The 12 Most Pivotal Books I’ve Ever Read

If books didn’t have the seemingly magical ability to influence the course of our lives I’d read a whole lot less. In my life I’ve been fortunate to have come across plenty of good books and quite a few great ones that have done just that to varying degrees. But there’s a third category of books which is the chief reason I continue to read as much as I do.

I call them pivotal books.1 They are books which have achieved a certain type of incredibly-hard-to-do alchemy: mysteriously mixing just the right combination of words with just the right timing that’s resulted in a chain of far-reaching and long-lasting consequences.

If you’ve known me for any length of time you’ve probably heard me talk about a few of these books. More than likely I’ve tried to persuade you to pick up at least one of them.

They are books I’ve been chewing on for years (I’ve only read two of the books on this list for the first time in the last year). They are books I’m constantly revisiting (I’ve read almost all of them cover to cover multiple times). They are books that have sunk deep into my bones. They have all in some way played a pivotal role not only in how I see the world, but more importantly, in how I live in it.

I believe anyone would benefit immensely from reading these books which is why I’m recommending them now. My hope being that just maybe, they’ll enrich your life in the same magical way they have mine.

What have you got to lose by finding out?

What might you gain?


antifragile-book-coverAntifragile: Things That Gain from Disorder – Nassim Taleb

Taleb draws on a wide range of deep thinkers as well as his own personal experience as a trader to provide the closest thing I’ve found to a guidebook for dealing with uncertainty and risk (AKA life). Persuasive, well written and often counter-intuitive, Taleb’s work has changed the way I evaluate risk and make decisions big and small.

GunsGermsSteelGuns, Germs, and Steel: The Fates of Human Societies – Jared Diamond

Jared takes a sweeping and systematic look into human history to answer the question: why did Eurasian peoples, rather than peoples of other continents, become the ones to develop the ingredients of power and expand around the world? His thorough analysis and surprising insights into how our world was shaped, or rather, how our world has shaped us, irrevocably altered the way I view our shared humanity and my own life within it.

MeditationsMeditations – Marcus Aurelius

It seems Marcus never intended for his reflections on living to be published which makes them all the more powerful. The beloved Roman Emperor’s personal writings on how he aspired to live —and what he practiced— read like a (surprisingly modern) manual for living today. Chalk-full of practical insights that take on new meaning and life with each reread; it’s the type of book worth leaving permanently near your bedside.

Letyour2Let Your Life Speak: Listening For the Voice of Vocation – Parker Palmer

The first time I read Parker Palmer I was inspired. The second time I read Let Your Life Speak, Parker’s words sparked an epiphany that led to my overnight decision to walk away from the business I had invested the last year and a half of my life to building.

LinchpinLinchpin: Are You Indispensable? – Seth Godin

This was the first book I read by Seth (but nowhere near the last). I picked it up while building and managing a rapidly growing startup business in my early twenties. Seth taught me how to navigate and lead in the chaotic, competitive and uncertain world of business. He’s helped me uncover my own values and shown me how to give and engage with others in business and in life. I’ve been reading Seth’s blog for seven years now. If you were to ask me for the one business book that I thought would give you the most mileage in your life this is the book I’d buy and give you. I’ve literally done just that for past employees and friends.

ManssearchMan’s Search for Meaning – Viktor Frankl

I picked this book up when I heard Tony Robbins say it was one of the most important books he’s ever read. Viktor shares his harrowing story of surviving four nazi concentration camps where his parents, brother and pregnant wife all perished. He writes about his struggle to find meaning in a world of meaningless suffering. Through his experience in the camps, as well as his later work as a practicing psychiatrist, he developed his theory of logotherapy and his powerful conviction that man is ultimately self determining: we find meaning where we make it. Incredibly moving, Viktor’s work on the subject of meaning is an invaluable gift for anyone grappling with meaning in their own life.

You're ItYou’re It! On Hiding, Seeking, and Being Found – Alan Watts

As he has done for countless others, Alan Watts opened the doors for me into the rich inner world of Eastern philosophy and spirituality. Those doors have never closed since. Entertaining, inspiring, and profound, his explorations on the nature of life sparked my own ongoing exploration. I revisit his lectures frequently which have remained as fresh and stimulating as the day I first heard them. This particular collection was carefully curated by his son, Mark Watts, and I’ve found it to be a much more impactful way to digest Alan Watts’ paradoxical teachings than the random Youtube videos that are so popular online.

*Alan Watts is a master orator and for this reason I’d recommend listening to this collection of his lectures.

What I Learned Losing A Million Dollars – Jim Paul & Brendan MoynihanWhatIlearned

It may be hard to appreciate this book fully until you have failed spectacularly and paid a heavy price in doing so. Lucky for me I picked this book up after having done just that. The authors’ reflections on losing everything and the process they’ve developed on the other side of that experience to prevent others from doing the same is objective, practical and dead-on. There were elements I knew to be completely true from personal experience and elements I had wished I had known to be completely true before personal experience.

The Antidote: Happiness for People Who Can’t Stand Positive Thinking Oliver Burkeman

AntidoteFunny and deep, The Antidote avoids the many traps and pitfalls common to this genre and delivers something with surprising weight and longevity. Oliver steers us away from the mainstream positive and motivational thinking to explore alternative, “negative paths” towards happiness. Instead of “10 easy steps” or a “proven system” I left with more (if not better) questions and a reinforced skepticism towards many of the contemporary gurus in our society who claim to have the answer. Don’t worry, Oliver also provides promising avenues for further self-exploration (you didn’t really expect the problem of happiness to be solved in a book did you?). There’s no doubt why I loved this book so much —it so closely summarized my own ten year journey through this hazardous and poorly marked terrain and provided another perspective on the subject that was both refreshing and clarifying.

*This is a great one to listen to on Audible.

QuietQuiet: The Power of Introverts in a World That Can’t Stop Talking

If you are an introvert or if you feel slightly out of place in the world and suspect you might be an introvert you need to read this book. If you don’t identify as an introvert Susan’s work will help you better understand the way in which one third to half of the population sees the world and operates in it. I was floored when I read this book and realized it’s not just me! Incredibly empowering and enlightening.

PowerofmythThe Power of Myth – Joseph Campbell with Bill Moyers

A great introduction to the Hero’s Journey and the Monomyth. It blew the doors open for me on the power of story and the common spiritual and psychological elements that are shared among all cultures no matter how removed from one another in space and time. Joseph Campbell, who wrote the book on the subject, shares his profound and practical insights into our need for story. His stimulating and engaging series of conversations with Bill Moyers is just plain good for the soul.

*Originally a conversation between Joseph Campbell and Bill Moyers, I’d recommend listening to this one.

WarofArtThe War of Art: Break Through the Blocks & Win Your Creative Battles – Steven Pressfield

A must read for anyone aspiring to create something new in the world who has run head first into Resistance. You’ll read it the first time for Pressfield’s in-the-trenches, hard-won lessons on writing and creative work. You’ll read it the second time because he’s such a damn good writer.



Happy reading! 😀

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  1. Although a couple of them aren’t actually books at all.

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Hello. I’m Alasdair.

Hello. I’m Alasdair.

I believe that being aware of who I am and mindful of who I am becoming is the best investment I can make in my life —and that when we focus our efforts within, the rewards naturally flow outward to those we love and through the communities we belong to.