Book Summary: The Pathless Path by Paul Millerd

Imagining a New Story for Work and Life

📖 The Book in 3 Sentences

1. Paul Millerd thought his job at McKinsey helping C-level leaders in business was a successful approach to life until he started to question himself on his values if this was the right way to live.
2. Paul started to contemplate if there was a different way and through a series of experiments, living in different countries, connecting with different people and communities globally to find his answers
3. Through his experiences and personal journey, Paul forms a set of ideas and principles that guide him from unfulfilled and burned out to a life that is true to himself

🖼 Impressions

The Pathless Path is a personal journey of awakening and is a recommend read for people looking into leaving traditional forms of work, finding a new path or ways of working by dealing with uncertainty that is common when navigating the unconventional "pathless path".

👥 Who should read it?

For anyone considering an exit from a traditional job and finding what way of life is true to one's self, The Pathless Path is a guide to navigating an unconventional way of living and working. If you are unsure about how to take the next step to find your authentic self then this book through the personal journey of author Paul Millerd will give you a perspective on ways to navigate this stage of your life.

💡 How the book changed me

• Helped prepare my thoughts around starting my journey with small experiments
• Encouraged me to find and reach out to people who are embarking on the journey of the pathless path
• That we must place efforts on to living our true selves and living our lives to our own desires, not for other people
• Focus on doing the work that makes you feel alive and also to reflect and look back what work activities made me excited
• Make constant efforts to reinvent oneself and constantly learn about what energizes me
• To be creative and share my work and to embrace the challenges of criticism along that journey

✍️ My Top 3 Quotes

Andrew Taggart believes that crisis moments lead to "existential openings" that force us to grapple with the deepest questions about life.  He argues there are two typical ways this happens.  One is the "way of loss", when things that matter are taken from us, such as loved ones, our health, or a job.  The other path is the "way of wonderment," when we are faced with moments of undeniable awe and inspiration.

As I started to feel better, a different kind of energy showed up in my life.  Professors Richard Tedeschi and Lawrence Calhoun have suggested that many people who face crises often experience "post-traumatic growth" and that this manifests as an "apprecaition for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer extensial and spritual 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.

📒 Summary + Notes

Section 1 - The Default Path

Chapter 1 - Introduction

The author gives an overview of what the pathless path, which is the idea of shifting from traditional societal thoughts on getting good grades, a good job and being achievement focused but at the sake of our own desires that give us a reason a live.

Paul mentions shifting away from a life built on getting ahead and towards one focused on coming alive. The intent is to shift our focus on realizing our deep desires to work on things that matter and bring forth what is inside them.

The Default Path

The default path is defined as the main societal expectations defined by pre-set "life scripts".  Researchers Dorthe Berntsen and David Rubin describe "life scripts" as "culturally shared expectations as to the order and timing of life events in a prototypical life course."

An example would be that expectations for a successful life mean that these moments occur should happen before age 35: graduating from school, getting a job, falling in love, and getting married.

Why This Matters

We must try to live our lives to what we are capable of, not just the ones other think we should live.

A key anecdote that Paul mentions is his parents, both without university degrees and navigating their life by working long hours, or going without recognition of their capabilities for example Paul's mother being the best candidate for the job but was not selected because she did not have a degree.

Chapter 2 - Getting Ahead

World Class Hoop-Jumper

Paul recounts his time in school and university where his life was influenced by other honors students who had impressive achievements to their name.  The key focus was landing good internships and/or jobs and getting accepted into graduate schools.

To get ahead, Paul started to find short cuts and not truly using his mind.

Strategy Consulting

Paul learns about the prestige of strategy consulting and starts to direct his career torwards landing a role in this space.

Chasing Prestige

Paul navigates the recruitment processes for various companies by attending networking events, landing interviews and ended up taking an offer with GE.

Upon working at GE, he found the organization slow and disengaging.  Found a job at McKinsey and after several interviews landed the job!

