9 Radical Questions to Shake Up Your Career Path

Ever find yourself at a crossroads in your career, unsure of what the next step should be? Maybe you're comfortable but wonder if you're missing out on something more?

Traditional career advice can sometimes feel too rigid. Questions like "What's your five-year plan?" often box you into your current trajectory, assuming that staying on your current path is the only option.

But what if you challenged those assumptions? What if you asked yourself bold, unconventional questions that force you to rethink everything you know about your career?

That’s the purpose of these "radical" questions. They're designed to break you out of the mold, encourage innovative thinking, and uncover possibilities that were hidden beneath the surface.

These questions aren’t meant to be practical. In fact, that’s the whole point. They're here to make you think differently, stretch your imagination, and maybe even lead you to a career you never considered before.

And while the answers might not immediately change your life, they could open up a new world of possibilities. As the saying goes:

"Once your mind is stretched by a new idea, it never returns to its original dimensions."

With that in mind, here are nine radical questions to help you rethink your career:

✍️ 1. If I could create a course about anything, what would it be?

Think about what you're passionate about teaching others. Maybe it’s something that lights you up every time you talk about it, whether it's a technical skill, a hobby, or a life lesson.

This question can reveal your deepest interests and passions. Who knows? It might even inspire a new career direction or a rewarding side project.

For example, the blogger who started writing about fitness for fun eventually built an entire business around their passion. Your course topic could be the beginning of something exciting.

🌀 2. What if I did the opposite of what I’m doing now, just for 48 hours?

Sometimes, the most unexpected changes lead to breakthroughs. Instead of following your usual routine, flip the script for two days. Try the opposite of what you've been doing and see where it takes you.

For instance, if you typically avoid networking events, spend two days actively reaching out to people. Or, if you always work behind the scenes, take on a more visible role for a bit. You'll learn a lot about what works—and what doesn’t—by shaking things up.

🔄 3. If I could swap jobs with anyone for a month, who would it be and why?

Think of someone whose career fascinates you. What would it be like to walk in their shoes? This exercise can reveal what you value in a job and what you might be missing in your current role.

Write down the aspects of their job that appeal to you and the ones that don’t. This list can guide your next career decisions.

🌟 4. What would the best version of myself be doing at work right now?

Picture the most idealized version of yourself at work. What are you doing? How are you spending your time? Who are you collaborating with?

Now, compare that to your current reality. What small changes can you make to bring your job closer to that ideal vision? Sometimes, it’s the little adjustments that lead to the biggest improvements in your work satisfaction.

💼 5. If money were no object, what would I choose to do every day?

The age-old question: what would you do if money didn’t matter? But let’s take it a step further. Imagine you've already traveled the world and checked off your bucket list. What would you do with your time after that?

This question helps uncover what truly drives you. Once you know that, you can start aligning your current work with those deeper motivations.

🔍 6. How could my biggest career challenge be a hidden blessing?

Sometimes our most difficult experiences teach us the most valuable lessons. Reflect on your biggest professional setback. How might it have actually been an opportunity in disguise?

Maybe that job rejection pushed you to pursue a passion project. Or perhaps a tough boss taught you resilience and grit. Reframing your challenges can reveal new paths forward.

👶 7. What kind of career would I want my kids (or future kids) to be proud of?

Imagine explaining your job to your kids or to your future children. What kind of work would you want them to admire? What values would you want your career to reflect?

This question isn’t about titles or achievements—it’s about impact and meaning. If your current career doesn’t align with what you’d want them to admire, that’s a sign that change might be needed.

🚀 8. How could I multiply my impact at work by 10x?

What if you were challenged to increase your impact at work tenfold, without simply working more hours? How would you approach your job differently?

Maybe you’d delegate more, focus on higher-level strategies, or learn new skills that could amplify your contributions. This question forces you to think big and push beyond your comfort zone.

🎁 9. What talent or gift am I holding back?

Many of us have talents or abilities that we keep hidden, often out of fear of not being accepted or feeling out of place. But holding back your gifts does a disservice not only to you but to those around you.

Ask yourself: What talent have I been keeping under wraps? How can I start sharing it with the world?

Remember, these questions aren’t about finding the "right" answer. They’re about breaking through the boundaries of your current thinking. So grab a pen, jot down your thoughts, and see where these questions take you.

You might just discover something extraordinary.

Your Career Buddy,

Bukola Bamidele