Should I leave my job? You're probably asking the wrong question

If you’ve typed "Should I leave my job?" into Google, you’re probably not looking for a checklist. You’re looking for permission, or clarity, or someone to tell you whether the thing you already half-know is actually true.

The problem is that "Should I leave my job?" is rarely the question that matters most. It’s the symptom of a deeper question you may not have sat with yet: who am I, what actually matters to me, and where do I want my life to go from here?

Until you can answer that, any decision about your job, whether to stay, leave, pivot, freelance, or start something new, is really just a guess.

Why the job question feels so impossible to answer

Most of the women I coach have been thinking about leaving their jobs for months, sometimes years. They’ve made pros and cons lists. They’ve talked it through endlessly with friends. They’ve Googled it at 2 am. And yet the decision won’t come, or it comes and goes, clear one day and completely murky the next.

This isn’t weakness or indecision. It’s what happens when you try to answer a complex life question with the wrong tool.

"Should I leave my job?" is a binary question. It sends the brain looking for a yes or a no. But underneath it are much richer questions about identity, values and purpose. Questions that can’t be answered with a pros and cons list, because they’re not cognitive questions. These are questions about who you are.

There’s also something else going on. By the time many women reach this point (usually in their 40s or 50s and mid-career), they’ve spent years being shaped by other people’s expectations. The job they’re in may have been the right choice for who they were at 32. The question isn’t really whether to leave it. The question is: who are you now, and what do you need?

The question worth asking first: what is your north star?

Before you make any decision about your job, it’s worth doing something that feels counterintuitive: stepping back from the job entirely.

Instead of asking “should I stay or go?”, ask yourself:

Who am I, authentically?

Not the version of you that shows up at 8 am for meetings, or the version that’s been quietly shrinking to fit a role, a culture, or a manager’s expectations. The version underneath all of that. What are you like when you’re most yourself?

What really matters to me?

Not what should matter, or what you’ve been told should matter. Your actual values. The things that, when you honour them, make you feel alive and aligned, and when you violate them, leave you feeling hollow. Autonomy? Creativity? Impact? Community? Joy? Financial security? Time?

Where do I see myself going?

Not just the next job title, but the broader picture. What kind of work do you want to be doing in five years? What kind of person do you want to be? What do you want your day-to-day life to feel like?

This is what I call finding your north star – the values, vision and sense of purpose that should be guiding every major decision you make. It’s not a goal to chase. It’s more like a compass: once you have it, it tells you whether the path you’re on is taking you toward the life you actually want, or away from it.

What happens when you find it

Here’s what’s interesting: for many women, once they’ve done the work of finding their north star, the job question starts to answer itself, and the answer isn’t always the one they expected.

Some women realise the job itself is fine. What isn’t fine is the way they’ve been showing up in it. Absorbing too much, saying yes to everything, shrinking their ambitions to avoid being difficult. Once they’re clear on their values and where they want to go, they can stay in the same role but with clearer boundaries, a stronger sense of purpose and a completely different relationship to the work. The job didn’t need to change. Their approach did.

Others realise the job genuinely isn’t aligned, but now they can see why, and that changes everything. Instead of a vague feeling that something’s wrong, they have specific information: this role doesn’t use the skills I care about most or this culture asks me to be someone I’m not, or I’ve outgrown this, and I know what I want instead. That clarity makes leaving (or pivoting) a purposeful move, not an escape.

And some women discover that what they actually want is to work for themselves. Not because employment is bad, but because autonomy is their highest value and they’ve known for years, somewhere underneath the practicalities, that they want to build something of their own. Once that’s named, the question becomes not "Should I leave?" but "How do I make this happen?"

The three possible answers, and what each one requires

Once you’ve found your north star, there are broadly three paths forward:

Stay, but differently

You remain in your current role, but with new clarity about your values and what you need. You set clearer boundaries, advocate for what matters to you, and stop treating the job as the whole story of your professional life. This works when the role has genuine potential to align with who you are, but you’ve been showing up in ways that don’t reflect that.

Leave for something more aligned

You move to a new employer, a different sector, or a new role that better fits your values and vision. This works when the issue isn’t employment itself, but the specific environment or type of work you’re currently in.

Go it alone

You start your own business, go freelance or build a portfolio career that gives you the autonomy and purpose you’ve been craving. This requires more planning and nerve than the other two, but for women whose north star points toward independence and ownership, it’s often the most fulfilling path.

None of these is theright answer. The right answer depends entirely on who you are and what you want from the next chapter of your life.

Where to start

If you’re sitting with the "Should I leave my job?" question right now, here’s the most useful thing you can do before you decide anything: take the question off the table temporarily. Give yourself a week. Not to research other jobs or rehearse conversations, but to sit with the deeper questions. Who am I? What do I value? Where do I want to go?

You might find the job question answers itself. And if it doesn’t, you’ll at least be answering it with information no search engine or chatbot can provide – your own.