The Inner Ring

Whilst at McKinsey, Paul started to adopt the norms of his colleagues and he focused his ambition on attending a top business school.  As part of the environment where success was getting into a top business school, Paul was accepted into a dual-degree program at MIT.

Existential Opening

Paul's grandfather is diagnosed with pancreatic cancer and whilst initially in denial, makes the trip to see him when his condition worsens.  He spends a significant amount of time with him and family and in his grandfather's final days learns that family, love, and relationships are the most important things in the world.  At the back of Paul's mind he is thinking about work and takes some time to check and respond to emails but realizes that this trivial activity might have caused him to miss key moments with grandfather but also to question what was he living for?  What did he really want? How did he want to look back on his life when it was his time to go?

Business School

Paul's memories of business school were ones where he lived life to the fullest - being present for everything and following his interests.  Upon conclusion of business school, he applied to various consulting companies and also McKinsey rejected him.

Health Crisis

Paul joined a boutique consultancy but during his 18 months started to deal with health issues with persistent fatigue and brain fog.  Paul was diagnozed with Lyme disease.  After struggling with his health condition at work where he was dealing with extensive pain and exhaustion, Paul worked with his company CEO to take several months of unpaid leave to manage it. To process his questions Paul took the time to write a blog called "Lyme Sucks". The experience of the illness was changing him as he wanted to restart his life.  Paul started to contemplate "What would people think if I don't work again?" and through each day of sickness and pain started to think about his own self-identity of being a high achiever.  He would give up his straight-A's and McKinsey career to feel OK for a single day.  Paul found a new doctor in Boston where with new treatments was able to help him improve to the point where he returned to full-time work. This is where Paul started to discover "the pathless path".

Chapter 3 - Work, Work, Work

Where Do Work Beliefs Come From?

Paul looks at the history of why we work.  How as humans we treat it as a duty and a reason to meet the needs of our families and communities. Sometimes it can be about a higher calling with regards to religion and determining one's status with God.  Catholic and Protestant perspectives on work focus deeply on the default path. As we grow up we never question this stance but based on human history - the sole focus on work was not always the case!

It Was an Anomaly!

Jim O'Shaughnessy:

We made a mistake and by that, I mean my generation and my parents' generation.  The mistake we made was thinking that the period from 1946 to 1980 was the norm.  No, it was not! It was the anomaly! We had just wiped out the manufacturing capabilities of anyone who could challenge us.  So, the idea that you had the job with the gold watch, and you could work there for your entire career and raise a family of four and all of that, that was an anomaly.

Peter Thiel:

During that stretch of time, it would have been a mistake to opt-out of the default path because as Thiel points out:

Whether you were born in 1945 or 1950 or 1955, things got better every year for the first 18 years of your life, and it had nothing to do with you.

Factors that support meaningful lives, like economic growth across all sectors, a young population, two-parent households, generous pensions, and company loyalty were anomalies of the past, as O'Shaugnessy points out.

The Meaningful Work Trap

Paul looks at how the current generation enter the workforce with high expectations that we want work to be meaningful and fulfilling.

It's high stakes when an entire generation of workers not only thinks that work should be the most important thing in their lives, but also that it should enable them to thrive in all aspects of their life.

Wage-based Society

In this section it gives examples of how people work a job for the sake of having a job.  Sometimes people are willing to spend their lifetimes completing pretend busywork or be in constant pursuit of more work for the sake of just working.

Chapter 4  - Awakening

Pebble in My Shoe

One can navigate a long and successful career with accolades, promotions but the discomfort never subsides or disappears.

A Daily Reminder

Paul starts observing his colleagues at work with new perspective and questions if they themselves are happy.  He starts to questions his values and think what his new priorities are which become: health, relationships, fun and creativity.  And to achieve this Paul states:

The answer, my dear reader is simple.  You start underachieving at work.

A Fool's Journey

Paul starts experimenting and starts a career coaching page and takes up a new job to setup a consulting practice that provides services to CEOs.  Landed two paid coaching clients, created an online course on resumes, started sharing writing publicly and several clients navigate career and life shifts.

