We’re often encouraged to look back at our career choices and ask ourselves what we would have done differently.

But what if the more useful question isn’t about regret at all?

I was asked a version of that question recently, after mentioning that I’ve had several career changes.

My answer was straightforward: No, I don’t regret any of them.

Every role and every change gave me the opportunity to grow, gain new skills, and build a strong, flexible experience. More importantly, it allowed me to connect with diverse people.

Even the choices that didn’t turn out as I expected became part of what I know about myself today. And perhaps that is what makes looking back at our careers so interesting.

Not everything makes sense when we look at it as an individual decision. But when we look at the bigger story, we can often see connections we couldn’t see at the time.

I was reminded of this recently when talking with two women about career change and what we wanted to become when we were children.

I was eight years old and wanted to become very rich. I had decided that being a butcher, owning a funeral home or becoming a notary would get me there. I know!

It sounds completely random now. But looking back, I can see some early clues: I was drawn to things that felt stable, established, and connected to planning for the future.

Of course, I had no idea what any of that meant at eight. But perhaps our career stories start before we ever have a career.

Long before we choose a degree or our first job, we are already absorbing ideas about work, success, security and what a good working life looks like.

Then life happens.

We gain experience. Our circumstances change. Our priorities shift. We discover new interests and new parts of ourselves.

And our values can evolve too. What mattered most to us at 30 may not be what matters most to us at 40, 45 or 50.

There isn’t one way to build a career. For a long time, the traditional career story was relatively simple:

Study → get a job → progress → become more senior → retire.

But careers don’t always work like that.

Some people follow a relatively linear path, developing within one profession or organisation.
Others move between industries, roles and organisations.
Some create businesses, take career breaks, change direction or reinvent themselves later in life.

One path isn’t intrinsically better than another. Research into careers increasingly reflects this complexity.

Mark Savickas’s work on Career Construction and Life Design, for example, starts from the idea that we are not simply choosing a career. We are constructing a career story from our experiences and the meaning we make of them.

Life Design also recognises that careers rarely unfold exactly as planned. Career adaptability is an important part of this thinking: our ability to stay curious, take some control, prepare for what might come next and have confidence in navigating change.

This connects with the idea of cognitive flexibility — our ability to adapt our thinking, behaviour and sense of identity as circumstances change.

As the Age Action Alliance recently highlighted, women often practise this kind of flexibility throughout their lives, through the many transitions and changing roles they navigate.
It is a reminder that the experience of change can itself build valuable adaptability.

The Protean Career perspective adds another dimension. It suggests that careers can be guided by personal values and fulfilment rather than traditional promotions or external metrics of success.

Together, these ideas challenge the assumption that a successful career has to be a straight line. They also offer another way of looking at the winding paths many of us have taken.

Perhaps they aren’t evidence that we got lost. Perhaps they are evidence that we changed.

This is where I think looking backwards can become useful. Not to question every decision. Not to rewrite your past. And certainly not to compare your path with someone else’s. But to notice the patterns.

• What have you repeatedly been drawn towards?
• What have you learned about the environments where you thrive?
• What skills have followed you from one role to another?
• What have you needed at different stages of your life? And what has changed?

Because the career that fitted you at 30 may not fit the person you’ve become at 40, 45 or 50. That doesn’t necessarily mean you made the wrong choices.

It may simply mean you’ve changed — and what matters to you may have changed too. Which is why, when we look back at our career paths, perhaps the most useful question isn’t:

“Why haven’t I followed a straight path?”
It is:
“What does my career story tell me about who I am, what matters to me and what I might need next?”

That is where career coaching can help. Not by telling you which career path to take. Not by giving you the answer.

But by helping you understand the path you’ve already travelled. The experiences that shaped you, the choices you’ve made and the patterns that keep appearing. Because you are the expert on your life.

My role is to help you see your story more clearly, and see what you already know about yourself to make a more intentional choice about what comes next.

You don’t need to regret the path you’ve taken. You can learn from it. And then decide where you want to go from here.