10 Essential Books to Help You Lead Through Uncertainty

After another week of pandemic and economic whiplash — these books can help you get comfortable with unpredictability

A businessman reading on his digital tablet while standing near a window, next to his filled bookshelves.
Photo: Thomas Barwick/DigitalVision/Getty Images

InIn the current climate of uncertainty, mainlining Twitter while trying to forecast impossible economic (and health) scenarios is not going to lift you from the morass of anxiety. Nor is it particularly useful. In fact, it’s a constant reinforcement of “negativity bias,” the hardwiring of our brains to seek out information that scares us. Bibliotherapy, however, uses reading to facilitate psychological healing, a growing field of research that actually dates back more than a century.

Whether you’re contemplating how to save your startup, raise money during a financial crisis, or what your “Covid-19 war room” should look like, this collection of books will shift how you think about and tackle uncertainty head-on.

1. Thinking In Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke

In 2004, Annie Duke won the World Series of Poker and raked in some $4 million before retiring to become a business consultant. High-stakes card players have to accept a level of uncertainty because you can never totally know when to hold or fold ’em. In Thinking in Bets, Duke shares tools to help shift away from a goal of certainty to a more accurate assessment of the variables of knowns and unknowns for better decision-making. One tip from the book: Before executing any plan, undertake a “premortem,” that is, imagine what failure will look like, then work backward to understand how to avoid it.

2. The Upside of the Downturn: Management Strategies for Difficult Times by Geoff Colvin

In the aftermath of the Great Recession, longtime Fortune columnist and editor Geoff Colvin decided to study the beacons of light rising out of the darkness. In his interviews with the world’s top business leaders, he found that those who followed the traditional rules of management during the recession and subsequent expansion were doomed. One interesting idea Colvin highlights from the 2008 recession, which will be a major issue in 2020, is to “protect your most valuable asset”—your workers. In a knowledge-based economy, people are the key assets, not giant machines, so hastily firing staff to save money today could come back to bite you tomorrow. Nobody knows what the global economy will look like when the pandemic ends, but at least Colvin offers proposals for the better days to eventually come.

3. Radical Uncertainty: Decision-Making Beyond the Numbers by John Kay and Mervyn King

If you’re sensing a theme here, it is the desire for humans to have a firmer grasp on present actions for future outcomes. At the outset of 2020, was anyone publicly warning of the virus causing a stock market collapse? Not really, and in Radical Uncertainty, two of England’s leading economic scholars, John Kay and Mervyn King, help explain why. Experts have become too secure in their quantitative forecasting while ignoring how humans actually live. Taking a pinprick to probability models, the authors encourage “narrative reasoning… the most powerful mechanism for organizing our imperfect knowledge.” Creating stories is more important than simply crunching the numbers.

4. Do Dice Play God?: The Mathematics of Uncertainty by Ian Stewart

Three months ago, the “c-word” on most of our minds was Christmas, not coronavirus. Or, as noted English mathematician Ian Stewart puts it, “Prediction is very difficult, especially about the future.” Do Dice Play God? is a cerebral look at centuries of brainiacs trying to anticipate what comes next. As “time-binding animals,” humans are always trying to hone our predictive capacities. Stewart breaks this down into “Six Ages of Uncertainty,” starting with the millennia of people believing in the fate of the gods up to the modern age, including the practice of forecasting medical research. In science there is solace.

5. The Fifth Risk: Undoing Democracy by Michael Lewis

Michael Lewis, the journalist’s journalist, has spent his career writing about successful risk mitigation in bestsellers like Moneyball and The Big Short. The Fifth Risk is not like those books. While recovering from surgery in the Trump transition period, Lewis grew anxious about the new administration’s lack of seriousness in staffing federal government positions and their disdain for the people holding the jobs keeping America functioning — and what could happen down the road as a result. Decisions such as the Trump administration’s firing of the U.S. pandemic response team in 2018 are just one example. The list of books here has primarily been culled to offer some semblance of helping get a handle on the current global madness. But it’s okay to be righteously fucking pissed off too. Lewis is. Check him out on CNBC absolutely dripping with contempt about the Trump administration’s approach to pandemics.

6. Ultralearning: Master Hard Skills, Outsmart the Competition, and Accelerate Your Career by Scott Young

You can spend your self-isolation binging on Twitter and watching your stock portfolio implode… or you could pick up a new skill. In Ultralearning, writer and speaker Scott Young provides strategies for aggressive self-directed learning. The book is well-researched and provides a clear set of principles to follow around things like experimentation, focus, and retention, to add any new talent to your arsenal. As Young points out in an entertaining talk he gave at the World Domination Summit, the hard way to learn something may be easier than you think.

7. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott

Hard times call for harder choices, but that doesn’t mean you have to turn into Bill Lumbergh, (aka “the boss from hell”). The heart of Kim Scott’s Radical Candor is simple, “Care Personally, Challenge Directly.” A manager during a crisis period shouldn’t be much different than during the boom days. Scott, who has led all kinds of teams from startups to Apple to a pediatric clinic in Kosovo, believes if you get to know workers on a truly human level, problems that arise can be addressed together, as adults. We all know in the weeks to come there is going to be an overwhelming number of layoffs, furloughs, and daily unpleasant decisions to be made. Scott’s perceptive understanding of what it means to be a humane boss in these uncertain times will help ease the pain.

8. Black Swan: The Impact of the Highly Improbable by Nassim Nicholas Taleb

For centuries, the Old (European) World believed the only color of swans was white. In 1697, a black swan was discovered by a Dutch explorer, out of which came the theory that you can’t rule out a thing that doesn’t exist just because you haven’t seen it. In 2007, the options trader-turned-professor Nassim Nicholas Taleb took that concept and extrapolated it to outlier events — World War I, World War II, 9/11, but also neckties and Harry Potter — in his hugely influential book Black Swan. He believes a Black Swan event has three components: it’s unpredictable, has a massive impact, and after it ends is “retrospectively predictable,” in that people assign causes nobody saw beforehand to make it seem less random. The coronavirus pandemic is a Black Swan event for the global economy. But what Taleb wants governments, businesses, nongovernmental organizations, even everyday citizens to take away isn’t helplessness, it’s robustness against Black Swan events.

9. Uncertainty: Turning Fear and Doubt Into Fuel for Brilliance by Jonathan Fields

In troubled times, it helps to have sherpas who have faced seemingly insurmountable obstacles to lead the way. Jonathan Fields has been there. He quit a high-paying lawyer job and with a baby at home and launched a New York City yoga studio on September 10, 2001. You can imagine what happened next. Fields realized that handling fear goes a long way in determining success or defeat. A tool Fields uses to lean into paralyzing fear is “question and reframe,” which means finding an alternative storyline for mobilization. For him, “Why quit law to be a $12 an hour trainer?” became “Why limit the next 40 working years based on the previous eight?”

10. The House on Pooh Corner by A.A. Milne

The books listed here so far can make for some heavy reading. So it only felt appropriate to end a list of books for uncertain times on a lighter note. Published following the brutality of World War I, by an author suffering from “shell shock” (now known as PTSD), the tales of Christopher Robin, his stuffed bear Winnie-the-Pooh, and their adventures in the Hundred Acre Wood, provided much-needed comfort in a time of great sadness. At the end of the book, before leaving his friend Pooh, young Christopher Robin says his favorite thing to do is nothing, which means “just going along, listening to all the things you can’t hear, and not bothering.” Trying to cope with uncertainty is important, but sometimes so is turning off your brain and, for a little while, doing nothing.

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