How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty

by Elizabeth Weingarten

“In a world stupefied by quick fixes and easy answers, Elizabeth Weingarten delivers a smart and urgent wake-up call.”—Daniel H. Pink

“An interesting, insightful, and surprisingly reassuring read.”—Adam Grant, #1 New York Times bestselling author of Think Again and Hidden Potential

Journalist and applied behavioral scientist Elizabeth Weingarten charts a new path to embrace the questions of our lives instead of seeking fast, easy answers.

What do you do when faced with a big, important question that keeps you up at night? Many people, understandably, seize answers dispensed by “experts,” influencers, gurus, and more. But these fast, easy, one-size-fits-all solutions often fail to satisfy, and can even cause more pain.

What if our questions—the ones we ask about relationships, work, meaning, identity, and purpose—are not our tormentors, but our teachers? Inspired by 150-year-old advice from Austrian poet Rainer Maria Rilke and backed by contemporary science, Elizabeth Weingarten offers a fresh approach for dealing with these seemingly unsolvable questions. In her quest, Weingarten shares her own journey and the stories of many others, whose lives have transformed through a different, and better, relationship with uncertainty.

Designed to inspire anyone who feels stuck, powerless, and drained, How to Fall in Love with Questions challenges us to unlock our minds and embark on the kind of self-discovery that’s only possible when we feel most alive—that is, when we don’t know what will happen next.

Genres: Nonfiction, Psychology, Self Help, Philosophy, Audiobook, Personal Development

302 pages, Kindle Edition

Published April 15, 2025

Reviews

[Chris Boutté · Rating 2 out of 5]

I’m a big believer in people embracing curiosity, which is why I was super excited for this book. It started out really good and had a lot of great studies and information. Then, it started to go up and down. The author includes far too many personal stories, and many didn’t really seem relevant to the topic she was writing about, and that kind of took me out of the book. There are some good nuggets of wisdom in here, but it’s not great overall.

[Ben Heisler · Rating 5 out of 5]

How to Fall in Love with Questions is an inviting guide to challenge our deep-seated need for certainty through both impactful research and heartfelt storytelling. It encourages us to embrace curiosity and patience amidst the unknown, gently reminding us that always having "the answer" at hand can actually distance us from owning the confidence to explore and learn for ourselves.

I enjoyed how Weingarten skillfully takes readers through the journey of uncertainty. Much like a trusted educator or therapist, the goal is profound self-discovery rather than quick fixes. Her writing comes through like a reassuring companion on a mountain trail, offering up a subtle nod of approval that it's okay to embrace "getting comfortable with being uncomfortable."

[Paul Ellis · Rating 5 out of 5]

Fantastic book by Elizabeth Weingarten. With wisdom, humilty, humor and commonsense, Weingarten sets out a smart, fresh way to navigate some of life's most difficult passages. The book is a must-read!

[Lia · Rating 5 out of 5]

I love how Weingarten weaves in her personal journey with spirituality, psychology, philosophy and more helpful approaches to uncertainty. It was hard not to relate to her story. I even bookmarked some pages with techniques for sitting with ambiguity and uncertainty. A must read!

[Daniel Lawlor · Rating 5 out of 5]

Thoroughly enjoyable!

[Aaron Stein · Rating 5 out of 5]

Must read for those who want to know themselves and others better! Super helpful in terms of knowing how to better introspect and empathize with others. Going to help me be a better human overall!

[Dave Freeze · Rating 2 out of 5]

The book was not what I expected or what I hoped it would be. It leaned heavily on the Rilke poem tool, returning often. This became tiresome and murky. The author’s choices of (many!) personal stories and interviews were too mystical for my tastes.

[C.D. · Rating 5 out of 5]

“How to Fall in Love with Questions” was such a helpful read. Elizabeth Weingarten has written an engaging, empathetic book that can help you figure out useful answers to all those questions that can nag at us about our life, relationships, job, or even why we question every decision we make. She uses stories — about her own life and those of others she interviewed — as examples of how asking the right questions can help you get to realistic answers that are right for you. She has a nice conversational tone (no lecturing), but reminds you that fast, one-size-fits-all answers are rarely the real answer.

