While I was entertained in my Intro to Philosophy class in college, I was not fully “awake” to ponder the questions I pretended to understand in my essays. In college and in grad school I studied Engineering and Business, which is to say that most of my mental energy was focused on the optimization type of thinking found in math, science, and finance. Find a problem and solve it. Asking questions like “What is the good life?” sounded great, but I had no idea how to really reflect and go deep.
As I started my career, I began my own sort of philosophical and liberal arts education. But given my limited background, I had to lay the groundwork to get to some of the deeper questions and mental models that helped me eventually take a leap to carve my own path beyond the corporate world.
I often see people suggesting deep philosophical books that question the meaning of life but realize given my own past mental models, that this approach doesn’t make sense for many people.
It is easy to dismiss books such as Dale Carnegie’s “How To Win Friends And Influence People” or David Schwartz’s “The Magic Of Thinking Big” but to someone indoctrinated in business, those may be the most reasonable books to start with. Alas, it was these kind of books that made me hungry to go deeper.
What follows are ten types of books that you can use as a roadmap to dream of a life beyond the corporate world. I’ve offered a “starting point” for each category which is probably the most accessible of the options:
- Thinking About What Matters
- Building “Human Skills” In The Workplace
- Know Thyself…In The Business World
- Questioning The Modern State Of The Business World
- Finding Some Hope In The Business World
- Mindfulness & New Emotional Mental Models
- Carving New Paths & Wandering Into The Unknown
- New Models For Seeing The World
- Grappling With The Role OF Work In Our Lives
- Going Deep – The Hard Questions
I. Thinking About What Matters
Start Here 👉 Tuesday’s With Morrie (Mitch Albom)
Helped me to think about life from the perspective of the end of one’s life. In this story, Morrie has lived a full life and has deep relationships as evidenced by the number of people who are constantly visiting him.
So many people walk around with a meaningless life. They seem half-asleep, even when they’re busy doing things they think are important. This is because they’re chasing the wrong things. The way you get meaning into your life is to devote yourself to loving others, devote yourself to your community around you, and devote yourself to creating something that gives you purpose and meaning.
Last Lecture (Randy Pausch)
Randy Pausch is a dying professor who decides to devote his energy into a literal last lecture. What transpires is a talk focused on never ignoring your inner child and a story that will likely deeply resonate with many.
Survival In Auschwitz (Primo Levi)
This book is a deep contemplation into what is means to live and survive in the darkest of places.
Sooner or later in life everyone discovers that perfect happiness is unrealizable, but there are few who pause to consider the antithesis: that perfect unhappiness is equally unattainable. The obstacles preventing the realization of both these extreme states are of the same nature: they derive from our human condition which is opposed to everything infinite.
II. Building “Human Skills” In The Workplace
Start Here 👉 How To Win Friends And Influence People (Dale Carnegie)
I know, I know! Cliche. So What? The simplicity of the book makes it powerful. It doesn’t need the latest and greatest psychology studies. It just offers principles about how to treat people and is a reminder that the norms and assumptions about behavior in the modern business world lead people astray. For example, if you want to change someone’s mind, focus more on getting that person to like you instead of attacking them with facts and to focus on simple things like listening:
Talk to someone about themselves and they’ll listen for hours.
Influence (Robert Cialdini)
This book was a bit mind-blowing, making me realize we are more susceptible to influence than we realize. Cialdini has written extensively about how things such as social proof, reciprocity, commitment, authority, liking and scarcity drive our behavior. Becoming aware of our behavioral biases will help you identify the decisions you really want to make as opposed to the ones you are just falling into
The Art Of Learning (Joshua Waitzkin)
This book is terrific. Waitzkin walks through how he became a chess champion at age 8 and brought Gary Kasparov to a draw at 11 years old. After quitting chess, he applied the same approach to Taiwanese push hands and became world champion. He introduces the concepts of “beginner’s mind” as well as his own framing of “numbers to leave numbers” which is a great way to show that to go fast, you first need to go slow.
III. Know Thyself…In The Business World
Start Here 👉 How Will You Measure Your Life (Clayton Christensen)
This book is a fascinating perspective on how to define success from within the corporate world. Christensen made me gain hope about leading with principles in the corporate world, positioning “management” as a way to have a positive impact on other people:
“If you want to help people, be a manager”
I thought I had a good understanding of introversion and extroversion until I read this book. This book also made me realize I was a lot more introverted than I realized. This is where I first heard of the term “ambivert” and realized I am energized by a mix of alone time and activity with others. I was fascinated by the history of how extroversion became such an ideal in modern society and the mistakes that can lead us to make.