With the lack of motivation at work, Paul focused on his side projects.  He say the best way to navigate these projectts is to embrace:

".. what author and educate George Leonard called "the spirit of the fool".  he argued that when you start learning anything new it will make you "feel clumsy, that you'll take literal or figurative pratfalls.  There's no way around it."

Pushing Forward

Paul talks to his boss about his desire to go on his own.  His own performance started to decline as he lost motivation at his day job.  In his own mind he is fighting the battle to stay on the default path, mentioning aiming for another raise and promotion.  Paul felt he was suffocating on this path and he had to take action.

What I Am I Worth?

Paul applies for another consulting job but is offered $50k less. This gets him thinking about the concept of money and how it is attached to self worth.  This is where he asks himself:

What if I paired making less with working less?

Chapter 5 - Breaking Free

Not Who I Wanted To Be

Paul questions himself that he is not being true to himself and he would need to get creative to bring forward his values of what he wants in his life.

Email from Sarasota

Paul quits his job.

Commuting in the Blob

Paul details his last 3 months at his job, processing his exit of the workforce and wondering how he will survive day to day.

Too Smart for Burnout

Paul talks about the aspects of burnout and how he writes about it on his first day being out of his job.  This event helps him move forward.

The Dynamics of Mourning

Paul celebrates the departure froms hib job by taking an extended trip in Europe.  Normally he books 2 week trips but this time he books 5 weeks making him realize this is outside his normal way of operating.  At the same time Paul mourns the end of his working career.

Fool with a Sign

Paul starts trying different jobs - interviewing people about Allbirds, helping a professor launch a non-profit in Boston.  Paul moves to Boston to reduce his living expenses as NYC.  Paul enjoys the newfound freedom and ownership over his life.

Am I Worker?

Paul contemplates the following question by Andrew Taggart.  "If work dominated your every moment, would life be worth living?" and he answers the question is no.  He references German philosopher Josef Pieper on the topic of work and leisure where leisure is a "condition of the soul".  He reaches out to Andrew Taggart who proposes three more questions:

1. Are you a worker?
2. If you are not a worker, then what are you?
3. Given who you are, what life is sufficient?

According to Taggart, living in a world dominated by total work undermines the "playful contemplation concerned with our asking, pondering and answering the most basic questions of existence".

Possibility

Paul ends six months of freelancing and decides to take a non-work sabbatical.  He wakes up and does whatever he feels like.  Paul starts to get drawn back into creative projects and is starting to live his life on his terms alinging to his intentions of : health, relationships, fun & creativity, and career.  He learns to live his life not oriented around work.

Paul covers the concept of Ikigai: "reason for being" or "something to live for".

One week before he departs to Asia on a month long trip, a freelance recruiting company calls Paul about an opportunity to build a consulting skills training program. Initially he is disappointed because he feels he may not be able to take the opportunity but instead he lists his terms of working 10-15 hours, double his normal rate with the ability to work from Asia.  They accept his proposal!

Paul works across Asia during his trip and he starts to explore where his journey takes him.

Chapter 6 - The First Steps

Protoype Your Leap

Paul investigates two examples of people who have successfully exited the default path.  Examples include John Zeratsky who sailed around the world for 18 months and Diannia Merriam who as part of the FIRE community through little side projects eventually left her fulltime job to work her new life. The emphasis on this chapter is the importance of running small experiments to your future life and see where things go.  Making small and deliberate changes to our life opens up opportunities, possibilities and connections that might illuminate the next steps of what comes next.

Wonder Tips the Scales

We stay in familiar environments that are painful because the unknown brings discomfort that is hard to predict.  We instead stay busy, adapt to our workplace challenges and get distracted by non-value add activities.

In summary: Uncertain Discomfort < Certain Discomfort + Coping Mechanism

People who have successfully made changes have done so through wonder.  Wonder is defined as:

state of being open to the world, its beauty, and potential possibilties.  The need to cope becomes less important and the discomfort on the current path becomes more noticeable.

