Four Books to Thrive in Uncertainty



All of the things you've read and heard about the difficulties of writing well are true. Writing is thinking. If you can’t make the words work, you don’t know yet what you think. I compare writing to meditation in that it also leads you down a path of discovery and self awareness.

Writing a book is a task that blends endurance, persistence, and creativity. The best books on a any topic are a mix of deep thinking, experience, and clear copy to minimize overwhelm.

Some books promise recipes—they're helpful when they keep the promise achievable, like in a niche topic, and deliver on it consistently. Technical manuals and pragmatic playbooks are in this category.

But the more enduring books are the ones that speak to the reader not just about the immediate tactics. They deal not in formulas but in asking and exploring important questions, so you can see more clearly… if you pay attention.

“When we are no longer able to change a situation,” said Viktor Frankl, “we are challenged to change ourselves.” In uncertainty, the one thing you can rely on is your self-control. That's what you can use to make decisions.

My selection of books is incomplete, I'm sure. But it's meant to make a difference in how you think about uncertainty and stack the odds in your favor.


Four books to navigate uncertainty

How often are you actually in control? Is a probabilistic question that takes work to think through. Your experience teaches you, but not well. Because you may not have gone through situations that are likely. Other people have, and you can live in their world through reading their story and learning from it.

The first thing then is being open to learning from the experience someone else had.


The Art of Learning: An Inner Journey to Optimal Performance by Josh Waitzkin (2007) is a book about chess and Tai Chi you can apply to life.

A public figure since winning his first National Chess Championship at the age of nine, Waitzkin was catapulted into a media whirlwind as a teenager when his father’s book Searching for Bobby Fischer was made into a major motion picture.

After dominating the scholastic chess world for ten years, Waitzkin expanded his horizons, taking on the martial art Tai Chi Chuan and ultimately earning the title of World Champion.

How was he able to reach the pinnacle of two disciplines that on the surface seem so different?

“I’ve come to realize that what I am best at is not Tai Chi, and it is not chess. What I am best at is the art of learning.”

Waitzkin believes that achievement, even at the championship level, is a function of a lifestyle that fuels a creative, resilient growth process. A well-thought-out, principled approach to learning separates success from failure.

Rather than focusing on climactic wins, he reveals the inner workings of his everyday method, from systematically triggering intuitive breakthroughs, to honing techniques into states of remarkable potency, to mastering the art of performance psychology.

Why did he switch from chess where he had fame and fortune to Tai Chi? After he became famous, Waitzkin figured out that being at the pinnacle in other people's eyes has nothing to do with quality of life. He saw the potential for inner tranquility and pursued it, finding himself in the process.

It's a fascinating story that I identify with on a much smaller scale.

Many years ago, I was on top of the lists of social media experts and bloggers. It was fun very briefly. I quickly realized it also brought undesirable effects with it. You end up paying more attention to the attention than to evolution of the work. The work suffers, and so does your potential and growth.

What we pay attention to is critical, especially in times of greater change. That's the topic of the next book.


The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win by Maria Konnikova is a book about understanding probabilistic thinking and putting it to work for you. Skill over luck for the long term.

The heart of the book is Konnikova's relationship with her poker coach, Erik Seidel, one of the game's all-time greats. A deeply wise and caring mentor, he dispenses advice that is not just timeless but applicable in many fields and endeavors. Things like, the goal of poker is not to win pots or chips but to make good decisions, defeat teaches you more than victory, don't play a tournament if you don't feel at your best.

The Biggest Bluff' is about how seemingly unlikely results can come within reach through persistence, planning, systematic training, and mindset management. Some seed funding probably also helps. World-class training isn't cheap, an important detail  to keep in mind.

As with so many facets of modern life, the qualitative elements of poker have been passed over in favor of the quantitative. Measurement presides over intuition. Statistics over observation. Game theory over 'feel.' We've seen the trend play out in areas as far afield as psychology —social psychology giving way to neuroscience—and music, who algorithms and experts quantifying not just what we listen to but how, to the fraction of a second, a song should be structured for maximum pop. [In poker] talk of frequencies trumps talk of feelings.

Probability by another name is luck. Some people invest it with meaning, direction, and intent: karma, fate, kismet. “Chance with an agenda.” Konnikova noted that Erik Seidel's style of play is psychological, based less on mathematical output and more on understanding the human element. He stays on top.

