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How to Not Know: The Value of Uncertainty in a World that Demands Answers
"Spectacular." —Daniel Pink
A guide to dealing with uncertainty at a time when our lives have never felt less certain.
From our careers to our politics to our personal lives, the future is unknown. And yet, our capacity to tolerate this uncertainty is in decline. How to Not Know will help you prepare for and even appreciate the uncertainty that surrounds us.
Through gripping stories of people grappling with big problems without easy answers from an economist trying to predict the next market crash to an island nation reckoning with the existential impact of climate change acclaimed journalist Simone Stolzoff shows how to develop comfort with ambiguity and build tolerance for the unknown.
Blending engrossing storytelling, research, and practical insights, How to Not Know is an essential guide to navigating uncertainty with courage and clarity.
A guide to dealing with uncertainty at a time when our lives have never felt less certain.
From our careers to our politics to our personal lives, the future is unknown. And yet, our capacity to tolerate this uncertainty is in decline. How to Not Know will help you prepare for and even appreciate the uncertainty that surrounds us.
Through gripping stories of people grappling with big problems without easy answers from an economist trying to predict the next market crash to an island nation reckoning with the existential impact of climate change acclaimed journalist Simone Stolzoff shows how to develop comfort with ambiguity and build tolerance for the unknown.
Blending engrossing storytelling, research, and practical insights, How to Not Know is an essential guide to navigating uncertainty with courage and clarity.
217 pages, Kindle Edition
Published May 12, 2026
About the author
Simone Stolzoff
5 books111 followersSimone Stolzoff is an author and designer from San Francisco. A former design lead at the global innovation firm IDEO, his work has been featured in The New York Times, The Atlantic, and on the TED Stage. He is a graduate of Stanford University and the University of Pennsylvania.
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Displaying 1 - 30 of 114 reviews
May 12, 2026
I had high expectations for "How to Not Know," and yet Simone Stolzoff managed to exceed them. What stayed with me most is how deeply human this book is. It’s the storytelling that makes it such a moving and impactful read.
Each chapter is anchored in a story—from an individual struggling with OCD to a community facing climate uncertainty. Through these stories, we learn how others have navigated the discomfort of not knowing. And through the lens of their experiences, we begin to recognize something both unsettling and freeing: uncertainty isn’t a "problem to be solved."
Perhaps my favorite sections were those that centered on control and decision-making. Two passages I keep coming back to: "A life that is fully optimized misses out on the serendipity and delight that live outside of our comfort zone," and "Whether we suffer from OCD or not, our brains play masterful tricks to help us avoid undesirable emotions. Decision-making is hard because before we make a choice, every option is available to us. Making a choice requires forgoing other opportunities, which can feel like loss. Rather than accept the consequences of commitment, our brains can convince us to perpetually stay in a place of indecision." I haven't stopped thinking about that second one.
Stolzoff so artfully blends research with reporting to examine our modern obsession with "the right answer." He doesn’t try to lecture us or simply cite studies. Instead, he brings us into the lives of others and lets us watch them grapple with uncertainty. As readers, we observe these situations with curiosity, recognize the familiarity of these struggles, and feel our own understanding begin to shift.
One of the things I appreciated most is that this isn’t a book that romanticizes uncertainty. As Stolzoff writes: "The goal of this book is not to direct you to always seek out uncertainty. Both certainty and uncertainty are important components of a fulfilling life. The problem occurs, however, when we search for certainty where there is none to be found." Stolzoff doesn’t try to tell us how we should live. More powerfully, he helps us shift how we relate to the unknown through the people whose lives he gives us a glimpse into.
Each chapter is anchored in a story—from an individual struggling with OCD to a community facing climate uncertainty. Through these stories, we learn how others have navigated the discomfort of not knowing. And through the lens of their experiences, we begin to recognize something both unsettling and freeing: uncertainty isn’t a "problem to be solved."
Perhaps my favorite sections were those that centered on control and decision-making. Two passages I keep coming back to: "A life that is fully optimized misses out on the serendipity and delight that live outside of our comfort zone," and "Whether we suffer from OCD or not, our brains play masterful tricks to help us avoid undesirable emotions. Decision-making is hard because before we make a choice, every option is available to us. Making a choice requires forgoing other opportunities, which can feel like loss. Rather than accept the consequences of commitment, our brains can convince us to perpetually stay in a place of indecision." I haven't stopped thinking about that second one.
Stolzoff so artfully blends research with reporting to examine our modern obsession with "the right answer." He doesn’t try to lecture us or simply cite studies. Instead, he brings us into the lives of others and lets us watch them grapple with uncertainty. As readers, we observe these situations with curiosity, recognize the familiarity of these struggles, and feel our own understanding begin to shift.
One of the things I appreciated most is that this isn’t a book that romanticizes uncertainty. As Stolzoff writes: "The goal of this book is not to direct you to always seek out uncertainty. Both certainty and uncertainty are important components of a fulfilling life. The problem occurs, however, when we search for certainty where there is none to be found." Stolzoff doesn’t try to tell us how we should live. More powerfully, he helps us shift how we relate to the unknown through the people whose lives he gives us a glimpse into.
May 11, 2026
The stories and research that Simon Stolzoff weaves together in this wholly approachable consideration of living with uncertainty is a book I’ll return to again just like his first book, The Good Enough Job. Would be a great book club read, rife with options for meaty discussion regardless of creed or differing values.
June 2, 2026
This is easily one of my favorite books of the year. I quickly realized this author wrote another book that I loved, and I wasn’t even surprised by how good this book is. A quality more people need in this world is how to not know. The issue is that we humans don’t do well with uncertainty. In this book, Stolzoff teaches the reader not only how to deal with uncertainty but the importance of embracing it.
The book is more stories than it is scientific research, but it’s just filled with solid advice, and I loved it.
The book is more stories than it is scientific research, but it’s just filled with solid advice, and I loved it.
May 27, 2026
the rare book on uncertainty that doesn't try to sell you certainty by the end of it :)
very well written, easy to read with great tidbits and supporting examples: an sf tech worker whose life had become too predictable, so he built a system to randomize where he ate, what he did, eventually where he lived. a chapter on OCD and the clinical hunger for certainty. social psych research and how selective publishing and incentives pushed a field towards certainty in situations where perhaps that wasn’t accurate. our fear of death. the finding, consistent across studies, that anticipating an uncertain outcome is psychologically harder than the outcome itself, and how we catastrophize the wait more than the result.
one thread that especially resonated was how every short-term move toward certainty atrophies our ability to sit with not knowing. the counter here, to strengthen the muscle, is the case for exposure therapy: small reps of uncertainty to rebuild it.
what i appreciated most is how accessible the book stays without thinning out. stolzoff has a good ear for examples that land well, aren’t covering already well-trodden ground. read quickly, really enjoyed. easy to recommend.
very well written, easy to read with great tidbits and supporting examples: an sf tech worker whose life had become too predictable, so he built a system to randomize where he ate, what he did, eventually where he lived. a chapter on OCD and the clinical hunger for certainty. social psych research and how selective publishing and incentives pushed a field towards certainty in situations where perhaps that wasn’t accurate. our fear of death. the finding, consistent across studies, that anticipating an uncertain outcome is psychologically harder than the outcome itself, and how we catastrophize the wait more than the result.
one thread that especially resonated was how every short-term move toward certainty atrophies our ability to sit with not knowing. the counter here, to strengthen the muscle, is the case for exposure therapy: small reps of uncertainty to rebuild it.
what i appreciated most is how accessible the book stays without thinning out. stolzoff has a good ear for examples that land well, aren’t covering already well-trodden ground. read quickly, really enjoyed. easy to recommend.
