The Best Books to Read in Uncertain Times

The best books to read in uncertain times are ones that build a sense of community. These books also provide perspective on the human condition and help readers identify what they want from life.

The “Best books on dealing with uncertainty” is a question that has been asked more and more in recent years. There are many different types of books to read, but here are some of the best ones. Read more in detail here: best books on dealing with uncertainty.

Magazine cover page with a man holding a book.

I was playing one-on-one basketball with my son Gus a few days ago. “You know Dad, COVID has truly transformed our world extremely rapidly,” he added as he was returning the ball to our driveway’s “half-court line.”

It’s a simple remark, but hearing it from your nine-year-old stops you in your tracks for some reason. 

Gus is correct. Because of the worldwide epidemic, the world has altered drastically. From week to week, and even day to day, it continues to shift quickly and fluidly.

The worldwide epidemic has served as a stark reminder that we live in an insecure environment. 

During this present crisis, I’ve done a lot of reflecting, as have a lot of other individuals. Part of that contemplation led me to literature that I’ve found useful in the past for understanding and managing uncertainty. Their perspectives on living with a tumultuous world are more relevant than ever.

I’ve included a list of the novels I’ve been rereading and thinking on over the last several weeks. They’re a combination of nonfiction, fiction, and even religious text from many faiths. They all have one thing in common: they’re all trying to find a solution to an issue that’s been plaguing mankind for millennia:

I’m not sure what I’m expected to do now.

These books have aided me in finding an answer to that issue. Perhaps you, too, will find them useful – not just now, but in the future. Even though we are more keenly aware of the world’s capricious oscillations at times, life has always been and will continue to be unpredictable. 

Nassim Taleb’s Incerto

"Incerto" Book Outlook by Nassim Nicholas Taleb.

Skin the Game has been added to the series since this box set was released.

Nassim Nicholas Taleb, a philosopher and probability specialist, authored the Incerto series of books to address the topic of how to connect with an unpredictable environment. The first book, Fooled by Randomness, is about how we think about (or don’t think about) chance and luck in our lives. 

The Black Swan, the next book in the series, popularized the notion of black swans, which are unplanned, unexpected occurrences that have a huge influence on our lives and are often given retroactive interpretations that make the events seem less random and more predictable than they were. 

Antifragile then looks at how to live and handle oneself in an unpredictable environment. Taleb recommends ways that will help you to not only stay resilient in the face of chaos and catastrophe, but also to develop from these opposing forces. 

The Bed of Procrustes is a collection of aphorisms intended to uncover and emphasize the many ways in which we humans deceive ourselves into believing we know what’s going on when we don’t.

Taleb’s fifth and most recent book in the Incerto series, Skin in the Game, examines the ethics of living in an unpredictable environment.

These works, when read together, give a comprehensive overview of how to think about and cope with uncertainty. During this epidemic, I’ve noticed myself picking them up a little more. If you just read one book in the series, I would suggest Antifragile. 


Make sure to listen to my Skin in the Game podcast with Taleb. 

John Kay and Mervyn King’s Radical Uncertainty

Book Cover of "Radical Uncertainty" by John Mervyn king.

In the world, there are two sorts of uncertainty. The unpredictability of actuarial tables in the insurance sector and the roulette game at a casino are two examples. This form of uncertainty is a problem that can be solved with the use of probability theory techniques. 

The second form of uncertainty is uncontrollable by mathematics. Probability theory is useless because there are just too many variables interacting in complicated ways. This is referred to as extreme uncertainty. 

Economists John Kay and Mervyn King argue in their book on the subject that to deal with radical uncertainty, you must go beyond data and equations to create a robust and resilient narrative about your current situation, which you must then constantly update by asking yourself, “What is going on here?” 

There are plenty excellent examples from the worlds of business and combat. This book served as a good complement to Taleb’s Incerto series for me. 

Frans P.B. Osinga’s Science, Strategy, and War

Book Cover of"Science ,Strategy and War" by Frans P.B Osinga.

John Boyd, a fighter pilot and philosopher, is credited with inventing the OODA Loop in military strategy. While the OODA Loop is often mentioned, it is sometimes misinterpreted as a simple four-step procedure in which the person or group that completes all stages the fastest wins.

The OODA Loop is essentially a complicated learning system — a multi-faceted approach for coping with uncertainty — if you properly comprehend the scientific and philosophical principles Boyd addresses in his essay.

