Beyond Answers: How Questions Can Transform Your Life

In our fast-paced world, we’re constantly bombarded with “ultra-processed information” —quick, easy answers that, much like junk food, offer fleeting satisfaction without genuine nourishment. We’re often driven by a desperate search for definitive answers to life’s most profound questions, fueled by social media, AI, and self-help culture. But what if true understanding doesn’t lie in the answers themselves, but in our relationship with the questions?

Elizabeth Weingarten, Director of Thought Leadership at Udemy, applied behavioral scientist, and author of How to Fall in Love with Questions: A new way to thrive in times of uncertainty, challenges our addiction to certainty. Drawing on behavioral science, philosophy, poetry and personal experience, Weingarten argues that instead of seeking a quick fix for life’s ambiguities, we should learn to love the questions.

Beyond embracing uncertainty

The popular advice to “embrace uncertainty” often rings as a “hollow platitude,” particularly when confronting truly painful questions about, for instance, navigating a failing marriage, coping with loss, or awaiting biopsy results. Weingarten suggests the advice to “embrace uncertainty” is a form of toxic positivity that can intensify suffering during challenging times.

Inspired by Austrian poet Rainer Maria Rilke, Weingarten proposes “loving the questions” instead. In the book Letters to a Young Poet, Rilke famously advised to the aspiring poet Franz Kappus to “love the questions themselves as if they were locked rooms or books written in a very foreign tongue,” encouraging us to “live the questions” now, and to gradually “live your way into the answer”. 

For Rilke, love is the most difficult task we undertake as humans, and we must “trust in what’s difficult” and lean into challenges. This perspective reframes uncertainty as a dynamic relationship to be nurtured, acknowledging its evolving, frustrating, and rewarding nature, which ultimately fosters growth and clarity.

The brain’s pull towards certainty

Did you know that our inherent discomfort with uncertainty is deeply biological? Our brains are wired to conserve energy, an adaptation from times of food scarcity. Uncertainty demands more cognitive resources, making it feel inherently aversive and taxing. This is known as the “selfish brain theory”. 

This biological drive to conserve energy renders us vulnerable to “charlatans of certainty” —individuals who exploit our desire for quick answers by sharing a kind of “ultraprocessed” content–, information that’s been stripped of its “nutritional value” and simplified to give us the illusion of certainty (think about anyone who gives you a five-step process to be happier or find your purpose). 

This can lead to a kind of information addiction, and a constant online search for answers that, according to the stories in Weingarten’s book, often masks a deeper craving for connection and community. 

We often mistakenly believe that knowing all the answers will provide safety and alleviate loneliness, when in reality it’s connection that we need during times of uncertainty. 

Categorizing your questions: The Fruit Tree Framework

To help individuals identify and reframe their most significant life questions, Weingarten introduces a practical framework comparing different question types to parts of a fruit tree:

• Peaches: these questions ripen quickly into answers on a short-term timeline, like “Will I get the job?”.
• Pawpaws: similar to the paw-paw fruit which ripens over five to seven years, these have a longer timeline. They are eventually answerable but require patience, such as “Is this the right relationship for me?” or “Will this career choice bring me fulfillment?”.
• Heartwood Questions: this part of the tree gives it stability and balance, staying with it throughout its life. Heartwood questions are our lifelong companions and are not permanently answerable but continuously explored. Examples include “Who am I?” or “How do I live a life of meaning and purpose?” The book How To Fall in Love With Questions: A New Way to Thrive in Times of Uncertainty fundamentally focuses on these.
• Dead Leaves: like fallen leaves, these questions no longer serve us and should be released, as they may keep us stuck in patterns of regret or rumination.

Identifying the type of question you’re asking is a crucial first step in cultivating a Questions Practice.

Tips for cultivating a Questions Practice

Weingarten suggests a “questions practice” can be cultivated like meditation or yoga, a structured ritual for understanding the questions guiding our lives. 

Key elements and tips include:

• Approach your questions with curiosity, not fear: when facing discomfort, pause and get curious about the underlying question instead of rushing for answers. Fear limits creative thinking and pushes us towards quick fixes. Curiosity, conversely, opens up possibilities and reduces anxiety. 
• Seek clarity, not just answers: the ultimate goal is not necessarily a definitive answer, but to gain clarity. Clarity enables forward movement, even when answers are elusive, and helps determine if you’re asking the right question.
• Foster conversation and community: questioning is not a solitary endeavor. Questions are an “interpersonal superpower” that builds stronger relationships. Sharing questions with a trusted community helps you feel less alone in uncertainty while often addressing the underlying craving for connection.
• Commitment to the process: loving questions, like any deep relationship, demands commitment. It means choosing daily to sit with your questions, even when difficult, recognizing the relationship will evolve.
• Reframe binary questions: great questions “blow the doors off of a room,” opening possibilities rather than limiting you to “yes” or “no”. For example, reframe “Should I have another kid?” to “How will I know if I want to have another kid?”.
• Use questions as an internal GPS: questions can serve as an “internal GPS,” guiding you back to your true self —what you authentically want and need— rather than external expectations or societal “shoulds”. This process fosters self-compassion and self-integrity.
• Cultivate patience and courage: these are twin virtues essential for navigating uncertainty. Patience involves “waiting well while we suffer,” holding onto difficult questions without giving up. Courage acts as a counterbalance, preventing disengaged passivity and encouraging movement.
• Practice listening: this is foundational, both to others and, crucially, to yourself. Often, seeking external answers disconnects us from our inner wisdom. Listening to your true self is key to a healthier relationship with uncertainty.

By shifting focus from immediate answers to cultivating a loving relationship with our questions, we can unlock a deeper sense of self, find clarity amidst chaos, and navigate life’s inevitable uncertainties with greater growth and possibility. It’s a journey of continuous self-discovery, leading to a richer and more fulfilling life, one question at a time.

You can buy Elizabeth Weingarten’s book “How To Fall In Love With Questions” on Amazon, Barnes & Noble, Harper Collins and wherever books are sold. 

Check out Elizabeth Weingarten’s take on Top Learning Trends for 2025 in this webinar.