May 12, 2026
I finally got around to reading this book and it felt incredibly relevant to the world we are living in today. In a time where everything is constantly changing and uncertainty feels unavoidable, this book offers a refreshing and thoughtful perspective on work, odentity, and how we navigate modern life. What I loved most were the personal stories and practical insights in the book. I genuinely think this is a book everyone should read, especially if you've ever felt overwhelmed by the pressure to 'have it all figured out'. Highly recommended!
May 25, 2026
Simone Stolzoff’s "How to Not Know" is a timely and deeply resonating read for anyone navigating complexity, especially those of us working in systems that are constantly evolving.
What struck me most is the tension between our desire for certainty and our persistent inability to accurately predict outcomes. We want and crave clarity. And yet, in practice, we are force to operate in ambiguity. Stolzoff captures this paradox in a way that feels both validating and challenging. It made me reflect on how often “comfort” becomes a quiet barrier to growth and how the pull toward familiar thinking can stall meaningful change, even when we know better.
I see this dynamic play out frequently in education systems. We talk about innovation and improvement, but too often decisions are shaped by perception rather than evidence. We "crowdsource" comfort instead of interrogating data. This book sharpened my thinking about that tendency and reinforced the importance of staying grounded in what we know, while also remaining open to what we don’t.
Another powerful takeaway was the role of external perspectives. Stolzoff highlights that groups with more cognitive diversity and outside viewpoints tend to make better decisions, even though they often feel less effective in the moment. That insight stayed with me. It reframes the discomfort of slower, more deliberative processes as a signal of stronger thinking, not weaker leadership. For those of us working in policy and systems change, that is an important reminder: inclusivity and rigor take time, and they should.
The discussion of leadership also resonated. Strong leaders are not those who eliminate dissent, but those who actively seek it out and align their teams around a shared purpose without distorting incentives. That’s harder than it sounds, especially in complex systems where pressures and priorities compete.
I was also struck by the framing of crisis management, particularly the idea that we consistently underinvest in emotional support. Strategic and operational responses are necessary, but insufficient on their own. Ignoring the human dimension is not just an oversight; it’s a missed opportunity to lead effectively through uncertainty.
And then there’s the line that has stayed with me: “The key is to keep rowing.” That image of rowing through fog perfectly captures what it feels like to start something new, to lead change, or to sit in the unknown without immediate answers. It’s uncomfortable, but it’s also where the real work happens.
This is a book I will return to, and one I would recommend to anyone working at the intersection of leadership, policy, and change. It doesn’t offer easy answers which is exactly the point.
What struck me most is the tension between our desire for certainty and our persistent inability to accurately predict outcomes. We want and crave clarity. And yet, in practice, we are force to operate in ambiguity. Stolzoff captures this paradox in a way that feels both validating and challenging. It made me reflect on how often “comfort” becomes a quiet barrier to growth and how the pull toward familiar thinking can stall meaningful change, even when we know better.
I see this dynamic play out frequently in education systems. We talk about innovation and improvement, but too often decisions are shaped by perception rather than evidence. We "crowdsource" comfort instead of interrogating data. This book sharpened my thinking about that tendency and reinforced the importance of staying grounded in what we know, while also remaining open to what we don’t.
Another powerful takeaway was the role of external perspectives. Stolzoff highlights that groups with more cognitive diversity and outside viewpoints tend to make better decisions, even though they often feel less effective in the moment. That insight stayed with me. It reframes the discomfort of slower, more deliberative processes as a signal of stronger thinking, not weaker leadership. For those of us working in policy and systems change, that is an important reminder: inclusivity and rigor take time, and they should.
The discussion of leadership also resonated. Strong leaders are not those who eliminate dissent, but those who actively seek it out and align their teams around a shared purpose without distorting incentives. That’s harder than it sounds, especially in complex systems where pressures and priorities compete.
I was also struck by the framing of crisis management, particularly the idea that we consistently underinvest in emotional support. Strategic and operational responses are necessary, but insufficient on their own. Ignoring the human dimension is not just an oversight; it’s a missed opportunity to lead effectively through uncertainty.
And then there’s the line that has stayed with me: “The key is to keep rowing.” That image of rowing through fog perfectly captures what it feels like to start something new, to lead change, or to sit in the unknown without immediate answers. It’s uncomfortable, but it’s also where the real work happens.
This is a book I will return to, and one I would recommend to anyone working at the intersection of leadership, policy, and change. It doesn’t offer easy answers which is exactly the point.
May 28, 2026
How Not to Know by Simone Stolzoff is a quietly provocative book that reframes our relationship with uncertainty. Rather than treating the unknown as a problem to be solved, Stolzoff argues that our tolerance for uncertainty is actually a skill — one that shapes how we think, decide, and lead.
Several ideas stayed with me. First, that uncertainty only threatens us when we treat it as an enemy. When we turn toward it instead of retreating, it becomes an invitation to think differently. Second, that good decision-making isn't about eliminating unknowns — it's about acting on what you know while accepting the unknowns that are simply part of any future-facing choice. This is harder than it sounds, especially for leaders, because slower, more reflective decisions carry a real cost that many aren't willing to pay.
Stolzoff also touches on some unexpected tools for navigating ambiguity. Brian Eno's Oblique Strategy cards make an appearance as a surprisingly useful resource in crisis situations. So does grief management — one firm profiled actually embedded it as a core component of their crisis practice, a reminder that loss and uncertainty are often inseparable.
Two lines I keep returning to: hold your hypotheses lightly and stay open to new evidence, and the idea that you have to trust your future self to handle future problems. That second one is almost a form of radical acceptance — a willingness to stop trying to solve everything now.
A thoughtful read for anyone navigating complexity, whether in leadership or in life.
Several ideas stayed with me. First, that uncertainty only threatens us when we treat it as an enemy. When we turn toward it instead of retreating, it becomes an invitation to think differently. Second, that good decision-making isn't about eliminating unknowns — it's about acting on what you know while accepting the unknowns that are simply part of any future-facing choice. This is harder than it sounds, especially for leaders, because slower, more reflective decisions carry a real cost that many aren't willing to pay.
Stolzoff also touches on some unexpected tools for navigating ambiguity. Brian Eno's Oblique Strategy cards make an appearance as a surprisingly useful resource in crisis situations. So does grief management — one firm profiled actually embedded it as a core component of their crisis practice, a reminder that loss and uncertainty are often inseparable.
Two lines I keep returning to: hold your hypotheses lightly and stay open to new evidence, and the idea that you have to trust your future self to handle future problems. That second one is almost a form of radical acceptance — a willingness to stop trying to solve everything now.
A thoughtful read for anyone navigating complexity, whether in leadership or in life.
May 31, 2026
Simone Stolzoff's new book is an insightful, easy-to-read exploration of the art and science of uncertainty in life. The book is split into three main sections - Comfort, Hubris, and Control - that cover the most common reasons people shy away from uncertainty in life. Combining anecdotal stories, research-driven facts, and linkages to philosophy and psychology, the book reads well and quickly. I think the volume is poised to be a great gift book for someone experiencing a transition in life - planned or otherwise. I can imagine sharing it with recent graduates, friends experiencing major life changes like job shifts or divorce, or even with someone experiencing a loss. The ability to understand our human tendencies and preferences, how they support us, and how they can hold us back, is a gift worth working for. I especially loved the ideas concerning how our desire to be in control makes us less tolerant of uncertainty. Given how clearly we all experience uncertainty on a regular basis, learning more about how uncertainty not only can be better tolerated, but also can support our growth, helps us manage the realities of being human, better.
May 20, 2026
Some sections of this really spoke to me, and I felt like it was worth a read even though I'm also feeling sort of saturated on this sort of book. I think it pairs well with something like Pema Chodron's Comfort With Uncertainty. That one obviously has a more cohesive philosophy behind it, where as this jumps around a bit more. It's very practical, with a lot of takeaways backed up by research and different frameworks along with anecdotes from people who handled uncertainty in novel or impactful ways. It shifted a bit from personal/individual to organizational behavior scenarios, which worked at times and at other times felt too meandery. The last chapter pulls together a bit of a framework from everything discussed in the book, and I thought that was helpful. Pretty good overall.