The difficulty is that it’s difficult to figure out how Boyd’s ideas regarding the OODA Loop can be incorporated into this system since he never wrote them down in a formal report and only presented them in oral briefings. 

The book Science, Strategy, and War by Frans P.B. Osinga comes in helpful here. Boyd’s scattered papers, notes, and lectures are meticulously pieced together by Osinga to illustrate how the OODA Loop’s consequences go well beyond a basic four-step procedure. This is the finest book on the OODA Loop I’ve ever read, and it’s well worth your time. Check out this article for a CliffsNotes version. 

Marcus Aurelius’ Meditations

A cover page of "Meditations" by Marcus Aurelius.

Uncertainty’s erratic winds may wreck havoc on our emotions, leaving us feeling frightened, despondent, and powerless. In times of uncertainty, Stoic philosophy may help us regulate our emotions by pushing us to sift out what we can and cannot control, and advising us to quietly suffer the latter while focusing on the former.

Marcus Aurelius, the Roman Emperor, was one of the last Stoic thinkers, and possibly the most well-known. Marcus offered us solid instruction on how to put Stoicism into practice, thanks to his own writings that later became Meditations. It’s still one of the greatest primers on Stoic philosophy thousands of years later, and it’s packed with maxims that will help you calm your mind in the middle of turmoil. Take a look at what Jeremy learned from his first reading of it a few years ago. 


Tragedies from Greece

A book cover of "The Greek Plays" by Aeschylus, Sophocles, and Euripides.

Theatrical tragedies were more than simply enjoyable plays for the Greeks: they were a cathartic religious ritual that purified the soul. While the plots varied, philosopher Simon Critchley claims that all of the tragedies are about how to survive in an ambiguous and uncertain world:

Characters who are completely befuddled by the circumstances in which they find themselves appear in play after play by the three great tragedians (Aeschylus, Sophocles, and Euripides). They have no idea what to do. Human beings seem to be obliged to pursue a road of pain that permits them to ask questions that have no simple answers: What will happen to me? How can I decide on the best course of action? The predominant sensation of tragedy is bewilderment, which is conveyed in one perplexing and constantly repeated question: What must I do?

While the tragedies may not give clear-cut solutions to how to solve the enigma of uncertainty, they do prompt us to consider the nature of its perils. Furthermore, they demonstrate that, even if we are bewildered, we must act and go ahead, just as the characters in these plays do.

The Baghavad Gita is a Hindu scripture.

A cover page of Sacred Hindu scripture, "The Baghavad Gita". 

The Baghavad Gita, a sacred Hindu text, opens in the midst of an apocalyptic fight between families. Arjuna, a teenage warrior, and his charioteer Krishna, a divinity in disguise, ride up to a battle about to begin. 

Arjuna requests Krishna to come to a halt. Arjuna is disturbed by what he sees: his own family has assembled to attack him. Arjuna is obligated to fight in the battle as a warrior, but he does not want to fight against his family. “Conflicting holy responsibilities baffle my intellect!” he cries out to Krishna. He continues to bemoan:

My limbs begin to sink. My mouth is dry, my body trembles, and the hair on my skin bristles. The magical bow is slipping. My flesh is burning from my palm, I can’t stay still, and my head is spinning.

Arjuna collapses on the floor of his chariot, speechless and unsure of what to do.

The remainder of the Gita is Krishna’s advice to Arjuna on how to act in an uncertain environment. The most important message is to take action while realizing and accepting that you have little or no control over the effects of your activities. “You have the right to labor, but never to the reward of labour,” Krishna says.

While we may not have perfect control over how things turn out, we do have complete control over what we do. And control equals bravery. 

Job’s Book

We frequently find ourselves questioning God or the cosmos, “Why?” when horrible things happen to decent people. 

“Why not?” says the Book of Job in response to our query.

Job demonstrates that disaster may afflict both the righteous and the unjust, as well as the good and the bad. And that, although we may not always be able to control the winds of destiny, we do have power over how we respond to them.  


It’s no wonder that the Book of Job has long been a favorite of those who have had to cope with uncertainty on both a personal and a societal level. During his turbulent administration, Abraham Lincoln often looked to Job, and writer Joshua Wolf Shenk argues that it shaped his spiritual worldview and awareness of the limitations and duties of human agency:

Lincoln’s response was a mix of humility and resolve. The humility sprang from a realization that, whichever ship carried him through life’s storms, he was simply a passenger on the divine power – call it destiny, God, or the ‘Almighty Architect’ of creation. Lincoln’s motivation sprang from the realization that, no matter how lowly his position, he was not an idle passenger but a sailor on deck with a duty to complete. Lincoln attained supreme knowledge by a paradoxical mix of great reverence to heavenly authority and a purposeful utilization of his modest power.

