Thinking About Quitting Your Job? Don't Do It Until You Ask These Seven Questions

If you're watching this video, there's a good chance you've been lying awake at 3am asking yourself whether you should quit your job. Maybe you dread Monday mornings. Maybe you've started updating your CV but haven't sent it anywhere yet. Or maybe you're just tired, bone-tired, and you can't tell if it's the job or just life.

I'm Lucy Caldicott, founder of ChangeOut and an executive coach with thirty years of leadership experience, including time as a CEO. I've seen hundreds of people wrestle with the stay-or-go decision, and I've made it myself more than once. What I've learned is this: the people who make the decision well, the one they don't later regret, ask themselves seven specific questions first.

Here they are.

1. Am I learning and growing?

If you can do your job in your sleep, if every Monday feels identical to the last and you've stopped feeling proud of your work, that's worth paying attention to. Comfort isn't the same as fulfilment, and maintenance mode is not a career strategy. Before you conclude there's no growth available, though, ask yourself honestly whether you've pursued what's on offer. Sometimes the opportunity exists and we simply haven't asked for it.

2. Is this affecting my health?

This is the one people ignore the longest, because we're taught that work requires sacrifice. I learned this the hard way during my time as a CEO, waking at 4am with my heart racing, developing headaches that wouldn't shift, telling myself this was just what leadership looked like. It took a series of panic attacks and a diagnosis of severe anxiety before I understood I was sacrificing my health for a job. No job is worth that. If you have chronic sleep problems, persistent anxiety, or physical symptoms that lift on holiday and return on Sunday evening, your body is giving you information. Listen to it.

3. Do my values align with this organisation?

This isn't about whether you like your colleagues. It's deeper than that. Do you fundamentally believe in what this organisation does and how it does it? I've worked with leaders who were brilliant at their jobs but were spending all their energy fighting a culture that contradicted everything they believed about good leadership. That kind of misalignment is exhausting in a way that's hard to explain until you've experienced it. If you feel like you're working against your organisation rather than with it, that's important information.

4. Is there a path forward here?

Sometimes we assume there's no path forward without ever actually checking. And sometimes we stay hoping for a path that doesn't exist. The honest question to ask your manager is: what would my growth look like here over the next two years? Listen carefully to the answer. Vague encouragement is not the same as a genuine plan.

5. Can I afford to leave right now?

I'm putting this fifth deliberately, not first, because I don't want money to be the only thing you consider. But it has to be part of the equation. When I left my CEO role to start ChangeOut, I spent six months planning before I handed in my notice. I built up savings, started developing the consultancy alongside my existing work, and had honest conversations with my partner about what adjusting our budget would look like. When I finally left, I was scared but not panicked. Financial constraints are real. If you can't afford to leave right now, that's not a moral failing. But don't let financial fear keep you trapped indefinitely. Start building your runway.

6. Have I done everything I can to improve the situation?

This is the uncomfortable one, because it asks you to look honestly at your own role. Sometimes the problem isn't the job. Sometimes it's our approach, our communication, or the conversations we haven't had yet. I've coached people who were convinced they needed to leave, only to find that one direct conversation with their manager changed things significantly. If you haven't genuinely tried to improve the situation, try that first. If you have tried, and nothing has shifted, you can leave knowing you gave it your best.

7. What's your gut telling you?

I've put this last because intuition matters, but it shouldn't be the only thing you listen to. Fear and exhaustion can cloud it. Work through the six questions above first, and then check in with what's underneath. In my experience, when people know they need to leave, they know. There's a quiet, persistent voice that says: this isn't right anymore. And when people know they need to stay, even through a hard season, there's a different voice that says: not yet. Trust that voice. It's been collecting data the whole time you've been in this job.

If you want to go deeper, I've created a 30 page workbook that takes you through each question with structured prompts and space to think properly. Get it here for £15.

Subscribe FREE to access the printable seven questions checklist below.

Here are your seven questions as a free printable PDF. Work through them at your own pace, and be honest with yourself. That's where the clarity comes from.