Questioning the question expert
5 questions for author and applied behavioral scientist Elizabeth Weingarten
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Times feel wildly uncertain, don’t they? It’s easy to get trapped in your lizard brain, want to hunker down, and control what is in your control (or control what you want to pretend is in your control?!). It’s easy to narrow and tighten and get tribal and scared.
But what might the opposite feel like? What might it feel like to widen and wonder? That’s what behavioral scientist Elizabeth Weingarten’s new book—at its core—is about. How do we ask big, open, beautiful questions when the world is trying to make us go ugly and small? I think it’s something so many of us are struggling with right now, me included, so I was so excited that Elizabeth was down to talk with us about her journey and this unusual book for these unprecedented times.
Meet Elizabeth…
Courtney Martin: I love the way you categorize different kinds of questions into parts of a fruit tree. What a totally original taxonomy! Can you explain what they are and also where that taxonomy came from?
Elizabeth Weingarten: I’m so glad this resonated with you! The book is about how to thrive in uncertainty (rather than being imprisoned by it) by forming a different relationship to the questions in our lives. Just like people, being in a relationship with questions requires getting to know them. A deeper understanding of the type of questions we’re asking of ourselves, and our loved ones, enables us to respond in more generative ways.
My fruit tree inspiration bloomed during a conversation with someone I met through Nearness, an organization that aims to foster deeper connection in part through the exploration of big questions (an experience I also write about in the book). When I told her about the book’s conceit, she said something off-handedly about a question “ripening into an answer.” It reminded me of something I’d once read about trees, and the concentric circles of wood you find if you cut the trunk. The tree may grow new bark on the outside, but it continues to hold its younger “selves” throughout its long life.
I began doing some tree-search, and started to find connections between the tree parts and our questions. For example, the core of the tree is known as the heartwood, and its purpose is to help the tree with balance, security and stability – much like some of the big questions we carry with us across our lives. I also learned not all fruit ripens at the same pace, which also reflects the fact that not all questions ripen into answers at the same speed. So I ended up with a four-part taxonomy.
First, you have your peach questions. Like peaches, these questions ripen into answers on a fairly quick time horizon. They’re questions like: “will I get the job?”
Next are paw-paw questions. It takes a paw-paw tree five to seven years to grow fruit (!), which means these questions are still answerable, but on a longer time horizon. Think about questions about whether a lengthy new fertility treatment will help you get pregnant.
The third category is the heartwood question. These big questions are your lifelong companions, and generally aren’t answerable in any permanent way. They’re questions like, “who am I?”
And finally, there are dead leaves. These are the questions that don’t ripen into answers, but are meant to be released. Clinging to them can keep us stuck in patterns of rumination and regret. Think of “why did we break up?” or “what if I’d just done it all differently?”
Knowing what kind of question you’re asking helps you to calibrate your expectations of that question. It may help you sit with it more patiently, or discern when to let it go.
The charlatans of certainty section challenged me a bit. I get that certain kinds of personality frameworks aren’t scientifically valid, and that they can’t be used to reduce people rather than acknowledging their multi-dimensionality, but I also find that some of them have been profoundly comforting and provocative - leading me to ask even deeper, more profound questions of myself and others. Can you say more about why you distrust them?
What you just described sounds to me sounds like the ideal way to use personality tests: as tools to help you ask deeper and more profound questions.
But let me take a step back for a moment to explain my perspective on this. In the book, I explore how we can form different relationships to questions in a world in which so many of us have become addicted to fast, easy answers. These can come in many forms (Google, generative AI, Tik Tok), but I specifically call out a group I’ve labeled the “charlatans of certainty.” These are the gurus and influencers who intentionally manipulate their followers into believing they have all of the answers to their deepest questions, giving them the illusion of certainty on complex topics, and signaling that their answers are the only ones that will solve their problems.
I’m not distrustful of all personality tests – particularly the scientifically valid ones, which come from the Big Five (as an aside: I highly recommend Olga Khazan’s new book Me, But Better, all about the science of personality).
My skepticism of certain tests is more about how we’re encouraged to use them in our lives, and how their powers are marketed. In some cases, they seem to be used not as thought starters, but thought stoppers. Instead of inviting deeper inquiry, they can promote more shallow categorization and thinking.
