Why Singapore’s work culture still makes you feel guilty for taking sick leave

Mia didn’t plan to wake up feeling this way. The pain started behind her ribs and bloomed like a bruise across her lower back, down her legs, and into her abdomen. It was the kind of fatigue that made sitting upright feel like a feat. But when she stared at the screen on her phone and hovered over the company’s group chat, guilt hit first—before any kind of relief.

She had the right to call in sick. She had a diagnosis—two, in fact. Endometriosis and an autoimmune disease, both medically documented, both known for causing flare-ups that made ordinary days feel like marathons. But instead of using the day to rest, she found herself bargaining. Could she push through? Could she take a half day instead? What would her teammates think? Would this make her look soft?

In Singapore’s fast-moving, responsibility-heavy work culture, sick leave isn’t just a health right. It’s a social signal. And that’s what many leaders still don’t realize.

The workplace doesn’t need to say, “Don’t take MC”—not out loud. It’s the looks, the unspoken assumptions, the way performance reviews still reward the ones who “show up” no matter what. It’s in the quiet hierarchy between the visibly present and the unseen.

Mia isn’t alone. Her internal battle reflects a larger emotional architecture that governs how many Singaporeans relate to illness and productivity. From civil servants to startup staff, a tension runs deep beneath the veneer of structured benefits and HR policies: you’re allowed to rest—but only if you don’t make it anyone else’s problem.

What’s striking is that the guilt rarely begins with external accusations. It begins with the employee themselves. The high performers. The ones who already care too much. These are not the slackers. These are not the people taking MC to skive off. These are the people who reply to Slack messages with a fever. Who join Zoom calls on antihistamines. Who feel bad for rescheduling meetings their body simply cannot handle.

And while some may argue that this is a matter of personal conscience or professional pride, we have to ask the harder question: why are we designing workplaces where guilt is built in?

The truth is, much of this starts with good intentions gone unexamined. Founders, managers, and team leads are often caught in the middle—juggling headcount constraints, project deadlines, and the ripple effects of absence in small teams. When someone calls in sick, it doesn’t just go unnoticed. Someone else picks up the extra work. The delivery timeline tightens. And in high-stakes, low-margin environments like early-stage startups or thinly staffed government departments, one day off can throw off the entire rhythm.

So instead of resenting the system, colleagues sometimes end up resenting each other. Quietly. Indirectly. A snide comment here. A silent judgment there. Over time, this erodes trust, especially for those managing chronic conditions.

But here’s where it gets dangerous: when organizations fail to name and address this dynamic explicitly, they turn illness into a character test.

Are you resilient enough to show up anyway?

Are you disciplined enough to plan your flare-ups around peak season?

Are you considerate enough not to let your pain inconvenience the team?

These are impossible standards. They don’t build accountability. They breed shame.

And shame doesn’t lead to better performance. It leads to presenteeism—when people show up physically but operate at half-capacity. It leads to burnout cycles that masquerade as productivity until someone collapses, resigns, or becomes a warning story whispered between departments.

Even worse, this culture creates a false binary between “real” illness and “mental” health. You hear it in the way people justify MCs. “It’s just a cold” doesn’t warrant rest. “It’s only burnout” is met with eye rolls. And yet, both of these experiences are entirely valid reasons for someone to step back and recover.

When we condition teams to think of sick leave as a favor rather than a fixture, we distort its function. It is not a reward. It is not a loophole. It is a fundamental part of a healthy work system—especially in today’s reality, where long COVID, autoimmune diseases, and mental health strain are more visible than ever.

Some employees know this. They advocate for themselves. They take MC unapologetically. But even they aren’t immune to the culture of performative responsibility. Take Tan, a young marketing executive in her mid-twenties. She believes that MC can be used for mental recovery too—and she has no issue faking it when needed. But her caveat? “Just don’t do it when you have big meetings or tight deadlines.” In other words, you can rest—but only if you choreograph it perfectly to avoid burdening others.

