This story is part of RICE Media’s Storytellers initiative, a mentorship programme for budding content creators to learn about the art of creative non-fiction. This piece is a product of a partnership between RICE Media and Singapore Management University (SMU) for its Professional Writing module.
Top image: Zachary Tang / RICE media
“So… what’s your game plan?”
It’s a question we usually ask in high-stakes moments of change, and as a 24-year-old Singaporean on the cusp of graduation, I’ve been asked that question countless times. Careers, relationships, goals. It’s almost second nature to plan for the immediate future when we’re young.
But I never thought I’d be asking my mum that question, one month into her retirement.
When my mum retired earlier this year, I expected her to finally enjoy the well-earned rest she deserved after decades of hard work. Instead, I found her unexpectedly bored, adrift, and quietly wrestling with a lost sense of purpose.
Retirement, in the Singaporean imagination, is the well-deserved rest after decades of toil—the endpoint. People assume that once you’ve gotten your finances in order, you can coast easily into your golden years. No further planning required.
At least, that’s what I believed until my mum unexpectedly retired. She’s 66, has worked since she was in her 20s, and has navigated everything from factory jobs to sales and administrative roles.
Never one to complain about her work, she rarely took leave and wore her work ethic like a badge of honour. I imagined that once she left her job behind, she would finally get to savour the chance to slow down, catch her breath, travel a little, or spend more time with friends and family.
Barely over a week after her last day of work, she looked at me in genuine frustration and asked: “Eh, girl, I’m so bored. Should I apply for a part-time job?”
My first reaction was to laugh—until I realised she wasn’t joking.
My mum was, in fact, craving the structure and purpose that work had provided her with. She had been so consumed by the daily Singaporean hustle, so used to the constant movement. Stopping felt like hitting a brick wall.
We rarely acknowledge that for some newly retired individuals, this transition can be terrifying. My mum felt restless, anxious, and, as she later admits, lonely.
At that moment, I found myself turning her own question back on her: “Mum, what’s your game plan?”
The silence that followed revealed more than any immediate answer could have. She simply didn’t have one.
Parallel Transitions, Shared Uncertainty
This realisation, that my mum and I were in oddly parallel positions, ignited a series of personal reflections. Me, at the threshold of working life, stepping onto the escalator for the first time, nervous but excited by the possibilities ahead. My mum, who had just stepped off the escalator, wondering what to do with all the time and space around her.
Both of us anxious, uncertain, and hopeful in our own ways. Both of us filled with questions about what comes next.
There’s a common assumption that what comes next after retiring is rest. Tell any group of friends, “My mum just retired,” and you’ll get the standard responses. Wah, good for her. She must be so happy and relaxed now.
But therein lies a glaring gap in our cultural script about retirement. Where are the nuanced, honest conversations acknowledging that leaving your job—especially one you’ve had for decades—can be jarring to your sense of self? Where are the stories about confronting post-retirement boredom, loneliness, and the need for a renewed sense of purpose?
Perhaps it reveals our own collective denial or lack of preparation for what it really means to grow old in Singapore.
Singapore is fast becoming a super-aged society. By 2030, one in four citizens will be over 65. We’ve spent years preparing for this shift economically by tweaking our CPF contributions, raising retirement ages, and promoting lifelong learning.
But while we’ve prepared well for the financial side of retirement, we’ve done far less to plan for what gives life meaning after work, like purpose, connection, and identity.
It’s the side effect of living in a society that often measures one’s worth by productivity. In a nation built on grades, careers, and industriousness, this emotional dimension of retirement remains underexplored, especially among the young. We treat it as a distant ‘later’, the reward for decades of hard work.
But when my mum retired, she already felt unmoored and purposeless just days into her new routine. Her experience has shown me that financial planning isn’t enough—we need emotional planning too.
Freedom or Free Fall?
My mum once had dreams of becoming a Chinese teacher. However, life nudged her towards sales, a stable job that paid the bills and helped raise me. Work was duty, not passion, and she only took leave when it was necessary.
As her hearing declined in her 60s, mentions of retirement came up more often. But the actual moment always felt distant, until her body decided otherwise. So, when she finally decided to retire at 66, it wasn’t a triumphant, decisive choice. It was a quiet surrender.
The first week of retirement, in my mum’s words, was “shiok”. She was sleeping in and catching up with relatives and friends, but by the second week, the novelty faded.
She found herself waking up at 7 AM out of sheer habit, only to lie in bed with nowhere to be. Restlessness crept in. She’d WhatsApp me during my classes, asking if I wanted dinner. If I said yes, she’d brighten up, but if I couldn’t, she’d reply with a half-hearted “Ok… nvm”. I could almost sense her deflating through the screen.
By day 10, she asked, “Should I go back to work part-time?”
She sounded genuinely lost, like someone trying to recalibrate without a compass. Boredom was gnawing at her, and in a rare moment of honesty, she said she’d wish she pursued teaching, and wondered aloud if she could still teach young children Chinese.
