SINGAPORE — For decades, the conventional career formula in Singapore appeared relatively straightforward: get a good education, secure a stable job, climb the corporate ladder, save consistently and eventually retire.
But a growing number of Singaporeans appear to be questioning one crucial part of that formula — whether a “stable job” can still be considered truly stable.
Stories of professionals leaving well-paying corporate careers, young workers building side hustles and people pursuing extreme versions of financial independence have increasingly captured public attention. The fascination may have less to do with wanting to copy these lifestyles than with something deeper: anxiety about how much control workers actually have over their careers.
A recent CNA commentary highlighted the story of Colin Lau, who reportedly retired at 35 after losing his job and now lives on less than S$150 a month, including by dumpster diving. His unconventional lifestyle generated sharply divided reactions online, ranging from admiration for his self-discipline to criticism of the extreme sacrifices involved.
But the bigger story may not be how little Lau spends.
It is that he managed to make employment optional.
Job insecurity is becoming a powerful career force
Concerns about employment are increasingly influencing how workers think about money and careers.
CNA cited research from human-resources company ADP indicating that only 15 per cent of Singapore workers felt secure in their jobs, with fears about retrenchment and artificial intelligence among the issues hanging over employees.
Official figures show why the issue is attracting attention.
Singapore recorded about 3,830 retrenchments in the first quarter of 2026, up slightly from 3,690 in the previous quarter. Preliminary Ministry of Manpower figures subsequently put second-quarter retrenchments at around 4,500, meaning job cuts increased even while the broader labour market continued expanding.
The increase should not be interpreted as evidence of a labour-market collapse.
Singapore’s Ministry of Manpower said employment expanded for the 19th consecutive quarter in Q2 2026, unemployment remained low and stable, and hiring sentiment showed signs of improvement. Retrenchments were concentrated mainly in selected outward-oriented industries and were largely linked to business restructuring.
That creates an unusual tension.
The economy can continue creating jobs while individual workers simultaneously feel that their particular job may disappear.
Side hustles are becoming something closer to career insurance
That uncertainty is helping change the purpose of the side hustle.
For some workers, earning money outside their main job is no longer simply about funding holidays, hobbies or additional consumption. It can provide another source of income if their primary employment suddenly disappears.
Among younger Singaporeans, that thinking is already visible.
A 2025 Prudential survey cited by CNA found that 41 per cent of Singapore Gen Z respondents wanted to create multiple income streams while working.
The concept has sometimes been described as “career cushioning” — building alternative income sources, skills or employment possibilities before they are urgently needed.
Similar behaviour is appearing internationally. Career analysts have increasingly described side businesses, freelance work and multiple professional identities as ways of reducing dependence on a single employer. The attraction is straightforward: if one income stream disappears, another may provide at least a partial buffer.
But diversification has its own costs. Maintaining a full-time job while operating another business or freelance career can mean longer working hours and burnout rather than genuine freedom.
Some Singaporeans are choosing control over salary
Perhaps more striking are workers who voluntarily leave comparatively lucrative careers.
CNA highlighted a former Meta professional who left the technology sector in 2025 to become a Hokkien mee hawker.
His reported monthly income fell dramatically — from roughly S$10,000 to S$4,000.
Financially, the decision looks like a major step backwards.
From another perspective, however, he exchanged income for something increasingly valuable: control over his livelihood.
The former tech worker told CNA that he preferred being responsible for his own decisions rather than potentially being removed from a job because of circumstances beyond his control.
A former fine-dining chef who established his own hawker business expressed a similar motivation. Having watched his mother experience retrenchment when he was young, he said the experience shaped his desire to avoid the same insecurity.
These examples do not mean entrepreneurship or hawking is inherently safer than salaried employment.
Quite the opposite: running a business can bring volatile income, long hours, capital risk and the possibility of failure.
But it changes who controls the risk.
That distinction may explain why such stories resonate so strongly.
Singapore’s labour market isn’t collapsing — but the employment bargain is changing
There is another side to the story that deserves emphasis.
Despite increasingly visible retrenchments, Singapore’s employment statistics remain relatively healthy.
In the first quarter of 2026, there were about 73,300 job vacancies, down from 77,700 at the end of 2025 but still equivalent to roughly 1.46 vacancies for every unemployed person.
The six-month re-entry rate among retrenched residents also improved to 60.7 per cent, from 57.4 per cent in the previous quarter. Improvements were recorded among PMETs, degree holders and workers below 30.
So the evidence does not support the idea that Singapore is facing a broad employment crisis.
Instead, something subtler appears to be happening.
Employment remains relatively strong, but confidence in permanent employment is weakening.
Workers increasingly understand that a profitable company can still restructure, eliminate departments, relocate functions or automate particular roles.
That changes the psychological contract between employee and employer.
A company can provide a salary.
It can provide training.
It can provide opportunities.
What it may no longer be able to promise is a job lasting decades.
AI adds another layer of uncertainty
Artificial intelligence is accelerating those concerns.
Not every occupation will disappear because of AI, and technology historically creates jobs as well as eliminating or transforming them.
But workers do not need to believe that AI will eliminate their entire profession to become nervous.
They only need to believe that automation could reduce the number of employees required to perform particular tasks.
That possibility encourages workers to accumulate skills, savings and alternative sources of income before disruption arrives.
In that sense, side hustles and unconventional careers may be less about rejecting work than about reducing dependence on any single organisation.
The new definition of security
For previous generations, career security could mean staying with one reliable employer for decades.
For the next generation, security may look very different.
It could mean maintaining several marketable skills.
It could mean having six or 12 months of expenses saved.
It could mean freelancing alongside a permanent job.
It could mean running a small business.
Or it could simply mean remaining employable enough to move quickly when an industry changes.
Companies also have a role to play. CNA’s commentary argues that employers can respond to declining perceptions of job security with greater transparency during restructuring, meaningful severance and transition assistance, while giving employees opportunities to develop broader skills through training and job rotations.
The objective is not to eliminate uncertainty. Modern businesses probably cannot promise that.
The challenge is giving workers enough capability to survive it.
And that may explain why stories about people abandoning conventional careers attract so much attention in Singapore.
Most workers probably have no intention of surviving on S$150 a month, dumpster diving or abandoning a professional salary to become a hawker.
But the lifestyles themselves may not be what people envy.
What they envy is the option to say no.
In an economy where workers increasingly understand that an employer can eventually walk away from them, having enough money, skills or alternative income to walk away first may be becoming the new definition of career security.
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