How to Actually Be Comfortable with Uncertainty

A new book explores how to actually do this thing anxious people are constantly told to do

ME, BUT BETTER, my book about personality change, is out now. If you haven’t yet, please pick up your copy today. And if you’ve read the book, it would mean the world to me if you could leave an Amazon review. Thank you!

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Photo by Towfiqu barbhuiya on Unsplash

When I was trying to bring down my Burj Khalifa-levels of neuroticism, a piece of advice that I often came across suggested that I should try to be “comfortable with uncertainty.” Neurotic people, the thinking goes, don’t like situations in which the outcome is unknown: Whether that person saw your email, whether you will get that job, whether this is the month you’ll get pregnant. (Feeling sweaty yet?) If we can maintain control, we think, we can more easily keep our anxiety at bay. This becomes a problem in the many, many situations in which we can’t maintain control.

The answer, duh, is to simply get comfortable with uncertainty! Every time I heard this piece of advice, I would think the same mental retort: I don’t know how to do that, either. When I was at my most anxious, telling me to get comfortable with uncertainty worked about as well as telling me to “just calm down.” If anxious people knew how to do that, they would! I even tried to read Comfortable with Uncertainty, the Buddhist Pema Chodron’s book that people beat you over the head with if they see you popping an emergency Xanax, but it was too esoteric for me.

This is why I was so happy to come across How to Fall In Love With Questions, a wonderful and profound new book by Elizabeth Weingarten that’s all about how not knowing the answer can be okay … sometimes even kinda fun! She doesn’t necessarily force you to embrace or learn to love uncertainty, but she walks you through a better way of thinking through life’s unresolved questions and uncertain moments.

I recently read the book, and had the opportunity to interview Weingarten about it. An edited transcript of our conversation is below:

OK: Why did you decide to write a book about being comfortable with uncertainty?

EW: My book is about how to change your relationship with uncertainty so that you can emerge feeling renewed, refreshed, and awake to what life has to offer.

My favorite definition of uncertainty is “a sense of doubt that stops or delays progress.” The book asks: How do we not let doubt stop us? How do you move forward in your life when you don’t have all of the answers?

I wrote the book because I was stuck. It was spring of 2021. I'd recently gotten married and my relationship was struggling. On top of that, I'd decided to leave a job to pursue a creative project that was failing. I was asking two big questions: Should I get a divorce? And – what the hell am I supposed to be doing with my life? I was feeling miserable: anxious, alone, and mired in my circumstances. I wished that someone, anyone, would tell me the answers so I could get on with my life.

It was around this time that I discovered Letters to a Young Poet, which is a book of correspondence between the Austrian poet Rainer Maria Rilke, and the 19-year-old aspiring poet Franz Kappus, written in the early 20th century.

In the book, Kappus peppers Rilke with questions. Rilke famously does not give him answers, but instead encourages him to “love the questions themselves as if they were locked rooms or books written in a very foreign tongue.” And he goes further telling him he ought to “live the questions.”

I had two reactions when I read this passage. The first was: wow, what a beautiful idea. The second was: yeah, right. As a journalist and applied behavioral scientist, I’d spent years not only revering questions as part of my craft, but also reporting and researching the power of questions in our lives. But I was struck by the fact that at that moment, I hated my questions. It made me wonder: was it even possible to love the most challenging questions of our lives – the questions about identity, love, meaning, loss, relationships, purpose? In other words – could we learn to have a different relationship to uncertainty?

I wrote the book because, at this very low point in my life, I was desperate to find out if Rilke’s words constituted a real way to live, or just an impractical poetic idea.

OK: Throughout the book, you follow the story of the Austrian poet Rainer Maria Rilke. I love Rilke! I feel like my wisest yoga teachers quote him right before savasana. Why did you decide to weave his story into this?

EW: I have also been in many yoga classes where Rilke is quoted. He was an original master of the sound bite – his poetry channels peace and profundity in only a few lines.

Rilke’s words were a big part of the reason I decided to write the book in the first place. But as I learned more and more about his life, I realized that his personal story also held lessons about the complexity of loving, and living, our biggest questions.