To me, personality tests should be treated not as final answers to the complex question of who we are, and who we’re becoming, but rather as one input among many that can help us continuously explore and discover ourselves. The distinction is whether they’re being used as tools to encourage rather than halt that kind of inquiry and critical thinking.
I loved the chapter on the way questions are born of relationships and communities. If America, as a collective, is asking a question of itself right now, what would you say it is?
I love this question, because it has really challenged me to consider the question that all of us might be asking right now, not just one political party or demographic group. At a time in which we so often focus on division and difference, what, if anything, might be a common experience at this moment?
I do think, no matter what party or group you belong to, a common collective experience is one of significant upheaval and uncertainty, a deep sense that we do not know what will happen in our personal and political lives from one day to the next. The question, then, might be something like:
If this kind of uncertainty is the rule rather than the exception, how might that change the way we live our lives? How can we continue to thrive, explore, and stay curious, rather than retreating to or clinging to what we know?
What is a questions practice and how does someone go about starting one?
Just like it’s impossible to develop a relationship with someone we never see or talk to, we can’t develop a different relationship to our questions without regularly communing with them.
Like in yoga or meditation, a questions practice is time to explore and commit to the questions that are guiding your life. It’s about building a regular ritual or habit of introspection and reflection.
In my work, I’ve found that there are four essential ingredients that can help you build a questions practice: curiosity, conversation, community, and commitment.
In part three of the book, I give readers a Questions Map with prompts that can help you reflect on each of the four Cs. The map is a tool to help you discern how to move forward when you don’t have all of the answers.
First, a questions practice is grounded in a mindset of curiosity. That means getting curious about the question(s) guiding your life.
I’d recommend starting your practice by identifying that question. One way to do this is by considering if there’s something you’ve been anxious, worried, or fearful about recently. Often, when we’re feeling those emotions, there’s a question lurking inside of them.
Next, you can ask: Is it the right question? The questions that help us feel empowered in uncertain times open up possibilities for our lives rather than closing them. For instance, binary questions are inherently limiting. At the beginning of my book, I shared that one of the big questions guiding my life was a binary: should I get a divorce? Along my journey, I discovered this question wasn’t right because it only gave me two options – yes or no – and I didn’t like either of them. When I changed the question to how can we continue to be together? it invited a much richer set of answers, and had a profound impact on my relationship.
Once you’ve identified the right question, the second ingredient is conversation. Questions are parts of the conversations we have with ourselves, but during times of uncertainty these inner dialogues can quickly spiral into catastrophizing. In the book, I share practices and ideas to help navigate that anxious mental chatter.
The third ingredient, community, is essential, as you alluded to in your last question. Community, after all, evolved to enhance our sense of security when we’re feeling uncertain. Neuroscience research shows that feeling embedded in community reduces stress-inducing cortisol, and activates the reward centers of our brain. Community, in other words, can help us feel safer, allowing us to more deeply explore and sit with painful questions.
Finally, we need to commit to the process of exploring our questions while observing which ones are no longer worthy of our attention. By connecting us with community and creating more structure around uncertainty, developing rituals - like a questions practice! - help us determine when to hold on to our questions and when to release them (like dead leaves).
I have this piece I wrote about how we often ask a question in childhood that follows us our whole lives in unexpected, wonderful ways. Do you have such a question?
What a beautiful piece. This line stood out to me: “Many of these first questions are asked from a painful place. So many of us didn’t get what we needed as children and we spend a lifetime looking for it. But the upside of that initial emptiness is that we create dynamic and beautiful things out of our yearning.”
The question that’s been following me my whole life is: how do I love myself unconditionally, even if I’m not receiving that love from the world, and even if I make mistakes?
I was fortunate to have a very loving family as a kid, but when I was very little, around eight months old, my mother became sick. For months, she couldn’t get out of bed, open her eyes, or even speak. Family videos show me toddling over to her bed, pulling at her arm, and then retreating despondently. At the time, doctors diagnosed her with chronic fatigue syndrome. (Years later, a psychiatrist suggested that what she experienced could have been severe postpartum depression). For nearly five years, she saw a variety of doctors, therapists, and homeopathic healers, sometimes spending months away from our family in therapeutic centers.
