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What If…?

What If…?

Polly May on asking the question that could change everything…

I’m 49, and I changed my job at 47. Not a little change. Not a promotion, a new title or a move to a slightly different role. A complete pivot.

I knew there was more I wanted to do. And with at least another 16 years before retirement, I knew I couldn’t ignore that feeling. But there was another consideration, and actually, it was the more important one: my family.

My children were heading into public exams and making big decisions about their futures. My husband had borne the brunt of the parenting for years because, as a freelancer, he had more flexibility. I was working 10- or 12-hour days, and although I was doing what I was good at, the balance was all wrong.

Something had to change. So I changed it. I retrained, set up a new business and started doing something that, on paper, looked completely different. But the funny thing is, I don’t think I really started again at all. At the heart of what I do now is something I’ve always done: helping people feel more confident and brave enough to make big decisions.

That experience has made me increasingly interested in a very simple question: what if?

It’s a small question, but it can open up an enormous amount of possibility. What if I went for the promotion? What if I started the business? What if I changed direction? What if I asked for more? What if I stopped doing something that no longer works for me? What if I stayed exactly where I am, but found a different way of working?

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I think “what if?” is particularly interesting for women in business because we often reach our forties and fifties carrying an enormous amount of experience, but somehow don’t always recognise its value.

We have spent years building careers, managing people, solving problems, raising families, running businesses and keeping everything moving. Yet when a new opportunity comes along, our first thought can still be: But am I qualified?

I see it all the time. Someone will tell me about a promotion they’re considering and immediately start listing the things they don’t have. They haven’t managed a team that size. They haven’t worked at that level. They don’t have every piece of experience mentioned in the job description.

And yet, when we actually look at their history, there’s a huge amount of evidence that they are capable. That’s why I often encourage people to look backwards before they look forwards. Think about something you’ve achieved that you’re genuinely proud of. It doesn’t have to be the biggest thing you’ve ever done. Perhaps you navigated a difficult period at work. Perhaps you built something from scratch. Perhaps you led a team through a particularly challenging time. Perhaps you dealt with something personally that you weren’t sure you could handle.

Really remember it. Where were you? Who was there? What did you do? What did it feel like when you realised you’d succeeded? It sounds simple, but reconnecting with those experiences can be incredibly powerful. We forget what we’re capable of. We remember the things that went wrong and the things we still haven’t done, but we don’t always give ourselves enough credit for everything we’ve already navigated.

That history matters. I call it historic worth: the value and capability contained within everything you’ve already done. And I think it becomes particularly important when we’re considering what comes next.

Because “what if?” doesn’t necessarily mean blowing everything up. It doesn’t have to mean quitting your job, starting a business or completely reinventing yourself. Sometimes the question is much smaller.

What if I asked for the promotion?

What if I stopped saying yes to everything?

What if I delegated more?

What if I finally explored the idea I’ve had sitting in a notebook for three years?

What if I admitted that the way I’ve always worked isn’t working for me anymore?

And sometimes the answer really is bigger.

A client of mine had spent 25 years in banking and reached managing director level. On paper, she had an extraordinary amount of experience. Yet when she started thinking about setting up her own consultancy, she struggled to see just how much she had to offer. She knew she wanted something different, but confidence was getting in the way.

That’s another thing I have learned: sometimes you don’t need someone to tell you what to do. You need someone to talk to while you work out what you want to do. That, for me, is where coaching can be so valuable. You can have the idea, the ambition or the niggling feeling that something needs to change, but when you’re inside your own head, it can be difficult to know which thoughts are worth pursuing and which are simply noise.

Having someone to throw an idea at can help you turn a tangled mess into something you can actually make a decision about. That’s what happened to me at 47.

I didn’t have every answer. I didn’t know exactly what the next few years would look like. I simply knew that the life I was living wasn’t quite working anymore. And I knew I had to pay attention to that. I’m not suggesting that everyone should change their career at 47. I’m certainly not suggesting that everyone needs to start a business or make a dramatic life change.

Sometimes the right answer is to stay exactly where you are.

But I do think it’s worth asking yourself some honest questions. How much of your working life do you genuinely love? What is your body telling you? What do you want your life to look like in five years? And what have you been putting off because you’re telling yourself you’re too old, too busy, too inexperienced or simply not ready?

Then ask yourself one more question.

What if?

You don’t have to know the answer immediately.

At 47, I didn’t.

But asking the question changed everything.