While I don’t have perfect answers yet for the questions I keep asking, my conversation has somehow turned into a full life, one filled with people, ideas, curiosities, and work that will keep me engaged for many years to come.”
A little about Paul:
- “As I was growing up, work was such an obvious goal of life that I never paused for a moment to question it.”
- “By my late 20s, I had oriented my entire life around work. I was always thinking about how I could get a better job or a higher salary.”
- “I always took all of my vacation days. Didn’t work crazy hours. Made time for friends and family. Changed jobs when I stopped learning.”
- “It wasn’t until my early 30s that I started to suspect something was amiss.”
- “After more than three decades of constantly planning for the future, I was able to start living in the present.”
- “So much of life is like this. We are surprised at the moment something happens, but looking back, we realize that everything makes sense. Losing my grandfather, getting rejected from jobs repeatedly, never finding the right fit, facing health challenges and hard questions were all events that sent me in an inevitable direction that was only obvious upon reflection.”
Default Path vs Pathless Path
“My story is not one of courage, but of pragmatic and safe experiments, experiences, and questioning over several years. This approach, one of prototyping a change, is not only a better way to think about taking bold leaps but is quite common across many people’s stories … It didn’t take me long to realize I had been on a path that wasn’t mine and to find a new way forward, I would need to step into the unknown.”
The story of the industrial world. An industrial, “bigger is better” mindset assumes that everyone is competing in a mass market. Thinking we have to serve a mass audience is default path thinking. You have to get the job before you can do the work.
- an obsessive focus on getting ahead (in my twenties).
- study hard, get good grades, get a good job (then put your head down and keep going, indefinitely).
- a series of decisions and accomplishments needed to be seen as a successful adult (these vary by country, but in the United States, we refer to this as the ‘American Dream,’ which means a life centered around a good job, owning a home, and having a family).
- the trap of prestigious career paths (instead of thinking about what you want to do with your life, you default to the options most admired by your peers).
- following a script (for most of my life, I had followed a script about how life should be, always trying to choreograph my future; I took classes with the sole intention of getting the best grade possible; I did not change radically as a person because nothing was at stake).
- keeps many trapped in a pseudo‑freedom where one is free from absolute oppression but not free enough to act with a high degree of agency (but has given us the freedom to earn money and spend it as we please, work in different fields, and have some control over our lives).
- optionality can be a trap (because you are trapped within your own career narrative).
The natural story for a digital‑native world in which nothing can stop us from finding others who share our desires, ideas, and questions. I’m in an indie economy, where over the long‑term I’m competing on learning, developing skills, and my reputation. This is a lot harder but also a lot more rewarding. You simply do the work first and then decide if you want to continue. In sum, the goal of being on this path is: Being able to get to a state of being where I can spend almost all my time helping, supporting, and inspiring others to do great things with their lives.
- an aspirational and alternative to the default path (a new story for thinking about finding a path in life; a call to adventure in a world that tells us to conform; a define-your-own-success adventure).
- the deliberate pursuit of a positive version of freedom (figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path).
- a mantra to reassure myself I would be okay (after spending the first 32 years of my life always having a plan, this kind of blind trust in the universe was new, scary, and exciting).
- an embrace of uncertainty and discomfort (a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved; making life changes requires overcoming the discomfort of not knowing what will happen; accepting that you might not know what you are doing and you might look like a fool.).
- shifting away from a life built on getting ahead and towards one focused on coming alive (releasing myself from the achievement narrative that I had been unconsciously following).
- most include some kind of prototyping (by experimenting with different ways of showing up in the world and making small, deliberate changes, we can open ourselves up to the unexpected opportunities, possibilities, and connections that might tell us what comes next).
- having faith (admitting that you don’t have all the answers for what comes next).
- worry is traded for wonder (people stop thinking about worst‑case scenarios and begin to imagine the benefits of following an uncertain path.
- curiosity about who they might become (if they embrace discomfort and are filled with a sense of urgency that says, ‘if I don’t do this now, I might regret it’; when I learned to be guided by my curiosity and pay attention, I started noticing that answers would spontaneously emerge as a byproduct of living my life; when people have time, they try new activities, revisit old hobbies, explore childhood curiosities, and start volunteering and connecting with people in their community).
- forces you to reckon with your fears no matter what (being aware of my fears and seeing them as tiny but manageable existential crises that are an inevitable part of an uncertain journey).
- offers profound personal growth but its benefits often remain invisible to others (when you are on such a path, you are hyper‑aware of this disconnect, and this can cause a lot of distress).
- ignoring the pull of needing to be a “good egg” and learning what truly enables you to thrive (what this really means is developing an appreciation for discomfort).
