3 Career Change Questions You’re Taught To Ask That Are Keeping You Stuck (And What To Ask Instead)

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Where do you start on your career change? Much of the 'advice' that's commonly given out (including key questions to ask yourself) is ineffective – and, as Natasha explains, can leave you feeling as frustrated and unclear as when you started. Here's why, and what to do instead.

When something as major as your career is at stake, there's nothing like a good Google with a cup of tea to get informed about the best course of action, right?

I was the queen of internet research at the beginning of my career change. Article after quiz after personality test – I ate them for breakfast. But with hindsight, after years of working with thousands of people going through career change, it turns out there's a lot of rubbish on the internet.

And when it comes to career change, this kind of rubbish can reinforce negative beliefs, perpetuate major career change myths, and keep you stuck for years.

How many of these questions have you come across online (and how many have you believed you had to answer before you could make a shift)?

1. Have you done the necessary self-reflection to find out what you really want?

This question sounds so straightforward at first glance.

And then you look again. And not only is it enormously ambiguous, it's also the kind of question that keeps people from making a career change for years.

It feels great to 'do self-reflection' – it really does.

There you are, on the couch, reflecting away, glass of wine lubricating the brain cogs. You're making lists, gazing into the distance, asking yourself big, lovely philosophical questions… it feels deep and meaningful and wonderful.

But it only gets you so far, doesn't it?

Self-reflection is a false friend – it looks and sounds like a great idea, but it can actually sometimes be exactly what's keeping you stuck.

Put it this way: you've probably been self-reflecting pretty hard recently. And you probably still have very little idea what you want to do next. Why? Because if the answer was inside your head, you’d have found it by now.

And how much self-reflection is the 'necessary' amount, anyway?

You're not going to suddenly remember a whole new skill set you'd forgotten you had.

You're very unlikely to draw up another list of values that contain a massive surprise, if you just give it one more try.

At what point can you put down your mirror and say "Right, I'm done reflecting now"?

Finding out what you want (from a career, from a relationship, from anything that matters) is not a theoretical process. It can't be 'figured out'.

And if you wait until you know what you want before you get started… you could be waiting forever.

Reflect powerfully. Ask yourself bold questions. But don't wait to have definite answers before you start your shift. Start now.

2. Are you being realistic?

As if you needed another voice to rain on your parade.

With the vast majority of career changers we work with at Careershifters, being 'realistic' is a habit we have to start by training them out of.


Because what people think is realistic for themselves and what's actually realistic are usually light years apart.

This absolutely doesn't mean that quitting your job today to become an astronaut by the time your savings run out in three weeks is a good plan. But before you know what you want to explore, and before you've tested out your ideas to find out what 'realistic' actually looks like outside of your head, asking yourself this question is 95% more likely to keep you stuck than it is to get you shifting.

If you'd asked me five years ago how realistic it was for me to get paid to coach people from the deck of a sailing boat in Greece, I'd have choked on my coffee with laughter.

If you'd asked Nina how realistic it was for her to make a career out of writing, she'd have giggled and shaken her head (and the sadness behind her eyes as she answered would have damn near killed you).

It's not 'realistic' to expect to shift into a career when you have no relevant experience on your CV. But Anna did it. So did Patrick.

It’s not 'realistic' to start a business when you've just had a child. But Gemma did it. Louis did, too.

How many ideas have you had and cast aside, on the basis that they weren't 'realistic'? And how many of those ideas do you know aren't realistic, and how many are you scared aren't realistic?

There is a difference. And on some level, you know the difference.

And the best way to find work you love is to take the ideas that really excite you and challenge your fears and assumptions about whether they're 'realistic' or not.

Instead of asking yourself if you're being realistic, get out there and ask the world. Challenge your assumptions through actions, Shift Projects, conversations with others.

See what 'realistic' really means.

3. Is this the right time?

Here's the answer to that one, boys and girls: no.

Disclaimer: the use of inverted commas in the following paragraph is for comedic and readability purposes only.

'Now' is not 'the right time'.

'Now' is never 'the right time', even when 'now' is the 'now' you were waiting for it to be six months ago because then wasn't 'the right time' and you were sure that 'now' would be.

Fact is, there is never a 'right time' to make a career change – at least not in the way that this question intends you to think about it.

