The Hills We Conquer

Childhood Adventures and Life’s Quiet Lessons

When I visited my grandma’s house on Keong Siak Street this week, just walking down the five-foot pathway stirred up waves of memories. Every step took me back to a simpler time, where Chinatown was my childhood playground and life felt full of possibility and adventure.

It’s funny, you don’t realise what stays with you until it comes rushing back, and suddenly, I was eight years old again, that fearless kid running wild with my cousins, my brother, and the neighbourhood kids. Back then, Singapore felt different. Our parents were off at work, leaving us to roam and explore, as long as we returned by dinner, alive and (hopefully) in one piece.

Some of my memories from those days are burned into my mind - the good, the funny, and the just plain ridiculous. Like throwing pebbles at the neighbour’s chicken coop and somehow survive the rooster on patrol at the coffee shop next door. (Yes, there was an actual rooster, and I had a habit of disturbing its peace…not my brightest idea.) That rooster wasn’t just a bird; it was a full-on, towering beast in my memory, chasing me down the back lane, wings flapping, his eyes dead set on me. To this day, I can still hear the flurry of squawks as I ran for dear life.

Or that haunted tree down the road, It had these vines that hung down just perfectly for swinging, or so I thought. One day, I decided it was my turn to play Tarzan, with all the courage in the world, I took a leap, grabbed a vine, and… SNAP. Next thing I knew, I was in freefall, landing in a not-so-graceful heap, sprawled out on the ground below. But hey, I got back up, and somehow, that moment only made the tree more legendary in my mind.

But my favourite memory, the one that means the most… was the day we conquered the “mountain” behind my grandma’s shophouse. Now, in reality, it was just a steep little slope. But to my young eyes, it was Everest, waiting to be conquered. Armed with a stolen cardboard box, I was determined to slide down and make it to the bottom like a hero. I barely made it halfway before my box stalled, leaving me stranded, paralysed with fear.

I yelled for help, and my brother, two years older, came charging up the hill. Without a second thought, he grabbed my hand, looked at me with the biggest grin, and yelled, “Run!” Together, we ran, sliding and stumbling until we hit solid ground. Out of breath, full of adrenaline, we threw our hands up like champions, fingers interlocked, cheering like we’d conquered something monumental. We laughed until we couldn’t breathe, rolling on the ground, feeling like we’d just taken on the world.

Looking back, I realise that this wasn’t just a “hill.” To us, it was a challenge, a shared triumph. That moment with my brother wasn’t about the thrill of sliding down a slope; it was about feeling unstoppable, together. This wasn’t my best event, but it was my best memory of him, and it’s stayed with me through the years, even as we grew up and life became more complicated.

The Power of Shared Experiences

My friend Tony Lukins shared this wise insight with me once, “Shared joy is double joy, shared sorrow is half sorrow.” Standing there on Keong Siak Street, I couldn’t help but agree. That moment with my brother is so vivid not because of what we did but because of what it meant. It wasn’t just about sliding down a hill; it was about courage, love, and the bond we shared.

Those memories aren’t just stories; they’re the foundations of who we are. They remind us of our fearlessness, our joy, and the connections we built. Looking back, it wasn’t about the size of the hill or the thrill of the chase… it was about the meaning we gave it.

Change Through Experiences

As adults, we’re quick to lose that sense of wonder. We get caught up in goals and plans, always looking ahead, always focused on the next thing. But the secret to life, I’ve come to realise, isn’t about “getting there” or achieving every last goal. It’s about experiencing experiences, fully and without restraint, just like we did as kids. We don’t crave to live forever; we just want more memories, more life.

But embracing life fully means embracing change, even when it feels hard. Change is where we often get stuck. We love stability when things go well, but when they don't, we fear it’s forever. I recall sitting as a child on the five-foot way outside my grandma’s shophouse in Chinatown. I was her "seat-warmer" until a friend joined her, and then they'd chat for hours, watching the world go by. And it did… Shops closed, buildings rose, streets reshaped. As Singapore transformed rapidly, I saw in my grandma’s eyes a quiet fear of being left behind.

Facing Change and Remembering Who We Are

I inherited some of that fear. As life moved on, I found myself trying to keep up, always one step ahead, afraid of what would happen if I didn’t. technology advanced, and life sped up even more. From adulthood to parenting, juggling work and family, then COVID and unexpected illnesses. Life kept piling things on - find your purpose, get a real job, play with kids, kid’s homework too, hit the gym, meditate, squeeze in date night, and oh, don't forget to breathe.

Then AI shows up,..? & we know, Life’s never going to be the same again. Again, we survive, fail fast, fail forward. I do the dance. I found my footing. Then when I left teaching, I felt lost, as if my whole identity was suddenly in question. Who was I if I wasn’t a professor, or a filmmaker? It’s funny how we define ourselves by what we do rather than who we are.

But looking back on that day with my brother reminds me that courage isn’t about facing giant challenges alone. It’s about finding strength in connection, in shared laughter, and in those moments when we feel like champions, even if only for a moment. That day, he didn’t just help me down a hill; he reminded me that fear doesn’t mean defeat. I may have lost my job title, but I hadn’t lost my identity. I’m still a storyteller, and I always will be.

A Lesson in Perspective

These memories remind me that it’s not the size of the hill but the meaning we give it that stays with us. It’s funny how the things that seemed so big in our minds turn out to be small, and how the smallest moments become the biggest memories.

So here’s my challenge to you: take a moment to look back, to remember a time when you felt brave or happy or just completely alive. Let it remind you of the person you were and the person you still are, deep down. Because sometimes, the best way to move forward is to take a look back and see how far we’ve come.

Key Takeaway: Sometimes, it’s not the hill but the meaning we place on it that stays with us. Let your memories remind you of the courage, joy, and connection that made those moments unforgettable. Because in the end, it’s those shared experiences that shape who we are.