- ignoring the shiny objects and distractions (and stripping away the stories that are not our own to remember who we are).
- creativity is more of an active choice and creative output is fuel (the removal of gatekeepers means that for the first time it might take more energy to deny your own creative expression than exploring it; the creative act is one of the most sacred things in the world and should be taken seriously in itself and not with any expected outcome).
- makes commitments (to a type of work, ways of living, creative projects, or a “conversation” with the world; finding ideas and principles worth committing to and seeing where you end up).
- the goal is to stay on the pathless path indefinitely (what author James Carse calls the “infinite game”; an infinite game for the purpose of continuing the play).
- optionality can pay consistent dividends (because you are not holding out for another job but leaving space for a little more life).
- opening yourself up to emergence (growing up and letting go).
- biggest problem is the paradox of choice (there are too many interesting things worth doing and too many places to visit).
10 Pathless Path Principles:
Crisis & Disconnect
“It was incredibly painful for me to realize that if I truly cared about living in a different way, I might need to leave the business world. The journey towards the pathless path often starts at this moment, with a willingness to investigate your disappointment and to wonder if there is a better way of defining success.”
Experiencing a crisis:
“My mother credits the health crisis I faced in my 20s for putting me on my current path. ‘It changed you,’ she says. While I don’t think it was the sole reason I left the default path, my illness did change my relationship to uncertainty.”
- “Without my health crisis, I probably wouldn’t have been so comfortable leaving my job without any clear plan for making money. This seems crazy now, but it didn’t occur to me to radically cut my spending until after I left my job.”
“Success for the company does not always align with what is best for the person, and over time, a disconnect can emerge. This is what happened to me.”
- “At that last job, I wasn’t a team player and I could have tried harder to say the right things, dress the right way, or spend more time pleasing my manager. But I couldn’t do it. The norms of the organization were pulling me too far away from the person I wanted to be and the energy I used to manage this disconnect undermined anything good I had to offer.”
- “I was physically present but detached. Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist.”
- “The disconnect between what we claim to care about and what we do (or don’t do) points out what matters to us.”
- “Based on the experiences of others who leave the default path, this stage of contradiction is common. You take a last stand, doubling down on the existing path despite all evidence that it is no longer working.”
- “Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it difficult to live in contradiction in your own life.”
Pre- & Post-Quitting
“In the months leading up to leaving my job and the year or two after quitting, I struggled to make sense of my journey. When others asked how I was doing, I felt compelled to give them proof that I had a plan and knew what I was doing.”
“I had no master plan to quit my job. Even now, several years after doing so, when people ask about my journey, I’m more confused than you might expect. Choosing to leave full‑time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path.”
- “It’s tempting to tell a simpler story. People want to hear about bold acts of courage, not years of feeling lost. On my way toward leaving my job, I never had a clear picture of my next step.”
- “Being at the frontier of your current reality is disorienting. Deep down you might have a sense that you should keep going in a certain direction, but you never know why.”
- “I was still searching for that elusive dream job and had not yet considered becoming self-employed.”
- “I split into two different versions of myself. One, ‘Default Path Paul,’ focused on continuing my career, looking for the next job. The other, ‘Pathless Path Paul,’ was finding his footing and starting to pay attention to the clues that were showing up. Clues that would lead me not to another job, but to another life.”
- “In the final months, I was in a liminal space between two worlds. I had decided to take a leap to a different path but had not yet changed direction.”
“People become aware of their own suffering. Often we don’t notice our drift into a state of low‑grade anxiety until we step away from what causes it, as I noticed the first day after I quit my job and realized I was burned out.”
- “Years of resentment, frustration, and confusion demanded to be released. While working, I always sensed that these feelings were there, but the daily inertia of a life centered around work kept them hidden. Now, without a plan and without anywhere to show up, I had to feel the full force of my emotions.”
- “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.”
- “Many people who leave the default path do so because they’ve become cynical and are driven by a desire to escape. But escaping is only the first step of leaving a certain path behind. In order to create a sustainable journey and path, it requires finding ways of orienting to the world that leave space for hope.”
Money, Money, Money
“On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It’s to actively and consciously search for the work that you want to keep doing. This is one of the most important secrets of the pathless path. With this approach, it doesn’t make sense to chase any financial opportunity if you can’t be sure that you will like the work. What does make sense is experimenting with different kinds of work, and once you find something worth doing, working backward to build a life around being able to keep doing it.”
Evolving relationship with money:
“Economist Daniel Kahneman found that ‘the importance that people attached to income at age 18 also anticipated their satisfaction with their income as adults.'” (Note: The Psychology of Money by Morgan Housel also talks about how views on money are formed early in life)
- “Behind my money fears was a longing to feel that my life mattered. I suspect this is the same for many, and money is one shortcut we use to ‘prove’ our worth. Yet in my experience, no amount of money ever seems to satisfy.”
