There comes a phase in adult life, somewhere in one’s thirties and doing well in their career, when property ceases to be merely shelter and begins to masquerade as judgment. It becomes a referendum on whether one is progressing at the correct pace, whether one is becoming the sort of person Singapore expects him to become, whether one has, in the eyes of relatives and friends, done well enough.
The upgrade path is laid out with such confidence that it acquires the quality of moral instruction: first the HDB, then the condominium, perhaps one day landed if providence and timing are kind. And yet I have found myself increasingly suspicious of this script, not because property is unimportant, nor because comfort is undesirable, but because the decision is so often framed far too narrowly, as though the only variables of consequence are square footage, postcode, and future resale value, when in truth what is really at stake is something much larger and more intimate — one’s flexibility, one’s peace of mind, one’s children’s psychology, and the shape of one’s life over the next twenty years.
What I have come to believe is that the question most people ask is not the real question at all. The question is rarely, in any meaningful sense, whether one can afford the next property move. Affordability, in Singapore, is often a dangerously shallow concept. Banks can tell you what you can borrow; agents can tell you what similar families are buying; friends can reassure you that prices only go one way in the long run. But none of them can answer the more consequential inquiry, which is this: what else could your capital, your headspace, and your freedom have become had you not held them inside a larger home and a larger mortgage? That, to me, is the true arithmetic, and it is astonishing how few people do it honestly.
Freedom
Even before one enters the world of businesses, index funds, or any formal investment framework, there is an argument for liquidity that has nothing to do with spreadsheet superiority and everything to do with existential room. Cash is too often described as idle, as though its highest virtue must be measured only by whatever yield it presently forgoes. But cash is not merely dormant return; it is optionality in its purest form. It is the ability to act when life suddenly presents an opening not visible six months earlier: a business whose owner is retiring and willing to let it go at a sensible price, an asset sold under strain, a partnership opportunity that appears only because one is ready before others are, a season in which boldness is required and boldness is impossible if one’s life has already been over-committed into granite, steel, and monthly obligations. And beyond opportunity, there is a more tender but no less real benefit to unencumbered capital — the ability to breathe. There is a psychological difference between living under a mortgage that is manageable and living under one that must be continuously serviced at the expense of one’s internal ease. The former leaves space for curiosity, for risk, for enjoyment, for the kind of lightness from which good decisions are often made. The latter can, over years, reduce a person without his fully noticing it, until the architecture he purchased to improve his life has instead become a low-grade occupier of his consciousness.
My own example sharpened this understanding for me. I sold my BTO and bought an executive apartment in Hougang Avenue 9 for about $730,000 instead of stretching for a condominium. I recognize the irony that I’m making an alternative status argument while critiquing status arguments. The difference, I hope, is that mine is made consciously. On paper, the condominium is supposed to represent advancement: the cleaner line of the narrative, the socially legible upgrade, the suggestion that one has crossed some invisible threshold. But lived reality is often more intelligent than appearances. Choosing the EA preserved more capital, reduced my carrying cost, and protected that most underappreciated of assets — flexibility, while letting me enjoy 1,500sqft of space.
It meant that a greater portion of my resources could remain alive rather than entombed. Alive to pursue opportunities, alive to absorb uncertainty, alive to be allocated where I believed value could truly be created rather than merely stored. And this distinction, though unglamorous, compounds in ways the market rarely celebrates because it is not easily photographed.
Investment?
To keep the comparison honest, one need not even use heroic assumptions. Suppose the difference between staying in a well-bought HDB and moving into a condominium is not some dramatic fantasy number, but simply an additional $2,500 to $3,000 a month once one accounts for the heavier mortgage burden, maintenance, and the general ownership drag that private property tends to bring with it. This is only an illustration, of course, not a claim that every family’s numbers will look the same. But illustrations, when reasonable, can still illuminate reality. If that same $2,500 to $3,000 a month were instead left flexible and compounded at an illustrative 8% a year, it would amount to roughly $457,000 to $549,000 over ten years, and about $1.47 million to $1.77 million over twenty. These are not decorative sums. They are large enough to alter the range of one’s choices, the resilience of one’s balance sheet, and the degree of calm with which one meets the future. In comparison, condominiums only rise by 3% annualized over the last 20 year period.
Then there is the peculiar mythology of condominium living itself, particularly the insistence that its facilities represent some obvious and universal lifestyle upgrade. Perhaps they do for some families. But I have found that people speak too lazily about “facilities,” as though a small pool, a modest gym, and a function room available through an app constitute a transcendence of ordinary life.
My own children enjoy the country club far more than a typical condominium facility, and it is not difficult to understand why. The scale is different, the atmosphere more generous, the range of experiences richer. There is more room to roam, more texture to the place, and a sense that leisure is not being squeezed into a developer’s checklist of amenities. In our case, the country club is not the compromise; it is the better experience.
And here too, the arithmetic is not trivial. My membership cost $12,000 upfront and $120 a month. If one compares that against a condominium arrangement where the facilities are effectively bundled into a much higher monthly carrying cost, even a modest recurring difference of $180 to $280 a month becomes meaningful when stretched across time. Again, that range is illustrative rather than universal, but it is hardly implausible. Compounded at an illustrative 8% a year, that narrower gap alone becomes about $33,000 to $51,000 over ten years, and roughly $106,000 to $165,000 over twenty. What is striking is not merely that the cheaper path can still build serious value, but that in our case it also happens to be the path my children genuinely prefer. The supposedly aspirational option is not even the more enjoyable one.