Mastery (Robert Greene)
Mastery is an incredible book for anyone with a creative bone in their body. Greene talks about the different phases one must undertake if they want to become a master at their craft or develop a wide range of skills. He helps people understand the hard decisions that need to be made, such as leaving a teacher (see: manager, leader) once you have learned enough so that you can go out on your own.
IV. Questioning The Modern State Of The Business World
Start Here 👉 The Halo Effect . . . and the Eight Other Business Delusions That Deceive Managers (Phil Rosenzweig)
A clear and convincing case that most explanation of who is “successful” and a failure in the business world is highly subject to market dynamics and the firms that happen to have the most profitable business model of the time. This book will make you highly skeptical of modern business “research” and stories praising or criticizing leaders.
Shareholder Value Myth (Lynn Stout)
This book is a must-read for anyone who has a suspicion that there may be other and better ways to measure success in the world than money and especially, “shareholder value.” This book helps show that our current state of affairs is a recent innovation.
Reinventing Organizations (Fredrik Laloux)
This book highlights organizations that are typically led by truly transformational leaders that have questioned the status quo and built organizations (sometimes very large ones) that start with deep trust in people and their ability to solve problems. This book shows that self-organization can work and that it is likely the only path forward if we want to build a better business world.
Skin In The Game (Nassim Taleb)
Taleb looks at the concept of “skin in the game” in terms of people, employees, and organizations. His perspective on the modern state of the employee/employer relationship:
So employees exist because they have significant skin in the game –and the risk is shared with them, enough risk for it to be a deterrent and a penalty for acts of undependability, such as failing to show up on time. You are buying dependability.
He argues that the modern employee is no longer a “company man” but rather a “companies man”:
A companies person is someone who feels that he has something huge to lose if he loses his employ-ability
V. Finding Some Hope In The Business World
A big part of my career in the business world was an obsession with trying to understand first why organizations seemed to drive so much stress and anxiety in people and then second, what we could do about it if anything. This led me to discover a number of books that not only helped me discover new ideas for business, organizations, and leadership but also develop my own perspective on what’s happening in the modern workplace.
Start Here 👉 Drive (Dan Pink)
Pink’s introduction of the concepts of autonomy, mastery, and purpose through research and company examples is a great way to discover self-determination theory, which is a foundational theory of what motivates people. If you look at modern organizations through the lens of motivation, you would assume that everyone had lost their mind.
Work Rules! (Laszlo Bock)
The key takeaway from this book was the fact that many things you can do to improve the employee experience are free. Too many organizations think that transformation comes at a major cost. But as Bock shows in many examples in his experience at Chief People Officer, the hardest things to do are to trust people and give them freedom to make mistakes.
VI. Mindfulness & New Emotional Mental Models
Start Here 👉 The Heart Aroused (David Whyte)
I wish I read this book at the beginning of my business life, but I wonder if it would have been too soon. Whyte speaks poetically about the experience of the business world in a way that well, arouses your heart. Whyte’s summary of the book:
(it) will look at the link between soul and belonging, creativity and failure, success and stasis, efficiency and malaise at work, but it sets as its benchmark not the fiscal success of the work or the corporation (though this certainly can be good for the soul) but the journey and experience of the human spirit and its repressed but unflagging desire to find a home in the world.
Nothing Special (Charlotte Joko Beck)
This was the first book I read about Zen Buddhism and mindfulness. The story is a conversation between Beck and her students and will resonate with anyone who is curious about mindfulness, meditation, and spirituality.
VII. Embracing The “Pathless Path”
Start Here 👉 My Book! The Pathless Path (Paul Millerd)
My book, The Pathless Path, was published five years after quitting my job and carving my own path. It’s sold over 25k+ copies with minimal marketing so people seem to like it. It’s not a how-to guide but an inspirational account of my journey combined with “recipes” on how to embrace an unconventional path.
Anything You Want: 40 Lessons For a New Kind Of Entrepreneur (Derek Sivers)
Sivers build a company selling CDs of independent artists in the early internet era. He ignored most of the advice about how to build a company. He also ignored the advice on how to write a book. This short book shows that “best practice” doesn’t always lead to happiness.