May 23, 2026
I greatly enjoyed reading How To Not Know. Carefully balanced with stories and research, this book felt like a cozy approach to dealing with the uncomfortable topic of uncertainty. But by painting a picture through example after example of how accepting uncertainty can help, heal and lead us forward, this book made me feel grateful to the author for capturing diverse perspectives and making the scary feel a little less so. I especially loved the powerful personal story at the end and the “invitations” to learn how to better manage uncertainty, staying true to the heart of the book with a soft hand and heart. I would definitely recommend this book to those interested in the topic, as it was easy to read and heartwarming.
May 31, 2026
This book offered one idea that I keep returning to: our tolerance for uncertainty is shrinking and constant access to information has created the expectation that answers should always be available.
Stolzoff even cites research showing that professional al uncertainty takes a similar toll on our healthy as actually losing a job.
His thesis is that the more we build that tolerance, the more we can meet life’s questions with curiosity instead of fear. He organizes the book around three traps-comfort, hubris, and control-with real examples of each.
If you’re new to thinking about uncertainty and how we relate to it, this is an accessible and worthwhile read
Stolzoff even cites research showing that professional al uncertainty takes a similar toll on our healthy as actually losing a job.
His thesis is that the more we build that tolerance, the more we can meet life’s questions with curiosity instead of fear. He organizes the book around three traps-comfort, hubris, and control-with real examples of each.
If you’re new to thinking about uncertainty and how we relate to it, this is an accessible and worthwhile read
May 24, 2026
As the proud owner of both a generalized anxiety disorder and a graduate degree in statistics, this book spoke to me.
This is not a ‘How-to’ book; instead it’s a book about acceptance. I enjoyed how the author approached the idea of uncertainty from so many different angles: from anxiety, to chance, to control, to faith, to hubris, to doubt, and more. Every chapter, every approach, had a story told helping to frame and reframe how the subjects in the story navigated through uncertainty.
Really enjoyed the book and the exploration into uncertainty.
This is not a ‘How-to’ book; instead it’s a book about acceptance. I enjoyed how the author approached the idea of uncertainty from so many different angles: from anxiety, to chance, to control, to faith, to hubris, to doubt, and more. Every chapter, every approach, had a story told helping to frame and reframe how the subjects in the story navigated through uncertainty.
Really enjoyed the book and the exploration into uncertainty.
June 14, 2026
I liked the premise of this book and the way the author broke down the fear of uncertainty into 3 key areas. The section on faith at the end was a little overdone and I felt distracted from the concrete concepts of the book. Otherwise I felt this was a very interesting and entertaining way to think about our discomfort with the unknown.
May 29, 2026
This was a well-written and well-narrated bit of pop science. The stories were compelling and wide-ranging, the author had a good tone, and the pacing felt perfect. It’s definitely my favorite NF book of the year so far.
Thanks to Libro.Fm for the ALC.
Thanks to Libro.Fm for the ALC.
May 20, 2026
Insightful, clearly grounded, and refreshingly honest read. This book will change how you approach uncertainty, helping you navigate the unknown with confidence and grace. A must read.
May 16, 2026
4.5 rounded up to 5.
Review of advance copy
Thank you to Norton for providing me with an ARC of this release.
Once upon a time, I voraciously read self-help books. By the end of that stint, I concluded that most rested on a highly individualist framing of suffering, which rarely addresses deeper issues of social stratification that are even further from our control, yet slip from our knowledge and awareness due to these very forces bent on imposing apathy and complacency through obligatory overwork and the subsequent lack of fulfillment one feels because of that drudgery.
Hot Not to Know by Simone Stolzoff mostly rides that same current, but approaches a more collective view, albeit conservatively. The chapter on economists refusing to own up to their false predictions invokes an image of working class peoples dangling from the strings of the wealthy and powerful; their hubris is particularly ludicrous, and it's this reality of powerlessness that underscores uncertainty intolerance--something that wasn't touched on meaningfully by drawing on criticism of neoliberalism and globalization which further alienate the individual from the collective.
Furthermore, the book suffers from colorblindness; the reader is assumed to be economically privileged and/or white, as egregious as the example of the white software engineer who makes it a point to go out of his comfort zone in the most materialistic manner--signing up for classes, venturing to restaurants he'd never visit otherwise, all speaking to his access and privilege. The chapter even insists that he is a well-intentioned white man, as if predicting the raised eyebrows. Consumerism drives uncertainty intolerance as well--"I buy, therefore I am,"--the temporary or imagined relief from that anxiety through buying an experience or product or culture becomes all the more irresistible, and I think this chapter exemplified this all too well.
Speaking more on the colorblindness: it's always expected of nonwhite peoples to be resilient and full of forbearance, and their anger is always misplaced, misdirected, or a waste of energy. The example of Tuvalu's varied responses to climate change did speak to the power of community resilience, but it was disheartening that they must be a "model" for others to follow, and anger or indignation at the reality of enduring imperialism and colonialism is mere complaining. There is a lot to be said about virtue signalling on the internet in particular, but the consequences of colonialism are not petty concerns, either.
The apolitical approach simply doesn't work when another reason that the threshold for uncertainty intolerance is so low is because in our current times, social stratification is getting even wider and starker, tyranny all the more blatant, and it's never been more obvious that "justice" and "law" do not exist if they do not serve the powerful and wealthy.
Barrier of access is also a pertinent issue raised by the chapter on false positives and the necessity of replication studies, in addition to the profit motive guiding research. Why isn't the takeaway that academia, to reiterate a previous point, is frightfully gatekept by the wealthy, titled, and influential, and that issues affecting marginalized groups are going to be sidelined if they are inconvenient to the former's interests?
The chapter on having faith also rang a discordant note; contextually, it's impossible for a "secular" definition of faith, as it cannot be divorced from its religious connotation. As a consequence, the chapter came off a bit preachy, pun intended. Perhaps it would have succeeded on its secular mission for the practice of "faith" if the author hadn't focused on an actual ordained minister within the chapter.
At the same time, the themes in the book did bring me to acknowledge my feelings about certain events in my life in the past year. The book itself is too shallow, though; it was more a springboard to bring up these issues with a therapist, or even with a discussion group, but with a lot more supplementary material. Speaking of shallowness, the chapter discussing OCD only scratched the surface, and it went too predictably in the direction of the option of psychedelics to treat mental illness--meanwhile addicts are maligned for using the same drugs in the "wrong" way. Thankfully, it doesn't purport that they are a cure for OCD or other mental illnesses, but the chapter came off as exploitative regardless.
Overall, the book suffers from a tension between the usual individualist framing of suffering that pop psychologists assure can be addressed by going to therapy or "practicing self-care", and acknowledging that, despite one's efforts, many factors are simply out of their control. These factors, however, aren't explored with the depth they deserve, and it's clearly a pamphlet to make better working cogs in the machine rather than expose social stratification and institutional oppression which makes the quest for the "right" choice even more tantalizing and imperative, all to avoid confronting the loss of agency and liberty in modern society.
Once upon a time, I voraciously read self-help books. By the end of that stint, I concluded that most rested on a highly individualist framing of suffering, which rarely addresses deeper issues of social stratification that are even further from our control, yet slip from our knowledge and awareness due to these very forces bent on imposing apathy and complacency through obligatory overwork and the subsequent lack of fulfillment one feels because of that drudgery.
Hot Not to Know by Simone Stolzoff mostly rides that same current, but approaches a more collective view, albeit conservatively. The chapter on economists refusing to own up to their false predictions invokes an image of working class peoples dangling from the strings of the wealthy and powerful; their hubris is particularly ludicrous, and it's this reality of powerlessness that underscores uncertainty intolerance--something that wasn't touched on meaningfully by drawing on criticism of neoliberalism and globalization which further alienate the individual from the collective.