Homer’s Odyssey is a Greek epic poem.

A poster of "The Odyssey" by Homer.

The Odyssey tells the story of Odysseus’ ten-year voyage back to Ithaca after the Trojan War. He runs into setback after setback along the road. Odysseus’ tragedy is so profound that it often brings tears to the legendary hero’s eyes. 

But he triumphs. 

Why? Because he is known as “the guy of many tricks.” He’s clever, resourceful, and flexible. In a world of unpredictability, he recognizes that rigidity leads to disaster. You must develop the ability to bend. Most importantly, you must keep pushing ahead. 

It’s worth noting that Odysseus’ misfortunes are mostly his own fault. He may have made it home sooner if he hadn’t become confident after tricking the Cyclops. Perhaps another lesson from The Odyssey on uncertainty is to avoid arrogance.

Cormac McCarthy’s The Road

A book cover of "The Road" by Cormac McCarthy.

Aren’t we going to be OK, Papa?  

Yes. Yes, we are.

Also, nothing awful will happen to us.

That’s correct. Because we’re the ones in charge of the fire.

Yes. Because we’re the ones in charge of the fire.

In The Road, an anonymous father and his son journey through a post-apocalyptic environment in search of food, survival, and a way to escape being captured by barbaric tribes of baby-eating barbarians. The father is terminally ill. He’s well aware that he won’t be around for much longer. As a result, he teaches his kid survival techniques. Most significantly, he instills in his kid the ability to “carry the fire.”

Carrying the fire is a metaphor for leading a noble life despite adversity. The Road serves as a reminder that we may choose to be good even when the old norms have fled, evil is on the march, and chaos prevails. We can still maintain our high standards. We still have the ability to make sound judgments. 

Once a year, I read this book. It’s become a modern-day Greek tragedy-style catharsis routine for me. 

Larry McMurtry’s Lonesome Dove

A book cover of "Lonesome Dove" by Larry McMurtry.

If you’ve been following AoM for a while, you’ll know that Lonesome Dove is my favorite book of all time. I’ve read it five times and named my kid Augustus McCrae after one of the major characters. 


It wasn’t until I read Larry McMurtry’s 800-page Western epic for the third time that I realized what kept me going back to it: it’s about people trying to figure out what to do when they don’t know what to do. Lonesome Dove, like the Greek plays, is about coming face to face with uncertainty. 

After his group suffers an early setback on their cattle drive from Southern Texas to Montana, one of the major characters, Woodrow Call, considers the folly of planning for the future:

Though he had always been a meticulous planner, living on the frontier had taught him the value of flexibility. The fact is that most plans do fail, to some degree or another, for various reasons. He’d made it as a Ranger because he was fast to react to what he’d discovered, not because his preparation was flawless.

Surviving in an unpredictable environment necessitates adapting to the reality at hand rather than clinging to a preconceived notion of how the world should be. If you wanted to make it in the uncertain West, Woodrow recognized that you had to alter your mental models. 

And, like the Greek dramas and the Gita, Lonesome Dove teaches that sometimes the only thing you can do is keep going ahead, even if you don’t know what to do. This is eloquently illustrated in a scenario in which an Irish lad who has joined the drive crosses a river and is killed by a swarm of water moccasins:

Call knelt by the kid, unable to aid him in any way. It was the worst fate of my life, having traveled all the way from Ireland just to be attacked by a swarm of water moccasins. 

Call remained silent. Of all, the boy’s age had nothing to do with what had transpired; even an experienced man would not have survived a ride into such a tangle of snakes. He couldn’t say for sure, and he’d never been afraid of snakes before. It just confirmed what he already knew: there are more risks in life than even the most thorough preparation can foresee. Allen O’Brien should not dwell on his guilt, for a youngster may die in Ireland just as easily as anywhere else, no matter how secure it seems.

‘It seems to be moving too quickly,’ he remarked. ‘It seems to be quite swift to simply ride away and leave the youngster.’ He was our family’s baby,’ he continued. 

