When “What’s Next?” Stops Working, Ask This Instead

Over time, careers tend to take their shape from life rather than from plans. The questions that once guided us often stop working in the same way.

In a recent session with women entrepreneurs, I kept hearing the same story in different forms. Not one job and one path, but two or three roles at once. A business alongside consulting. Paid work alongside community leadership. Working lives shaped around reality rather than a neat career ladder.

Against this backdrop, decisions are shaped as much by context as by ambition. People take on work that looks right on paper but never quite lands. Or they stay with something sensible long after it has stopped fitting.

An exercise I first wrote about in Now It’s Clear invites clients to draw their careers as they feel right now. You do not need to be an artist. The value is not in the picture itself, but in the act of making something visible before trying to explain it.

What often emerges is a sense of loosening. Familiar anchors are still present, but they no longer hold in the same way. Seeing that on paper gives people a different perspective than words alone ever could.

My clients are not lost exactly, but many feel untethered. I hear this most from mid career professionals and dual career couples who are managing not only their own trajectories, but how two lives and two sets of commitments move together. It can feel less like following a familiar path and more like walking a tightrope you have not crossed before, where balance matters more than speed.

When the ground shifts, uncertainty and restlessness tend to follow. Change begins to move faster than our ability to absorb it. And still, the question that surfaces most is the same one we have always asked.

What’s next?

Once, it pointed the way forward.

Now, it doesn’t.

Some questions carry assumptions that we may push aside. We think momentum equals progress. If you just keep going, clarity will follow. For many people right now, that is unlikely.

We work in a world described as stable, even as it keeps moving underneath us. Careers are shaped by far more than aspiration alone. Economic uncertainty, shifting expectations, global mobility, caregiving responsibilities, and identity transitions all play a role. Ambition still matters. But so does the ability to pause long enough to notice what is changing beneath the surface.

In this context, what’s next is the wrong question to lead with.

A better one, and one I am hearing more often, is quieter and more revealing.

What still fits?

Sometimes the question is even simpler.

Do I?

This question invites a different kind of attention. It asks you to notice whether your work still fits your life as it is now, not as it once was or as you imagine it should be. Whether it fits your energy as well as your capability. Whether it fits your values, not just your role or title. And whether it fits what you are holding on to, rather than what you are choosing.

I sometimes share a short manifesto for clients when they reach this point. Not as advice, but as a way of naming what they already sense.

Walk the Path of Most Resistance

Career paths are never straight lines, so appreciate the curves.

Wield an artist’s brush to paint your future.

Feeling unmoored does not mean there is anything wrong with you or with the work itself. Often, both are strong. The tension comes from the gap between how things appear from the outside and the quiet sense that something has shifted. What once felt coherent now feels like a suit made for a different season of life.

There is nothing wrong with you if this is happening. More often, it means you have outgrown an earlier version of your career, even if that version once served you well.

Why clarity does not come from more advice

When uncertainty shows up, the instinct is to move faster. To find answers. To fix something. To gather opinions or look for the right solution. Advice is plentiful, and much of it well intentioned.

But clarity rarely comes from more input.

It comes from space to think.

Thinking time without distraction. Time where you are not interrupted or rushed toward a solution. I often encourage people to go for a walk and leave everything behind. No phone. No podcast. No agenda. Just walk. Not to optimize yourself or fix anything, but to allow thoughts to bubble up, settle, and linger.

As Sylvia Boorstein writes, “Every moment of awareness is accompanied by a feeling tone. We tend to notice pleasant or unpleasant moments more than neutral ones, because they attract or alarm us.” She suggests a simple practice while walking, gently asking yourself: What is true?

When real listening happens through uninterrupted thinking time, something shifts. The noise quiets, patterns emerge and options become visible again, without the pressure to act on them.

One question often bubbles up, ‘what are you noticing now that feels different from before?

Holding on with steadiness

Careers are adaptive responses to a changing system. This is not about predicting the next move. It is about staying connected internally long enough to notice what still fits, and what might need to change.

Clarity comes from taking time to think. So here is the question I will leave you with. What are you standing in the middle of right now?