Furthermore, the book suffers from colorblindness; the reader is assumed to be economically privileged and/or white, as egregious as the example of the white software engineer who makes it a point to go out of his comfort zone in the most materialistic manner--signing up for classes, venturing to restaurants he'd never visit otherwise, all speaking to his access and privilege. The chapter even insists that he is a well-intentioned white man, as if predicting the raised eyebrows. Consumerism drives uncertainty intolerance as well--"I buy, therefore I am,"--the temporary or imagined relief from that anxiety through buying an experience or product or culture becomes all the more irresistible, and I think this chapter exemplified this all too well.
Speaking more on the colorblindness: it's always expected of nonwhite peoples to be resilient and full of forbearance, and their anger is always misplaced, misdirected, or a waste of energy. The example of Tuvalu's varied responses to climate change did speak to the power of community resilience, but it was disheartening that they must be a "model" for others to follow, and anger or indignation at the reality of enduring imperialism and colonialism is mere complaining. There is a lot to be said about virtue signalling on the internet in particular, but the consequences of colonialism are not petty concerns, either.
The apolitical approach simply doesn't work when another reason that the threshold for uncertainty intolerance is so low is because in our current times, social stratification is getting even wider and starker, tyranny all the more blatant, and it's never been more obvious that "justice" and "law" do not exist if they do not serve the powerful and wealthy.
Barrier of access is also a pertinent issue raised by the chapter on false positives and the necessity of replication studies, in addition to the profit motive guiding research. Why isn't the takeaway that academia, to reiterate a previous point, is frightfully gatekept by the wealthy, titled, and influential, and that issues affecting marginalized groups are going to be sidelined if they are inconvenient to the former's interests?
The chapter on having faith also rang a discordant note; contextually, it's impossible for a "secular" definition of faith, as it cannot be divorced from its religious connotation. As a consequence, the chapter came off a bit preachy, pun intended. Perhaps it would have succeeded on its secular mission for the practice of "faith" if the author hadn't focused on an actual ordained minister within the chapter.
At the same time, the themes in the book did bring me to acknowledge my feelings about certain events in my life in the past year. The book itself is too shallow, though; it was more a springboard to bring up these issues with a therapist, or even with a discussion group, but with a lot more supplementary material. Speaking of shallowness, the chapter discussing OCD only scratched the surface, and it went too predictably in the direction of the option of psychedelics to treat mental illness--meanwhile addicts are maligned for using the same drugs in the "wrong" way. Thankfully, it doesn't purport that they are a cure for OCD or other mental illnesses, but the chapter came off as exploitative regardless.
Overall, the book suffers from a tension between the usual individualist framing of suffering that pop psychologists assure can be addressed by going to therapy or "practicing self-care", and acknowledging that, despite one's efforts, many factors are simply out of their control. These factors, however, aren't explored with the depth they deserve, and it's clearly a pamphlet to make better working cogs in the machine rather than expose social stratification and institutional oppression which makes the quest for the "right" choice even more tantalizing and imperative, all to avoid confronting the loss of agency and liberty in modern society.
Review of advance copy received from Author
As a leadership and grief coach, I spend much of my time sitting with people in the in-between e.g. career transitions, identity shifts, anticipatory grief, profound loss. In those liminal spaces, certainty is scarce. That’s why Simone Stolzoff’s new book (out May 2026) "How to Not Know: The Value of Uncertainty in a World That Demands Answers" feels not only timely, but essential.
Simone beautifully normalizes what so many of us experience as personal failure: discomfort with the unknown. He writes, “When we experience uncertainty, it activates two parts of our brain simultaneously, the amygdala, which is responsible for alerting the brain to potential threats, and the prefrontal cortex, which is responsible for analytical and deliberate thinking…Increasing our uncertainty tolerance allows us to slow down our decision-making process.”
So much of my work with leaders is exactly this: slowing down. When the amygdala is triggered, we default to fight, flight, or freeze. Decisions become reactive. Teams feel the turbulence. From a neuroscience perspective, grounding practices like breathing, orienting, naming what we feel, help regulate the threat response so the prefrontal cortex can reengage. Simone names something I see daily: uncertainty isn’t only fear, it’s anxiety. And the antidote is not control, but emotional intelligence. Trust and curiosity become the way through. When leaders can say, “I don’t know—yet,” and stay open, they cultivate psychological safety and deeper dialogue.
One gem that stood out to me: “What does this choice say about me?” That question invites us to tether decisions to values and identity. As Simone notes, “When our decisions are rooted in our values and identity, we are more likely to stand by them regardless of the outcome.” In seasons of transition, whether stepping into a new executive role or navigating the loss of a loved one, clarity of identity becomes an anchor when outcomes are unknowable.
Simone’s reflections on control resonated deeply with me, especially after losing my mother. He writes that when we live “in an unpredictable and chaotic world, we try to find a sense of security and predictability by seeking to control the uncontrollable.” Grief shatters the illusion of control. What remains is integration: the evolving version of ourselves shaped by loss. Creativity, curiosity, and leadership requires trust in what cannot yet be seen.
Between Simone’s work and others exploring uncertainty, I am reminded more than ever that none of us are meant to navigate these transitions alone. Having a leadership or grief coach to sit with you in the unknown, to regulate the amygdala’s alarm, to reconnect you to your values and your future self is not a luxury. It is an investment in becoming more fully human in uncertain times.
Simone beautifully normalizes what so many of us experience as personal failure: discomfort with the unknown. He writes, “When we experience uncertainty, it activates two parts of our brain simultaneously, the amygdala, which is responsible for alerting the brain to potential threats, and the prefrontal cortex, which is responsible for analytical and deliberate thinking…Increasing our uncertainty tolerance allows us to slow down our decision-making process.”
So much of my work with leaders is exactly this: slowing down. When the amygdala is triggered, we default to fight, flight, or freeze. Decisions become reactive. Teams feel the turbulence. From a neuroscience perspective, grounding practices like breathing, orienting, naming what we feel, help regulate the threat response so the prefrontal cortex can reengage. Simone names something I see daily: uncertainty isn’t only fear, it’s anxiety. And the antidote is not control, but emotional intelligence. Trust and curiosity become the way through. When leaders can say, “I don’t know—yet,” and stay open, they cultivate psychological safety and deeper dialogue.
One gem that stood out to me: “What does this choice say about me?” That question invites us to tether decisions to values and identity. As Simone notes, “When our decisions are rooted in our values and identity, we are more likely to stand by them regardless of the outcome.” In seasons of transition, whether stepping into a new executive role or navigating the loss of a loved one, clarity of identity becomes an anchor when outcomes are unknowable.
Simone’s reflections on control resonated deeply with me, especially after losing my mother. He writes that when we live “in an unpredictable and chaotic world, we try to find a sense of security and predictability by seeking to control the uncontrollable.” Grief shatters the illusion of control. What remains is integration: the evolving version of ourselves shaped by loss. Creativity, curiosity, and leadership requires trust in what cannot yet be seen.
Between Simone’s work and others exploring uncertainty, I am reminded more than ever that none of us are meant to navigate these transitions alone. Having a leadership or grief coach to sit with you in the unknown, to regulate the amygdala’s alarm, to reconnect you to your values and your future self is not a luxury. It is an investment in becoming more fully human in uncertain times.
May 26, 2026
Review of Advanced Copy
3.5 ⭐️ so guess I’ll have to round up (looking at you, Goodreads).
This book worked best when it leaned into real stories and interviews with people willing to admit they don’t have all the answers. That vulnerability — especially in fields obsessed with certainty — was the most interesting part for me. There are some genuinely strong lines and concepts here too: the relationship between ambiguity and creativity, hindsight vs. insight, trusting your future self, and how certainty protects our self-image from scrutiny.