Manufacturing Hunger
Yet the deepest layer of this question, for me, has less to do with finance or governance than with children, culture, and the invisible moral atmosphere of a home. My sons are still young. They are six and eight, at the age where the world does not yet present itself as explicit ideology but as feeling, rhythm, and norm. And one of my private fears — not always easy to explain because it sounds harsher in literal language than it feels in the heart — is that comfort, if introduced too early and too completely, can become corrosive. Not overtly, not all at once, but subtly, like humidity entering wood. I have known children from very wealthy families, or families that appeared wealthy in every outward sense, and what struck me was not that they were bad people, nor that comfort made them useless, but that something essential seemed prematurely blunted in them — a hunger, a tensile curiosity, a refusal to settle too quickly into the given world. They had been furnished, too early, with the psychological conclusion that much of life was already arranged.
I do not mean to romanticise hardship. Children do not need deprivation; they do not need to feel unloved, diminished, or lesser. But I do believe they need some friction. They need to feel that life is not entirely padded for them, that there are gradients to climb, that not every desire is instantly normalised into entitlement.
This is why I am wary of moving into private property too early, even if I could afford it. The issue is not simply whether the condo or landed house is financially justifiable. It is whether it alters the emotional climate in which my children are being formed. Houses teach, whether parents admit it or not. They teach what is normal, what is impressive, what is expected, what sort of comfort one need not question.
My sons have already started asking why we don’t live in a condominium. I use it as an opportunity to tell them that it’s something they can work towards and earn themselves. I don’t mention that I’ve spent considerable time concluding it may not be worth the trade. The hunger I’m trying to preserve in them doesn’t need to know my reasoning — it just needs room to grow
A family can of course live in a very expensive home and still raise grounded, resilient children; the house does not determine the soul. But neither is the material setting morally inert. If the move into a more affluent housing context subtly communicates that one’s life should now be smoother, easier, and more ornamented than before, then it may, over time, erode precisely the instincts I most hope to preserve in them: gratitude, resourcefulness, appetite, and the desire to build rather than merely inherit.
Optimization
And perhaps that is the point at which the property conversation becomes inseparable from philosophy. What am I trying to optimize for? If the answer is only net worth on paper, then one could debate price indices, recovery periods, leverage, opportunity cost, and relative performance between HDB, condos, and equities. Those are worthwhile discussions. But beyond these measurable things lies another question that no official dataset can answer: what sort of life do I want my family to inhabit, and what sort of interior life do I want my children to develop? A home is not merely an asset class. It is a field of formation. It shapes tempo, expectation, identity, and the stories a family silently tells itself about what matters.
My Advice
I’m speaking here to families who have genuine optionality — where the question is not survival but direction. If space or ageing parents or logistics are the real constraint, that’s a different and more urgent calculation.
So when younger people in their thirties ask how they should think about their next property move, I find myself wanting to rescue them from the provinciality of conventional advice. Do not ask only what property is likely to appreciate.
- What is your capital being prevented from becoming?
- Are you buying freedom or prestige?
- Will this move make your children more grounded, or merely more comfortable?
I suspect that for many families, the wisest move is not the most socially aspirational one. It is often to stay put longer than expected, to resist the coercion of comparison, to preserve liquidity, to build one’s life before decorating it too lavishly, and to remember that there is a difference between wealth and the performance of wealth.
One can be entirely too rich in appearances and strangely poor in room to move. One can also live more modestly and yet possess something rarer: the ability to act, to choose, to breathe, and to shape one’s family without being overruled by the demands of an unnecessarily expensive life.
That, to me, is the real property decision. Not whether a condominium is a “better class” of home, nor whether landed property is the ultimate destination, but whether the next move enlarges your life in the ways that matter most. And if it does not — if it merely makes the balance sheet heavier, the obligations firmer, the children softer, and the soul more managed — then perhaps the wiser decision is not to move at all.
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Addendum: A reader, Leonard Tye, kindly shared this which I will add here:
Condos didn’t only appreciate 3% annualized over the past 20 years. They appreciated 4.6%. HDBs on the other hand, appreciated 5.2%. So his empirical financial case for upgrading is far narrower, unless the household genuinely values the non-financial benefits of private housing
On the other hand, housing services aside, a condo purchase is usually leveraged. A 4-5% return on a leveraged property can produce a higher return than the suggested by the (raw) price index suggests. At the same time, larger property moves face non negligible. BSD topped 6% since 2023 and as of last year the seller’s stamp duty holding period has been extended to 4 years with higher rates. This erodes the returns even on leveraged property
Additionally, to add on to his argument about affordability: while the TDSR cap at 55% of gross income and housing loan repayments at 30% of gross income of HDBs/ECs imply that affordability is regulated, this is very different today
Structural employment is setting in. Optimism labs just laid off today, that’s the industry I work in. Atlassian laid off today, an industry I was part of. Singapore has not felt the full brunt of AI layoffs yet. And we have virtually no protection against layoffs in Singapore
Especially since the government is pushing for higher fertility rates. The probability of losing your job is higher, and the resulting weighted risk of being unemployed with children and a mortgage is higher
His linkedin profile is here: https://www.linkedin.com/in/leonard22/
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