Field Guide To Getting Lost (Rebecca Solnit)
Rebecca Solnit puts words to the journey of “getting lost” and wandering into the unknown. If this quote resonates with you, you are ready for this book:
That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.
Linchpin (Seth Godin)
Godin has been a self-employed solopreneur and freelancer for decades. He helps people re-frame their thinking away from needing to be “chosen” for a job towards a world where the world depends on you expressing your creativity and daring to “make a ruckus.”
Designing Your Life (Burnett & Evans)
This book by two Stanford professors was designed to help undergraduate students figure out what they want to do with their lives. Based on design thinking, they have a number of useful question prompts and exercises that push you to expand the number of ideas and options you can come up with, rather than picking from default options. If you want to imagine new possibilities, this is the book for you.
Crossing The Unknown Sea (David Whyte)
Whyte is my favorite writer and this book is a beautiful reflection of his own journey from naturalist to non-profit worker to poet. He talks about the inner game of doing the thing which is scary (people thought he was crazy to quit his day-job) and living full out.
The Good Life & Sustaining Life (Andrew Taggart)
A practical philosophical reflection on what it means to live the “good life” in the modern world and the many approaches one might take to sustain such a life.
There may be no greater vexation in our time than the question of how to make a living in a way that accords with leading a good life. Yet if nearly every thinking person has faced this vexation at one time or another and doubtless throughout most of his adult life, virtually no one has ventured to think it through in a well-considered, systematic fashion.
VIII. New Models For Seeing The World
Start Here 👉 A Lesson On Worldly Wisdom (Charlie Munger)
This fantastic graduation speech from Munger highlights the need for many different “mental models” for seeing the world and how to move between them. Worth reading in full.
The Righteous Mind, Why Good People Disagree On Politics & Religion (Jonathan Haidt)
This book made me rethink how people arrive at their beliefs. Haidt shows that morality is something that is highly influenced by your environment and biology. This book made me much more understanding of a wider range of ideas beyond politics and religion.
Wanting (Luke Burgis)
The self-employed path is filled with hustle traps and the most powerful one is “mimetic desire.” Luke walks through his own personal journey of awakening and helps steer people toward finding their “thick desires” – things they can sustain over the long term.
Sacred Economics (Charles Eisenstein)
A bold re-imagination of our world to one based on generosity, connection, and embrace of the environment. This book is a beautiful mix of technical economic analysis with a spiritual questioning of the status quo:
I think ultimately what is happening is that our deep ideologies and belief systems, and their unconscious shadows, generate a matrix of synchronicities that looks very much like a conspiracy. It is in fact a conspiracy with no conspirators. Everyone is a puppet, but there are no puppet-masters.
IX. Grappling With The Role Of Work In Our Lives
Start Here 👉 Bullshit Jobs (David Graeber)
Graeber looks at the modern workplace through his definition of a “bullshit job” which is when employees define their job as pointless and without meaning. He looks at the history of work and shows that our current relationship with employment, time and money was not always the way it was and challenges readers to think beyond the status quo.
Rest (Alex Pang)
Pang’s incredible book on rest covers sabbaticals, unplanned breaks, naps, and sleep while challenging our modern understanding and definition of things like time, leisure, idleness and rest. He boldly challIf your work is your self, when you cease to work, you cease to exist,” shares counterintuitive results from people who worked 2-5 hours a day and shows the benefits of not following the conventional wisdom that more = better.
As a result, service workers and professionals are rewarded not just for performing work but also for “performing” busyness at work.
Reclaiming Work (Andre Gorz)
Gorz argues that “real work is no longer what we do when at work” and that a lot of what we are doing in the workplace is performing a social ritual we have decided is necessary to “earn a living.” This book imagines a world “beyond the wage-based society.”
The Normal Chaos Of Love (Beck & Beck-Gernsheim)
While this book is very much about love and relationship, it also frames those relationships and our modern ideal of a family in contrast to the workplace. The authors (a married couple) argue that the modern reality of having everyone be workers is great for the workplace and freedom, but creates chaos and complexity at home – complexity that we have yet to fully grapple with:
Everybody – including parts of the women’s movement – has the right to expect that offers once made to men should now be extended to women, and assert that women are as useful as members of the job world as men are. They should however realize that this road does not lead to a happy world of co-operative equals but to separateness and diverging interests.
