5 Questions to Ask Before You Upskill

By 2030, 70% of our current job skills may no longer be relevant.

Yet despite this urgency, many Singaporeans have yet to act.

Since SkillsFuture’s launch in 2016, seven in ten have not used their credits.

When it comes to upskilling, many of us tend to have several questions: Should you study full-time or part-time? Which course actually moves the needle in your career?

Here are five common considerations to help you make more confident decisions and save you time, money, and missed opportunities.

Let’s break them down.

1. Some Skills Demand Full Immersion

Some skills grow well with part-time effort. Others demand full focus.

When I picked up angel investing, personal finance and digital marketing, progress came easily alongside my day job.

These skill sets involved reading and applying weekly, creating a steady feedback loop.

Learning Business Mandarin was a different ball game.

Language learning is not just about knowledge. It rewires how we listen, think, and respond in real time.

Unlike business concepts, Language can’t be retrieved on demand, it must become instinctive

That is why one lesson a week and two additional hours of revisions only increased my vocab slightly.

Real gains in language come from consistent exposure and real-world interaction—something only full immersion can truly offer.

In fact, three months of immersion often achieves what longer part-time study cannot: confidence, fluency, and the ability to use the language in daily life.

2. How Demanding Is Your Current Role?

After work, your brain’s learning capacity drops. Decision fatigue sets in. Working memory shrinks. Reflection becomes difficult.

Yet effective learning requires exactly that:

• Time to process

• Space to reflect

• Opportunities to apply

If you are too mentally drained, it is hard to practise deliberately. Without deliberate practice, there is no real growth.

Ask yourself: Do I truly have the bandwidth to learn after work?

That answer can guide whether part-time or full-time study is more realistic.

3. Understand Your Learning Style

Your learning style shapes how well you process and retain information.

During COVID, I attempted various online courses to improve myself.

Despite having more available time during lockdown, little knowledge stuck when I took courses with on-demand e-learning.

I discovered I was not suited for this format and instead thrived on the energy of a live interaction.

When I later enhanced my enterprise SaaS sales skills through live coaching, my retention skyrocketed. The immediate feedback and peer discussions matched my learning style.

Do you learn better through conversation or reflection, structure or flexibility?

The environment that matches your natural style will dramatically impact your success.

4. Do your due diligence on courses

Before committing to any program, do your homework.

While some SkillsFuture and online programs are heavily marketed, not all deliver meaningful outcomes in terms of career progression or practical skills.

Here's how to evaluate program quality effectively:

1. Track record: Research the career outcomes of those who attended the course. This can be done via LinkedIn or asking the school directly

2. Industry recognition: Speak with hiring managers in your target field about which certifications they actually value.

3. Instructor expertise: Research your potential teachers' practical experience, not just their academic credentials.

As the Workers' Party has highlighted, there is a need to track the effectiveness of skills training.

Currently, there are no published metrics around each course take-up rates among eligible workers, duration of unemployment and post-training placement into related employment.

Until we raise the accountability of these initiatives, your own due diligence remains essential in choosing courses that are truly worth your time and money.

5. What are my personal financial and family circumstances?

Your life stage and financial situation shape how you approach learning.

A parent with young children faces different time and energy constraints than someone without caregiving responsibilities.

Financial preparedness is equally critical, especially if you are considering full-time study.

I would recommend one calculates and set a realistic saving budget. This will ensure one does not keep shifting the goal posts due to financial anxiety that can come when quitting without a job.

For instance, a software developer enrolling in a full-time bootcamp may need $10,000 for tuition and $12,000 for six months of living expenses, totalling $22,000 before making the leap.

Given the job market, it might also be good to add 3-6 months worth of expenses of additional buffer. This would ensure one does not need to rush into a job after the course.

Your journey will depend on your goals, capacity, and season of life.

Upskilling is not an expense, it’s an investment. The right skills can boost your income and build resilience in a changing economy.

The most expensive course is not the one with the highest price tag.

It is the one that fails to meaningfully upgrade your capabilities.

Forward this email to a friend if you feel the advice is helpful.

Jeraldine Phneah focuses on the challenges working adults face - rising costs, burnout, job insecurity, and caregiving - and offers reflections to drive meaningful change.

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