Book Notes: The Pathless Path

In One Sentence

“I want to see people live the lives they are capable of, not just the ones they think they are allowed to live.”

Paul Millerd, The Pathless Path

Top 3 Takeaways

1. There’s an alternative to the default path of doing what most people do (getting good grades -> studying -> working in a mediocre office job), it’s not as straightforward but more fulfilling.
2. Think and reflect deeply about your life. Figure out which social norms and values truly resonate with you and accept them. Also find and reject the ones you were just told over and over but not actually match with how you think about the world. Write down your findings, for example your Definition of Success and your Definition of Enough.
3. I want to try out this «Pathless Path» and not find myself later in life regretting to only have spent my time unhappy in a corporate job. Working is not bad, but spending 40 hours a week at a job you don’t like is.

About The Author

Paul Millerd started his career in what he calls «the default path» by working as a strategy consultant in high-profile firms. He noticed that he wasn’t really happy in his well-paying job and started to figure out if there are any alternatives.

Who Should Read This Book?

• People feeling stuck in their job
• People feeling unfulfilled and wondering if the traditional 9-to-5 job is what they really want
• People that like to think, reflect and question on how to live life
• People that got «traditionally successful» and wondered if that’s really it once they reached their goals

How The Book Changed Me

• I created my own Definition of Success and put it online
• I created my own Definition of Enough and put it online
• Although the real lasting effects of reading this book will be seen once I return from my travels and I have to decide on what to do with my time, it made me question really hard if I want to go back to «just» being a Software Engineer in a traditional employment.

Best Quotes

If you can see your path laid out in front of you step by step, you know it’s not your path. Your own path you make with every step you take. That’s why it’s your path.

As I’ve lived in different places around the world and focused on different kinds of work, I’ve created mini-experiments that help me learn more about how I want to live my life.

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. Many people say things to me like ‘I could never live like you do!’ All I can think, however, is ‘Have you tested that?’

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 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.

Alan Watts

Summary & Notes

DISCLAIMER:
The following notes are my raw notes for each chapter in the book. They are meant to be used as a quick overview and not to be read as fully fleshed-out and thought-out sentences.

Questions to ask yourself

• What am I living for?
• What do I really want?
• How do I want to look back on my life when it’s my time to go?
• While observing your colleagues in their job:
  • Are they happy?
  • What kind of pain or challenge are they dealing with?
  • Is this how they want to spend their time?
• Why am I trying to get a raise when I know I am not in a good working environment?
• What if I paired making less with working less?
• If work dominated your every moment, would life be worth living?
  • Are you a worker?
  • If you are not a worker, then who are you?
  • Given who you are, what life is sufficient? What is your definition of enough?
• What if I took working for a paycheck out of the center of my life, what would my life look like? What would I do all day if it wasn’t for the money?

Action items

• Have a daily reminder list with your life priorities, so you see that work is (probably) not the most important thing in your life. Example:
  1. Health
  2. Relationships
  3. Fun & Creativity
  4. Career
• Create your own Definition of Success
• Create your own Definition of Enough like Paul Jarvis
• Work backwards by defining the person you do not want to be and then doing the exact opposite of what that person would do

Chapter 1 – The Default Path

• The default path = study hard, get good grades, get a good job, work hard until retirement
• On the default path filled with impressive names and achievements, no one asks «Why are you doing this?»
• The pathless path = alternative to default path, call to adventure, embrace of uncertainty and discomfort
• You work hard, but get laid off anyway. You have the perfect life on paper, but no time to enjoy it. You retire with millions in the bank, but no idea what to do with your time.
• People try to escape feeling stuck instead of having a deeper conversation with themselves.
• Leo Rosten about purpose of life: «to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.

Chapter 2 – Getting Ahead

• Paul Graham on prestige: «a powerful magnet that warps even your beliefs about what you enjoy.»
• Alan Watts: «the desire for security and the feeling of insecurity are the same thing.»
• «My friends all had impressive plans after graduation, and I didn’t want to be left behind. People were impressed by the job I was taking, and I liked how the attention made me feel. I felt smart.»
• 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.

Chapter 3 – Work,Work, Work

• Work nowadays is an obvious goal and constantly reinforced by society. People barely pause a moment to question why and for what they work so hard all the time. For most of human history, this was not the case.
• «The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve.» – Seth Godin
• The author claims that the current view of work-life stems from the booming years after World War II and that these views may not fit the current realities. You can’t just work 40 hours for 40 years in the same job and easily buy a house and feed a big family. «Since tracked careers worked for the baby boomers, they can’t imagine that they won’t work for their kids, too.» – Peter Thiel in «Zero to One»
• The booming era was an anomaly, not the normal way in life. If you were born in that time, life got better each year and it had nothing to do with what you did.
• Reference to Bullshit Jobs by David Graeber: «Why the hell are so many grown adults spending their time on obviously pointless tasks?»

Chapter 4 – Awakening

• Working in an unsatisfactory job is like having a pebble in your shoe: you’re walking and something is off, and it’s mildly uncomfortable. Promotions and salary raises make this feeling go away temporarily, and you start to become a passive participant in your life as you get accustomed to this mild discomfort.
• Once you start asking yourself questions and thinking about your life you will come to the question of: «How do you design a life that doesn’t put work first?»
• Austin Kleon on creative work: «it runs on uncertainty; it runs on not knowing what you’re doing.» The creative work of finding a new life path is similar.
• In the first few years of a new job/career you learn a lot (presenting, communication, technical skills, research) but after a few years you just learn company-specific behaviors and attitudes.
• Once the pebble in your shoe gets too annoying and you start to break down and think about leaving your job, often the phenomenon of doubling down surfaces: you convince yourself that this career is the real deal for you because it’s safe and easy and you start to work hard once again to «get over the slump» despite all evidence that this career does no longer work for you. It’s easier to aim toward another raise or promotion than daring to ask myself deeper questions –> Boiling Frog Theory.
• Making more money is probably not on your priorities list, so why are people so attached to having a stupid high paying job rather than a fulfilling lower paying job?
• What if I paired making less with working less?

