Why we keep waiting for certainty before we change

A few years ago, I was working with an executive who had become increasingly restless in a role that, by most measures, was exactly where he had spent years trying to get.

He was well compensated. His CEO trusted him and his team respected him. In fact, there were no obvious signs anything was broken.

And yet every few months, our conversations would drift back to the same place.

“Do you think it’s time for me to leave?” he’d ask me.

At first, I assumed there was something driving his concern. Maybe he was frustrated by the culture, or perhaps he was comparing himself to someone else’s trajectory or he was quietly attracted to a more attractive role elsewhere.

But every time I pushed deeper, the answer was essentially the same.

“No, that’s not it.”

To be honest, this really stumped us. After all, he wasn’t miserable or burned out or struggling with FOMO.

But something inside him kept wondering whether he had outgrown his current situation.

The question wasn’t urgent enough to force action, yet it wasn’t quiet enough to disappear. So it kept returning.

Many of us know this feeling.

We tell ourselves we’re waiting for certainty before making a change. We imagine there will be a moment when the fog lifts, the future becomes obvious, and the right answer presents itself with such clarity that moving forward feels easy.

But if you’ve ever made a significant life decision, you know that’s rarely how it works.

People leave careers without knowing whether the next chapter will fulfill them.

They become parents without understanding how profoundly their lives are about to change.

They move across the country without knowing if it will feel like home.

They decide to start a business or write a book, or retire or make countless other life-changing decisions without guarantees.

Looking back, the path often appears obvious. But looking forward, it almost never does.

What we’re actually searching for

For most of my life and in my career advising others, I assumed certainty was what we all wanted. Now I’m not so sure it’s that.

I think what most of us are really searching for is the permission to trust ourselves.

Certainty is attractive because it removes responsibility for the decision. With certainty, we would already know it’s the correct choice. It would protect us from regret and it would guarantee that our judgment was sound.

But life doesn’t work that way.

The most consequential decisions can’t be validated in advance and only understood in hindsight. Should I take that job? Should I leave this relationship? Should we have a child? Should I stay where I am or bet on something new?

The challenge isn’t that these questions have hidden answers we’re failing to uncover. (And who hasn’t googled or asked AI for more information than is even helpful at some point for some of the decisions we face?)

Rather, the challenge is that we’re demanding a level of certainty that life was never designed to provide.

Nobel Prize winner Daniel Kahneman spent much of his career studying how people make decisions under uncertainty. One of his key findings was that we tend to experience potential losses more intensely than equivalent gains.

I think that helps explain why transitions feel so difficult. When we’re considering change, our attention naturally gravitates toward what we might lose rather than what we might discover.

We may lose income, our reputation, our relationships, even our identity. And what’s so hard about letting go of past identities to make room for something new is that you’re not releasing something that failed; often you’re saying goodbye to something that was really going great.

So when you can sense something needs to change but can’t figure out what it is, it’s time to trust in something other than certainty: yourself.

The moment things changed

Eventually, the executive I referred to above made his decision about whether to stay or leave. He told me that he kept waiting to feel certain but the a-ha moment came when he realized it never was coming. That was unsettling to him but it was also liberating.

Once certainty is no longer the goal, a different question can emerge. Instead of asking “what if this goes wrong and I lose?” Consider asking, “Do I trust myself to handle what happens next?”

That’s a different question and one that builds courage and motivation instead of triggering fear and advance regret. It also places agency in your hands about what is possible in an uncertain future.

And you still may answer that question with hesitation, unsure whether you can trust yourself either.

But if you look back on how you’ve arrived where you are, you’ll find that your current station is a function of trusting yourself many times before when you didn’t know what was ahead.

A question to consider

Where in your life have you been waiting for certainty, when what you may actually need is greater trust in yourself?