- “When I was getting paid on a steady basis, the relationship between making money and my motivation was hard to understand. Without a paycheck, the combination of insecurity, fear, and my desire to prove myself made it much clearer. This ignited a period of frenzied activity, one which I’ve noticed is a common stage for people that leave their jobs without an income.”
- “When I quit, my mindset shifted immediately and I looked at every monetary transaction with the intensity of a financial auditor.”
- “When I left my job, I expected that working on my own would be challenging, but I did not expect my entire relationship to money and its role in my life to change.”
- “With money coming in and a lower cost of living, my financial insecurity decreased, leading to a chain reaction in my understanding of work. If I wasn’t working for money, why was I working?”
- “As my money anxieties receded, I realized I wanted to go deeper. Not with freelance work, but in my life. In those first six months, I experienced a remarkable sense of freedom and ownership over my life. Most days I decided when, where, and how I worked.”
- “No amount of money can buy the peace of mind that comes with finding a path that you want to stay on. Once we know, as Vicky Robin argues in her book Your Money or Your Life, that ‘money is something we choose to trade our life energy for,’ it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.”
- “No money is worth it if it undermines your desire to stay on the journey.”
Minimizing spending & defining enough:
“On the pathless path, knowing you have enough is what gives you the freedom to say ‘no’ to clear financial opportunities and say ‘yes’ to something that might bring you alive and might even pay off much more over the long term.”
- “If we don’t define ‘enough,’ we default to more, which makes it impossible to understand when to say no.”
- “Minimizing spending is a useful step in lowering the pressure of making money, but it’s not a lifestyle. While it gave me the confidence to make drastic changes without sacrificing my happiness, it kept me in a mindset of scarcity instead of leaning into possibility.”
- “People aim for ‘financial independence‘ only to realize when they achieve it that they’re only independent in the narrow sense of being able to pay for everything.”
- “Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. 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.”
Retirement & mini-retirements:
“On the pathless path, retirement is neither a destination nor a financial calculation, but a continuation of a life well-lived. This shifts attention from focusing on saving for the future to understanding how you want to live in the present.”
- “While I’m still saving for retirement, I’m not putting all my faith in reaching certain financial milestones as the most important thing. I’m much more focused on spending time and money now to experiment with different modes of living such that when I reach the latter stages of my life, I won’t be making a dramatic shift in life priorities, but continuing on the pathless path.”
- “For me, testing out different ways of structuring my life now is a win‑win proposition. I’m lowering the odds that I’ll be unhappy in the future all while crafting a life I’m more and more excited to keep living.”
- “I try to think about time in blocks of one to three months and within each block, I pick one or two things I want to prioritize and test. It might be living in a different type of place, working on new projects, traveling, or learning something new. My goal is to test my beliefs to get a better understanding of what really makes my life better.”
- “Right now, I’m orienting my work around taking every seventh week off from work no matter what.”
Identity & Ikigai
“If the culture doesn’t work, don’t buy it. Create your own. This is what the pathless path is all about. It’s having the courage to walk away from an identity that seems to make sense in the context of the default path in order to aspire towards things you don’t understand. It’s to experiment in new ways, to remix your own path, to develop your own personal definition of freedom, and to dare to have faith that it will be okay, no matter how much skepticism, insecurity, or fear you face.”
“According to Robert Kegan, a psychologist at Harvard, we are shifting away from a world where we need to fit in towards one where we must develop the skill of ‘self‑authoring.’ Instead of looking to external cues to learn how to live, we need to have a coherent internal narrative about why we are living a certain way. This is the ethos of the pathless path and if you don’t know or understand your own story, you will struggle.”
- “So much of my identity had been connected with being a high achiever.”
- “At the time I could not imagine any other existence. Where I lived, what I did, how I thought about money, and the people I hung out with were all connected with my work identity.”
- “When I became self‑employed, I was surprised at how strongly I had internalized a worker identity.”
- “I had loosened my attachment to ‘Paul as a successful person,’ but was still firmly located in that successful world.”
- “Even if it was never spoken, when I left the default path I felt as if I had immediately crossed an imaginary boundary where I was some sort of rebel that needed to defend my recklessness.”
- “Simple questions from others like ‘what do you do?’ will expose your own uncertainty and can feel like a death blow to the soul.”
- “Embracing a new identity can be a useful way to enter the uncertain world of the pathless path. At a minimum, it gives you an answer when people inevitably start asking about your plans. However, many people quickly realize that they’ve created the same conditions that they sought to escape.”