Konnikova's personal story is weaved into the book. I find it strengthens my understanding of why this is important. There's a reason why story has plots and archetypes—we can rely on a certain number of scenarios for characters to measure themselves in their journey. They feel familiar.

The explorer is in all of us. As is the hero, the lover, the creator, the sage, the outlaw, the ruler, the innocent, the caregiver, the every-man, the jester, and the magician.

For the next selection, I've chosen a book about a magician who saw all the other parts in him, too. It's a biography faithful to his teachings.


The Warrior Within: the Philosophies of Bruce Lee by John Little is a biography.

Bruce Lee thought about life force as energy:

I feel I have this great creative and spiritual force within me that is greater than faith, greater than ambition, greater than confidence, greater than determination, greater than vision. It is all these combined… Whether it is the godhead or not, I feel this great force, this untapped power, this dynamic something within me. This feeling defied description, and there is no experience with which this feeling may be compared. It is something like a strong emotion mixed with faith, but a lot stronger.

We do have a warrior within, if we let it speak to us, we can learn to appreciate that we have more options, talent, and capabilities than we may think. It's your journey. “Research your own experience,” “absorb what is useful,” “reject what is useless” and “add what is specifically your own.”

Maintaining a coherent self is important to be able to attend to projects and life. Which is why it's important to understand what's worth paying attention to and what to value.

But we don't learn as well as when we have a stake in the outcome. Learning how complex things work is hard. It takes your full attention and energy. You'll make mistakes, and they will cost you.

Social media is seemingly full of certainties—people present opinions and beliefs as such to others. Yet, would they bet their personal health on them? That of their loved ones? Personal accountability is the path to credibility and trustworthiness.

The hard thing about change is going through it. High uncertainty makes the process very stressful. Under high stress, people tend to curl up in a ball, physically or metaphorically, and harden even more around belief. That's what's happening to people today.

I have a secret I'd like to share with you. A simple thing that can really make a big difference in your mindset and outlookand that is engaging with learning for the joy of it.


Lost in Thought: The Hidden Pleasures of an Intellectual Life by Zena Hitz is a timely invitation to readers from every walk of life to rediscover the impractical splendors of a life of learning.

“Learning for its own sake” is her simple theme. But she admits that justifying a life that is considered, superficially, as “useless” remains a formidable task in today’s activity-based culture.

Hitz has a strong premise:

If human beings flourish from their inner core rather than in the realm of impact and results, then the inner work of learning is fundamental to human happiness, as far from pointless wheel spinning as are the forms of tenderness we owe our children or grandchildren. Intellectual work is a form of loving service at least as important as cooking, cleaning, or raising children; as essential as the provision of shelter, safety, or health care; as valuable as the delivery of necessary goods and services; as crucial as the administration of justice. All of these other forms of work make possible, but only possible, the fruits of human flourishing in peace and leisure: study and reflection, art and music, prayer and celebration, family and friendship, and the contemplation of the natural world.

In nature, humans are not as resilient and robust as other forms of life. But we are a thinking being, that has value. It's something wise people have discovered centuries ago. In Pensées, Blaise Pascal says:

Man is but a reed, the weakest thing in nature; but he is a thinking reed. The entire universe need not arm itself to crush him. A vapor, a drop of water suffices to kill him. But, if the universe were to crush him, man would still be more noble than that which killed him, because he knows that he dies and the advantage which the universe has over him; the universe knows nothing of this. A thinking reed.—It is not from space that I must seek my dignity, but from the government of my thought. I shall have no more if I possess worlds. By space the universe encompasses and swallows me up like an atom; by thought I comprehend the world.

My caution is that learning is not just a sentiment of connecting with our universal humanity. You can also invest energy in learning with others to further your ability to make sense of what you're thinking about by talking it out with them.

Cultivating an interior life serves to engage your curiosity and imagination, to take the foot off the competitive pedal for a pause. Health is creating dramatic changes to how we must do things. Some of which may need to endure.

The shock of these changes in not just physical. Things are changing faster than the pace of human response. There's a gap and we're trying to fill it with activity. Hence the burnout.

We've been here before. History is full of examples of things we've tried and failed at because we didn't understand uncertainty and our odds. I believe perspective is valuablethat's why we say perspective is something you gain.


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