Over the past few years, I’ve explored in therapy how this experience may have impacted not only the relationship I have with my mom, but the relationship I have to myself.
After something happens that doesn’t make sense, we conjure stories to explain it. When my mother left and could no longer care for me, I suspect the story in my head was something like: She’s gone because I did something wrong, and now, in order to earn her love and make her stay, I need to be perfect.
In the book, I talk about my struggle with self-love and perfectionism, which I discovered is intimately bound up with the journey of loving the questions of our lives. In this way, I think the question that’s been following me may have led to the book itself – an offering of hope and support from a place of emptiness and yearning.
There you have it, the amazing Elizabeth Weingarten. Buy her book here. And tell us in comments - Do you have a questions practice? What was your first question? In what ways do you see personality inventories opening us up vs. narrowing us down? I can’t wait for your insights.
Thank you for this helpful opportunity to ask questions and dig. How does one relate to the younger minds of children about how it is that we may always be growing and learning from life experiences; both from the painful experiences as well as the ones that fill us with good feelings and that we will be doing this through our last breath?, unlike many children’s book endings. I don’t want my young nephew to ever feel like he has to deal with disillusionment with big life questions.
My nephew is old enough to start questions of his own and has done the math on the mortality of his grandmother as well as his mother, especially in the face of hospice care in the home. How many years months and days will he have with his loved ones?, are his questions. The first answer to his question came from my 80 year old friend. She found that while going through life, that one never stops learning or feeling life, whether it be in pain or in joy but that she learned not to “hide” by being more open to life’s discoveries and self discovery. My therapist and I also asked questions about knowing ourselves in life and living with uncertainty and I felt like my nephew for a moment, until I was soothed by nature about what disappears.
My thoughts: ”Before bed while closing the shades, the first fireflies of the year appeared, from their mysterious portals of existence. Suddenly generating more than a glowing flicker for the eye, they significantly altered my heart and mind into being their own luminary wonder worlds, never needing to give emphasis about the origin or source of light or source of going dark. They seemed to disappear and appear, perhaps as I do in the way that I change moment by moment in my life. I can never point to any one firefly and know exactly when it will light up or fly in the dark. I only know to wait for the luminosities happily, maybe like worlds in myself through life…seeing another and another appear and disappear, while still being present.
My sense to sort of an answer, is that maybe we can’t really fully comprehend and know one another and life, much less ourselves in the vastness of life’s variables and uncertainties but maybe we can always learn each other with curiosity and see and care for each other and ourselves and be open to wonder as we go. If there is mystery in the universe then why not in ourselves. But if I really try my best to attentively express love and be vulnerable to both hope and mystery, it feels like a gift to look again and again as I disappear brightly into the discoveries I find in the dark.
One might say I have a 'questions practice,' though it looks less literally like questions and more like a practice for the consideration of ideas that, of course, ripen over time, as ideas do.
It began as a system for bringing myself to ground enough to think when I felt like my mind was flying around all over the place not particularly productively.
So, of course, it involves writing.
Over years of reading, I have and do come across a sentence here and there that resonates with me either as true or as provocative. As an example, from the recent Ocean Vuong novel I took this one: 'How he would pull this off, there was no telling - but it was a narrow passage worth taking, a feeble tributary that should at least end up somewhere.'
I record these in a document I call the Weaving Room. It has about 600 entries at present, growing only slowly.
Every morning I pull three or four at random (using a random number generator) and reflect on their intersection, which will automatically entwine with whatever my concerns are, recognized or unrecognized, of the moment.
I do this, as I said, to ground thinking, to build out the tree, or the tapestry, as it were.
But I make no mistake of feeling reassured that quiet, curiosity, and thought are adequate in themselves for living a meaningful and worthy life. Right now I am particularly grateful each day for Valarie Kauar's example. She does engage in quiet, curiosity, and prayer, but is also out there every day, body and soul, on the streets of Los Angeles, standing between threatened people and forces of terror.