- “Opting out of work and opting in to other aspects of your life can create questions about who you used to be. It feels weird at first, but over time, you start to change what you value.”
- “If you lean into your own unique psychology, interests, and sense of humor, your journey will be a little more fun and much more meaningful.”
Finding your ikigai:
“A lot of our confusion around work results from ideas like meaningful work and the widespread belief that we can always make money doing something we love. The blogger Marc Winn supercharged this idea in a viral meme. Winn translated a diagram created in 2011 by Andrés Zuzunaga and replaced the Spanish word for ‘purpose’ with ‘Ikigai.’ In Winn’s version, finding your Ikigai means aligning what you love, what you are good at, what the world needs, and what can be paid for … While many people have embraced this version of Ikigai, having discovered work I love doing that doesn’t come with a paycheck, I’ve realized that it’s wishful thinking. Plus, in Japanese, Ikigai is none of these things. Rather, its best translation is simply that it is a ‘reason for being’ or ‘something to live for.’” (Note: I got a footnote in the book regarding the truth about ikigai)
Figuring out what you love:
- “Most people desire a path that aligns with what matters uniquely to them.”
- “Most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them.”
- “The search for work worth doing is the real work and one of the most important pursuits in life.”
Figuring out your unique talents/gifts:
- “The pathless path has helped me see that quitting my job was never about escaping work or living an easier life, it was about using the gifts I received from my parents to benefit others.”
- “When you find the work you want to keep doing, what makes it meaningful is that you are drawn to do it for its own sake.”
- “Far too many people limit their imagination of work worth doing to things that either come with a paycheck, require qualifications, or have a socially accepted story of impact. If I limited myself in the same way I would have lost all energy to continue. For me, I was finding that the act of creation was the reward itself.”
Figuring out how you can help the world/others:
- “Figuring out who you want to serve is an important element of the pathless path.”
- “In my travels around the world, meeting a diverse range of people that have left the default path, nothing has been more consistent than the reality that most people want to engage with the world and to be useful.”
- “The need to feel useful is a powerful one. This is the hidden upside of the pathless path and a reason why finding work that aligns with what matters to you and makes you feel useful is so important. When you find the conversations you want to take part in and the work you want to keep doing, you start to feel necessary and the whole world opens up.”
A virtuous cycle (or flywheel):
- “You can experiment with your work and your life until you stumble into a virtuous cycle that helps you continue to move in a positive direction. By a virtuous cycle, I mean being able to do work that you enjoy that naturally leads to opportunities and people that help make your life better.”
Making money as an optional byproduct of the flywheel:
- “While money is important on the pathless path, using it as a filter for finding the work worth doing, especially at first, is a mistake. More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer. Fighting for the opportunity to do this work is what matters, whether or not you make money from it in the short term.”
- “One of my most important is the mantra ‘coming alive over getting ahead.’ I embraced this fundamental shift when I left my previous path, and the mantra reminds me that I don’t want to create another job for myself. When I see an opportunity to make money, scale something, charge more money, or move faster, this phrase reminds me to explore all possibilities first, including doing nothing.”
- “I’m not in the business of being a business. I’m embracing the work of building a life and all of the connections that will make that meaningful.”
Putting it all together:
- “The work that I want to keep doing is writing, sharing stories, helping people, and doing other experiments online.”
- “What I want to keep doing, such as mentoring young people, writing, teaching, sharing ideas, connecting people, and having meaningful conversations, is worth fighting for.”
- “Nothing good gets away, as long as you create the space to let it emerge.”
Find the Others
“The internet has made it possible for people from anywhere in the world with access to the internet to create and share their ideas, stories, and creations without permission.”
- “On the pathless path, powered by digital communities, we can surround ourselves with people that inspire us and push us to improve in the ways we care about. The longer I’ve stayed on this path and the more effort I’ve put into connecting with people heading in similar directions, the better my life has become.”
- “While the pathless path is a solo journey, it is important that you have at least one close friend with whom you can have these kinds of intimate conversations. They will help you remain aware of your own emerging conversation with the world.”
- “When you meet others on a similar path, there is an instant bond and a deep sense of knowing about the challenges you are both going through. You can smile in a way that says, ‘I know, I know,’ skip the ‘what do you do?’ question, and start a deeper conversation.”
You May Also Enjoy:
- 📘 Ikigai 2.0: A Step-by-Step Guidebook to Finding Life Purpose & Making Money Meaningfully (+ Bonus Workbook)
- A Systems Approach to Lifestyle Design: “Early Retirement Extreme” by Jacob Lund Fisker (Book Summary) + 🔒 Premium Synthesis
- Everything from Money to The Meaning of Life: Wisdom from “The Almanack of Naval Ravikant” (Book Summary)
Leave a Reply