The scariest thing about being a woman is not what you think

As we near the end of October and rummage through old costumes for yet another Halloween party, it dawned on me that the scariest thing isn’t the ghosts or ghouls, but the mask we wear every day.

Research shows that women, including adolescents, often report a higher fear of failure than men – and this fear directly affects life satisfaction. I remember being that young person: constantly second-guessing myself, lacking confidence, and trying to be someone I wasn’t. I was, without a doubt, a fearful young person who avoided risk at all costs.

But over the years, through shedding the weight of those expectations and the false mask I used to wear, I’ve learned something liberating – I’m actually fabulous at failing. And I’m totally okay with that. I learned over time that even when I hit rock bottom, it wasn’t the end of the world, and, miraculously, there was learning and a silver lining.

The trap of perfectionism

In Singapore, we’re raised to keep it all together. From a young age, we’re told to suppress negative feelings, to soldier on, to smile and stay strong. But studies have shown that this façade doesn’t build resilience – it actually weakens it. Real resilience comes from accepting our limitations, being unafraid to try, and being willing to stumble. Our society, teachers, and parents must truly embrace this narrative if we want to aspire to be more progressive and resilient.

Singapore, for all its success, can also be a breeding ground for perfectionism. From school grades to career milestones, we’re taught that anything less than perfect isn’t good enough. And that message follows us into adulthood.

When I talk to my clients, many of them working women, I often see the same thing: a mask of fear. They’re doing incredible work, but they don’t believe in themselves. The imposter syndrome creeps in quietly, whispering, “You’re not good enough.” A senior banking client of mine just a few months ago felt crippled at work, lacked confidence, and was on the brink of quitting after pouring years of hard work into her role.

Through coaching, self-reflection, and looking inwards, she’s shifted her mindset to believe she can – and deserves to – stay, and has carved out a new trajectory at the company, feeling more empowered and motivated than ever before. By ripping off her mask that led her to accept what others told her, she moved away from self-doubt to self-belief.

Social norms reinforce the idea of the “perfect woman” – one who excels at everything: career, family, appearance, caregiving. But the constant striving for flawlessness only feeds self-doubt, avoidance of risk, and that paralyzing fear of failure.

Taking off my own mask

Several years ago, I had to face one of my own biggest fears – the fear of being seen as a failure.

For seven years, I ran House of Sheens, my handbag brand. It was a passion project that I had poured my heart, creativity, and endless hours into. Yet, after years of building it, I realised something had shifted. The business hadn’t lost money – but it had stopped giving me joy. I felt stretched thin between running House of Sheens and my consulting business, Sheens Consulting, and I knew deep down that I wanted to spend more time as a life coach rather than designing and selling handbags.

Admitting that to myself was agonising. For months, I wrestled with guilt and fear – what would people think? Would they see me as someone who couldn’t keep a business going? Would they think I had failed? I lost sleep, turning the thought over and over, trying to convince myself it wasn’t time to let go.

But eventually, I realised that the fear wasn’t truly mine – it was the voice of societal expectation echoing in my head. The day I finally decided to close House of Sheens, I expected to feel regret or sadness. Instead, I felt relief. Relief that I had honoured what was right for me. Relief that I had listened to my gut. And pride – pride for the seven-year journey, the lessons learned, and the courage to say, “This chapter is complete.”

That experience taught me something profound: sometimes, the fear we carry isn’t fear of failure at all – it’s fear of disappointing others. But at the end of the day, our choices have to serve our happiness, not our image.

Underneath it all

During Halloween, we wear masks for fun. In real life, women wear masks to survive – masks of perfection, of competence, of calm. We hide our trembling, our uncertainty, our vulnerability.
But perhaps it’s time to take them off.

To walk confidently, not expecting to get everything right, but to be brave enough to know that even if we stumble, we can stand back up again.

Because the real monster behind the mask isn’t failure – it’s the fear that keeps us from ever trying.

And in a society like ours – fast-paced, high-achieving, and often silent about emotional struggle – this fear can quietly erode our well-being. But when we allow ourselves to be real, to speak about our fears, and to embrace imperfection, we create a more resilient and happier society. As more women in Singapore learn to drop the mask, to fail forward, and to choose authenticity over perfection, we not only strengthen our own mental health, but we help redefine what success and happiness really look like.

Shireena Shroff Manchharam is a Her World Tribe member, the founder and principal consultant of Sheens Consulting, and the founder and creator of Getting To Happy, a mental health movement to inspire our community and society to live happier, more mindful lives.