There are always going to be reasons to wait. Maybe if you just get this promotion first, you'll have more money in the bank. Maybe if you just get through this big project, you'll have more time. Maybe if you just wait until your partner has finished their marathon training… Maybe if you just wait until your boss… Maybe if you just wait…

But there's always something you can be doing right now toward your career change, no matter what your circumstances. Taking yourself into new environments to stimulate new ideas. Connecting with new people who can provide new perspectives and support you. Creating mini Shift Projects to build your experience and learn more about your interests.

And the more actions you take along these lines, the closer the gap will get between where you are now and where you want to be. Until one day, all there is to do is take the final step.

"The best time to plant a tree was 20 years ago. The second best time is now." – Chinese Proverb

So if these questions aren't helpful starting points, what should you be asking before you get started?

1. Am I committed?

Career change can be tough.

You're navigating uncertainty at every turn, asking yourself some big, challenging questions, and aiming to transform an area of your life that triggers all your survival instincts.

It's easy to daydream about finding work you love from your desk. It's quite another matter to actually start making it happen.

And if you're only interested in doing it if it's easy – if you're happy to fantasise but not to fight – you will likely fail.

Unless you're committed, the safety and warmth of the devil-you-know will always be stronger than you.

And you don't have to know how you're going to make it happen. Commitment isn't about agreeing to do something that's clear and obvious. It's about choosing your destination and creating a path.

"This is going to happen. I don't yet know how I'm going to make it happen, and I might encounter some big challenges, but this is non-negotiable: I will make a shift into work I love."

That blind, unequivocal commitment is what carries you through the moments of fog and the uncertainty and the constant, insistent pull of familiarity.

It's also what gives your voice gravitas and passion and bravery when you're talking to someone who could help you make a shift. It's what has them see you're serious, and take you seriously as a result.

It pushes you into creativity and finding solutions to problems you'd usually give up on.

And it's the one thing that we see, over and over, separate the people who make successful shifts from the people that don't.

"Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one's favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way. Whatever you can do, or dream you can, begin it. Boldness has genius, power, and magic in it." – William Hutchinson Murray

2. Who can I get in my corner?

If commitment is the first key indicator of people who are likely to make a shift, community is the second.

Making a career change alone is possible, but it's much, much harder than having a team of supporters around you.

People to bounce ideas around with, to challenge your fears, to connect you with interesting people, to accompany you on your journey – people are the oil to your career change machine.

There are going to be moments in your shift when you wake up panicking that it's all too big and too much. There will be moments when you doubt your own bravery. You'll come across situations that you just don't know what to do about.

And having a bunch of cheerleaders to call on in those moments? It's priceless.

On our Launch Pad, people consistently tell us how much of a difference the group dynamic made to their shifts:

"The group was so supportive; it was a big melting pot of backgrounds and influences and perspectives, and it popped me out of the bubble I was in. I don't know if I'd have been able to do what I did without the group. I'm a very self-motivated person, but I would have struggled to do everything I did on my own." – Alison, Launch Pad participant

Alison put a community of career changers and coaches around her as she started this journey. But you don't have to join the Launch Pad to create your own crack team of career change supporters.

Friends and family, trusted colleagues, people you meet along your career change journey – the woman who owns the shop where you go to buy milk in the mornings could become an accountability buddy for you.

Whatever your situation, wherever you are, there are people in your life who can play this role for you.

Who are yours going to be?

3. What is the first thing I could do in the real world to start exploring?

A while ago, I wrote an article about why I feel uncomfortable writing career change articles. The irony of this is not lost on me.

But the sentiment still stands.

If there's one question you should ask yourself today to start your career change process, it's this one.

Career change is not a single event. It's a series of tiny actions – Micro Shifts – that lead you to a meaningful result.

And because Micro Shifts are tiny, and they're active, and they give you real-world feedback, and they feel great, there's no reason why you can't start your career change today.

Ultimately, there are no 'right' questions to ask before you start a career change

All there is to do is start.

But if you do find yourself on the internet one day, browsing through career change guidance and wondering if you should be asking yourself the questions they're insisting you ask, I implore you – check in with yourself. Do these questions feel good? Do they inspire you? Do they call you to action?

And then, begin.

What career change questions have kept you stuck? And what are your answers to our alternatives? Let me know in the comments!

Natasha Stanley's picture

Natasha Stanley is head coach, writer, and experience designer for Careershifters. When she's not working, you'll find her listening to neuroscience podcasts, learning pottery, and dreaming up her next adventure.