In a world obsessed with being right, the real leaders are learning how to be wrong—well.

I usually charge $300 an hour to coach leaders and entrepreneurs. But on 29 May 2025, I gave that hour away for free. Not because I had spare time, but because I saw myself 18 years ago—in the eyes of a 20-year-old girl.

She was my junior from Monash, reaching out for help. It was her first time asking someone to mentor her. And strangely, it was also the first time I said yes to mentoring someone so much younger, so fresh, so unsure. In that hour, I gave her more than coaching. I gave her space. I gave her a mirror. I gave her the beginning of unlearning. And what she gave me in return was even more priceless: clarity on what mentoring is really about.

From Teaching to Mentoring

Unlike my usual sessions with entrepreneurs who pay for breakthroughs and come in already seasoned by failure, this was different. She was high-performing, respectful, excellent in grades—but she was standing at a cliff edge. She was deciding whether to stay in Melbourne or return to China. She was unsure if getting internship experience was worth risking her perfect GPA. She was worried that the “wrong move” could cost her everything.

I realized that my biggest responsibility wasn’t to give her answers. It was to make sure she didn’t stay frozen. So I told her what I wished someone had told me earlier: study is the easiest part of life. The real test begins when there are no grades.

I knew I had to be careful. It wasn’t about how much I knew. It was about how much she could receive. I couldn’t coach her like I coach CEOs. I had to enter her world, not pull her into mine. So I designed the session intentionally. I chose presence over performance.

If I could tell my 18-year-younger self one thing, it would be this: You don’t need to be perfect to move forward. You don’t need to have all the answers to be okay. What you need is to keep going, even when it feels messy. Seek. Fall. Get up. That’s where real growth happens. And those were exactly the words I offered to her—the one standing across from me, 18 years behind.

And maybe, that’s what I needed to hear too—18 years ago.

The Real Curriculum They Never Taught Us

She reminded me how deeply conditioned many of us are by school. Especially those raised in Asian education systems—systems that train us to listen, memorize, regurgitate, and ace exams. In that world, success means not failing. It means getting the right answer.

But in the real world? Success means failing forward. It means making 5,000 mistakes to get one thing right. Just ask James Dyson. If you’re afraid to fail, you’re not ready to innovate. In schools, we’re penalized for wrong answers. In life, we’re promoted because we keep trying.

In fact, a 2020 study in Educational Psychology found that students who made and corrected mistakes retained 45% more information than those who didn’t. Failure isn’t a flaw—it’s a feature of real learning.

I wish to share stories with her:

Dyson and his 7,000 prototypes before a working vacuum.

Nokia, who famously said, “We didn’t do anything wrong, but we lost.”

WeChat, who had the foresight to kill their own product (QQ) before someone else could. That’s not failure. That’s boldness. And boldness isn’t natural. It has to be trained.

Seekers, Not Solvers

The more we talked, the more I realized she didn’t need a roadmap. She needed permission. Permission to seek. Permission to not know. Permission to be unsure.

She thought she was lost. But what if she wasn’t lost at all? What if this wasn’t a season of being lost, but a season of seeking? We’re told as children: if you’re lost, stand still. Wait for help. But real life doesn’t work that way. Real life asks us to move, explore, experiment. Even when it’s messy. Even when it’s unclear. Even when we fall.

Like learning to ride a bicycle, clarity doesn’t come from reading a book. It comes from falling, bruising, getting up, and suddenly, one day—finding your balance. And when that moment comes, you don’t just ride. You fly.

A recent Pew Research study showed that 74% of Gen Z feel anxious about making life decisions because of a fear of failing or getting it wrong. But seeking is not failing. It’s growing.

A Parallel Classroom: My Children, My Teachers

As I finished the session with her, my thoughts drifted to my own children, playing nearby. A few months ago, they didn’t believe they could ride a bike. But they fell. They cried. They tried again. And now? They ride like the wind.

That’s education. Not worksheets. Not theory. Not moral exam questions with predictable answers. “When an old lady crosses the road, what should you do?” “You help her.”

But life doesn’t hand you scripts. Life throws you uncertainty. Like today, when one of my sons injured another while playing, and his first instinct was to shout, “I didn’t do anything!” That was his version of the Nokia mindset: “We didn’t do anything wrong, but somehow, we still lost.”

So I told him, “It doesn’t matter if you caused it or not. What matters is whether you care.” That’s responsibility. That’s leadership. That’s what I wished someone taught me when I was 20.

Mentorship Is Not Rescuing

I didn’t give my mentee a plan. I gave her something more enduring. I reminded her that answers are overrated. That seasons of uncertainty are sacred. That fear is normal, but paralysis isn’t.

In today’s hiring landscape, even LinkedIn’s Global Talent Trends Report shows that 92% of employers believe soft skills like adaptability and emotional intelligence matter more than technical scores or grades. Yet we’re still preparing students to ace exams—not to navigate ambiguity.

I didn’t rescue her. I walked with her. And that’s what mentorship should be. It’s not telling someone where to go. It’s helping them trust their ability to move.

Just like my children. Just like that junior. Just like the version of me from 18 years ago, who thought grades were the whole story. They weren’t. The real story began when I started unlearning.

The Reverse That Redefines It All

We teach children that when you’re lost, stay still. But what if the ones who truly grow are the ones who move anyway?

We live in a world obsessed with being right. But maybe, the real leaders are learning how to be wrong—well. And that is how you unlearn to win.