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Books to Cultivate Wisdom for What Lies Ahead

you take time away from work this holiday season, please, read a book that builds wisdom.  Read one, and challenge someone else to read it too. 

Why? Well in general, what’s not great about reading? A great book informs your mind, rests your body, enlarges your horizons, challenges your assumptions, and builds your vocabulary all while connecting you with other cultures, times, and viewpoints.  

More specifically, the right books – books that require wrestling – inform our minds and shape our worldviews.  That combination of informed head and shaped heart builds wisdom.  Understanding, applied well. The right knowledge for the right time, to build something good not just effective.  Wisdom is what we need in this season, more than ever.

My recommendations this year are books that were incredibly helpful to me in 2020 specifically, and to my approach for 2021. Out of the 65 I read, here are the four I believe most furthered and fashioned wisdom and right orientation to life in this unusual season:

by Nassim Taleb

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Understand uncertainty and grow stronger in chaos.

How it applies to 2020/2021

You cannot find a book that would have better prepared us for 2020, nor one that better encapsulates the ways we should think and make decisions in great uncertainty, than Antifragile.  Nassim Taleb is a fascinating author who communicates with the full force of his personality.  A trader-turned-thinker, he writes on risk, chaos, and what we can do about it.  He starts the book with the question: None of us want fragility (in our health, our society, our businesses), but what is the opposite of fragility? The natural answer is: robust! Fragile things break under shock, robust things hold up to much stronger shock.  Right? Wrong. That answer hides the much deeper truth, and the point of the book: The opposite of “something that breaks under stress” is “something that gets stronger under stress.” The opposite of fragile is antifragile.  Think of your muscles – the more you stress them, the stronger they get. From finance to evolution, antifragility is everywhere, with massive implications.

The book can get long and pedantic at parts (he explores antifragility in many different settings) but I believe it’s well worth reading for any serious thinker. The book gives us an important lens to see the world, to question our own assumptions, to better understand risk, and to build antifragility into our lives, businesses, and societies.

Throughout his writings, Taleb pillories economists and experts in prediction, and he emphasizes the need to align with principles of antifragility, so that stresses and chaos make us stronger.

We used the principles in this book as a guide to our early COVID recession planning. The concepts of antifragility prepared us for many futures and lifted much of the emphasis on prediction and stability. When I look at the Mainstay team and the results of this year, there is no question that 2020’s stresses have made us stronger. This book has given us the language, focus, and understanding to more directly harness the power of antifragility.  While it is not a light read (Taleb gets fairly technical) I think this concept is so critical that I cannot recommend it highly enough.

Note: Taleb has written five books on risk and decision making in a series called “Incerto,” of which Antifragile is the third book. It stands alone, but he writes in a fractal way – each book unpacking a concept introduced in the previous book.  If you like Antifragile, I’d recommending working your way through the full Incerto series. Skin in the Game was my second favorite to Antifragile.

The House of Belonging
by David Whyte

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Connect with the importance of belonging.

How it applies to 2020/2021

An artform of staggering power and beauty, poetry uses words to point to, hint at, and illuminate deep truths that cannot be grasped by our minds directly.  It bridges the gap between our left brains (where we communicate) and our right brains (where we intuit and feel) by using language to impress upon us things of beauty and depth.

If there were ever a season we needed poetry, it is now. After months of isolation, months of video conferencing, months of global anxiety – we need this book especially – a book about belonging. Belonging to our home, to those we know, to our place, to another person.

This is a small book by a poet of amazing depth. David has spent his life traveling the world and using language to point at the deeper reality we live in. In this year of disembodied communication and frantic anxiety and claustrophobia, The House of Belonging takes on new dimension and depth.  Feed your soul. Buy this book, stick it by your bedside, and read at leisure. Be reminded of what it is to be human, to ponder, and to belong.

Leadership: in Turbulent Times
by Doris Kearns Goodwin

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How suffering can transform and prepare us.

