“This is the pathless path. Where the journey leads is to the deepest truth in you.”

“My restlessness was easy to hide because my path was filled with impressive names and achievements, and when you're on such a path, no one asks, 'Why are you doing this?'"

“I was able to shift away from a life built on getting ahead and towards one focused on coming alive.”

“The hardest questions often don’t have answers.”

“The best option available for my parents was the default path. This worked remarkably well for them, which is what made leaving it so damn hard. I know how much they sacrificed so that I would have better career opportunities.

However, what they really gave me was so much more than the ability to succeed in school and work. It was space to dream, take risks, and be able to explore more possibilities for my life."

"The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained to others."

“The modern world offers an abundance of paths. In one sense this is great. It's the result of an industrial system and resulting prosperity that has created opportunities for people around the world.

However, the proliferation of paths presents a challenge. With so many options it can be tempting to pick a path that offers certainty rather than doing the harder work of figuring out what we really want."

“The desire for security and the feeling of insecurity are the same thing.”

“The house became not only a second home, but a gathering space for friends, family, and acquaintances. The door was open to everyone as long as they agreed to eat my grandfather's food. He never talked about his childhood, but according to his siblings, after their mother died, he was sent to live on a farm with his uncle.

Sometime around fourth grade, he stopped going to school so that he could start working with his uncle. He didn't have a childhood filled with love and support. He chose to deal with it by trying to do better for his children and grandchildren and he succeeded.

Like many of my cousins, we feel like we won the lottery growing up with a family like ours, where thanks to my grandfather we had access to a magical world filled with love, laughter, and possibility.

Sitting in the house in Arizona, I knew I was about to lose him, one of the most important people in my life. Those few days were filled with tears and overwhelming emotion, but also with beauty and a profound sense of meaning. The proof of his life's work was in front of us. He had succeeded in creating a world better than the one he had grown up in. It was clear to me in those moments that family, love, and relationships were the most important things in the world.

Despite this clarity, I struggled to remain present in the days before he passed. I couldn't stop thinking about work. What if my colleagues needed me? To settle my anxiety, I drove to a local cafe and checked my email. Everything was fine. A colleague messaged me, 'What are you doing!? Go back with your family, we got you!' I smiled and closed my laptop.

Driving back from the cafe, I was angry at myself. Why had I been so worried about work, something that was clearly not important? As I walked back into my grandfather's house, the house was silent. He was taking his final breaths. Had I nearly missed this moment because of some silly emails? I joined hands with my family, said a prayer, and left my worries aside for the next few days."

“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."

“The Ancient Greek translation for 'work' was literally 'not-at-leisure.' In Aristotle's own words, 'we are not-at-leisure' in order to be-at-leisure.' Now, this is flipped. We work to earn time off and see leisure as a break from work.

Pieper pointed out that people 'mistake leisure for idleness, and work for creativity.' To Pieper, leisure was above work. It was 'a condition of the soul,' and the 'disposition of receptive understanding, of contemplative beholding, and immersion - in the real.'"

"In stepping away from my temporary identity as a freelance consultant, I let myself fully lean into what I would later call the pathless path. As I wandered Asia, my mind exploded with possibility. If it was possible to work from a laptop in Bali, what else had I not yet considered? My imagination was open, and I was ready to see where it might take me."

“We must let go of the life we have planned, so as to accept the one that is waiting for us."

"The incommunicable trees begin to persuade us to live with them, and quit our life of solemn trifles."

"The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we're too poor to buy our freedom."

“Why not take the usual 20-30-year retirement and redistribute it throughout life instead of saving it all for the end?"

“No amount of money can buy the peace of mind that comes with finding a path that you want to stay on.”

“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.”

“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.”

"Whatever takes us to our edge, to our outer limits, leads us to the heart of life's mystery, and there we find faith."

“The fact that our next steps are unknown to us is exactly the point.”

“This is not just a lesson for individuals to unlearn, but one for society to unlearn, and we'll be amazed at the energy that's liberated when we do."

"If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you."

"Whereas money today embodies the principle, 'More for me is less for you,' in a gift economy, more for you is also more for me because those who have, give to those who need it. Gifts cement the mystical realization of participation in something greater than oneself which, yet, is not separate from oneself. The axioms of rational self-interest change because the self has expanded to include something of the other."

“It’s the generous person who is the wealthiest.”

“For most people life is not based on all-or-nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state. We simplify life transitions down to single moments because the real stories are more complex, harder to tell, and attract less attention.

The headline, “Quits to Live on a Sailboat” seems more impressive and is easier to talk about than “Couple Slowly and Purposefully Tests Out a Life Transition while Aggressively Saving Money Over Five Years.” As a result, we hear fewer of the real stories, most of which include some kind of prototyping.”