The structure around comfort, hubris, and control gave the book a clear framework, but at times it felt like the author was trying to fit too many ideas into too small a book. Some chapters became dense and overexplained when a lighter touch would have flowed better. The “false positives” section especially felt more academic than accessible unless you already enjoy scientific theory and research discussions.
I personally loved the crisis communications chapter and the Department of Doubt material — probably because those sections felt grounded in real-world complexity instead of abstract self-help language. The book shines most when it explores uncertainty through lived experience rather than ancient quotes and motivational framing.
As a creative person, I kept wanting one deeper layer the book never fully reached: how to sustainably create, protect your energy, and make decisions while living inside ambiguity long term. The argument that uncertainty is valuable is compelling, but I wanted more practical insight into existing there without burning out.
Book clubs can make you tolerate books you wouldn’t otherwise, which is useful socially, but it also made me ask: would I stay in this if no one was watching? Weirdly, that question ended up feeling very connected to the entire theme of the book; how often certainty, performance, and identity shape the choices we make more than genuine curiosity does.
The “12 Invitations” ending felt a little thesis-like, but I did genuinely love one idea: trusting your future self to handle future problems. The version of you that meets hard things will be born into existence in that moment — with more experience, more information, and more capacity than the version of you has now. That was probably the thought I’ll carry with me most.
Nothing here felt earth-shattering, but there were enough memorable ideas and strange little details (the Donald Duck “flippism” comic fact somehow stuck with me) to keep me engaged. Interesting, thoughtful in parts, occasionally dense, and ultimately decent, but not one I’d actively recommend or pass along afterward.
3.5 ⭐️ so guess I’ll have to round up (looking at you, Goodreads).
This book worked best when it leaned into real stories and interviews with people willing to admit they don’t have all the answers. That vulnerability — especially in fields obsessed with certainty — was the most interesting part for me. There are some genuinely strong lines and concepts here too: the relationship between ambiguity and creativity, hindsight vs. insight, trusting your future self, and how certainty protects our self-image from scrutiny.
The structure around comfort, hubris, and control gave the book a clear framework, but at times it felt like the author was trying to fit too many ideas into too small a book. Some chapters became dense and overexplained when a lighter touch would have flowed better. The “false positives” section especially felt more academic than accessible unless you already enjoy scientific theory and research discussions.
I personally loved the crisis communications chapter and the Department of Doubt material — probably because those sections felt grounded in real-world complexity instead of abstract self-help language. The book shines most when it explores uncertainty through lived experience rather than ancient quotes and motivational framing.
As a creative person, I kept wanting one deeper layer the book never fully reached: how to sustainably create, protect your energy, and make decisions while living inside ambiguity long term. The argument that uncertainty is valuable is compelling, but I wanted more practical insight into existing there without burning out.
Book clubs can make you tolerate books you wouldn’t otherwise, which is useful socially, but it also made me ask: would I stay in this if no one was watching? Weirdly, that question ended up feeling very connected to the entire theme of the book; how often certainty, performance, and identity shape the choices we make more than genuine curiosity does.
The “12 Invitations” ending felt a little thesis-like, but I did genuinely love one idea: trusting your future self to handle future problems. The version of you that meets hard things will be born into existence in that moment — with more experience, more information, and more capacity than the version of you has now. That was probably the thought I’ll carry with me most.
Nothing here felt earth-shattering, but there were enough memorable ideas and strange little details (the Donald Duck “flippism” comic fact somehow stuck with me) to keep me engaged. Interesting, thoughtful in parts, occasionally dense, and ultimately decent, but not one I’d actively recommend or pass along afterward.
May 20, 2026
If You Can’t Predict the Future, Don’t Worry About It
In How to Not Know: The Value of Uncertainty in a World That Demands Answers, Simone Stolzoff offers sage advice for those who dread uncertainty. He argues that we make things more difficult for ourselves when look at every fork in the road of our life journey “represents a choice between utopia and damnation.” And, Mr Stolzoff points out, this is exacerbated because, as research has shown, “people dramatically and regularly mispredict the emotional consequences of future events.” So, when dealing with hard choices, we are often overcome by fear of the unknown. He suggests that sometimes there simply is no single best option, and that “acknowledging that there is no best option frees us to create the reasons for why we make a particular choice.
In one of his carefully drawn case studies, Mr Stolzoff brings to life concepts like Intolerance of uncertainty and being a prisoner of our preferences. Another focuses on hubris, and how “Hubris blinds us from reality by convincing us that we are right in situations we might not be. However, like trying to hear your own accent, hubris is notoriously hard to recognize in ourselves.”
I particularly enjoyed Mr. Stolzoff’s discussion of a conversation he had with science expert and former professional poker player Annie Duke about two heuristics for cutting through the noise in our heads and determining whether decisions are of high or low consequence: the Happiness Test and the Only-Option Test.
The book is filled with nuggets of wisdom that help us make a mental shift and acknowledge that uncertainty is NOT a problem to be solved, such as :
- [ ] “…we have to normalize changing our minds. It’s easy to believe that admitting you are wrong might forever tarnish your reputation. But a growing body of research has found the opposite to be true.”
- [ ] “If we want to get better at dealing with uncertainty, we have to be willing to admit what we don’t know.”
- [ ] “If we knew exactly what the future held, we’d only need to rely on data and evidence. But we don’t—so we must choose where to place our hearts without knowing how things will turn out.”
- [ ] “When faced with existential uncertainty—whether personal or planetary—taking initiative can restore a sense of agency. In the face of fear, action itself becomes a kind of hope.”
- [ ] “As much as we try to impose certainty on or uncertain world, the universe has a way of reminding us of the true nature of things.”
I highly recommend this book to every reader who is looking for better ways to deal with uncertainty and doubt.
In How to Not Know: The Value of Uncertainty in a World That Demands Answers, Simone Stolzoff offers sage advice for those who dread uncertainty. He argues that we make things more difficult for ourselves when look at every fork in the road of our life journey “represents a choice between utopia and damnation.” And, Mr Stolzoff points out, this is exacerbated because, as research has shown, “people dramatically and regularly mispredict the emotional consequences of future events.” So, when dealing with hard choices, we are often overcome by fear of the unknown. He suggests that sometimes there simply is no single best option, and that “acknowledging that there is no best option frees us to create the reasons for why we make a particular choice.
In one of his carefully drawn case studies, Mr Stolzoff brings to life concepts like Intolerance of uncertainty and being a prisoner of our preferences. Another focuses on hubris, and how “Hubris blinds us from reality by convincing us that we are right in situations we might not be. However, like trying to hear your own accent, hubris is notoriously hard to recognize in ourselves.”
I particularly enjoyed Mr. Stolzoff’s discussion of a conversation he had with science expert and former professional poker player Annie Duke about two heuristics for cutting through the noise in our heads and determining whether decisions are of high or low consequence: the Happiness Test and the Only-Option Test.
The book is filled with nuggets of wisdom that help us make a mental shift and acknowledge that uncertainty is NOT a problem to be solved, such as :
- [ ] “…we have to normalize changing our minds. It’s easy to believe that admitting you are wrong might forever tarnish your reputation. But a growing body of research has found the opposite to be true.”
- [ ] “If we want to get better at dealing with uncertainty, we have to be willing to admit what we don’t know.”
- [ ] “If we knew exactly what the future held, we’d only need to rely on data and evidence. But we don’t—so we must choose where to place our hearts without knowing how things will turn out.”
- [ ] “When faced with existential uncertainty—whether personal or planetary—taking initiative can restore a sense of agency. In the face of fear, action itself becomes a kind of hope.”
- [ ] “As much as we try to impose certainty on or uncertain world, the universe has a way of reminding us of the true nature of things.”
I highly recommend this book to every reader who is looking for better ways to deal with uncertainty and doubt.