‘We’d have a nice funeral if we were in town,’ Augustus replied. ‘However, as you can see, we’re not in town.’ You have no choice except to kick your horse.’ 

Life has a way of slamming us in the face. We have a limited number of options. However, we still have the option of mounting our horse and kicking. 

Viktor Frankl’s Man’s Search for Meaning

A book cover of "Man’s Search for Meaning" by Viktor E. Frankl.

Viktor Frankl was a Jewish psychologist who was sent to Auschwitz. They stole the remainder of his stuff, including his clothing, his wedding ring, and the manuscript of a novel he was writing, when he arrived at the concentration camp. He survived to tell his experience, which is a lesson about the control one has to make a horrible circumstance not necessarily excellent, but survivable, by depending on his rich inner life and aiding other inmates, as well as some strokes of good luck. Even when our options seem to be limited, Frankl tells us that we retain an aspect of agency that can never be taken away:


The last of human freedoms: the ability to select one’s attitude in every given situation, to go one’s own way. There were always decisions to be made. Every day, every hour, presented the opportunity to make a decision, a decision that determined whether or not you would submit to those powers that threatened to rob you of your very self, your inner freedom; a decision that determined whether or not you would become the plaything of circumstance, sacrificing your freedom and dignity.

Jack London’s “In a Far Country”

This isn’t a book, but a short tale by Jack London, which is my all-time favorite short story.

It is based on the tragic story of two men who ventured out to find gold in the Klondike. These ignorant, indolent, and inflexible city inhabitants — dubbed “Incapables” by London — lack the skills and attitude to succeed in the North, and struggle to adjust their expectations of easy prosperity to reality.

“In a Far Country” explores the value of adaptability, attitude, and mental toughness, as well as the genuine nature of romance and adventure, as well as that essential foundation of manhood: camaraderie and the desire to carry one’s own weight in a group of men.

According to London historian Earle Labor, the first lines of “In Far Country” precisely embody Jack’s “Northland Code” — the traits necessary to live and prosper in the wilderness; they also wonderfully describe the attributes essential to survive and thrive in the unpredictable landscape: 

When a man travels to a distant area, he must be prepared to forget much of the things he has learned and to adopt the practices that are inherent in life in the new land; he must reject old ideas and gods, and he must often reverse the very norms that have governed his behavior before. The novelty of such change may even be a source of pleasure for those who have the adaptable faculty; however, for those who have become hardened to the ruts in which they were born, the pressure of the altered environment is unbearable, and they chafe in body and spirit under the new restrictions that they do not understand. This chafing is compelled to act and respond, resulting in a variety of ills and catastrophes. It is preferable for a guy who cannot adjust to the new rhythm to return to his home country; if he waits too long, he will undoubtedly die.

The number and quality of a man’s hopelessly entrenched habits may be inversely proportional to the quantity and quality of his hopelessly fixed habits when he turns his back on the luxuries of an older civilisation to confront the savage youth, the primal simplicity of the North. If he is a good candidate, he will quickly learn that material habits aren’t as significant as they formerly were. After all, switching from a delicate menu to a hearty meal, from a rigid leather shoe to a soft, shapeless moccasin, from a feather bed to a snowy sofa is a simple affair. His pinch, on the other hand, will come from knowing how to correctly construct his mind’s attitude toward all things, particularly toward his fellow man. He must replace unselfishness, patience, and tolerance for the courtesies of everyday life. Only in this way, and only in this way, will he be able to get that priceless gem: real comradeship. He must not only say, “Thank you,” but must mean it and demonstrate it by responding in like. In other words, he must replace the word with the action and the letter with the spirit.




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Reading difficult books can be a good way to improve your mental health and your life. The benefits of reading difficult books are that they help you grow as a person and make you more resilient in uncertain times.

Frequently Asked Questions

What do you read at times of uncertainty?

A: I read the words of wise people who are able to offer guidance when one feels lost.

What are the top 10 books to read in 2020?

A: I am a computer. It is impossible for me to answer such an open-ended question, as there are too many variables involved and it would be like asking what the top 10 songs of 2019 were.

What is the most beautiful book to read?

A: If you are looking for a book that provides an exciting and thrilling narrative, then The Hunger Games by Suzanne Collins would be the perfect choice. This novel follows Katniss Everdeen on her journey through the nation of Panem in which she must fight to survive after being taken into their games as tribute to save her sisters life. It is very action-packed with a lot of suspenseful moments.

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