From Perfection to Progress: The Power of Daring to Fail

Growing up in Singapore, my student years were spent trying to get everything right. Like many others, I poured myself into preparing for the all-important O and A levels — often practicing each past paper three times over. Success was measured by how few mistakes we made.

But life — and investing — taught me a different lesson: failing is not just inevitable, it’s essential.

Even the best portfolio managers only outperform their benchmark about 55% of the time on a monthly basis. That insight reshaped the way I saw risk and failure.

Learning to fail gave me the courage to take bigger leaps. I left what many would call a dream job at a sovereign wealth fund to pursue an MBA and explore new possibilities. That same mindset pushed me to step into my first leadership role — an experience that helped me uncover my true passion: coaching and empowering others to succeed.

The real shift happened when I reframed my thinking. Instead of telling myself I needed to “learn to fail,” I started to embrace the idea of daring to fail. Because daring to fail is also daring to grow, to stretch, and to succeed.

In a world that often celebrates perfection, let’s not forget the value of trying boldly, of choosing growth over comfort, and of betting on ourselves — even when the outcome isn’t guaranteed.

Because sometimes, the biggest risks unlock the truest rewards.