Is it worth working two full-time jobs in Singapore for financial freedom?

For some, financial freedom means early retirement. For others, it simply means not lying awake at night calculating how many days until the next paycheck. In Singapore, where the cost of living continues to rise and salaries in many sectors remain stagnant, some workers are going to extreme lengths to get ahead. One man’s story recently struck a nerve when he posted on Reddit about juggling two full-time jobs—back to back, day and night—for the past three months. The comments flooded in, not with judgment, but concern. The core question wasn’t whether he was hardworking, but whether this was sustainable—and whether the payoff justified the toll on his body, mind, and life.

The man’s schedule sounded almost impossible. He worked the night shift from 8 p.m. to 8 a.m., then reported to another job at 9 a.m. and stayed until 5 p.m. That left him, at best, three hours to shower, eat, commute, and sleep—before doing it all again. He took just one day off each week. His reason was clear and, to many, relatable: he was working to pay off his debts, build a basic emergency fund, and start investing. With no obvious pathway to a S$4,000 or S$5,000 salary in a single job, much less S$10,000, he saw doubling up as his best option.

At first glance, the logic makes sense. If one job won’t pay enough to get you ahead, take two. But as the weeks wore on, the man’s post revealed something deeper. He was proud of his dual paychecks. But he was also exhausted, pale, and beginning to experience heart palpitations. He described feeling like a zombie. His social life was gone. His health was starting to erode. And he asked, out loud: is this really what success looks like in Singapore?

This story deserves attention not because it’s exceptional—but because it’s becoming more common. More people are quietly taking on second jobs, freelance shifts, or gig work to stay afloat or speed up their savings. It’s often framed as admirable sacrifice, the kind of hustle that deserves applause. But behind the discipline, there’s a creeping unease. If financial freedom comes at the cost of your health, is it freedom at all?

Working two full-time jobs isn't illegal in Singapore, but it's not typical either. It brings up questions about employment terms, rest periods, and long-term consequences. But the core tension is financial: in a city where basic expenses—from rent to food to transport—are among the highest in Asia, many feel like one job simply isn’t enough to achieve stability, let alone progress. Yet doubling your workload doesn’t automatically double your financial safety. And over time, it may jeopardize the very stability you’re trying to build.

Let’s start with the most obvious cost: health. Several large-scale studies have shown that working more than 11 hours a day significantly increases your risk of cardiovascular disease. In fact, the Scandinavian Journal of Work, Environment & Health found that those who consistently exceed that threshold are three times more likely to suffer a heart attack and almost four times more likely to develop type 2 diabetes. Add in a sleep deficit—common among people working two shifts—and the risk of burnout, immune dysfunction, and emotional instability multiplies.

Working 60 or more hours a week also correlates with a higher likelihood of early disability retirement, meaning that even if you’re technically earning more now, your career horizon may shrink in ways you didn’t plan for. In other words, short-term income gains could trigger long-term income losses—through hospital bills, missed career development opportunities, or even job termination due to performance dips. And once your health is compromised, regaining it often takes more time and money than you expect.

From a financial planning perspective, the real concern isn’t just about overwork—it’s about direction. There’s a meaningful difference between using a second job strategically and defaulting into it because you see no other option. A strategic second job comes with a clear time limit, a concrete goal, and a well-defined exit point. For example, someone might take on an additional role for six months to clear a S$10,000 debt. That’s different from drifting into two-job mode indefinitely, hoping more money will fix what is ultimately a structural mismatch between income, expenses, and long-term goals.

The idea of “more work equals more security” can be seductive, especially in a culture that celebrates perseverance. But sustainable financial planning requires more than effort. It requires systems. Earning more is only one part of the system. The other parts include health preservation, rest, skill building, long-term income visibility, and clarity about what you’re trying to achieve.

Let’s say your plan is to work two full-time jobs for a year and save S$40,000. On paper, that might be possible. But how will your expenses shift? Will you spend more on transport, food delivery, or coping mechanisms like online shopping? Will your body hold up for 12 months at that pace—or will you face medical leave halfway through? Will you be able to continue investing time in upskilling, networking, or job applications that could offer you a single, better-paying role? Without answers to these questions, your plan may be more fragile than it appears.

That doesn’t mean working multiple jobs is always a bad idea. There are windows in life where taking on more can make sense. If your physical health is strong, your financial target is short-term and specific, and you’ve accounted for recovery time and exit plans, then using a second job to create a buffer or launchpad might be worth it. But it should always be a tactic—not a lifestyle.

There’s also a silent cost to overwork that rarely gets attention: the missed opportunity to build leverage. When all your time is consumed by work, there’s little room left for education, networking, or personal development. Ironically, the very thing that could lift you into a better job—a portfolio, a certificate, a professional course, even a side project—is often what gets sacrificed first. That’s the trap. You can become so busy earning, you stop growing. And without growth, your earnings will eventually hit a ceiling.

Singapore offers various upskilling pathways through SkillsFuture and other subsidized programs, yet many workers feel they can't take advantage of them because they’re too exhausted or financially stretched. But consider this: a one-year investment in training that leads to a 25% pay bump could have more compounding value than a year of grinding through two unsustainable jobs. Time, like money, needs to be invested with intention.

There are also personal finance considerations. Working two full-time jobs may not double your CPF contributions, depending on how your employment contracts are structured. You may be contributing more to Medisave, but not necessarily building up your Special or Ordinary Accounts at twice the rate. That could affect your long-term retirement picture. Additionally, employer insurance coverage often doesn't extend across two jobs, and you could fall through the cracks in terms of workplace protections, especially if one of your roles is freelance, temporary, or outside the scope of MOM enforcement.

Beyond income, the structure of your budget matters. If you’re working 18 to 20 hours a day and your lifestyle spending increases in parallel—through convenience purchases, stress-related spending, or medical costs—you may find that your net gain is far less than you hoped. In financial planning, margin matters. Earning more only helps if you’re able to keep more—and if what you keep moves you closer to your goals.

This is where having a financial system becomes vital. A system might include a basic 50/30/20 budget, where 50% of your income goes to needs, 30% to wants, and 20% to savings or debt repayment. But it should also include routines: a monthly check-in on progress, a rest day to recalibrate, and an intentional review every three months to assess whether the current plan is still serving your long-term objectives. If you’re working two jobs, the system needs to work harder than you do.

The man on Reddit ended his post with uncertainty. He asked, “Is this what success feels like, or am I crazy?” The responses were telling. Many urged him to slow down, not because he wasn’t admirable—but because they saw what he couldn’t from the inside: that he was building something unsustainable. A few shared similar stories. Some shared regrets. And others offered practical advice—rest, upskill, shift to a higher-margin role, set an end date.

What was missing from the discussion wasn’t intelligence or effort. It was structure. Financial freedom isn’t a one-size-fits-all formula. But it does require boundaries, clarity, and an honest view of what your body, mind, and future self can withstand.

Singaporeans are not lazy. Quite the opposite. But overwork is not a reliable plan. And exhaustion is not a milestone on the way to success. If you are considering—or currently living—the two-job lifestyle, ask yourself: do I have an exit strategy? Is this plan moving me toward something, or just keeping me busy? Can my health, relationships, and energy levels hold this rhythm for another six months?

If the answer is no, then perhaps it’s time to shift the question. Not “How much can I earn?” but “What will make this income sustainable?” The answer may not be easy. But it will be honest. And financial freedom built on honesty, clarity, and health is worth more than any paycheck.