Chapter 5 – Breaking Free

• Burnout
  • People dedicate themselves to being «good workers», and being successful means keeping clients, customers, and managers happy while fitting into a company’s cultural norms. Unfortunately, success for the company does not always align with what is best for the person, and over time, a disconnect can emerge.
  • When burned out, people may start being cynical about their working conditions and their colleagues and may distance themselves emotionally and start feeling numb about their work.
  • Before World War II: «We are not-at-leisure to be-at-leisure». Today this is flipped in the mindset of total work. We work to earn time off and see leisure as a break from work.
  • People mistake leisure for idleness and work for creativity.

Chapter 6 – The First Steps

• Don’t do all-or-nothing decisions out of the blue. Start with small steps and «prototype your leap».
• 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.
• Many people dislike some parts of their jobs. But they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown and change brings discomfort in hard to predict forms. So people avoid change and develop coping strategies. They learn to sidestep the manipulative manager, or change jobs every couple years, plan vacations, stay busy, and get drunk during the weekends.
  • Uncertain discomfort < Certain Discomfort + Coping Mechanism
• Instead of coping, start to wonder and think about who you might become if you embrace the discomfort. «if I don’t do this now I might regret it.»
• Find the others: at first online resources will be good enough but then you need to get to know real people that know what you want to do and understand what you are trying to achieve.
• The pathless path is an aspirational path and can never be fully explained to others.

Chapter 7 – Wisdom of the Pathless Path

• «We must let go of the life we have planned, so as to accept the one that is waiting for us.» – Joseph Campbell
• Curiosity re-emerges: when people have time they try new activities, revisit old hobbies, explore childhood curiosities, and start volunteering and connecting with people in their community.
• Misery Tax, concept by Thomas J. Bevan: The spendings an unhappy worker allocates to things that «keep you going and keep you functioning in the job.» Examples: alcohol, expensive food, vacations, unnecessary tech gadgets.
• Many people are convinced that the formula for living on their own terms is saving up money. But actually, the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is.

Chapter 8 – Redefine Success

• “Arrival Fallacy” defined by Dr. Ben-Shahar: the idea that when we reach a certain milestone we will reach a state of lasting happiness.
• Don’t try to achieve someone else’s goals.
• On the default path, you are automatically a «good egg». On the pathless path, people default to seeing you as a «bad egg». Even if it was never spoken, when the author left the default path he felt as if he had immediately crossed an imaginary boundary where he was some sort of rebel that needed to defend his recklessness.
• On the pathless path at first, you will sense that you are doing something wrong, or at minimum, don’t know what you are doing. Simple questions from others like «what do you do?» will expose your own uncertainty and can feel like a death blow to the soul.
• When you work for yourself, you spend zero minutes a year blaming other people for your circumstances. It forces you to take complete ownership of your life and continue to experiment, reflect, and try again.
• Don’t play to not lose, play to win.

Chapter 9 – The Real Work of Your Life

• 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. It’s a shift from the mindset that work sucks towards the idea that you can design a life around liking work.
• We want to be useful. Sebastian Junger: «humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary. Modern society has perfected the art of making people not feel necessary.»
• With the internet, you don’t need permission to show yourself and your creativity no more. You can just go and do it.
• People get stuck by thinking «what will people say?». This is valid. It’s scary to share with the world, and if you do it over a long enough period, criticism is inevitable. But: at first you don’t have no audience at all which can be a good thing because it enables you to experiment while building up your confidence slowly. At first, no one really cares about what you do.
• Don’t adapt to conform to haters that don’t share your values or don’t get you. Know who you serve. Seth Godin: «once you figure out who you intend to serve, you can go all-in and focus on what it takes to become great.»
• Believe in People:
  • «Any time I consume something from an individual that inspires me, I have to send them a note to let them know. Creating and sharing in public takes an incredible amount of courage and I remember how awkward and scared I was at the beginning of my journey. It’s easy to tell people what they got wrong but much harder to say “I love what you are doing. I hope you keep going and let me know if I can help.”»
• It doesn’t matter how you start but that you start.
• William Zinsser on Writing: «Believe in your own identity and your own opinions. Writing is an act of ego, and you might as well admit it. Use its energy to keep yourself going.»

Chapter 10 – Playing the Long Game

• To find out what you want to do, work backwards by thinking about what you don’t want to be doing.
  • Imagine what kind of person you do not want to be. Then find out how you could become this person and do the opposite.
• Be Antifragile (by Nassim Nicholas Taleb) by building up multiple income streams even if it means to decrease your income in the short term.
• It’s important that you play for the infinite game of staying on the pathless path. Don’t play for the finite game where you go for fast one-time success.
• Don’t fall for the End of History Illusion. You and the world around you will change in the future. Take an active part to shape those changes instead of reacting to change by denying, delaying or rejecting it.
• Embrace giving gifts but also be comfortable with receiving gifts.
• Final summarizing 10 actions to do
  1. Question the default
  2. Reflect
  3. Figure out what you have to offer
  4. Pause and disconnect
  5. Go make a friend
  6. Go make something
  7. Give generously
  8. Experiment
  9. Commit
  10. Be patient