Guest: Elizabeth Weingarten | Book: How to Fall in Love With Questions: A New Way to Thrive in Times of Uncertainty
Uncertainty has a way of stopping us in our tracks. We tell ourselves we can’t move until we know the outcome. Yet paradoxically, uncertainty is also the very condition that allows us to grow, create, and lead with purpose.
That paradox is at the heart of my recent Working on Purpose conversation with journalist and behavioral scientist Elizabeth Weingarten, author of How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty.
Learning to Love the Questions
Elizabeth didn’t write her book from the comfort of hindsight. She wrote it while standing inside her own uncertainty—newly married, newly uncertain about her career, carrying questions that felt unbearable. The usual advice to “embrace uncertainty” fell flat, until she found Rilke’s words to a young poet: “Try to love the questions themselves.”
That became her compass. And it could be yours, too.
The Shape of Our Questions
Elizabeth offers a metaphor worth holding onto: our questions are like parts of a fruit tree.
- Some ripen quickly, like peaches.
- Others take years, like pawpaws.
- Some are lifelong companions—the heartwood.
- And some, the dead leaves, must be released.
The wisdom is knowing the difference: are you clutching dead leaves, or tending to your heartwood?
When Uncertainty Enlarges Us
Uncertainty doesn’t always diminish us. Sometimes it expands us. Elizabeth shared the story of Barbara, a consultant whose life changed after a paralyzing accident. Terrifying as it was, Barbara felt unexpected relief—the old identity she had clung to shattered, making space for a larger one to emerge.
This is the paradox: uncertainty is not only something to endure; it is the soil from which new life grows.
Why This Matters for Workplaces
The workplaces people cherish—the ones they stay for, fight for, and grow inside—aren’t magnetic because they have all the answers. They are magnetic because they dare to live the questions.
At the Gusto, Now! Academy, we help leaders do exactly that: hold the heartwood questions with courage, prune the dead leaves with wisdom, and invite curiosity into their culture. This is how Destination Workplaces are born—places people don’t just work, but places they come alive.
Listen and Learn
🎙 Hear the full conversation with Elizabeth Weingarten on Working on Purpose [insert link].
📚 Explore her book How to Fall in Love with Questions.
🎓 Discover how the Gusto, Now! Academy can help you build a culture where purpose, belonging, and growth thrive.
Closing Thought
Questions are not tormentors. They are companions, catalysts, and—if you let them—teachers.
