Where Do You See Yourself in Five Years? Maybe You’re Asking the Wrong Question

“Where do you see yourself in five years?”

It’s one of the most common interview questions. You may have even asked it yourself when recruiting new staff.

It’s also a question many of us ask ourselves when planning our careers.​ But here’s my perspective ... I actually think it’s the wrong question.

Why a Five Year Career Plan Doesn’t Make Sense Anymore

Think about where you were five years ago. Would you have predicted where you are today?

I certainly wouldn’t have.

When I look back five years, I never imagined I’d be where I am now. My career has taken unexpected turns, opportunities have appeared that I couldn’t have planned for, and my priorities have evolved in ways I never anticipated.

Now add another layer.

Think about how quickly technology is changing (insert scared face emoji)!

Artificial intelligence, automation and digital innovation are transforming the way we work at a pace we’ve never experienced before. According to the World Economic Forum’s Future of Jobs Report, technological advancement continues to be one of the biggest drivers reshaping the future of work.

Five years ago, many of the tools businesses rely on every day either didn’t exist or weren’t widely adopted. New platforms emerge constantly. Entire industries evolve. New careers are created while others disappear. Need I say more?

How can any of us confidently predict exactly where we’ll be in five years when the world itself is changing so rapidly?

A Better Question to Ask Yourself

Instead of asking:

“Where do I want to be in five years?”

Try asking:

“How do I want to FEEL about my career and my life one year from now?”

Notice the difference. The focus shifts away from predicting a job title and towards creating a career that supports the life you actually want to live.

The keyword here is feel.

The Question That Changed My Career

Back in 2016, I was heavily pregnant with my first child. I was working in an incredibly stressful role. What started as managing one centre quickly turned into managing 13 centres due to organisational restructuring and staff departures, all within my first few months in the role.

I remember driving to work so exhausted that I’d catch myself fighting to stay awake behind the wheel. It wasn’t sustainable.

During that time, I stopped asking myself what job I wanted next. Instead, I asked myself something much more important.

“How do I want to feel when I return to work after having my baby?”

I knew exactly what I didn’t want. I didn’t want to feel constantly stressed. I didn’t want to be burnt out. I didn’t want a career that competed with the kind of mother I wanted to be.

Instead, I wanted work that:

• allowed me to prioritise my family

• gave me flexibility to work from home

• enabled me to make a meaningful difference in people’s lives

• supported my wellbeing instead of sacrificing it

• Those feelings became my compass

Fast Forward Ten Years

Today, I’m still working remotely, and I’m still building a career centred around flexibility, purpose and making a meaningful impact, just in a different way than I imagined all those years ago.

Has everything unfolded exactly as I planned?

Not at all.

But the way I wanted to feel has remained remarkably consistent.

And that’s what guided my decisions.

Don’t Start With the “How”

One of the biggest mistakes I see people make is jumping straight to the logistics.

“How will I find a flexible job?”

“How will I change careers?”

“How will I earn enough money?”

“How will I make it work?”

The truth is, you don’t need all the answers yet.

Start with the what.

What do you want your career to give you?

What kind of lifestyle are you trying to create?

What values matter most?

What do you want your work to feel like?

Once you’re clear on the destination, you can begin exploring the different pathways that could get you there.

The “how” often becomes much clearer once you’ve defined the “what.”

Your Career Doesn’t Need a Five Year Prediction

It needs a clear direction. The future of work is changing faster than ever before. Your career will likely evolve in ways you can’t currently imagine.

But your values, your priorities and the way you want your work to support your life can become your guide. So instead of asking yourself where you’ll be in five years…

Ask yourself:

How do I want to feel one year from now?

You might be surprised how much clarity that question brings.

If you’re feeling uncertain about your next career move, you don’t need to have your entire future mapped out. You simply need clarity on what matters most to you.

Ready to explore what’s next? Book a Career Clarity Session today and start designing a career that feels aligned and sustainable.