[Ray Wang · Rating 5 out of 5]

A heart warming book that most people can relate to


Elizabeth wrote a heartwarming book that most people can relate to. She is brave in sharing her own struggles and other lessons in her life, and never hesitates to admit doubt, pain and regrets that she has encountered throughout her life.

Her book is based on solid, dissertation level research but yet full of interesting details of her own life journey which are both endearing and inspiring.

The whole book is extremely well written and an absolute joy to read in a couple of sittings. Her journalist parents must be proud of her. I highly recommend this book.

[Lewis B. · Rating 5 out of 5]

I could not put this book down. Interesting topic that is thought provoking and continuously has you thinking about your own life and experiences. Extremely well written and honest and open based upon Elizabeth’s facinating and extraordinary life experiences as well as documented examples of many others dealing with the topic. A must read for the intellectually curious .

[Bill Rodriguez · Rating 4 out of 5]

Great read, we don't need am the answers. It is fine living with questions.

[Jung]

In "How to Fall in Love with Questions", Elizabeth Weingarten invites readers to see uncertainty not as a threat but as an opportunity. In a world that often glorifies knowing the answers and projecting confidence, this book offers a fresh approach: embracing questions as a vital path to growth, innovation, and deeper human connection. Weingarten draws on history, science, and personal stories to show how curiosity can transform our understanding of ourselves, our relationships, and the environments we inhabit. Rather than treating questions as mere stepping stones to answers, she urges us to inhabit them fully, allowing them to unfold and shape us over time.

Curiosity, Weingarten argues, is one of the most underappreciated capacities we have. Although we’re born with an innate desire to explore, this tendency often fades as we age. We become more focused on appearing knowledgeable than remaining open to new ideas. Yet it is precisely this openness—this willingness to admit what we do not know—that leads to deeper insight. Our brains are wired to seek certainty, a trait that once kept our ancestors safe but now limits us in an increasingly complex world. To counter this, we must intentionally nurture curiosity. It can be as simple as reflecting each day on what new thing we learned, or noticing how our assumptions shift when we encounter new perspectives. The act of regularly asking questions, especially those that don't have immediate answers, keeps our minds agile and receptive.

Historical examples illustrate how transformative curiosity can be. When Alexander Fleming discovered penicillin, it was not through deliberate intent but because he allowed himself to be intrigued by a failed experiment. Rather than discarding the moldy Petri dish, he looked closer and asked why bacteria had stopped growing near it. This small act of paying attention and questioning what others might have ignored led to a revolution in medicine. Weingarten uses stories like this to emphasize that great discoveries often come not from certainty but from an ability to pause and explore what doesn’t immediately make sense.

In relationships, questions serve as bridges. They show others that we value their perspectives and want to understand their experiences more deeply. Too often, conversations are dominated by the impulse to give advice or share our own stories, especially when someone opens up about a challenge. But when we shift from giving answers to asking sincere questions, we create space for others to explore their own thoughts. Weingarten highlights the work of Studs Terkel, the oral historian who was able to elicit rich stories from people across all walks of life. His secret wasn’t fancy interviewing techniques, but rather a deep, authentic interest in what others had to say. This kind of curiosity makes people feel seen and heard, building trust and intimacy. We can apply this same approach in our own relationships by asking thoughtful, open-ended questions like 'What feels hardest about that?' or 'What support would be most helpful to you?' These types of questions encourage reflection and foster a sense of connection.

Weingarten also explores the role of questions in self-understanding. Just as we can use inquiry to connect with others, we can turn those same tools inward to better understand ourselves. Life often pulls us into routines, and without self-reflection, we can end up living on autopilot. By regularly asking ourselves questions—about what we value, what we’re afraid of, what we want to change—we disrupt these patterns and start making choices that align with our true selves. The author points to Eleanor Roosevelt as someone who used internal questioning to evolve far beyond the roles expected of her. Rather than accept her limitations, Roosevelt asked what she could do in spite of them. Her habit of challenging her own fears allowed her to grow into a powerful advocate for justice and change. We can adopt similar practices by making time for regular reflection, or by imagining what advice a trusted mentor might give us in a difficult moment. These practices deepen our insight and increase our sense of agency.