In summary: Uncertain Discomfort + Wonder > Certain Discomfort

This concept covers the dilemma that we face. If we continue to avoid our true "self" by continuing to work - we will look back on our life with regret.  When making life changes overcoming the challenges of discomfort of not knowing what will happen will reveal themselves.  We should ignore the impulse to revert back to what we are comfortable with but we should open ourselves up to discover what wonderful things might also happen.

Seeing the World in a New Way

Starting this journey will bring a sense of vagueness about the journey.  But really it is the beginning of seeing the world in a new way.

Find the Others

Connect with other people who are taking the same journey.  Don't be shy to reach out to them because they will also be wanting to learn from you.  Most people on this path have family members on the traditional path and it's important to seek lessons learnt from others along the journey.  When you meet others there's a common bond where both of you understand the struggles of walking the pathless path.  Working a traditional job, the consistent financial rewards help one live a smooth existence needing to rely less on others.

Tame Your Fears

You must confront your fears.

Complete Tim Ferris' "fear setting" reflection exercise.

The exercise has six steps. The first four are straightforward:

1. Write down the change you are making.
2. List the worst possible outocomes.
3. Identify the actions you would take to mitigate those outcomes.
4. List some steps or actions you might take to get back to where you are today.

Writing about fears helps to translate them into issues.  However not all fear issues can be resolved and we must accept them.

The second two are:

5. What could be some benefits of an attempt or partial success

6. What is the cost of inaction in three months, 12 months, and in a few years?

It's important to be true to oneself.  The author mentions the blog of Bronnie Ware: https://bronnieware.com/regrets-of-the-dying/

Will They Still Love You?

The author discusses having different points of view with family members and friends who maybe on the traditional path that values comfort and security.  The pathless path offers significant personal growth however not everyone may see this and one may ask themself "will the people in your life love you less?" to address the deepest and scariest issues.

Section 2 - The Pathless Path

Chapter 7 - Wisdom of the Pathless Path

The Life Changing Magic of Non-Doing

The author starts living a phase of "non-doing" in Taiwan and starts to embrace a way of living that is not filled with anxiety and tension, but reflective and open.

Give Me A Break

The author lists examples of individuals leaving work on a sabbatical only upon return to make a decision to pursue a "non-work" journey.  Each person talks about how different life feels when it is not purely orientated around work.  This opened up the possibilities torwards different kind of lives which were formerly hidden and restored the energy back into living.

Waiting For Retirement

The author talks about and challenges the notions of retirement.  He adopts Tim Ferris' idea of mini retirements from the book The Four Hour Work Week.  Rather than pack a vacation into 2 weeks, take 1-6 months off throughout one's life.  The mini-retirement is not an escape from life but a re-examination of it.

He asks three questions during these breaks:

1. How do your decisions change if retirement isn't an option?
2. What if you could use a mini-retirement to sample your future plans now?
3. Is it really necessary to commit fully to work to live like a millionaire?

You can work intensely for a few weeks and then take a break in a sustainable and energizing way over the long term.  On the default path this variability is difficult to achieve.

Have Fun on the Journey

The pathless path may not have a specific destination or "fixed points".  Fixed points are defined as a non-negotiable goal one intends to achieve, no matter what.  Home ownership is a popular fixed point, making partner etc. Whilst it's important to have goals according to Venkatesh Rao, it's important to find unique fixed points that align to our true self that energizes us.  John Stuart Mill gives similar advice in his book On Liberty that people need to embrace their individuality and perform "experiments in living".  By choosing a unique and personal fixed point, you raise the odds of finding a path to stay on and serving an important role in pushing culture forward.  Tech entrepreneur Sean McCabe takes every 7th week off.  More info on Sean here: https://nathanbarry.com/051-sean-mccabe-building-successful-creator-business-starts-writing/

Reimagine Money

The author rethinks how money affects him.  He has to find a lower cost of living, become a minimalist to build financial security. With the reduce income came increased freedom and started doing things he cared about.

