Teachable moments #39 - When the Punishment is a Fine, the Poor Pay More

Let’s talk about something we rarely question — fines.

In Singapore, like many parts of the world, fines are a common way to enforce rules. Park illegally? Fine. Litter? Fine. Miss a payment deadline? Fine.

It feels fair on the surface — break the rule, pay the price. But here’s the uncomfortable truth: when the punishment is a fine, it only really punishes the poor.

For someone earning six figures, a $500 fine is a slap on the wrist. An inconvenience, not a consequence.

But for someone living paycheck to paycheck? That same $500 could mean not paying rent on time. It could mean skipping meals or delaying bills. Same fine, completely different impact.

It’s not just about money. It’s about power.

This idea doesn’t just live in legal systems — it shows up in corporate policies too.

Take company penalties, for example:

• Late to work? Pay docked.

• Need time off for urgent childcare? Marked as unpaid leave.

• Can’t afford to dress to corporate standards? Judged as unprofessional.

Who do these policies really hurt?

Usually, not the senior managers with flexible hours, car allowances, or remote work options. It’s the lower-wage employees, the frontline workers, the interns trying to prove themselves.

When "rules" are enforced with monetary consequences, they don’t affect everyone equally.

And the deeper problem is when we accept this as normal — when we don’t challenge the idea that fairness means everyone paying the same amount, regardless of how much they earn or what they can afford.

But fairness isn’t about equal treatment. It’s about equitable impact.

Imagine a company where instead of just slapping fines or rigid consequences on people, they looked at why someone was late, why a mistake happened, or why someone couldn’t comply — and responded with empathy, not just punishment.

That kind of workplace doesn’t breed entitlement. It builds loyalty, trust, and long-term performance.

Because here’s what happens when we ignore this imbalance:

• Talented people from humble backgrounds burn out faster.

• The workplace becomes less inclusive without anyone realising it.

• We reward privilege while punishing struggle — all under the name of "discipline" or "professionalism".

What can we do instead?

If you’re in a position to shape policies — whether as a manager, business owner, or HR leader — ask these questions:

• Does this policy have a disproportionate impact on lower-income or junior staff?

• Are there non-monetary ways to reinforce accountability?

• Can we create flexibility without compromising performance?

And most importantly — are we using punishment where support would do better?

It’s time to move away from lazy leadership models that rely on fear or fines to get results. True leadership is about understanding context, building systems that uplift, and holding people accountable in ways that help them grow — not just suffer.

Because when punishment is designed for wallets, only the wealthy walk away unscathed.

Let’s tear that system down — and build one that sees people, not just policies.