The workplace, according to Weingarten, is one of the areas most in need of a questioning mindset. Too often, organizations reward quick answers and discourage inquiry, which stifles innovation. People fear looking uninformed, so they stay silent instead of asking questions that could lead to better outcomes. But true progress happens when we challenge assumptions and explore problems more deeply. Claude Shannon, known as the father of information theory, didn’t merely try to improve communication systems—he asked what information really is and how it could be measured. His questions laid the groundwork for the digital world we now live in. Professionals can apply this same spirit by preparing thoughtful questions before meetings, debriefing with colleagues after projects, and exploring what success would look like before jumping to solutions. These habits not only improve performance but also foster a culture of curiosity and continuous learning.

At the heart of Weingarten’s message is the idea that uncertainty is not something to be feared, but a space where transformation begins. Even when we embrace questions, we won’t always get clear answers. In fact, the most important questions may only lead to more questions. But this is not a flaw in the process—it is the point. Learning to live within the discomfort of not knowing is a skill that allows us to stay open to growth. The physicist Richard Feynman embodied this mindset. He delighted in the mysteries of the universe, often saying he was in a state of 'confused wonder.' For him, not knowing wasn’t a failure—it was an invitation to explore. This attitude didn’t just lead to scientific breakthroughs; it made the process of discovery itself more joyful.

We can develop the same resilience by practicing patience with our own uncertainties. Instead of rushing to resolve every question, we can give them space to evolve. Some of the most significant insights in life don’t arrive all at once—they unfold gradually. Keeping a journal of meaningful questions and revisiting them over time is one simple way to build this capacity. It allows us to track how our thinking changes, how our relationship to the unknown matures. Over time, this practice transforms uncertainty from a source of stress into a fertile ground for insight and creativity.

In sum, "How to Fall in Love with Questions" offers a compelling argument for rethinking how we engage with uncertainty. By replacing the urge for immediate answers with a habit of thoughtful inquiry, we open ourselves to new ways of thinking, connecting, and growing. Curiosity becomes more than a personality trait—it becomes a way of being in the world. Whether we are navigating personal challenges, building stronger relationships, or seeking innovation at work, questions provide a powerful guide. Weingarten’s message is clear: living the questions doesn’t mean we give up on finding answers—it means we value the journey of asking just as much.

[Kevin Stecyk · Rating 5 out of 5]

Different Than I Expected

Because Weingarten and I are much different—gender, of course, and vastly different ages—How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty did not resonate with me as much as it likely does to those who are younger and beginning their life adventure. That said, she did meet and discuss with people so various ages how to ask and live with questions that cause us to reflect on who we are and what we want to achieve.

I would encourage those who are younger and have an introspective bent to read this book.

[Kim · Rating 4 out of 5]

Accessible and interesting. No mind blowing revelations but nice to spend some time thinking about questions and uncertainty and how to better live with the emotions they bring up.

[Cheryl · Rating 3 out of 5]

Multiple studies suggest that we prefer certain pain or loss to uncertainty and that we tend to avoid ambiguity at all costs. We humans are wired to avoid or reduce uncertainty and to minimize surprise by changing the way we respond to our environment.

There’s a ubiquitous assumption of our “impatient age,” Harned writes. That’s the assumption that real life is characterized by action, agency, and productivity—that we are most fully human when we are in control and doing things. Far from being passive or weak, patience is an essential ingredient not only to achieving goals but to living well and actively during periods of uncertainty.

A fresh take on the wisdom of Rilke and modern studies around personality with a tad too much about the author’s life and anxiety, but still worthwhile. It seems to be that curiosity and patience are superpowers and helps us hold more uncertainty in our lives, which seems to be healthy and anxiety-fighting.

With each answer smartphone users looked up, they missed out on an opportunity to “sit with not knowing in relatively safe environments,” he told me. “We know from mental health disorder treatments that exposure-based therapies can be very powerful to help people overcome anxiety. And a big part of anxiety management can be learning to tolerate uncertainty, to become comfortable with not knowing. There I am with a cell phone, and all of a sudden, I don’t need to tolerate that. I now have a device that can build in certainty, or perceptions of it, into every part of my life, taking away opportunities to practice tolerating uncertainty.”