How it applies to 2020/2021

This beautifully written book profiles Abraham Lincoln, Theodore Roosevelt, Franklin Delano Roosevelt, and Lyndon B. Johnson.  But it isn’t simply a brilliant biography series. Rather, it is a book of suffering, character, and leadership during dark days.  The author looks at each leader in the light of the trials and suffering that prepared him to lead through times of great adversity. She delves deeply into the times of greatest pain and confusion before the leader’s triumph.

The pandemic broke in February when I was in the middle of reading this book.  Reading of the trials that others have endured motivated me, steeled me, and granted me great hope for each of us.  Reading of the leadership that rose above great national struggles incited great sadness at the state of modern political leadership throughout this crisis.  And reading of these four individuals made me more determined than ever to embrace suffering, set my face resolute towards what is right, and pull as many as I can towards a better place.

To be Told
by Dan Allender

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Dealing with the emotions and frustrations of life.

How it applies to 2020/2021

2020 has been a year of collective trauma. For many of us, our normal coping systems have broken under the strains of lockdown, and the careful balance of our lives has been thrown off.  Anxiety, loneliness, frustration, despair, rage, and pain have been a part of so many lives this year.

That pain so often comes not just from the present, but from the way the present-day pain interacts with our story – with our past, our stories of who we are, how we are raised, what harm we have experienced in life, and what we have done with that.

My life significantly changed when I began to understand how much our past is present with us, today.  We are born into this world seeking meaning, love, and belonging. As babies, infants, toddlers, children, and adults, we learn based on our interactions with others. We literally build a physical structure of neurons in our brain based on conclusions we reach of how the world works, starting from before we have memory.

There have been immense breakthroughs in neuroscience and psychology in the last 30 years, unlocking an understanding of how we work and, more importantly, how we can heal. Dan Allender has been a pioneer in this movement, giving language to what happens within us, why we have emotional responses that don’t always make sense, why we often feel “stuck” with feelings, pain, or desires, and how we can begin to journey into and through that pain, to a place of flourishing.  He calls this “our story” – the story of how we became who we are. Unless we understand that story, we will not understand ourselves, nor what power we possess to change our present.

Ever pet a dog who was abused as a puppy, and seen the dog flinch?  That’s because of the dog’s story – the past of abuse is still present today in a physical way (by stretching out your hand you are interacting with neural structures of meaning – to the dog’s limbic system, the hand translates to “pain is coming” in an entirely subconscious way).  The same things happen with us in a myriad of ways.

This book is written by a believer in God, written to those who have some belief in God, as I do.  I believe Dan’s lifetime of working with victims of trauma has given him deep and profound wisdom for all, but I understand not all may be want to engage a book so overtly focused on how God co-authors our story with us.  If so, I still encourage you to wrestle with this topic, but I recommend reading The Body Keeps the Score by Dr. Bessel van der Kolk instead.  It is focused on trauma victims, and if you don’t see yourself as a trauma victim, please recognize that life is traumatic for all – we have all experienced harm in some way, just in various ways.  And the understanding of who we are is vital to being a human, fully alive.

On reading…

I love reading. I value it so highly, that I set annual “reading goals.” My goals include quantity (averaging at least five books per month), quality (plus books that are well written and that challenge my thinking), and breadth (a variety of topics and both fiction and nonfiction). This helps me prioritize the time and encourages the exploration of my curiosity, and I encourage you to consider setting similar goals as we turn to the New Year.

If you’re looking to read more, consider creating a reading space.  Consolidate your books onto a bookshelf, stick your comfiest chair next to it, throw a blanket on the chair, put a space heater next to it, and set a warm lamp at a good angle. 

And fill your house with books! Books on your bedside table can encourage the health-giving habit of reading both before bed and before the day starts (indefinably better than checking email or the news at those times!).  Note titles that have been recommended to you, purchase books you know you’ll want to read someday, and buy books that are on sale.  You’ll read more, I guarantee it.  And as a bonus, research has shown that the number of books in the home has a large effect on the literacy and education levels of children later in life.

Here’s to 2021, the books we’ll read, and the wisdom we cultivate!