And that is the deeper problem. When the only acceptable version of rest is the kind that doesn’t affect anyone else, then we are telling employees that their health only matters when it’s invisible.

This isn’t just a generational thing. Older employees aren’t immune. Ms. Eswary, a 62-year-old school administrator, rarely takes leave herself—even when she’s sick—because she’s afraid of troubling others. She’s been on both sides of the equation, having seen colleagues abuse MCs and leave others scrambling. But her belief that “you only need MCs if you don’t take care of yourself” speaks to a silent moral code: if you’re often unwell, you must be doing something wrong.

The truth is more complex. Some bodies require more maintenance than others. Some illnesses aren’t preventable or predictable. And some workplaces are structured in ways that actively sabotage well-being through poor boundaries, unrealistic expectations, or hyper-responsibility.

Managers may argue that they’re only watching out for performance. And that’s fair. But when sick leave frequency becomes a proxy for productivity, you start rewarding the wrong things.

A team member who shows up every day but delivers mediocre work is not inherently more valuable than one who takes occasional medical leave and produces excellent outcomes. Yet when attendance is tied—formally or informally—to bonus structures or promotion metrics, it sends a chilling message: rest is disloyal.

HR experts agree. Tracking medical leave is fine. Penalizing it is not. When you attach performance consequences to legitimate sick leave, you don’t incentivize wellness—you incentivize silence. And silence leads to avoidance, overwork, and delayed recovery.

What’s worse, this can backfire in retention. Talented employees managing chronic conditions won’t stay in environments where they’re made to feel like liabilities. They’ll go where they feel trusted. Where their health doesn’t need to be hidden. Where support doesn’t come with strings attached.

So what can founders and team leaders actually do?

It starts with clarity. Policy without culture is just paperwork. You can have the best HR manual in the world, but if your leadership team subtly resents or penalizes people for using their entitlements, no one will feel safe taking them. Leaders need to model the behavior they say they support. If a founder never takes sick leave, the message is clear: rest is weakness. If managers treat MC as an inconvenience, employees will downplay symptoms until they break.

Clarity also means decoupling medical leave from performance reviews. Make it explicit that using sick leave does not affect bonuses or promotion prospects. And don’t leave this in fine print—say it at town halls, reinforce it in one-on-ones, and remind middle managers that empathy is a core leadership skill. You also need structural support. If every absence causes chaos, the problem isn’t the absence—it’s the lack of coverage. Cross-train teams. Build buffers. Normalize flexible scheduling. Chronic conditions don’t have to derail workflows if you plan for them.

Transparency helps too. Employees with long-term health issues should be encouraged—not forced—to have open conversations with their managers about what support looks like. That doesn’t mean disclosing private medical details. It means co-designing realistic working arrangements that protect both output and dignity.

This also requires empathy from the top. You don’t need to understand someone’s illness to respect their experience. You just need to trust that if someone says they need time off, they do.

And if you're worried about people abusing the system? Build in feedback loops. Track patterns. But don’t default to suspicion. Design systems that assume good intent—then hold people accountable if that trust is broken. That’s very different from creating a culture of distrust from the start.

Most importantly, create space for new norms to take root. Culture doesn’t change overnight. But it does change when leaders stop rewarding martyrdom and start celebrating boundaries.

It changes when someone says, “I’m taking today off to rest,” and the reply is simply: “Thanks for letting us know. Feel better soon.” It changes when founders realize that the strongest teams aren’t the ones who never rest. They’re the ones who know when to—and feel safe doing so. So if you’re a founder reading this and thinking, “But what if people take advantage?”—flip the question.

What if your best people are burning out quietly because they don’t feel safe stepping back? What if the reason you’re losing talent isn’t performance—but guilt? And what if the thing that makes your team more resilient isn’t more hustle—but more permission?

Leadership is not about rewarding endurance. It’s about building systems that don’t break people. And that starts with the simple act of saying: rest is not a weakness. It’s part of the plan.