“There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself."

“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."

“The purpose of college, to put all this another way, is to turn adolescents into adults. You needn’t go to school for that, but if you’re going to be there anyway, then that’s the most important thing to get accomplished. That is the true education: accept no substitutes.

The idea that we should take the first four years of young adulthood and devote them to career preparation alone, neglecting every other part of life, is nothing short of an obscenity.

If that’s what people had you do, then you were robbed. And if you find yourself to be the same person at the end of college as you were at the beginning – the same beliefs, the same values, the same desires, the same goals for the same reasons – then you did it wrong. Go back and do it again.”

“The system manufactures students who are smart and talented and driven, yes, but also anxious, timid, and lost, with little intellectual curiosity and a stunted sense of purpose: trapped in a bubble of privilege, heading meekly in the same direction, great at what they’re doing but with no idea why they’re doing it.”

“This is your shot. This is your chance to become, not the person that you want to be, not the person you’ve decided that you’re going to be, but the person that you never could have dreamed of being.”

“Normally man’s mind is composed only of a consciousness of his immediate needs, which is to say that this consciousness at any moment can be defined as his awareness of his own power to satisfy those needs. He thinks in terms of what he intends to do in half an hour's time, a day's time, a month's time, and no more.

He never asks himself: What are the limits of my powers? In a sense, he is like a man who has a fortune in the bank, who never asks himself, How much money have I got?, but only, Have I enough for a pound of cheese, for a new tie? etc."

“Man’s moments of freedom tend to come under crisis or challenge, and when things are going well, he tends to allow his grip on life to slacken.”

“Let us summarize our conclusions briefly: The Outsider wants to cease to be an Outsider. He wants to be 'balanced.' He would like to achieve a vividness of sense-perception (Lawrence, Van Gogh, Hemingway). He would also like to understand the human soul and its workings (Barbusse and Mitya Karamazov). He would like to escape triviality forever, and be 'possessed' by a Will to Power, to more life.

Above all, he would like to know how to express himself, because that is the means by which he can get to know himself and his unknown possibilities. Every Outsider tragedy we have studied so far has been a tragedy of self-expression."

“The first and most fundamental threat to your Future Self is not having hope in your future. Without hope, the present loses meaning. Without hope, you don't have clear goals or a sense of purpose for your life. Without hope, there is no way. Without hope, you decay."

“You can expect the future to take a definite form or you can treat it as hazily uncertain. If you treat your future as something definite, it makes sense to understand it in advance and to work to shape it. But if you expect an indefinite future ruled by randomness, you will give up trying to master it."

“Anything that isn’t taking you toward your Future Self is a lesser goal."

“The lesson is that the things we had thought were most important - achievement, affirmation, intelligence - are actually less important, and the things we had undervalued - heart and soul - are actually most important."

"It turns out that freedom isn't an ocean you want to spend your life in. Freedom is a river you want to get across so you can plant yourself on the other side - and fully commit to something."

“Life is not a solitary journey. It is building a home together. It is a process of being formed by attachments and then forming attachments in turn. It is a great chain of generations passing down gifts to one another."

"The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time and still retain the ability to function.”

#1: “If work dominated your every moment, would life be worth living?”

#2: "Are you on the default path now? How comfortable are you? Are you tempted to leave? Motivated to make a change? What might that look like?"

#3: "When was the last time you heeded a Call to Adventure - some event, conversation with a friend, or inner stirring that caused you to reevaluate your current path?"

#4: "How much money do you need to maintain your current lifestyle? Can that be reduced? By how much? By reducing your fixed expenses, can you open some space for greater freedom and possibility in your life?"

#5: "Of all the things you currently spend money on, how many of those things did you buy in order to show other people how successful you are? Did they even notice? And if they did notice, do you think they're still thinking about you when you're not there?"

#6: "Have you ever tried eliminating something from your life that you believed you could never live without? What would that be? Can you experiment with eliminating it from your life for 30 days?"

#7: "If you embarked on the pathless path tomorrow, what could be some benefits of doing so? What would success, or even a partially successful attempt look like for you?"

#8: "If you don't make a change, what might be the cost of inaction? In 3 months? In 3 years? At the end of your life?"

#9: "Who are you? No really, who are you? If you asked yourself this question five times in a row and kept asking 'Who are you beneath that?' who would you be then?"

#10: "Are you willing to let go of the life you have planned in order to make room for the life that's waiting for you?"

"Judge a man by his questions, rather than by his answers."

"The path to success is to take massive, determined action.”