5 Unconventional Questions To Get You Unstuck In Your Career Change

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Sluggish, frustrated, and running the same old circles in your head? Craving a fresh perspective but don’t know where to look? Natasha shares 5 things you can ask yourself to see your shift (and the reasons you’re stuck) in a new light – so you can get moving faster into more fulfilling work.

At the start of my career change, the space under my bed was a source of major embarrassment.

Not because of dust bunnies and long-lost hair ties (although there may have been a few of those, too).

Under my bed was my collection of self-help books, and an embarrassing number of pieces of paper covered in lists, angry scrawlings and mournful, unattainable dreams. It was the place where the chaos inside of my frustrated brain was visible to the outside world.

And what frustrated me most about those pieces of paper was how much of their content was the same. I felt like every time I opened one of those self-help books and started writing my thoughts in response, I was answering the same questions.

  • What did I really want to do with my life? (I didn’t know – no matter how many times I tried to answer the question)
  • What was holding me back? (The same things as were holding me back yesterday, and the day before...)
  • What would I do if I knew I couldn’t fail? (I didn’t know – I still had no idea what I wanted to do with my life)

And I was doing things to move my career change forward. I was spending hours on it every week. But for all my efforts, I wasn’t getting very far.

What I really wanted was a wake-up call – an angle to look from that cast my career change in a new light, and gave me a way to get over my blind spots and blockages in a hands-on, productive way.

Now, with the benefit of hindsight on my side, I’ve been thinking about the questions I wish someone had asked me back then: questions that are action-focused, a little challenging, and certainly not the ‘classics’ I was beating myself up for not having answers to.

So here are five questions you may not have asked yourself before – inspired by real-life career changers and a handful of unexpected experts – to help you reveal the blind spots that could be holding you back, and start moving forward with more speed, confidence, and clarity.

Are you doing real work or fake work?

“One person wrote to me saying she turned down a job working in French. She didn’t feel her French was good enough yet. So instead, she planned to listen to podcasts at home every day until she was ready.

“You know what would have helped her get good at French? Working at the job in French.

“Working at a job in the language she wanted to speak was the real thing for her. Listening to podcasts at home to prepare was the fake alternative she chose instead.”


– Author and ‘Ultralearning’ expert, Scott H. Young

Fake work tends to show up when you’re avoiding something, or you’re not clear on exactly what you need to be doing. It’s ‘filler’, largely passive and solo: researching industries, tweaking your CV, writing lists… It often takes the form of preparation; getting-ready-to instead of doing. It sounds rational: you can always produce a solid-sounding reason for why you’re doing it, but ultimately it doesn’t move you forward. Which is a real shame, given how draining and exhausting it feels regardless.

Real work, on the other hand, consists of the actions that produce tangible results.

  • It’s writing articles to deadline over and over again – not reading a book on how to write.
  • It’s getting up on stage and speaking, over and over again – not watching videos of amazing public speakers on YouTube.
  • It’s actively reaching out to people in industries that interest you – not trying to craft your LinkedIn profile in the hope that they’ll come to you.
  • It’s going to an event related to an industry you’ve got a vague interest in – not reading articles I’ve written online.
  • It’s offering a scaled-down version of your service to the public – not spending hours on your logo.

Real work gets sidelined in favour of fake work because real work involves risk. It normally includes other people, and the possibility of failure. Real work often elicits immediate, real-world feedback on what you’re doing – and that can feel scary. And yet it’s exactly this kind of feedback that gives you the information you need to progress.

In other words, the longer you fart around in the shadows, the longer you’ll be stuck in the dark.

Real work is also often, oddly, harder to identify than fake work. Why? Because there are far more people out there doing fake work every day than there are going directly to the real stuff. We’re often trained to ‘look busy’ and ‘get ready’ more than we are practised in producing direct results. So it might take an extra level of thought to identify the difference… but if you want to make meaningful progress faster, it’s worth it.

Write down the things you usually do when you spend time on your career change. How many of them are real work, and how many are fake work? And what’s the first piece of real work you know you need to do?

Are you doing enough negative thinking?

“My optimism and confidence come not from feeling I'm luckier than other mortals, and they sure don't come from visualizing victory. They're the result of a lifetime spent visualizing defeat and figuring out how to prevent it.

“Like most astronauts, I'm pretty sure that I can deal with what life throws at me because I've thought about what to do if things go wrong, as well as right. That's the power of negative thinking.”


– Astronaut, engineer and fighter pilot Chris Hadfield

Many people come to us at Careershifters saying they’ve been paralysed by fear in their career changes for months and years. The fear of taking a financial hit, of looking bad in front of family and friends, of having to become a beginner again.

