Should I Stay or Should I Go? 3 Questions to Ask Before a Career Change
If you’ve landed on this post, chances are something in your career feels… off.
Maybe your work looks good on paper but feels hollow. Maybe you’ve outgrown your role, your industry, or even your values. Or perhaps you’re just bone tired—and you don’t know if it’s burnout or a deeper misalignment.
This is one of the most common crossroads I support my clients through. And while there’s no one-size-fits-all answer, there are powerful questions that can help you get clearer on what’s really going on—and what to do next.
Here are three I recommend you start with:
Is it the job? Or is it me?
Before overhauling your entire career, it’s worth getting curious: Is it this particular role or company that’s draining me—or is it the whole direction I’ve been heading in?
Ask yourself:
Would I feel differently doing the same work in a different environment?
Am I frustrated with leadership, culture, or a lack of growth—or have I fundamentally changed?
If I could magically change one thing, what would it be?
Often, clients come to me thinking they need to leap into something new, but discover they can create more meaning, purpose, and sanity where they are—if they have clarity.
2. What do I long for — and am I listening to it?
Mid-career is a natural time to shift priorities. What used to excite you might not anymore. That doesn’t mean you’re broken—it might mean you’re evolving.
Ask yourself:
What do I find myself daydreaming about when no one’s watching?
What kinds of work or conversations energise me?
When have I felt most alive in my career?
That quiet sense of longing? It’s not foolish. It’s feedback. The question is: are you paying attention?
3. What would I regret not doing in five years?
When we’re stuck in the thick of career indecision, it helps to zoom out.
Imagine yourself five years from now, looking back at this moment. What would you be proud of having explored? What decision would feel brave, even if it wasn’t the easiest?
This question doesn’t promise certainty—but it does cut through the noise. Because regret doesn’t usually stem from failing. It stems from not trying.
Final Thought: You Don’t Have to Figure This Out Alone
There’s no shame in feeling stuck. In fact, many of the most fulfilled professionals I know once stood at this very same crossroads.
What made the difference? They paused. They reflected. And they got support.
If you’re ready to explore what’s next—whether it’s making peace with where you are or preparing for a more meaningful shift—I’d love to help.
🟢 Book a free discovery call here and let’s explore what’s possible, together.
