Hello Monday with Jessi Hempel · LinkedIn

How to Live With Uncertainty: Asking Better Questions About Work and Life

December 22, 2025·28 min·2 clips

Jessi Hempel confesses she hates the feeling of not knowing and challenges the toxic positivity of 'embracing uncertainty.'

Just knowing would feel easier. Jessi Hempel starts with that familiar wish to be told what to do when uncertainty feels painful, scary, and hard to sit with. The episode does not dress uncertainty up as a cheerful mindset. It treats it as something that can freeze a person, but can also make room for curiosity. Work is one entry point, not the whole story. Questions about the economy, jobs, AI, fertility, career change, family decisions, and meaning all carry the same unsettled feeling. Weingarten offers a way to sort them. Some questions answer themselves fairly soon, like whether a job comes through after a few weeks or months. Those have a shorter clock. Other questions need more time. Weingarten compares them to pawpaw trees, which can take five to seven years to grow fruit. Fertility treatment, a career switch, or the question of what kind of school a child may eventually need can belong to that slower season. Jessi takes the idea personally and finds relief in realizing that some answers may come later, even if now is not the moment for them. Then the frame gets deeper. Heartwood questions are the ones that grow with a person: identity, relationships, love, loss, meaning, and purpose. They do not resolve cleanly. They become part of how someone stays balanced while changing over time. Some questions, though, need to be put down. Dead leaf questions keep a person circling the job not taken or the relationship not kept. The episode lands on a practical question of its own: is this question helping imagine a future, or keeping life stuck in the past?

As heard by us

A calm framework for questions that do not resolve on command.

The episode treats uncertainty as a work and life pressure, not a slogan. Jessi Hempel keeps the focus on what happens when people freeze in the face of an unclear future, and Elizabeth Weingarten gives that problem some shape by separating quick questions from pawpaw questions,…

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Why you'd press play

When uncertainty is louder than your next move.

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