Here, we face a paradox: We’re able to sustain our ability to love the questions of our lives only when we embed ourselves in the right relationships and community. But the act of entering relationships can often mean facing even more uncertainty. “This fear of the inexplicable has done more than impoverish the life of the individual,” Rilke writes. “It has also constricted relations between people, lifting that relationship out of the riverbed of infinite possibilities, as it were, onto an unseeded plot of land on the shore, where nothing is accomplished. For it is not laziness or inertia that makes human relationships repeat themselves from one case to the next, with such unspeakable monotony and stagnation—it is also our shrinking away from any new, unpredictable experience we don’t feel able to handle.”

After analyzing survey results across ten years, the researchers found that, indeed, higher curiosity scores were associated with fewer symptoms of anxiety and depression. One takeaway from the research is that the more you can anchor yourself in questions, letting them fuel your curiosity and deepen your understanding of who you are and what you want, the less anxious you’ll be.

[Greg Talbot · Rating 3 out of 5]

"Unknown carries two beautiful resonant almost underground vowel sounds echoing through it's very center. The unknown itself resonantes through every minute structure of our never fully articulated life." - [David Whyte poem "Unknown" from Consolations II]

Oh what a joy to search for questions instead of answers. Rainer Maria Rilke's "Letters to a Young Poet" is what prompts Weingarten's deeper search. Although "living the question" is not articulated by Rilke (p.7), many of the deep truths we impart are incommunicatable but nevertheless present. This is a joyfully written book with deep heart and vulnerability. Sometimes I find an author's voice seems to strognly resonant with my own inner own, and Weingarten did this multiple times when she vulnerably discussed issues of marriage, community, and inner acceptance.

What struck me most reading this book is that Weingarten avoided the ptifalls of our screen-based world. She connected with real people to discuss grounding practices and psychodelics and Dialetic behavior therapy. It's very powerful to read someone's experience to find their inner self even if it doesn't directly map onto our own. Passages when she was climbing Mt. Rainer with her fiance or going deep into her psyche with MDMA were riveting. She will write expressively on others too, such as her writings on the Heterodoxy group.

The times I was most engaged with the book were when Weingarten stayed close to her emotional experience. She articulates the feeling-felt experience of being in a loving relationship with depth. Many people will relate to those feelings of getting close to someone, and loving them, but feeling some barriers toward the life-partner intimacy that could blossom into a beautiful marriage. Stories about pregnancy, her studio experience with koans, and people pleasing were some highlights.

I generally enjoy "self-help" books that are more prescriptive, perhaps something like Pema Chodron's "When Things Fall Apart" or Tony Robbins "Awake the Giant Within", but Weingarten successfully weaves literary and personal stories into a thoughtful collection. Because we cover so much ground with topics and methods of tranformation, there are times I thought the momentum waned a bit, or left me wanting more. But with that said, there is plenty here to enjoy and appreciate.

[Cherryl · Rating 5 out of 5]

How to Fall in Love with Questions is such a thought-provoking read! Elizabeth Weingarten really challenges the idea that we need quick, definitive answers to life’s biggest questions. Instead, she encourages us to lean into the uncertainty and see questions as opportunities rather than obstacles. I loved how she blends her personal experiences with insights from psychology and even poetry – especially drawing inspiration from Rainer Maria Rilke. It’s one of those books that makes you pause and rethink how you approach decision-making and self-reflection. Rather than rushing to find solutions, Weingarten argues that we can actually grow and learn by just sitting with the questions.

What really stood out to me was how practical and relatable the book felt, even though it tackles some pretty abstract concepts. It’s not just about theory – Weingarten shares real stories of people who have embraced uncertainty and found new perspectives because of it. It’s refreshing to read a book that doesn’t pretend to have all the answers but instead teaches you to embrace the journey of figuring things out. If you’re someone who feels stuck or overwhelmed by big life choices, this book might just give you the permission you need to slow down and appreciate the process.

