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July 9, 2025 39 mins

What if the secret to navigating life's uncertainties isn't about finding quick answers, but about embracing the questions themselves?

In this episode of Glass Ceilings and Sticky Floors, Erica Rooney sits down with Elizabeth Weingarten, author of How to Fall in Love With Questions. Elizabeth's unique career path, spanning journalism, public policy, behavioral science, and tech, is driven by a lifelong curiosity about why people behave the way they do and how to design spaces where everyone can thrive.

Together, they dive into the art of embracing uncertainty by loving the questions—a liberating approach that moves beyond the often-unrealistic expectation of "embracing uncertainty" in difficult times. Elizabeth shares powerful strategies for navigating life's messy middles, from career pivots to personal crises, by reframing how we interact with the unknown.

Inside the Episode:

  • The "Messy Middle": How curiosity has connected Elizabeth's non-linear career path across diverse fields.
  • Beyond Embracing Uncertainty: Discovering why "loving the questions" offers a more authentic and liberating path forward.
  • The Charlatans of Certainty: Identifying and avoiding sources that offer quick, often misleading, answers to deep personal questions.
  • The "Questions Map": A powerful tool to identify, refine, and commit to the right questions for clarity and progress.
  • Cultivating a Questions Practice: The four key elements—curiosity, conversation, community, and commitment—for transforming your relationship with uncertainty.
  • Finding Courage in the Questions: How shared questions and community can provide the strength to move forward, even when answers are elusive.
  • Redefining Self-Worth: A crucial question for women in particular: how to define your self-worth outside of achievements and accomplishments.

If you're ready to transform your anxieties about the unknown into a journey of deeper understanding and empowered action, this episode is your guide.


Connect with Elizabeth on LinkedIn or Buy Her Book Here!


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