Have a Little Faith

Paul takes a leap of faith and follows Angie to Thailand but he emphasizes existing with the fears of no money, no stability and not having the answers to these prbolems.  Rather than trying to tame or control them learn to accept they exist and co-exist and open up to the world.

Chapter 8 - Redefine Success

The Second Chapter of Success

Tells the story of Kevin Durant chasing a championship and after he eventually won one, felt unfulfilled.  Accomplishments don't bring lasting happiness and even after each achievement we still continue to ratchet up the next goal and continue which is why maybe disappointment is a way to re-evaluate what success means. Re-orientating to different goals like feeling alive, helping people and meeting one's own needs meant Paul wasn't competing with anyone else.  This increased the odds of him continuing his journey on the pathless path.

Prestige and "Bad Tests"

Prestige and status that comes from joining top tier companies sometimes hides our short comings.  We spend time navigating bad tests ("gaming the system") by clever tricks in corporate jobs by getting certain senior leaders to like you, dressing a certain way and speaking a certain way.  Paul Graham often finds young founders trying to hack bad tests as a way to success and struggles to convince them that their true success is building a product that people love. When freelancing or being indepedent, one must really focus on the quality of ideas and the ability to do good work.  There is less people to impress and empahsis on brand but on skills, learning and reputation.  Bad tests are a product of how corporations see the world and by taking the pathless path we can escape these silly games.

Find Your Tribe

Paul interacts with other people online through his writings and mentions that there are communities of people you can connect with going through the same journey.  You should find them and connect with them.

You Are a Bad Egg

Release yourself from the concept of full-time employment and realize that there are an infinite amount of possibilities out there.  The term "good egg" and "bad egg" is used to describe the traditional path of a corporate job as being a "good egg" - there are no "good eggs" or "bad eggs".

Find Your "Enough"

Book: Company of One by Paul Jarvis

Enough is the antithesis of unchecked growth because growth encourages mindless consumption and enough requires constant questioning and awareness. Enough is when we reach the upper bound of what’s required. Enough revenue means our business is profitable and can support however many employees/freelancers we have, even if it’s just one person. Enough income means we can live our lives with a bit of financial ease, and put something away for later. Enough means our families are fed, have roofs over their heads and their futures are considered. Enough stuff means we have what we need to live our lives without excess

Paul's version of enough:

Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand. Enough is knowing that the clothes, fancy meal, or latest gadget will not make me happier, but also that buying such things won’t mean I’m going to end up broke. Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me.

Beyond Scarcity Mindset

After being unemployed for several months, money was once a consideration was now a very important aspect of life.  Paul was experiencing "scarcity mindset".  By being starved of a paycheque, Paul did not look into the root cause of his insecurities.  Unfortunately no amount of money ever seems to satisfy.  The only way to overcome these insecurities is to live a life that is heroic - grapple with your insecurities and seek a life that is uniquely yours.

Behind our money fears are existential fears, like the fear of death or the fear of not being loved, respected, and admired. These fears are likely not solvable but we can learn to coexist with them. This is also why financial worries can be infinite and people can chase more and more their entire lives. The flip side of this is that if we can learn to coexist with our financial insecurities, we can turn them into a secondary concern. This opens you up to the real secret: the opportunities of the pathless path are infinite too.

Chapter 9 - The Real Work of Your Life

Finding Your Conversation

Open oneself to the world and ask it questions:

What matters?

Why do we work?

What is "the good life"?

What holds people back from change?

How do we find work that bring us alive?

In our daily lives we should try to exist at the "frontier" of reality - by not pushing torwards our "frontier" we risk missing out on a "deeper, broader, and wider possible future that's waiting".

Have at least one close person to have conversations with about your journey - to help with ideas, engagement and maintaining curiosity.

Design For Liking Work

The founder of Ghost, John O'Nolan spent many years trying to build a million dollar company.  After many failed attempts he reevaluated and instead built a company he wanted to be stuck with.  All his decision are based on his goal that his organization is purely focused on what he wants to do.