[Lauren Smith · Rating 5 out of 5]

“How to Fall in Love with Questions” was such a beautiful, resonant read—and made even more special by the chance to explore it through a book club. Elizabeth Weingarten’s writing is both insightful and grounding, weaving in powerful personal stories and interviews with researchers that brought the themes to life.

What stuck with me most was the idea of sitting with the discomfort of the questions in our lives—learning to recognize which ones will be answered quickly, which ones we'll work through over time, and which are our heart questions, the ones we may carry with us forever. This book gently invites us to release the pressure to have all the answers and to step away from binary thinking. Instead, it teaches us to fall in love with the questions themselves.

Since reading it, I’ve found myself applying these lessons in everyday life—giving myself (and others) more grace in moments of uncertainty, and learning to hold space for the unknown with curiosity instead of frustration.

A truly special book that I’ll keep returning to.

[Deborah Laskero · Rating 5 out of 5]

Elizabeth Weingarten has presented a historical, spiritual, philosophical, as well as a personal journey into the importance of asking questions to move forward. The book is a guide for all of us seeking our own truths by asking the questions that can generate growth and change. I highly recommend this book for therapists, teachers and mentors of any kind. There is so much to gain and I plan to refer to it often as it shares much wisdom and positivity. This is not a commentary on one particular phase of life nor does it offer a simple fix. What is presented is a true companion that can be unleashed by us developing the practice of asking questions and and then listening to the the answers.

[May Samali · Rating 5 out of 5]

This is one of the most important books of our time! Elizabeth does an incredible job giving us our agency back—replacing the platitude of embracing uncertainty with a call to action: love the questions. This book is thoroughly researched and beautifully written. It is both philosophical and highly practical. I recommend this to anyone who wants to lead their life with more confidence and to find solace and community during uncertainty.

[Conor Smith · Rating 5 out of 5]

Timely and refreshing. I found that the book offers a great guide to navigating uncertainty in this crazy time. I'm constantly trying to find quick answers to solve my and my loved ones' problems, but I like how this book teaches that, rather than rushing to find answers, we should slow down and stay curious. How to Fall in Love with Questions is a book I’ll be returning to often — highly recommend for anyone in transition or just seeking a framework and philosophy for navigating these times.

[Carolyn Tubekis · Rating 5 out of 5]

This book is crucial reading for all who are stressed by this world we live in today. I loved this book because it truly forces you to slow down and look inward - with hope. It makes you realize that everyone has some inner turmoil that is unique to them. It’s part of being human. Elizabeth calls that out in a way that is comforting, inspiring and highly educational. She weaves her research beautifully into the intimate corners of her own life questions.

[Fuzz Hogan · Rating 5 out of 5]

Really insightful book on how to embrace uncertainty as you confront major decisions or moments in your life. Very well written and deeply researched. A good book to keep on the shelf and refer to often!

[Mary · Rating 5 out of 5]

Good mix of personal stories and scientific research. I really appreciated the actionable insights and the soulful treatment of the subject matter. I think it’s worth a second read and plan on coming back to this book in a few months.

[The · Rating 1 out of 5]

I couldn't get through this book. What is it with modern self-improvement books that the author needs to make themselves the focus? Cringey. And author came away from this looking pathetic. It is too bad as it is a topic for which I am all in. She spoiled it fully.

[Joe V · Rating 2 out of 5]

At the core of this book I find the author asking over and over: "is it going to be ok and will I be happy" that I find a bit impulsive. I enjoyed the chapter on embracing patience, but if the author takes that advice, there might not be a book to write. There evolves this struggle between tackling big questions contemplatively or actively. The "New Way" lacks a certain spirituality that could be drawn from traditions and anecdotes of the past, but a sense of subjectivity overrides the collective opinions of those who encountered the same timeless struggles before.

[Joshua Macdonald · Rating 5 out of 5]

Insightful and full of sage wisdom on embracing uncertainty

[Tony Jay · Rating 5 out of 5]

I’m about a hundred pages in…. loving this so far!!!!

[Michelle Woods · Rating 5 out of 5]

Highly recommend for anyone navigating uncertainty or weighing decisions large or small. Great perspective, delivered with wide ranging examples and levity.

[Sara · Rating 3 out of 5]

I liked the premise but had a hard time paying attention