Rilke excelled at loving and living the questions of his professional life, and floundered at loving his personal, and relational, ones. He was able to sit and explore his artistic work patiently – it took him more than a decade to finish one of his most famous bodies of work, the Duino Elegies – but not so with his closest relationships. He famously abandoned his wife and baby, and was as itinerant (and philandering) as they come.

There are two larger points here: Even the people who we might perceive as all-knowing sages, or gurus, also struggle with cultivating a different relationship to uncertainty across all of their life circumstances. Grappling with uncertainty and questions unites all of us.

And also: no one – not Rilke, not me, not any social media influencer – has all of the answers to this big question of how to live our lives. In this way, Rilke’s story is a bit of a cautionary tale. For many years, he chases after mentors who he thinks will be able to tell him how to live, how to be an artist (for instance, the sculptor Auguste Rodin). He fails to find that omniscient person, because there is no one person out there who can give us all of the answers we seek, or someone who can eliminate our uncertainty. This doesn’t mean they can’t still help us in times of need. But hopefully, this is also liberating: we are empowered to be able to find those answers ourselves rather than relying on someone else.

OK: One thing I was struck by is the importance of looking for answers in the right places. For instance, you wouldn't ask a friend who has never had a job for career advice. Can you talk about how you came to that realization, and how we can make sure we look for answers in the right places?

EW: In the book, I recount an experience I had with an astrologer while I was dating my then-boyfriend, now-husband.

A little bit of background: Even before we were married, I had my doubts about our relationship. We both had different ways of expressing love and care, and hadn’t yet learned how to communicate in each others’ styles. On the one hand, I’d never felt so attracted to someone – intellectually and physically – before. On the other, he challenged me in ways that were also unlike any other relationship I’d had. To him, care meant questioning and constructive debate. To me, it meant validation and agreement. We argued a lot. I wondered: was this normal? Was it worth it?

One summer, a few years into our relationship, a family member gave me the gift of a session with an astrologer. As a journalist and applied behavioral scientist, I did not “believe” in predictive powers of astrology. It’s a practice that has been debunked as a science.

And yet for years, I’d been occasionally going to psychics, getting my Tarot cards read, perusing astrology apps, and seeking out answers to my big life questions from alternative sources. There was something inside me that wanted to believe that these practitioners could give me the answers I sought.

During my session with the astrologer, I asked her about whether my then-boyfriend and I were a good fit and if we would stay together. Her response: no. She told me it wasn’t going to work, according to our charts.

This session haunted me, even after I got married, and especially when I was considering divorce. It wasn’t until I interviewed another astrologer, Jessica Lanyadoo, that I realized my mistake. When I recounted my experience to Lanyadoo, she pointed out that I’d gone to the astrologer for entertainment but then had asked this astrologer a deep and meaningful question. It wasn’t just about asking the right questions, she told me, but also about asking questions from the right sources. If the question was that important and sensitive to me, why would I pose it to a practitioner I didn’t trust?

This is a lesson that can also apply to the answers we seek from therapists to technology, particularly generative AI.

One of the biggest ways to make sure we’re looking for answers from the right sources is simple: slow down, and get to know your question a little better first. Try to understand what you’re really seeking – is it answers, or might it be something different, like connection? In the book, I share tools (like a questions map and guided prompts) to help guide people through this exploration.

OK: How does trauma play into our discomfort with uncertainty?

In general, we humans are wired to want to reduce uncertainty in our environments. That’s partly because of how we adapted to live in a world where food was more scarce: by conserving metabolic energy whenever we could. Navigating uncertainty forces us to use more metabolic energy, which means we feel a powerful drive to resolve it to conserve future energy. This is known as the selfish brain theory.

Of course, not everyone feels the same level of discomfort with uncertainty, and people feel different levels of comfort or discomfort across contexts and situations. There are many variables that can influence this. One is our personality (which you know all about!), and particularly our levels of openness to new ideas and experiences. In other cases it can be influenced by our upbringing, and whether or not we experienced trauma. Trauma can warp our sense of security, creating the specter of threats in the shadows of uncertainty when they don’t always exist, and making it harder for us to relate differently to our questions. It’s the difference between seeing the future as threatening, full of potential, or something in between.