May 31, 2026
Overall, this book was an easy read. It features real case studies from the author’s interviews, tons of research references and best practices to help us all have a more positive outlook and strategy for managing uncertainty. Tackling the subject of uncertainty is an ambitious one - every person deals with it differently and there are already a ton of books about it. However, the author has done a thoughtful and deliberate way of writing about it with compassion and respect for the people he featured.
I gave four stars not because it wasn’t great but I felt some of the examples were hard to relate to. For example, a tech guy who prided himself on using algorithms to randomize his life seemed indulgent and a bit elitist to me. Certain classes of people might find this cool but I also thought about folks who are not in the tech bubble or do not have this luxury of time and money to embrace such a lifestyle. Just my two cents but I think there are more compelling and practical examples to illustrate openness to variety and change.
With the example of Kate in Chapter 1, I also found it hard to relate to how her story was told. I applaud her for an impressive turnaround in her life but in reality, the aha moment after a significant life crisis doesn’t happen overnight. I’ve lived and survived many heartbreaks and unforeseen changes in my life and each of them was always a journey to growth. I wish the author focused a bit more on the in-between where uncertainty is usually the strongest.
The first three chapters were certainly hard to get through because of the examples he chose and the first chapter was overwhelming with stats that it felt too academic. As I read through, I was hoping to get a more personal take from the author, and so when I got to the last chapter where he spoke about his own journey, it was so satisfying. I loved the chapters of the book from Chapter 4 onwards and I read them in one sitting. I thought the examples were spot-on - very inspiring and the interweaving of research and best practices were subtle and just gracefully written.
I especially appreciated reading this book and I finished it right before the news of my deceased father in law. It really helped me have a more balanced perspective on life and death, and so I’m facing my personal grief focused on how he added so much good in our life, and the lessons he imparted in us.
I gave four stars not because it wasn’t great but I felt some of the examples were hard to relate to. For example, a tech guy who prided himself on using algorithms to randomize his life seemed indulgent and a bit elitist to me. Certain classes of people might find this cool but I also thought about folks who are not in the tech bubble or do not have this luxury of time and money to embrace such a lifestyle. Just my two cents but I think there are more compelling and practical examples to illustrate openness to variety and change.
With the example of Kate in Chapter 1, I also found it hard to relate to how her story was told. I applaud her for an impressive turnaround in her life but in reality, the aha moment after a significant life crisis doesn’t happen overnight. I’ve lived and survived many heartbreaks and unforeseen changes in my life and each of them was always a journey to growth. I wish the author focused a bit more on the in-between where uncertainty is usually the strongest.
The first three chapters were certainly hard to get through because of the examples he chose and the first chapter was overwhelming with stats that it felt too academic. As I read through, I was hoping to get a more personal take from the author, and so when I got to the last chapter where he spoke about his own journey, it was so satisfying. I loved the chapters of the book from Chapter 4 onwards and I read them in one sitting. I thought the examples were spot-on - very inspiring and the interweaving of research and best practices were subtle and just gracefully written.
I especially appreciated reading this book and I finished it right before the news of my deceased father in law. It really helped me have a more balanced perspective on life and death, and so I’m facing my personal grief focused on how he added so much good in our life, and the lessons he imparted in us.
May 24, 2026
I enjoyed Simone's book How To Not Know. The stories he used were compelling, and he placed the right hooks at the right moments to keep you coming back for more. The book is divided into three parts: Comfort, Hubris, and Control.
Simone's main thesis is to push us to embrace the discomfort of uncertainty. He then provides examples of the advantages of doing so along with actions to manage that uncertainty. I wondered how he would wrestle with the reality that many of us grapple with anxiety — embracing uncertainty, for the anxious, is usually a recipe for disaster. But he does address that in the final part, Control. As a scientist, I particularly enjoyed the chapter on the perils and possibilities of the scientific method and the chapter where he invokes my favorite decision scientist, Annie Duke. We get clear frameworks from Annie: the "kill criteria" and the control-versus-impact 2×2 matrix.
The Department of Doubt chapter was particularly interesting, where the critical role of devil's advocates was discussed. But I was left wanting more after reading that, rightfully so, devil's advocates come at a high cost and are usually the first ones to go. I also caught myself wondering: how does one project certainty while still grappling with doubt? How does one embrace uncertainty without drowning in self-doubt?
Simone provides actionable frameworks to deal with uncertainty while adding the dimension of control to the matrix. If you can control something, then what steps can you take? All of this made me think of the Bhagavad Gita, which asks you to simply perform your duty, for that is what you can control. Funnily enough, the next chapter got into the topic of faith and the idea that you can keep the faith by doing the action — belief comes as a result. While the Gita was not used as an example in the chapters on faith and how "action" is the way you practice it, it was interesting that this seems to be a through line across many religions and Stoic thought.
All in all, I loved Simone's book and all the heartfelt stories he wove to make it a compelling narrative. This book provides actionable frameworks for embracing uncertainty. As we all know the cliché (which are usually always true): change is the only constant.
June 16, 2026
As someone who prefers certainty, I found this to be an interesting read, particularly since my tendency has been to approach uncertainty with a sense of trepidation. This a well-researched book that engages the reader through various means including psychology and stories.
The book is divided into three sections: comfort, hubris and control. The quotes at the beginning of each chapter hit the mark on what the chapter was about and provides food for thought. The author states that often the desire for control is rooted in a fear of uncertainty.
The author opens with the story of a couple who designed an experiment titled “The Year of Living Dangerously.” This hooked me into wanting to read the book. I wondered about the outcome was and I was tempted to skip ahead to find out. There are many lessons learned through the experiences and stories in the book.
I found the lessons about managing uncertainty to be quite useful, and the author’s framing his "recommendations as invitations, rather than mandates" to align with curiosity, particularly the following:
1. "Find Your Anchors" – as I reflect on my values (the most important anchor per the author), I feel confident when my decisions align with my values and untethered when they don’t.
2. "Choose curiosity over comfort" – this is an invitation I am focused on. I had previously dwelled on choosing courage over comfort (Brene Brown), but I find that replacing courage with curiosity is softer and inviting. Through stories, the author shows how individuals have grown and persevered when they ventured outside their comfort zone.
3. "Trust your future self to handle future problems" – “Trusting in your future self is a way of preventing unnecessary suffering.” This one resonated with me. We sometimes tend to worry about potential future problems which in most cases, don’t materialize and we end up wasting time and suffering unnecessarily.
At the end of this book, you’ll have recommendations that you could implement and perhaps a willingness to embrace uncertainty with curiosity rather than fear. Highly recommend this book particularly if you want insights on how to approach uncertainty with a sense of curiosity.
The book is divided into three sections: comfort, hubris and control. The quotes at the beginning of each chapter hit the mark on what the chapter was about and provides food for thought. The author states that often the desire for control is rooted in a fear of uncertainty.
The author opens with the story of a couple who designed an experiment titled “The Year of Living Dangerously.” This hooked me into wanting to read the book. I wondered about the outcome was and I was tempted to skip ahead to find out. There are many lessons learned through the experiences and stories in the book.
I found the lessons about managing uncertainty to be quite useful, and the author’s framing his "recommendations as invitations, rather than mandates" to align with curiosity, particularly the following:
1. "Find Your Anchors" – as I reflect on my values (the most important anchor per the author), I feel confident when my decisions align with my values and untethered when they don’t.
2. "Choose curiosity over comfort" – this is an invitation I am focused on. I had previously dwelled on choosing courage over comfort (Brene Brown), but I find that replacing courage with curiosity is softer and inviting. Through stories, the author shows how individuals have grown and persevered when they ventured outside their comfort zone.
3. "Trust your future self to handle future problems" – “Trusting in your future self is a way of preventing unnecessary suffering.” This one resonated with me. We sometimes tend to worry about potential future problems which in most cases, don’t materialize and we end up wasting time and suffering unnecessarily.
