Career Transitions and How to Navigate the Discomfort of Uncertainty

Most people knock on my door hoping I'll be able to help them figure out what they should do next in their career. Should they leave? Stay? Start the business? Accept the promotion? Go back to school? Move across the country?

The assumption underneath all of those questions is the same: somewhere out there is a correct answer, and if we think carefully enough, gather enough information, or speak to enough wise people, we'll eventually uncover it.

The longer I do this work, the more I realize my job isn't to help people decide what to do next. My job is to help them ask themselves better questions, listen more carefully to their own responses, and cultivate the discernment to recognize what those questions are revealing.

When Uncertainty Feels Like Stuckness

The challenge is that the moment uncertainty enters the picture, our curiosity often disappears.

Psychologists call this the need for cognitive closure: our tendency to want an answer simply because not knowing is uncomfortable. Instead of asking questions that expand our perspective, we begin asking questions that promise certainty.

From the outside, this often feels like being stuck. In my experience, most people aren't stuck because they lack options. They're stuck because they're waiting for uncertainty to disappear before they're willing to make a move.

Where the Real Work Begins

Recently, I began working with a woman in her late forties, a senior executive at a large multinational company. By every conventional measure, she had built an extraordinary career. She had lived overseas, taken risks, moved countries, and climbed steadily into leadership. She wasn't lacking courage – far from it. In fact, she'd spent much of her life doing things other people were too afraid to try.

And yet she found herself sitting across from me, saying something I hear all the time: "I don't know what I want."

As we talked, it became clear that wasn't entirely true. She knew what she didn't want. And when pressed, she did know what she wanted. What she didn’t know was whether she could trust that wanting as real, or just another level up on the hedonic adaptation treadmill. We’re sold a bill of goods about adulthood, and if you’ve got a job that can pay for a nice life, friends and family, that should be enough, right? Stop wanting more. More than 90% of the world lives on $30K or less a year. You have champagne problems!

While gratitude is critical and much of our culture does get stuck on this treadmill, there is a difference between your life being out of alignment with what is important to you, and seeking newness for newness’s sake, or because you’re hoping a material leveling up will heal an existential or soul-level longing. But I digress…

This client could feel that her life had become less than she really wanted, and truthfully, less than what she was capable of or deserving. What she wanted wasn't another new opportunity. She wanted certainty before she moved. She wanted to know she was choosing the "right" future before taking the first step.

Better Questions, Better Data

Unfortunately, life has never agreed to those terms. So instead of trying to answer the question she arrived with, we began by asking a really simple, yet powerfully challenging question to open space for more: 

“Fast forward one year. You and I (client and coach) are reconnecting. It’s been the best year of your life. Tell me all about it. Start with the prompt, ‘It’s been a really great year…’ ”

First, this client wrote the version of the year she predicted, because she had to clear that version out. Then, after having allowed her Very Responsible Adult Brain to have its say, she wrote the second version. The true version. The version her heart and her gut and her soul were longing for, but were afraid wasn’t possible. 

We can’t create a better future if we don’t even allow ourselves to imagine it, or trust that imagining.

One Stone at a Time

This is how many career transitions actually unfold, rarely through one dramatic realization, and much more often through a growing collection of observations, shifts, and imaginings that slowly become impossible to ignore. One conversation changes how you think about your work. A question lingers longer than you expected. You notice a feeling of being unexpectedly energized by a project, or drained by something that once excited you.

At first, those moments feel unrelated, like scattered stones stretching across a stream. But for anyone who has crossed a stream in the woods that was too wide to leap over in a single bound, you need those stones to reach the other side.

(A quick aside: if you're in the middle of a career transition, I'd add Working Identity by Herminia Ibarra to your reading list. This book helped me, and countless other clients, see that you don’t need to leap from Point A directly to Point B. Your transition can be gradual, like crossing that river one stone at a time.)

Over time, you stop searching for the opposite bank and begin paying attention to the next stone – another conversation, another experiment, another observation. Looking back, the path feels obvious. Standing in the middle of it, you rarely see more than one or two stones ahead.

We spend so much of our lives believing confidence comes from knowing what to do next. It comes from something else entirely: from trusting yourself (and the great mystery that is life) enough to step onto the next stone before you've been shown where the rest of the path will lead.

What is Hedonic Adaptation? It is, acorrding to Yale professor Dr. Laurie Santos, “The process of becoming accustomed to a positive or negative stimulus such that the emotional effects of that stimulus are attenuated over time.” 

Source: Laurie Santos, PhD, “The Science of Hedonic Adaptation” https://www.youtube.com/watch?v=MJr-43grEzw.