This was the realization of one of the men I profiled in the book, Mateo. He began using the Internet heavily when he was a kid to help him cope with a traumatic childhood experience. Searching for information and answers online gave him the illusion of safety and security, like he could control his world. He ended up learning, through a long and painful struggle with what eventually became a technology addiction, that what he’d been searching for all along were not answers. Instead, he was looking for connection and community.

OK: Why is community so important to being comfortable with questions?

EW: On a basic level, community evolved to enhance our sense of security during uncertain moments. Research shows that a sense of being connected in community reduces cortisol, and activates parts of our brain that indicate we’re getting a reward and are safe. It puts us in an optimal place to explore questions, rather than rushing towards fast, easy answers.

OK: What are koans, actually, and how can they help us feel more at peace?

EW: A zen koan can be a paradox, or a question, or even a snippet of poetry, that’s designed to guide your mind past rational, conscious thought and onto another plane of understanding. A classic example of a koan is: ‘what is the sound of one hand clapping?’

You can’t understand a koan by thinking your way to a logical answer. You have to live it, to carry it around with you and start to relate it to experiences and conversations. Working with a koan isn’t about determining what it means objectively, but rather what it means to you. How might it help you see your own question, or problem, in a new way?

You can think of koans like uncertainty training wheels. They’re designed to help you get more comfortable with big mysteries in life by starting with small ones.

Koans also contain communities. When you carry a koan with you, you become linked to people who, across centuries, have asked the same questions and struggled with similar uncertainty.

In the book, I tell the story of Megan Rundel, who found a koan at a time in her life when she was feeling alone and rudderless, trying to figure out who she was and wanted to become. The central question of the koan she carried was essentially: how could someone who feels destitute and insignificant actually be rich and venerable?

Though the koan didn’t give her the answer, it helped her feel less solitary in her struggle, allowing her to see it as not just a “her” problem, but part of the human condition. This gave her more space to ask other questions that ultimately helped her find the right path.

OK: What is the "need for cognition," and what is its role in all this?

EW: The need for cognition measures how much someone is drawn to deep thought; there’s some evidence to suggest that higher levels of it are also associated with greater tolerance of uncertainty, and more wellbeing in general. In the book, I write about one study conducted by researchers at Harvard Medical School and Pennsylvania State University, where they wanted to investigate the connection between the need for cognition and symptoms of anxiety and depression. What they found is that people with lower NFC scores also had lower tolerance for uncertainty and were less curious. Conversely, they also found that higher NFC scores were associated with fewer symptoms of anxiety and depression. One of the takeaways is that curiosity – and question-asking – is a tool that may help reduce your anxiety during times of uncertainty. Anxiety isn’t always bad, but sometimes it can make it harder for us to cope, or to see different possibilities for the future.

OK: Talk about the role uncertainty played in your pregnancy, and how your approach to uncertainty has changed as a parent. (The ovulation strips didn't work for me either and I got "surprise" pregnant because of them too!!)

EW: Pregnancy, and parenthood, has been a constant test of my relationship to uncertainty. The greatest challenge in parenthood for me thus far has been letting go of the illusion of control, surrendering to the uncertainty of every hour. It’s. So. Hard. Especially when you aren’t sleeping much!

Like Mateo, one of the characters I mentioned earlier, one of the ways I tend to seek control is through gathering information. And in some cases, this is an okay way to cope: There are parenting questions that can be answered through information.

But not always. And these days, I try to be much more aware of when I’m seeking an actual answer, something that I can research and feel relatively certain about, and when my discomfort is about a bigger question that doesn’t have a fast, easy answer. Sometimes, these are questions about my finding my own identity as a mother, about co-parenting with my husband, or about how some of my own challenges with anxiety might impact my kid.

When I’m tumbling around with these larger questions, I know from my research, and my own experience, that the best thing to do is to seek out people who are going through something similar, or have in the past. I’ve found a lot of comfort in talking to other moms, even when none of us know the answers to these big questions. There’s something powerful in simply stumbling through the morass of uncertainty together, and knowing that we’re not alone.