Books about Embracing Uncertainty

Not knowing can be uncomfortable. In school and at work, we’ve likely seen people with the most confident answers (regardless of correctness) get acknowledged and rewarded, while those seeking clarification are dismissed. When faced with options, from the banal to significant, we often wish we knew what the right choice was. But Uncertainty is inevitable, and you need to learn to acknowledge, if not embrace, the certainty that you don’t always have the information to discover the right answers, much less the answers themselves. I recently read How Not to Know , a book about embracing uncertainty, and it brought to mind two other books on this essential subject.

Uncertain, by Maggie Jackson, offers insight (and data) into why being uncertain can improve conversations, innovation, and even AI. Jackson helps you to understand the value of uncertainty in domains as varied as team dynamics, interviewing, problem-solving, and politics. Uncertain doesn’t just show you how to accept uncertainty. Jackson provides a guide to understanding the power in not being sure, something we might all need help with.

Think Again, by Adam Grant is a must-read book for anyone who is certain that they understand a complex issue. Whether it’s something related to your profession or an “important” argument on social media, Think Again provides some insights into how to step back from the desire to convince and to win an argument and into a position of wanting to understand and find solutions. Unlike the other two books on this list, Think Again isn’t explicitly about uncertainty; rather, it demonstrates the value of maintaining a curious approach. Grant uses the archetypes of Preacher, Prosecutor, Politician, and Scientist to describe different approaches to understanding a problem. The Scientist does best in most cases because the scientist’s approach is inherently about questioning and revisiting what we know. This is a book about critical thinking, adaptability, and most of all humility: all things that can help us to learn and to persuade. We can benefit from the approaches here, especially if our goal in conversation and debate is to have an impact rather than to simply be judged “right” and win the argument.

How Not to Know, by Simone Stolzoff, is a more recent work that really resonated with me. While he refers to the work of Adam Grant, he adds the context of how embracing uncertainty in various aspects of our lives, ranging from relationships to religion to OCD, to coping with illness and death. And he calls out one reason this is particularly relevant in current times: with so much access to information, we feel like we should be able to know. But the truth is that more information can make knowing harder. The book ends with some guidelines to keep in mind when you find yourself struggling with uncertainty. These guidelines are more like prompts than a summary of the book, so don’t replace reading the work. If you find yourself wanting to be certain when you are in fact not, you may well want to give this book a read.

Each of these books offers different perspectives on why certainty can mislead us and hold us back. That’s something we all need to understand better.