And unfortunately, a lot of classic guidance on how to make big life changes focus on quite the other end of the success spectrum.

“Dream big!” they tell you. “Make a vision board”. “Visualise yourself in your new life for 60 seconds every night before you go to sleep.” “Get really clear on what success would look like.”

Which is all well and good, until you remember what’s at stake as you work your way toward this glowing new reality.

Instead, try the reverse. What’s the absolute worst that could happen? And if that situation were to arise, how could you handle it?

Astronaut Chris Hadfield trained for years to learn how to imagine, visualise, and prepare for the worst. And given that ‘the worst’ for him meant burning to a crisp while attached by a wire to the outside of a spacecraft hurtling through the universal void, he knows a thing or two about it:

“In my experience, fear comes from not knowing what to expect and not feeling you have any control over what’s about to happen. When you feel helpless, you’re far more afraid than you would be if you knew the facts. If you are not sure what to be alarmed about, everything is alarming […] Anticipating problems and figuring out how to solve them is actually the opposite of worrying: it’s productive.”

Write a list of absolute worst-case scenarios (think really, REALLY bad) and a contingency plan for each one. What do you notice?

Is your best foot tripping you over?

“I am the Big Baroness of Preparation. When life gets tough, some people open a bottle of wine – I open a spreadsheet.

I organised my own wedding. I got my husband and I and our (then) four-year-old twins around India for three weeks with a military-style itinerary. I managed all my emotions about putting my elderly mother into a care home by researching the living daylights out of every service in the county. Research and organisation had never, ever failed me.

Until it came to my career change. It clearly wasn’t working, but I couldn’t conceive of any other way of doing things. I felt like one of those robot vacuum cleaners when they get stuck in a corner – repeatedly bumping into a wall, not realising I’d find a big open space behind me if I just turned around and tried a different approach.”


– Lisa, Career Change Launch Pad participant

What do you do when you want to get results?

If you need to achieve something, or solve a problem, what’s your success strategy?

For Lisa, it was lots of planning and preparation. For you, it might be focusing on the long game and the big picture. Perhaps you succeed at the important stuff by gathering lots of opinions and ideas – or perhaps it’s the reverse – maybe you’re fiercely independent, so nobody gets in your way. Maybe your way of getting results is just to work really, really hard for as long as it takes. Or perhaps in emergency situations you’re utterly charming.

The approaches and skills we draw on when we need to produce results are our strong suits. (One playful way I get my clients to identify theirs is by thinking about the following scenario: you’re working in a hotel and a very well-known VIP client complains that there are no Moostrangs in her suite. She’s going out for the evening, you have no idea what a Moostrang is, and you have just three hours to solve the problem. What’s your approach?)

We default to our strong suits when something important shows up in our life. This matters, so we pull out the best tool in our toolkit, and put our best foot forward. And 99% of the time, it happens on autopilot. You may not even realise you’re doing it.

But not every situation benefits from the same approach.

Sometimes, the thing that we depend on for our success is exactly what’s holding us back.

Lisa found that her dream career wasn’t like India. There wasn’t a map for her to build an itinerary around. Nobody had made this career change before, so she couldn’t find any reviews or recommendations online like she could when she was researching her mother’s care home. And while spreadsheets were useful for organising facts and figures, her fears and hopes and daydreams were messier and fuzzier than Excel could hold.

The more she tried to ‘logic’ her way forward, the more frustrated she felt.

She needed to try a different approach – taking steps without knowing where they would lead; trying things she’d never tried before; giving some space to the mess and the uncertainty in her heart.

Knowing what your strong suits are can be a huge benefit.

Knowing when NOT to use them is an even greater one.

What do you do when you need to produce results? Write down your strong suits, and then take a look: in what ways might they actually be blocking your career change progress?

Are the weeds in your way?

“I got so dragged down by the day to day of my career change. I felt like I was just taking actions for the sake of taking actions, not because they were part of a greater plan or strategy that actually meant something.

It really helped me to step back and look at the long game, with a bit of compassion for myself.”


– Carl, Career Change Launch Pad participant

Something we hear a lot at Careershifters is that it’s much easier to help someone else than it is to help yourself.

When you’re down in the weeds of a career change, trying to figure out each little step and feeling all the feelings and caught up in the here and now, it’s really hard to find a clear path forward. But if you can step outside of yourself, even only briefly, and look objectively at what’s going on, it’s far easier to see what’s required.

So, play a little game with me for a moment.

Picture yourself, sitting across a table for a conversation with someone.

Imagine that that ‘someone’ is you – the ‘you’ that you’ll be a year from now.

We don’t know where Future You will be, yet.

But what we can be sure of is that who they are, and where they are, and how they feel, is dependent on you. So in this conversation, they would probably have some requests to make.