At the end of this book, you’ll have recommendations that you could implement and perhaps a willingness to embrace uncertainty with curiosity rather than fear. Highly recommend this book particularly if you want insights on how to approach uncertainty with a sense of curiosity.
June 29, 2026
Patient Readers Will Be Rewarded
Simone Stolzoff writes with a curious, journalistic eye. The book is rich with stories, and therein lies both its strength and its occasional challenge. There were moments mid-book where I found myself drifting, wondering how all these threads would eventually connect. Is this an objective collection of reporting, or did these stories hit the author personally? Stolzoff keeps you guessing, and that ambiguity is actually very much on purpose.
The final chapter, "The End of the Beginning," is where it all crescendos to a deeply personal and beautiful conclusion. The payoff is real, but you must be patient and stay focused to get there.
One pattern I appreciated is when Stolzoff pauses to offer precise, etymological definitions of key words. Learning that "crisis" comes from the Greek krisis, a medical turning point between recovery and decline, reframes the word. Or that in Pali, the language of early Buddhist texts, the word for faith (saddha) translates roughly to "that which you place your heart on." These small moments to pause and really digest the language felt unique.
The final chapter uses death as the ultimate exercise in accepting uncertainty and through it revisits the book's three core tensions: comfort vs. possibility, hubris vs. humility, control vs. openness.
The hermit crab analogy near the end gave me a fun visual for what comfort looks like. These creatures must continually abandon their shells as they grow, seeking new ones to protect their soft bodies. As Stolzoff writes: "To embrace uncertainty means being okay with the fact that your current shell may not be where you will live forever." Sometimes you can accept that you’re outgrowing your environment, and it's OK to seek another experience.
Ultimately, this book is a simple reminder to let go and flow. Having a specific goal or destination is often worthwhile, but sometimes moving in a general direction without knowing the outcome is its own kind of fun. Life should be a little mysterious. Predictable is boring.
Disclosure: I received an advance copy of this book, but this review reflects my honest thoughts and experience as a reader.
Simone Stolzoff writes with a curious, journalistic eye. The book is rich with stories, and therein lies both its strength and its occasional challenge. There were moments mid-book where I found myself drifting, wondering how all these threads would eventually connect. Is this an objective collection of reporting, or did these stories hit the author personally? Stolzoff keeps you guessing, and that ambiguity is actually very much on purpose.
The final chapter, "The End of the Beginning," is where it all crescendos to a deeply personal and beautiful conclusion. The payoff is real, but you must be patient and stay focused to get there.
One pattern I appreciated is when Stolzoff pauses to offer precise, etymological definitions of key words. Learning that "crisis" comes from the Greek krisis, a medical turning point between recovery and decline, reframes the word. Or that in Pali, the language of early Buddhist texts, the word for faith (saddha) translates roughly to "that which you place your heart on." These small moments to pause and really digest the language felt unique.
The final chapter uses death as the ultimate exercise in accepting uncertainty and through it revisits the book's three core tensions: comfort vs. possibility, hubris vs. humility, control vs. openness.
The hermit crab analogy near the end gave me a fun visual for what comfort looks like. These creatures must continually abandon their shells as they grow, seeking new ones to protect their soft bodies. As Stolzoff writes: "To embrace uncertainty means being okay with the fact that your current shell may not be where you will live forever." Sometimes you can accept that you’re outgrowing your environment, and it's OK to seek another experience.
Ultimately, this book is a simple reminder to let go and flow. Having a specific goal or destination is often worthwhile, but sometimes moving in a general direction without knowing the outcome is its own kind of fun. Life should be a little mysterious. Predictable is boring.
Disclosure: I received an advance copy of this book, but this review reflects my honest thoughts and experience as a reader.
May 30, 2026
I have to admit, going into this book I wasn't sure I would align with even the premise, let alone the content. As someone that places a high value on being certain whenever possible, the subheading of this book "the Value of Uncertainty in a World that Demands Answers" felt as if it was challenging something in my core right out of the gate. I must also admit, I couldn't be happier to be so wrong. After reading Stolzoff's work, I've realigned my thinking to not only see value in not knowing, but am finding more things that I am leaning into the discomfort of uncertainty in. One quote early in the book that stuck with me throughout the reading is a simple, concise way of framing this work, "The more we build a tolerance for uncertainty, the more we can meet life's questions with curiosity instead of fear." While the sentiment seems simple, for me the impact of that statement queued this book up with a completely different lens than I began it with (and this was in the first 10 pages). The author does a remarkable job of balancing research with specific stories, woven together masterfully to take the reader on a journey that challenges conventional thinking in a way that, if one can stay curious, really can shift our approaches - and even our comfort in not knowing. Citing research from people like Daniel Kahneman (and his famous and seminal work, "Thinking, Fast and Slow), Stolzoff makes sure to lean into some of the great works out there but from a fresh and different angle. For me personally, many of the stories carried personal weight that made the book even more interesting - some of the specific stories touched on Obsessive Compulsive Disorder (OCD) which runs in my family, to tackling the mystery (and uncertainty!) of death - which having lost both of my parents was at times a bit close to home but also sparked more curiosity than resurfacing feelings of loss or grief. I cannot recommend this book enough to anyone willing to challenge their own beliefs, wanting to become more comfortable with "grey areas", or just wanting a very well written and executed exploration of what it truly means to not know.
June 1, 2026
Simone Stolzoff’s latest work explores what he calls the “certainty trap” — how comfort, hubris, and the desire for control distort the way we see the world and make decisions.
What immediately caught my attention was the idea of control: planning everything in pursuit of a specific outcome. If I’m honest, that has been my primary operating mode for much of my life.
I took a sabbatical during the holiday season last year, and during that time I pursued many different paths and possibilities, eventually following what energized me rather than forcing a predetermined outcome. This book gave me language for a journey I had already begun but struggled to articulate.
One idea I’ll carry with me is what. Stolzoff describes this as “choosing curiosity over comfort.” While I connect with that framing, for me it feels even closer to choosing what I genuinely care about over comfort.
Another practice that deeply resonated with me was the idea of finding your anchors. This period of uncertainty helped me gain clarity about my professional life. I realized that while I can be many things, I’m someone with forward-moving energy, a healthy appetite for growth and risk, and deep inquisitiveness. That’s how I show up, and those are strengths I want to continue building on. I also became clear that environments centered on maintaining the status quo or prioritizing cultural assimilation over culture add are simply not the right fit for me — and I’m not the right fit for them.
This is the book I wish I had before my sabbatical.
A few ideas and quotes that stayed with me:
“We are drawn to the allure of certainty when we feel unsure of our own capabilities.”
And perhaps the biggest takeaway: certainty is not especially appealing to people who want to shape what the future holds. The future, by definition, asks something different of us — openness, experimentation, and trust in what energizes us. We are not here to do what has already been done.
What immediately caught my attention was the idea of control: planning everything in pursuit of a specific outcome. If I’m honest, that has been my primary operating mode for much of my life.
I took a sabbatical during the holiday season last year, and during that time I pursued many different paths and possibilities, eventually following what energized me rather than forcing a predetermined outcome. This book gave me language for a journey I had already begun but struggled to articulate.
One idea I’ll carry with me is what. Stolzoff describes this as “choosing curiosity over comfort.” While I connect with that framing, for me it feels even closer to choosing what I genuinely care about over comfort.
Another practice that deeply resonated with me was the idea of finding your anchors. This period of uncertainty helped me gain clarity about my professional life. I realized that while I can be many things, I’m someone with forward-moving energy, a healthy appetite for growth and risk, and deep inquisitiveness. That’s how I show up, and those are strengths I want to continue building on. I also became clear that environments centered on maintaining the status quo or prioritizing cultural assimilation over culture add are simply not the right fit for me — and I’m not the right fit for them.
This is the book I wish I had before my sabbatical.
A few ideas and quotes that stayed with me:
“We are drawn to the allure of certainty when we feel unsure of our own capabilities.”