But in that same breath, she’d shut herself down. “But I’m too old, who would want to learn from me?”
Generations in Transition
What struck me most was how similar her predicament was to what I feel now. I’m on the brink of graduation, and I’ve asked myself countless times: What if I choose the wrong path? What if I’m not good enough?
The difference here is that I’m at the start of my career journey, brimming with optimism that I still have time to figure it out.
My mum, on the other hand, feels that time is not on her side. I felt that she was continuously grappling with the question: At 66, is it too late to start something new?
Here’s something to think about: If we frame a person’s life as having multiple seasons (Season One being our education and career-building years), then maybe Season Two can be a season for reinvention.
As an aged person, one will have the advantage of life experiences, financial stability and the wisdom from work. While there are physical constraints and cultural biases about what seniors can or cannot do, a limiting belief is the narrative that a person is “too old” or “not qualified” enough.
Listening to my mum’s dream of teaching Chinese, hearing her self-doubt and watching her navigate her sudden expanses of free time made me question why we place so many constraints on older people’s possibilities.
But it wasn’t just self-doubt I heard—it was the quiet internalisation of an entire culture that equates worth with output. Retirement, for her, hasn’t meant rest. It meant disorientation. She’s spent a lifetime moving, and suddenly there’s nowhere she has to be.
Maybe that’s the real issue. Here in Singapore, we’ve been conditioned to fear stillness. Rest feels unnatural; shameful even. If you’re not doing something, you’re either irrelevant or failing. So of course we struggle to imagine older people starting over. We’ve barely allowed ourselves to imagine stopping.
There are other ways to measure a life beyond productivity, but my mum’s generation was never taught how. Maybe ours hasn’t either.
Branching Pathways
Not everyone sees retirement as a time for reinvention, and that’s fair. After decades of working, many just want to rest. To finally enjoy slow mornings, long walks, and kopi with old friends—free from deadlines and morning alarms.
For some, that quiet freedom is the dream. No pressure, no hustle, just space to breathe. And there’s deep value in that.
Culture plays a role, too. In families where caregiving and tradition are prized, some retirees find meaning in being there for children and grandchildren—cooking meals, helping with school runs, offering their quiet wisdom.
Unfortunately, not everyone has the luxury of choice. Health issues can limit movement. Financial stress may force older folks to keep working. For many, picking up a new hobby or ‘finding purpose’ just isn’t realistic.
I’m grateful to have the privilege of being able to romanticise growth and change. But someone in their 60s might feel they’ve done enough of that. Maybe what they want now is peace. And that’s valid too.
In reflecting on my mum’s journey and on all these swirling perspectives about retirement, one thing became clear to me:
We need to start talking about retirement in our 20s and 30s. Not merely in terms of finances, but in terms of what we want our lives to look like when we’re older.
I’ve had countless chats with friends about ‘adulting’, but almost none about how we picture our lives at 65. We file it away as a future problem, but perhaps it’s time to start weaving the idea of retirement into our personal and collective imagination—not as a single vision, but as a spectrum of possibilities.
Just as we plan careers and families with intention, we can shape our later years with curiosity and care. That means rethinking how we want to spend our time—long before retirement hits—and accepting that what we want at 25 will evolve by the time we’re 45 or 65.
I’m beginning to see that life isn’t a simple arc that peaks at 40 or 50, followed by decline. It’s a series of peaks and valleys, fresh chapters and second winds. That idea is both liberating and daunting.
It’s liberating because I now believe I can still chase dreams at 65. It’s daunting because time isn’t limitless, and I want to make the most of it.
Living With Intent
So, what’s your game plan?
Not just for the next five years, but for who you’ll be at 60 and beyond.
My mum is asking herself that too. After a lifetime of responsibility, she’s taking small steps toward something new—trying out new elaborate recipes, thinking about volunteering, even considering fun part-time jobs just to meet new people.
She’s not chasing ambition; she’s following curiosity. And that, to me, is courage.
I hope she finds something that makes her feel alive. It doesn’t have to be big. Maybe it’s joining a hiking club. Maybe it’s teaching a few neighbourhood kids. Maybe it’s simply cooking and hosting weekly dinners. What matters is knowing it’s not too late to want something more out of life.
And for the rest of us—especially those still figuring life out—it’s time to see retirement differently. Not as an ending, but a beginning. Because if we wait until we get there to decide what it should look like, we might arrive restless, bored, and unprepared.
This isn’t about hustling to the end. It’s about giving ourselves—and our parents—permission to dream again. To feel purposeful, even after the titles and paychecks are gone.
So the next time someone retires, ask them what they’re excited about. Then ask yourself the same question—because one day, that person will be you. The earlier we start imagining our Season Two, the more intentional our lives become today.
I didn’t expect my mum’s restlessness to spark such existential thoughts. Her search for purpose made me realise: I don’t have to wait decades to ask those questions.
Watching her start over gave me permission to begin, too.
Because the real game plan isn’t just about preparing for the end. It’s about daring to begin—again and again.