The point here is to keep finding work that you actually enjoy doing.   And you should always experiment with different types of work to find out which work you like the best and build your life around the type of work that you enjoy.

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.

Book: Stephen Cope, The Great Work of Your Life

The author interviewed multiple notable people in his book and found that each person worked hard to bring forth what was inside them - they worked hard to protect their time to focus on what mattered.  We should be resolutely faithful to what we are.

We Want 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.

Remembering What You Forgot

Reflect on what activities in the past brought you alive.  We should strip away the stories and expectations that are not us and embrace the work we truly enjoy.

You Are Creative

We are all creative and we should not wait for the opportunity to start being creative.  The internet and today's technology allows us to start creating and producing content immediately without the need ot ask for permission to do so.  We should also not be worried what other people think about our creative endeavours.  Criticism will always come but our first challenge is building an audience.

Who Do You Serve?

When making your content or pursuing your creative outlets.  Remember to remind yourself who your core audience/supporters are.  Once you work this out you should focus in on what makes your content great for your target audience.

The World Is Waiting

Get out there and start creating/sharing.

Virtuous Meaning Cycles

This is possible on the pathless path. 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.

When being creative, never start with frustration or cynicism.  Lead with curiosity, vulnerability and passion to attract the right people you'd like to meet.

Chapter 10 - Playing the Long Game

Working Backward

Start from the worst case scenario and work backwards.  For example, What does a miserable life entail? What actions would make achieving such a life more likely? Then we try to figure out how to make sure these do not come true.

Write a description of who you don't want to be then brainstorm actions that might create that outcome.

The Positive Side of Freedom

With the pathless path there comes a lot of free time - it's important to be constantly deliberate about finding out what we want by constantly learning and exploring.

Reinventing Who You Are

Change is always going to disrupt and interfere with our plans. Therefore it's important that we keep evolving with the times and taking the perpetual mindset of constant reinvention of ourselves to keep pace with change.

Embracing Abundance

1. Find ways to give without expectation of anything in return
2. Be willing to receive gifts in any form and on any timeline
3. Be open to being wrong about all of this and adjust my approach as necessary

Coming Alive Over Getting Ahead

Be cognizant about the paradox of choice and priortize accordingly:

Everyone on the pathless path eventually needs to develop a strategy for approaching their journey. On the pathless path, once you open yourself up to possibilities and start experimenting with different ways of working and living, the biggest problem is the paradox of choice. There are too many interesting things worth doing and too many places to visit. To prioritize, developing a set of principles to help you make decisions is essential.

Explore all possibilities

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.

Remember your purpose, you want to do what is true to what you set out to do.

After my initial frenzied efforts to land freelance projects, I reflexively said “no” to many paths to making more money. This meant more financial insecurity, but I was doing it because I didn’t want to fall into the trap of creating another “job” for myself. This ultimately paid off as the space I created enabled me to be creative, become more resilient, and find a positive way to engage with my work and the world.

Create Your Own Culture

The author tells the story about Morrie and Mitch from the book "Tuesdays with Morrie".  Morrie and Mitch reconnect and discuss lessons on living life.  A key theme to the book is to have the courage to walk away from an identity that seems to make sense in the context of the default path in order to aspire to things we don't understand.

After Morrie passed, Mitch made some drastic changes to the activities in his life from being centered around work to instead focused on helping people.  He created his own culture.

Some assumption on life to create a culture for yourself:

• Many people are capable of more than they believe.
• Creativity is a real path to optimism, meaning, and connection.
• We don’t need permission to engage with the world and people around us.
• We are all creative, and it takes some people longer to figure that out.
• Leisure, or active contemplation, is one of the most important things in life,
• There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself.
• Finding the work that matters to us is the real work of our lives.

Unfortunately, embracing the pathless path means accepting that you might not know what you are doing and you might look like a fool. This is exactly how I felt in those first few months.

Go Find Out

Have a go!

10 lessons from this book in summary:

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