And perhaps the biggest takeaway: certainty is not especially appealing to people who want to shape what the future holds. The future, by definition, asks something different of us — openness, experimentation, and trust in what energizes us. We are not here to do what has already been done.
June 1, 2026
In How to Not Know: The Value of Uncertainty in a World That Demands Answers, Simone Stolzoff tackles a challenge that feels increasingly relevant: how to live well when the future is unknowable and certainty is impossible.
What makes this book stand out is Stolzoff's ability to blend compelling storytelling, behavioral science, and practical wisdom without ever becoming preachy. Rather than offering simplistic formulas or false promises, he explores how real people—from economists and scientists to individuals facing deeply personal decisions—navigate ambiguity, risk, and doubt. The result is a book that feels both intellectually engaging and deeply human. (Goodreads)
One of the book's greatest strengths is its central message: uncertainty is not a problem to be eliminated but a reality to be understood and, perhaps, even embraced. In a culture obsessed with optimization, prediction, and having all the answers, Stolzoff makes a persuasive case that some of life's most meaningful experiences require us to move forward without complete certainty.
The writing is accessible and engaging, making complex psychological and philosophical ideas easy to understand. Each chapter offers insights that are immediately applicable, whether you're facing career decisions, relationship questions, financial uncertainty, or simply the anxiety that comes from living in a rapidly changing world.
If you enjoyed books such as The Good Enough Job, The Psychology of Money, or works that explore decision-making and human behavior, you'll find much to appreciate here. More than a self-help book, How to Not Know is a thoughtful reflection on what it means to live courageously in an uncertain world.
Highly recommended for anyone who has ever felt stuck waiting for the "right" answer before taking the next step.
What makes this book stand out is Stolzoff's ability to blend compelling storytelling, behavioral science, and practical wisdom without ever becoming preachy. Rather than offering simplistic formulas or false promises, he explores how real people—from economists and scientists to individuals facing deeply personal decisions—navigate ambiguity, risk, and doubt. The result is a book that feels both intellectually engaging and deeply human. (Goodreads)
One of the book's greatest strengths is its central message: uncertainty is not a problem to be eliminated but a reality to be understood and, perhaps, even embraced. In a culture obsessed with optimization, prediction, and having all the answers, Stolzoff makes a persuasive case that some of life's most meaningful experiences require us to move forward without complete certainty.
The writing is accessible and engaging, making complex psychological and philosophical ideas easy to understand. Each chapter offers insights that are immediately applicable, whether you're facing career decisions, relationship questions, financial uncertainty, or simply the anxiety that comes from living in a rapidly changing world.
If you enjoyed books such as The Good Enough Job, The Psychology of Money, or works that explore decision-making and human behavior, you'll find much to appreciate here. More than a self-help book, How to Not Know is a thoughtful reflection on what it means to live courageously in an uncertain world.
Highly recommended for anyone who has ever felt stuck waiting for the "right" answer before taking the next step.
May 24, 2026
How to Not Know is about something most of us are bad at: sitting with uncertainty. Stolzoff's basic argument is that needing to feel certain about everything actually makes us worse at thinking clearly, leading, and living well.
The book works through three traps he calls comfort, hubris, and control. Comfort keeps you safe but stuck. Hubris tells you that you already know best. Control convinces you that planning everything will protect you — but the more control you seek, the more enslaved you become by the illusion of it. Each trap gets real stories and solid research behind it.
A few things stayed with me. Leaders who admit what they don't know come across as more trustworthy, not less. People with lower uncertainty tolerance are actually more likely to accept misinformation as true. And organizations that can tolerate ambiguity tend to be more innovative — they're willing to take the kinds of risks that lead to breakthroughs.
There's also a good chapter on discomfort. The idea that feeling uncomfortable might mean you're on the verge of a breakthrough — not that something is wrong — reframes a lot. Same with the concept of a "prison of your preferences," where a life that's fully optimized for what you already like misses everything outside of it.
The chapter on "resulting" — judging a decision by how it turned out rather than whether it was a good call at the time — is worth the price of admission by itself. So is the simple line the author comes back to: "This is what I believe right now, based on what I know."
It's a quick read and sometimes covers familiar ground. But it's well-researched and doesn't overpromise.
The book works through three traps he calls comfort, hubris, and control. Comfort keeps you safe but stuck. Hubris tells you that you already know best. Control convinces you that planning everything will protect you — but the more control you seek, the more enslaved you become by the illusion of it. Each trap gets real stories and solid research behind it.
A few things stayed with me. Leaders who admit what they don't know come across as more trustworthy, not less. People with lower uncertainty tolerance are actually more likely to accept misinformation as true. And organizations that can tolerate ambiguity tend to be more innovative — they're willing to take the kinds of risks that lead to breakthroughs.
There's also a good chapter on discomfort. The idea that feeling uncomfortable might mean you're on the verge of a breakthrough — not that something is wrong — reframes a lot. Same with the concept of a "prison of your preferences," where a life that's fully optimized for what you already like misses everything outside of it.
The chapter on "resulting" — judging a decision by how it turned out rather than whether it was a good call at the time — is worth the price of admission by itself. So is the simple line the author comes back to: "This is what I believe right now, based on what I know."
It's a quick read and sometimes covers familiar ground. But it's well-researched and doesn't overpromise.
June 5, 2026
I listened to 6 hours audio books. It was easy to listen to and includes a number of stories according to each chapters. I think It doesn’t mean you are not prepared for what’s coming, but to not let your concerns of the uncertainty to stop doing things altogether.
Below is internet’s words not mine:
1. Uncertainty is unavoidable. Many of life’s biggest questions don’t have clear or permanent answers.
2. The desire for certainty can mislead us. We often prefer a confident wrong answer over an honest “I don’t know.”
3. Hubris limits learning. When we become too sure of ourselves, we stop noticing information that challenges our beliefs.
4. Intellectual humility is a strength. Recognizing the limits of your knowledge makes you more adaptable and wiser.
5. Expertise has limits. Even highly trained professionals can be wrong, especially in complex systems involving people and society.
6. The future is difficult to predict. Many major events happen because of factors nobody fully understands or controls.
7. Curiosity is more valuable than certainty. Asking better questions often matters more than finding immediate answers.
8. Identity can become a trap. When our beliefs become part of who we are, changing our minds can feel threatening.
9. Good decisions don’t guarantee good outcomes. Sometimes you can make a thoughtful choice and still get an unfavorable result because of chance.
10. A meaningful life doesn’t require complete certainty. Wisdom comes not from knowing everything, but from acting thoughtfully despite ambiguity.
The goal is not to know everything—it is to become comfortable, curious, and thoughtful in a world where complete certainty is impossible.
Below is internet’s words not mine:
1. Uncertainty is unavoidable. Many of life’s biggest questions don’t have clear or permanent answers.
2. The desire for certainty can mislead us. We often prefer a confident wrong answer over an honest “I don’t know.”
3. Hubris limits learning. When we become too sure of ourselves, we stop noticing information that challenges our beliefs.
4. Intellectual humility is a strength. Recognizing the limits of your knowledge makes you more adaptable and wiser.
5. Expertise has limits. Even highly trained professionals can be wrong, especially in complex systems involving people and society.
6. The future is difficult to predict. Many major events happen because of factors nobody fully understands or controls.
7. Curiosity is more valuable than certainty. Asking better questions often matters more than finding immediate answers.
8. Identity can become a trap. When our beliefs become part of who we are, changing our minds can feel threatening.
9. Good decisions don’t guarantee good outcomes. Sometimes you can make a thoughtful choice and still get an unfavorable result because of chance.
10. A meaningful life doesn’t require complete certainty. Wisdom comes not from knowing everything, but from acting thoughtfully despite ambiguity.
The goal is not to know everything—it is to become comfortable, curious, and thoughtful in a world where complete certainty is impossible.
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