20
Last Friday night, I gathered friends across all stages of my life and hosted a little rooftop party to celebrate my twentieth birthday. Dipped in the infinity pool, we oversaw the landscape of Orchard, Singapore’s retail heart. The evening was extra hot (what gives, Singapore?) and getting wet in the pool — a usually horrible idea — became the highlight of that night.

At twenty, I sit in the awkward stage between high school and college. Being a Singaporean male, this awkward stage is occupied by mandatory military service, where I haven’t had much time to meet friends regularly. Furthermore, I would leave Singapore in a few days for college, so it seemed ripe for me to reconnect with friends one last time.
I am so grateful for everything that has led me to this moment. Dreams that seemed far-fetched in high school are actually materializing. To think that just 5 years ago, I didn’t know a single US college other than Harvard and Yale (I only knew Yale existed after watching Gilmore Girls then).
During the party, my friends, clutching their wine-filled plastic cups, congregated in a circle and exchanged their most memorable stories of us. It was hilarious how distinct yet similar their recollections were. In my nineteen years alive, I’ve been a poet, a music critic, a Middle East researcher, a #studygram influencer, a holy Christian boy, a chorister, a Taekwondo player. Nevertheless, all of them remembered me as a writer through these different eras.
This reminded me never to lose touch with my love for writing, but to also be open to reinventing myself. Last year, I read The Defining Decade by Dr. Meg Jay, an enlightening book teaching twentysomethings — people in their twenties — how to live a fulfilling life. Now that I am in the twentysomething threshold, I recall her advice to revise my stories. As we grow, we repeat stories to ourselves to feel a sense of coherence between our place and identity. I must revise my stories consistently so I am always shedding away old traumas, and embracing new perspectives.
There have been moments when flashbacks of my previous eras strike my mind. A bubble of shame then bursts within me, flooding my face red. You mean I wrote poems about a crush, unabashedly published them on a blog, unabashedly told friends about it, and that person * shockingly * found out? But now I realize I had to undergo each and every of these awkward phases to evolve into who I am today. Just as Taylor Swift remarked during her commencement speech at NYU last year, “Learn to live alongside cringe. No matter how hard you try to avoid being cringe, you will look back on your life and cringe retrospectively.”
One of my friends commented during the party, “We know that while Shaun always works hard, he never takes things too seriously.” I was grateful he noticed this trait about me, because I’ve always aimed to be someone who can both get good grades and live an interesting life. (I just am * not like the other nerds *) In fact, I wrote the exact phrase “take work seriously but not myself too seriously” in a college application essay two years ago.
Truth be told, I sometimes wish I took school a little more seriously, and dedicated less time to my silly goofy pursuits outside. I could have pushed myself a little harder to get first place in this, a top-in-that. But all of this sounds exceptionally cringey to me now. I am living the vision I’ve painted for myself since four years ago, even as I am not a straight A student, and have failed Math multiple times. At the same time, had I just kept my head down in the books 24/7, the multitude of memories I’ve written in my youth would not have unravelled.
For most of my teenage years, especially during the Covid-19 lockdowns, I thought I would live my adult life eloped with a lover. Off the grid. Today I understand how untenable such a plan would be. I can’t stress enough how much the cliche “nobody is an island” holds true. All of us need our communities to survive and thrive.
More than friends, I hope to embrace weak ties, as Dr. Meg Jay also advised. Stepping out of my current networks and forcing myself to forge new friendships is essential to expanding my worldview. In high school, I clung to my clique of friends, and didn’t mingle much with other classmates. I do regret that somewhat. I don’t need to be besties with everyone, but I need to interact with more people, more histories, more cultures.
My last hope for myself is to stop obsessing over the future, and follow the flow. “Avoid lock-in,” Dr. Jay wrote. In behavioral economics, consumer lock-in is the decreased likelihood to search for, or change to, other options once an investment in something has been made. Even if I have made a plan, I must be ready for tweaks and iterations. Never succumb to sunk costs.
When I was eight, I was singing Katy Perry every day and didn’t think much about my future. Unexpectedly, I stumbled into the highest-performing class next grade (in hyper-competitive Singapore, we once had this controversial system where classes were formed and changed based on your results every grade). Surrounded by academically driven students for four years, the air of ambition seeped into me. I started to discover and harbor heavier aspirations.
When I was twelve, I didn’t get into my first choice of middle school; I missed the entrance examination’s cut-off point by decimals. It was only after appealing that I sneaked in. I could very well have ended up in my second choice, and undergone a drastically different teenage life with a different crowd.
When I was eighteen, I ended my high school career with an illustrious C for A Level Math. I thought this meant that the doors to the overseas colleges I wanted were shut. Somehow I am here, writing this beside two big luggages in my bedroom, days before I would leave Singapore for at least a year.
I say all this because I’ve spent the past few months feeling frightened about my future and my twenties. I should remember twists, turns and mistakes characterize my past. And my favorite word: serendipity. I need to breathe, be present, and look life in the face.
“Dear Leonard. To look life in the face. Always look life in the face. And to know it for what it is. At last to know it. To love it for what it is, and then, to put it away. Leonard. Always the years between us. Always the years. Always the love. Always the hours.” Virginia Woolf in The Hours by Michael Cunningham

