14 Provocative Questions To Get You Thinking About Your Career Change In New Ways

Image: Roberto Hund

Feel like your shift is taking up a lot of energy, but going nowhere fast? Sometimes what you need is to ask yourself something new. Head coach Natasha shares a set of questions that challenge, surprise, and offer new paths forward… if you’re willing to give them the time they deserve.

The inside of your head during a career change can feel like a bit of a broken record.

The same ideas popping up on repeat; the same frustrations doing endless drive-bys; and the same questions on a loop: 

“What do I even want? Why can’t I figure this out? What am I going to do? What’s wrong with me? Is this just ‘it’ for me now? When are things going to change?”

What’s required to break the loop is something disruptive – a record-scratch moment that will send your thinking down a whole new path.

These disruptive moments normally come through action; doing something completely different that brings in fresh, real-world data and opens up possibilities you hadn’t realised existed.

But sometimes, a new question can be the thing that gets you moving. 

Each of these questions will ask something of you that you may not immediately want to look at. 

It’s likely you’ll be tempted to skim through the list, scanning for a low-hanging light-bulb moment. 

(Maybe you’ve already done that, before coming back up here to read this. And that’s fine – that’s what humans do.)

But it’s unlikely you’ll find one here.

These questions will require a little… stretch. A bit of chewing. 

So, give them a chew. Sit with the ones that make you uncomfortable – those are probably the ones that matter. Talk about them with friends; journal about them, take them for a walk.

And then come back and let me know what emerges. 

1. If I lost my memory and had to piece my identity back together, what would I instinctively be drawn to?

2. What am I pretending not to know about what I want?

3. When will I be 'ready'? How will I know?

4. Who is the person to help me with this that I'm discounting, whether consciously or unconsciously?

5. What discomfort am I avoiding, and what is that avoidance costing me?

6. If someone had broken my future career up into 10 tiny clues and scattered them throughout my daily life, where would I find them?

7. What am I telling myself is an obstacle that, deep down, I know almost certainly isn't?

8. When the little voice inside my head tells me I'm being unrealistic, or I'm not good enough, whose voice is that?

9. Which part of me is growing faster than I'm letting it?

10. If I weren't so focused on making the right choice, what would I allow myself to try?

11. Which version of me is driving my career change thinking right now?

12. What would the person I want to be do now?

13. What's one small act of courage I could take today that the 'me' of next week, or next month, would be grateful for?

14. If my life were a movie, what would the audience be yelling at the screen for me to do?

Which of these questions feels like the one you need to start with – and what answers are already bubbling up? Let me know in the comments below.