Why Are Successful Women Staying in Jobs That Make Us Miserable?

As women, we’re often taught to be resilient at work: navigate the difficult boss, adapt to the culture, keep performing, push through. But what if our ability to adapt, accommodate, and keep going is the very thing keeping us stuck? Drawing on three decades of experience spanning the boardroom, the head-hunter’s interview room and the therapy room, psychotherapist and former C-suite head-hunter Kathleen Saxton explores how toxic power is protected and excused — and asks at what point resilience becomes endurance, and whether sometimes the strongest career move is knowing when to walk away.

Is It Time to Quit Your Job? A Psychotherapist Explains How to Know When to Go

Connie is a highly successful executive who moved from New York to Hong Kong for a newly created global role, becoming the only woman on the leadership team. She had been recruited because she was experienced, creative, direct and confident. Instead, she found herself caught between two very different forms of toxic leadership.

One boss was openly aggressive. He had been there for over twenty years; people were frightened of him, and the organisation had learned to work around his Emperor-like behaviour rather than confront it. His number two was almost the inverse: a phantom lieutenant, covert, evasive and difficult to pin down. Questions went unanswered, decisions disappeared, and goalposts moved. Where one created fear through force, the other created uncertainty through absence.

Connie ricocheted between them. One encounter left her braced for impact; the next left her wondering whether anything had actually been agreed. Promised resources failed to materialise and conversations dissolved into silence. Overt aggression at least announces itself. Covert obstruction is more slippery because it leaves you working harder to establish what is real.

Like many capable people, Connie’s response was not to leave but to try harder. She prepared more carefully and began adapting herself to the personalities around her. From the outside, this looked like conscientiousness. Inside, she was becoming disconnected from the instincts and confidence that had helped her succeed.

She later described what happened to her as “forgetting how to be myself”.

Connie is one of the women I write about in my latest book, Sly & Mighty, but her experience speaks to a question I have spent more than thirty years considering as a senior executive, executive head-hunter and now psychotherapist: at what point does resilience become endurance?

We talk a great deal about resilience at work. We are encouraged to manage difficult personalities, navigate office politics, cope with pressure and learn to thrive in demanding environments. Resilience has become such an unquestioned professional virtue that we rarely ask what happens when the thing we are being resilient to is the problem.

Put my three professional perspectives together, and something striking appears. The woman privately wondering whether she has lost her ability to lead may be the same woman a board fought hard to recruit a few years earlier. So what happened in between?

The psychoanalyst Donald Winnicott wrote about the True Self and False Self. In my clinical work, I often think about an Adapted Self that develops when we learn that being entirely ourselves carries a cost. In a healthy workplace, adaptation is flexible and temporary. We adjust without losing contact with who we are.

The danger comes when adaptation becomes a survival strategy. People begin changing how they speak, behave and think to become acceptable to the environment. I see this particularly in conscientious women, because the qualities that helped them succeed can be enlisted against them. They work harder, prepare more, become more agreeable and try to become impossible to criticise. They begin trying to become unassailable.

This is where resilience can become a trap. When colleagues privately sympathise but publicly comply, or an executive team learns to work around one powerful person, silence starts to distort our calibration. We ask why everyone else seems able to cope instead of why everyone has agreed not to name what is happening. Organisations can become remarkably good at normalising behaviour when the person responsible is considered valuable.

Most people do not suddenly collapse under a toxic leader. The change is incremental. Confidence becomes caution, then self-questioning. Someone may still be performing exceptionally well while privately becoming less certain of her own perceptions. This is why Connie’s description of “forgetting how to be myself” stays with me.

Perhaps what we need alongside resilience is fortitude. Resilience is our capacity to recover and retain ourselves through difficulty. Fortitude is the courage to hold onto reality when the group would rather look away. Sometimes that means speaking plainly, finding allies or forcing an organisation to confront what is happening. Sometimes it means accepting that staying would require too great a psychological compromise.

The hidden cost of staying too long

From the headhunting side of my career, I know how frightened people can become about leaving. Women tell me they worry a short tenure will make them look weak, that resignation means they failed, or that walking away from a prestigious company will damage their career.

But careers are often more robust than they feel from inside a difficult job. What concerns me far more is staying until the experience damages the confidence, judgement and appetite for leadership needed for whatever comes next.

There are, of course, legitimate reasons to stay for a time. Mortgages, children, visas and financial obligations are real. Sometimes the wisest thing is to remain while preparing your next move. But there is an important psychological difference between consciously choosing to stay and enduring because you have stopped believing you have a choice.

Eventually, Connie forced the organisation to confront what was happening. She was told the company was no longer ready for the very role it had recruited her to perform, and her employment ended. She left her job, the country and, a year later, her industry.

On paper, it might look disastrous. But she took her severance and took her time. She retrained and eventually re-entered the working world.

That doesn't mean leaving necessarily feels triumphant. People may grieve the job they thought they were taking and the future they imagined there. The experience can follow them into their next role, too: someone may enter a healthy workplace and still brace when a new boss asks for a meeting.

And this is perhaps why we need to interrogate our idea of resilience in the first place. Not every difficult boss or demanding period is toxic. Good work should stretch us, and good leadership will sometimes challenge us. But challenge should enlarge us over time, not steadily diminish us.

Perhaps the better question is not whether we are strong enough to stay, but what staying is gradually asking us to become.

If remaining somewhere requires us to become less trusting of our judgement, less confident in our abilities and less recognisable to ourselves, walking away may have very little to do with failure.

Kathleen Saxton is a psychotherapist, executive coach, author and former global CMO who spent two decades as an executive head-hunter selecting senior leaders for some of the world’s biggest organisations. Her latest book, Sly & Mighty: How to Recognise, Resist and Rise Above Toxic Power, is out on 24 September 2026.