Have you ever felt stuck in your career, unsure of your next move? Or perhaps you're content but curious about what else is out there?
Traditional career advice often falls short. Questions like "Where do you see yourself in five years?" can be limiting. They keep you thinking inside the box of your current situation, assuming your path will stay relatively unchanged.
But what if we could break free from those constraints? What if we could ask questions so provocative, so outside-the-box, that they force us to reconsider everything we thought we knew about our career aspirations?
That's where my "frame-breaker" questions come in. They're designed to challenge your assumptions, spark creativity, and uncover possibilities you might never have considered otherwise.
They're not meant to be practical or realistic - that's the point. They force us to look at things from different angles. To find out what you truly want from your career.
And while you might not even use the answer…
“A mind exposed to a new idea will never go back to its original shape.” (I love that quote)
So, with that said….
Here’s 9 questions to ask yourself:
(Btw, to get the most out of these, grab a piece of paper and write your answer down.)
👨🏫 1. If I had to teach something, what would it be?
Think about what topics get you excited. What do you love explaining to others? It could be anything from coding to cooking.
This can show you what you're passionate about. It might lead to a side job or even a new career.
For example, Mark Manson started a blog giving dating advice. He enjoyed coaching and writing about relationships and personal development so much that he blogged about them. Now he's a bestselling author. Your teaching topic might reveal a similar path.
↔️ 2. What if I did the opposite for the next 48 hours?
When author Tim Ferris was in his twenties, he was selling data storage to CEOs but couldn’t get cold-calling between 9-5 to work.
So, he asks himself:
What if I did the opposite of what I’m doing now for the next 48 hours?
I.e what would happen if he made his calls outside of 9-5?
Turns out, because his calls went straight to the CEOs instead of their 9-5 secretaries, he started out-selling the entire LA office of his competitors.
So I ask you:
What if you did the opposite for 48 hours?
Similarly:
- If you've been solely looking at corporate jobs, what if you explored startups?
- Hate public speaking? Volunteer to give a presentation. Doing the opposite can help you find new skills or interests you didn't know about.
🔄 3. If you could swap jobs with someone you know for a month, who would it be and why?
Think about your friends who love their jobs. Not influencers (who portray a mostly BS version of their careers), but people you actually know. Who seems really fired up about their work?
Pick one and imagine swapping places. What parts of their job would you enjoy? What parts wouldn't you like? Write these down.
This list can show you what you want (and don't want) in your own career. It might give you ideas for your next move or ways to improve your current job.
☀️ 4. What would the ‘ideal’ me be doing right now?
If you could snap your fingers and have your perfect job, what would it be?
What would you be doing day-to-day? Who would you be working with? What problems would you be solving?
Now, look at your current job. Is there any way to bring in a bit of that ideal scenario? Even small changes can make a big difference in how you feel about work.
💸 5. If money was no object, what would I do for work?
A classic. An inheritance lands in your lap from your long-lost great aunt, and you’re sorted financially for life.
What do you do now?
If your first thought is something like "I’d travel the world!", I urge you to think a little deeper. What would you love to do for work? What's a task you've done in the past that you would've done even if you weren't compensated?
And if it is traveling the world, note that down too. There are ways to incorporate traveling into your job. (Though, speaking on behalf of all the consultants I know, ‘forced’ traveling for work kinda sucks.)
This helps figure out what you actually enjoy doing. Once you know that, you can look for ways to do more of it in your current job (or start planning a career change).
😳 6. What if the worst thing that happened to me was actually the best thing?
Batman only became Batman because he was traumatised by bats as a child. J.K. Rowling was rejected by 12 publishers before Harry Potter was accepted. She's said that failure taught her valuable lessons. What if your setbacks are setting you up for something better?
Look at your biggest career challenge. How could it be a hidden opportunity?
🌳 7. What career path do you want your kids (or future kids) to admire?
Picture explaining your job to your kids (real or imagined). What do you want them to think? What values do you want your career to represent?
This isn't about having an impressive title. It's about the impact of your work and if it aligns with your values.
If your current job doesn't match up with what you'd want your kids to admire, that’s a useful signal. If it doesn't, what needs to change?
🎯 8. What if you had to 10x your impact at work?
Imagine your boss says you need to make 10 times the impact in your job. Not just work more hours, but truly increase your value.
What would you do differently? Would you need new skills? Different resources? Would you change how you work entirely?
Maybe you'd automate repetitive tasks to focus on strategy. Or you'd start mentoring junior colleagues to multiply your knowledge.
This question can reveal where you can grow in your career and what's holding you back from making a bigger impact.
🎁 9. What gift am I not giving?
In “Coach Carter”, Timo Cruz is a very troubled young man who’s holding his talents back so he can feel “accepted” in gang-life.
Throughout the movie, Coach Carter asks him, “What is your deepest fear, young man?”
Finally, at the end, Timo stands up and replies,
“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won't feel insecure around you. We are all meant to shine, as children do. It’s in everyone. And as we let our own light shine, we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.”
My point?
Most of us, if we’re honest with ourselves, are holding back something we should be giving, for fear that we’ll not be accepted by others.
My question to you:
What is that thing?
I hope these questions (and your answers to them) get you thinking about your career in new ways. If you do jot down your answers to any of them, send them through — I’d love to read them confidentially.
