Thinking About Leaving Your Job? Here's What to Figure Out Before You Decide

The thought arrives quietly at first. A Sunday evening feeling you can't quite name. A meeting that drains you in a way it didn't used to. A moment where you catch yourself thinking: is this it?

By the time most women I work with come to me, the question "should I leave my job?" has been living rent-free in their heads for months, sometimes years. They've lost sleep over it, they’ve made endless pros and cons lists and talked it to death with their friends.

And yet the answer still won't come.

Here's what I've noticed after working with women at this crossroads: the reason the answer won't come isn't because the decision is too hard. It's because they're trying to answer the wrong question.

"Should I leave my job?" is the wrong starting point

It feels like the right question. It's the one that's burning. But it's actually a surface question - a symptom of something deeper that hasn't been named yet.

When you ask "should I leave my job?", your brain goes into yes/no mode. It starts scanning for reasons to stay and reasons to go, weighing them up, trying to tip the balance one way or the other. This is why the pros and cons list never works. The moment you write down a reason to leave, your brain finds a counter-argument. The moment you commit to staying, something shifts and the doubt comes rushing back.

The reason this happens is that you're not actually wrestling with a career decision. You're wrestling with an identity question. And identity questions can't be resolved with logic.

What's really underneath "should I leave my job?" is something more like: who am I now, what do I actually want my life to look like, and is the path I'm on taking me there?

That's a much harder question to sit with. But it's the one worth answering first.

Why this hits hardest in your 40s and 50s

There's a reason this kind of career crossroads tends to arrive with particular force in midlife.

By the time many women reach their 40s or 50s, they've spent a significant portion of their career being shaped by company cultures, managers' expectations, the need to prove themselves and the invisible pressure to be agreeable and accommodating and not ‘too much.’ The job they're in may have been a genuinely good fit for the person they were a decade ago.

But people change. Values evolve. What felt like ambition at 32 can feel hollow at 47. What once looked like stability can start to feel like a cage.

The question isn't really whether to leave the job. It's whether the job still fits the person you've become, and whether you've taken the time to get to know who that person actually is.

The question to ask before anything else

Before you research salaries, update your CV, or fantasise about handing in your notice, I'd encourage you to do something that feels counterintuitive: put the job question to one side entirely. Just temporarily.

Instead, ask yourself three things:

Who am I when I'm most myself? Not the version of you that shows up for Monday morning meetings or says yes when you mean no. The version underneath all of that. What are you like when you're not performing?

What do I actually value? Not what you've been told you should value, like security, status, a good pension, but what genuinely matters to you. Autonomy? Creative work? Time with people you love? Making a tangible difference? When you're honouring these things, you feel like yourself. When you're not, something quietly goes wrong.

What does the next chapter of my life look like, in an ideal world? Not just the next job title. What does a good day feel like? What kind of work energises you? What kind of person do you want to be?

This is what I call finding your compass, your own internal sense of direction that tells you whether any given path is moving you toward the life you want, or away from it. Once you have it, the job question becomes much easier to answer, because you're no longer guessing. You're checking.

What clarity actually makes possible

Here's something that surprises a lot of the women I work with: when they finally do this deeper work, the job question often becomes clearer much faster than they expected - but the answer isn't always what they thought it would be.

Some women realise the job was never really the problem. What wasn't working was the way they'd been showing up in it – zero boundaries, saying yes to everything, shrinking to fit a culture that didn't always deserve their best. With clearer values and a stronger sense of what they need, they can stay, but completely differently. Same role, different relationship to the work.

Others find that the job genuinely isn't aligned with who they've become, but now they understand exactly why, and that makes the decision to leave feel purposeful rather than like an escape. They're not running away from something vague. They're moving toward something specific.

And some discover that what they've really been craving is to work for themselves. Not because employment is inherently wrong, but because autonomy is their highest value and somewhere, underneath the practicalities, they've always known they wanted to build something of their own.

None of these are the right answer. The right answer is the one that's true for you.

Three paths forward (and what each one actually takes)

Once you're clearer on who you are and what you need, there are broadly three directions available to you:

Stay — but with intention. You keep your current role, but you stop treating it as the sum total of your professional identity. You get clearer on your boundaries, advocate for what matters, and show up as the full version of yourself rather than the version you've been editing down. This path works when the role has real potential but you've been operating below your own values.

Move to something more aligned. A new organisation, a different industry, a role that uses your skills in a way that actually feels like you. This path works when the issue isn't employment itself but the specific environment or type of work you're in right now.

Build something of your own. Go freelance, start a business, create a portfolio career that gives you the freedom and purpose you've been looking for. This takes more planning and courage than the other two, but for women whose compass points toward independence, it's often the most fulfilling direction there is.

Where to begin

If you're sitting with the job question right now, here's the most useful thing I can offer you: don't make any decisions yet. Not because the decision doesn't matter, but because you don't yet have the information you need to make it with zero regret.

Take a week. Not to research other opportunities or prepare for difficult conversations, but simply to sit with the deeper questions. Who am I? What matters to me? Where do I want to go from here?

You might find the job question answers itself. And if it doesn't, you'll be answering it from a place of genuine self-knowledge rather than exhaustion, fear, or the vague sense that something needs to change.

That's the difference between a decision you can trust and one you'll spend the next year second-guessing.

Lauren Johns is The 'Should I Stay Or Should I Go' Coach, working with women in their 40s and 50s facing life-changing decisions in work, relationships, and beyond. She is ICF and AC certified and an NLP Master Practitioner. If you're sitting with a big stay-or-go question and want support working through it, get in touch.