What would they ask you for?

They might ask you to do something. They might ask you to treat yourself a certain way. They might ask you to practise something, or to give them a chance at something.

They’d likely be kind, compassionate. They’d hope you’d want the best for them. They’d understand how you’re feeling – after all, they’ve been there before.

And they’re not telling you what to do in order to get to where they are – after all, we don’t know where they are yet. But they are appealing to you to take the best care of them that you can.

What would they ask you for? What would you tell them, and how would they respond?

Take some quiet time and map out, in whatever way gets your ideas flowing best, how that conversation would go.

You might write the script. You might speak it out loud to yourself, or draw a picture of the two versions of yourself. In whatever way feels most natural, play out the dialogue between You Today and Future You.

Then, choose the three most important principles that showed up. What have you learned?

Are you afraid of the thing, or afraid of the feeling?

“I’m just really scared of reaching out to people in sustainability, when I don’t have any experience.”

“And what specifically are you afraid will happen if you do?”

“I’m scared that they’ll think badly of me, or they won’t respond at all.”

“And what part of that is scary, specifically?”

“Well… I’d just be really embarrassed.”

“Got it. Anything else?”

“No. … … Oh.”


– Coaching conversation with a client

Fear is the single biggest blocker of any career change.

It’s a greater obstacle than the experience catch-22, a more potent problem than a tight financial buffer, and even more problematic than a complete and utter lack of ideas.

And we humans have a funny habit of hanging it on the wrong hooks.

Sometimes, what we’re afraid of are real, deeply problematic consequences. But (shockingly often) what we’re really afraid of is not the action itself, or even its practical consequences. What we’re afraid of is feeling a not-so-pleasant feeling.

Here are some examples...

Perhaps you say you’re afraid of taking a pay cut… but actually, if the required pay cut for a role was so significant that you couldn’t make it work, you wouldn’t make that particular shift. You’d look for something else. So maybe what you’re actually afraid of is feeling disappointed.

Or you say you’re afraid of offering a stripped-back version of your product or service to the public, because it’s not fully ready yet. But there would be no real negative consequences to that – certainly none that you couldn’t address, learn from, or rectify. So is it making the offer you’re scared of? Or are you scared of feeling vulnerable?

Are you afraid of having to start from the bottom of the ladder, or are you afraid of feeling nervous?

Are you afraid of telling your family you want to make a shift, or are you afraid of feeling annoyed or sad?

Are you afraid of the thing, or are you afraid of the feeling?

And is an emotion significant enough a reason to stay stuck?

Especially when we consider that, according to neuroanatomist Dr. Jill Bolte Taylor, emotions only actually last for 90 seconds at a time...

“When a person has a reaction to something in their environment, there’s a 90-second chemical process that happens in the body; after that, any remaining emotional response is just the person choosing to stay in that emotional loop.”

“Something happens in the external world, and chemicals are flushed through your body which puts it on full alert. For those chemicals to totally flush out of the body, it takes less than 90 seconds. This means that for 90 seconds you can watch the process happening, you can feel it happening, and then you can watch it go away.”

“After that, if you continue to feel fear, anger, and so on, you need to look at the thoughts that you’re thinking that are re-stimulating the circuitry that is resulting in you having this physiological reaction, over and over again.”
– Dr. Jill Bolte Taylor, Neuroanatomist

A lot of time is spent in career change on trying to ‘fix’ the external sources of our fears.

But if what you’re really afraid of is feeling afraid, ‘fixing’ the facts won’t get you into motion any faster.

Write down your immediate career change fears (ones that are related to actual actions you’re currently faced with, not way-off-in-the-distance ‘what-if’ fantasies).

Ask yourself: what is the specific real-world fear, and what’s the feeling you’d have if your fear came true?

And then see if you can identify: are you actually afraid of the thing, or are you afraid of the feeling?

What have you realised about why you might be stuck?

The classic career change questions – about the content of what you want to do in your future career – can be helpful in directing your focus and attention, especially before you’re ready to take specific, practical action.

But once the rubber hits the road, the way you’re approaching your shift is just as important to pay attention to. 

The people who make the fastest progress into fulfilling work are the ones who can identify their blind spots, and adjust their actions accordingly. It might feel uncomfortable at first, and answering these questions might force you to confront some challenging truths about what you’ve been spending your time on thus far.

But if you’re really committed to making a career you love a reality, not just a pretty daydream, it’ll be worth it.

Which of these questions might change the way you’re thinking about your shift? Let me know in the comments below.

Natasha Stanley's picture

Natasha Stanley is Head Coach for Careershifters. She also speaks, writes and facilitates events on the art of human connection.