Leisure: The Basis Of Culture (Josep Pieper)
In the late 1940s, Pieper wrote of a crisis of “overwork” and a disconnect from the classical sense of leisure. He wrote that we “mistake leisure for idleness, and work for creativity” and was skeptical of Max Weber’s assertion that “One does not only work in order to live, but one lives for the sake of one’s work.” In today’s world, “leisure” often just means a break from work. Pieper argued instead that leisure was:
the disposition of receptive understanding, of contemplative, beholding, and immersion – in the real. In leisure, there is, furthermore, something of the serenity of ”not-being–able–to–grasp,” of the recognition of the mysterious character of the world, and the confidence of blind faith, which can let things go as they will; there is in it something of the ”trust in the fragmentary, that forms the very life and essence of history.
X. Going Deep – The Hard Questions
Start Here 👉Not a book, but perhaps better than a book? Brain Pickings is perhaps the best source for wisdom on the web. A voracious reader and learner, Maria Popova pulls the most powerful parts of great writers in history on topics such as love, creativity, art, poetry, philosophy, life and work into compelling synthesized posts. Start with one post and you’ll end up opening up a ton of tabs in no time.
- Recommended posts: 10 lessons from 10 years of BrainPickings, Ursula K. Le Guin on Busyness, Reclaiming Our Human Dignity in a Culture of Workaholism, or David Whyte on Work/Life Balance
The Great Work Of Your Life (Stephen Cope)
Stephen Cope’s The Great Work of Your Life is a spiritual guide to finding your life’s purpose. The book uses the ancient text of the Bhagavad Gita to frame stories of famous people who have followed their dharma, including Tubman, Whiteman, Frost, Keats, and Susan B. Anthony.
Zen And The Art Of Motorcycle Maintenance (Robert Pirsig)
This book has been around since the 1970s and its central argument still rings true (perhaps more so?) that in our continued acceleration towards the future, we are losing touch with a deeper, spiritual side of ourselves. Pirsig contemplates what got us to this point:
The range of human knowledge today is so great that We’re all specialists. And the distance between specialization has become so great that anyone who seeks to wander freely among them almost has to forgo closeness with the people around him.
At the Existentialist Café: Freedom, Being, and Apricot Cocktails (Sarah Bakewell)
What does it mean to be free? How should one act in accordance with that belief. Bakewell tackles these tough questions through the lens of the existentialist philosophers that emerged in the early and mid 1900’s featuring the philosophies of Kierkegaard, Sartre, de Beauvoir, Heidegger and more.
The Wisdom Of Insecurity (Alan Watts)
Watts contemplates our desire to continue to put life into neat little boxes:
The more one studies attempted solutions to problems in politics and economics, in art, philosophy,and religion, the more one has the impression of extremely gifted people wearing out their ingenuity at the impossible and futile task of trying to get the water of life into neat and permanent packages.
and on following the default path:
To keep up this “standard” most of us are willing to put up with lives that consist largely in doing jobs that are a bore, earning the means to seek relief from the tedium by intervals of hectic and expensive pleasure. These intervals are supposed to be the real living, the real purpose served by the necessary evil of work. Or we imagine that the justification of such work is the rearing of a family to go on doing the same kind of thing, in order to rear another family . . . and so ad infinitum.
Meditations (Marcus Aurelius)
While it was written over 2,000 years ago, we get a peek into the Empreror of Rome’s private journal and his meditations on life:
When you arise in the morning think of what a privilege it is to be alive, to think, to enjoy, to love …
Leisure lives on affirmation. It is not the same as the absence of activity; it is not the same thing as quiet, or even as an inner quiet. It is rather like the stillness in the conversation of lovers, which is fed by their oneness.
Essays (Ralph Waldo Emerson)
Emerson’s collection of essays are a great read and accessible for being written in the 1800’s. Emerson on self-reliance:
There is a time in every man’s education when he arrives at the conviction that envy is ignorance; that imitation is suicide; that he must take himself for better, for worse, as his portion; that though the wide universe is full of good, no kernel of nourishing corn can come to him but through his toil bestowed on that plot of ground which is given to him to till. (Self-Reliance)
The incommunicable trees begin to persuade us to live with them, and quit our life of solemn trifles.
The book, the college, the school of art, the institution of any kind, stop with some past utterance of genius. This is good, say they,—let us hold by this. They pin me down. They look backward and not forward. But genius always looks forward. The eyes of man are set in his forehead, not in his hindhead
41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here