The 5 Hard Truths I Learnt About Career Change & Money

What does it take to confidently walk away from a six-figure salary? Here are 5 game-changing insights I learnt from my career break…

I went on The Financial Coconut to share my story on how I walked away from a 6-figure career, why I chose to join the financial advisory industry as an investment advisor, and all the life stories and money lessons in-between.

Why You Need to Make Your Move Before 50 (Seriously)

“At my age, if you cross 40, you’re going to want to think that this is probably the last chance you might try something different. You can’t be 50 years old and say that, okay, I’m a manager in hospitality and suddenly I want to try banking.”

One of the strongest messages is about timing your career transitions strategically, especially as you approach your 40s. I mentioned on the podcast that crossing 40 often marks your last real opportunity to try something completely different. It becomes exponentially harder to pivot at 50, especially if you want to switch industries drastically. Instead of waiting until then, you should start planning your transition during your 40s to maximise your chances of success and avoid getting stuck in roles that don’t fit your passions or goals.

Action Step: If you’re approaching 40, start planning your transition now.

Stop Hiding Behind Your Degree – Show What You Can Actually Do

“Certificates are just certificates. I rather show people you want to hire someone who knows what they’re doing. I spent time after I got out of the army to create three different websites… to show people I know how to build websites, get traffic, and monetise them.”

Credentials only tell a part of the story, and increasingly, real-world skills matter more than formal certificates. When I was interviewing for my first job, I shared about how I went beyond his diploma by creating multiple websites to showcase my practical abilities in the digital marketing space by building websites, driving traffic, and monetising content.

Don’t rely solely on degrees or certificates. Instead, demonstrate what you can actually do through tangible projects or portfolios that give employers confidence in your capabilities.

Action Step: Create side projects that showcase your expertise.

How Much Money You Actually Need Before You Quit

“I need to make sure that I probably have two years of savings in terms of covering my expenses because one year is not working. Then you at age 40, in Singapore, you probably take another year to find a job.”

Money management plays a critical role in making a career break feasible. I explained that before quitting, it’s essential to precisely know your annual expenses and save at least two years’ worth of living costs.

This calculation covers one year of no income during the break plus an additional year to find a new job, which is particularly relevant for those at age 40 or older in high-cost cities like Singapore.

Tracking your spending meticulously for several months is needed to get an accurate picture and build a reliable financial safety net.

Action Step: Track your spending for 6 months to get accurate numbers (check out my ebook for templates and cheat sheets).

Why You Should Keep Your Investments Boring (While You’re Climbing the Corporate Ladder)

“The biggest monetary reward isn’t through investing. The biggest monetary reward is really doing my job well then climbing the corporate ladder. Anything that distracts me from doing my job well… is a distraction.”

When you are in your prime earning years, the best financial move is often to put your focus on excelling in your career. I highlighted in the podcast that the most significant financial gain comes from climbing the corporate ladder and not from trying to beat the market through complicated investing strategies.

Keeping investments simple through passive index funds reduces stress and distraction. Automating investments and sticking to this low-maintenance approach will keep your energy where it counts: on career success.

Action Step: Automate your investments and focus on excelling at work (contact me if you need help with that).

The Insurance Mistake That’s Costing You Money

“Nobody should get ILP in most cases unless you’re very different, but most people are not very different. Buy term and invest the rest.”

Insurance and investments should be treated as separate entities. In the podcast, I advised against costly, complex products like Investment-Linked Policies (ILPs), which tend to lock you into long commitments with high fees that don’t serve most people well.

Instead, the smarter strategy is to buy term insurance to cover risks like death, disability, or critical illness, and then invest the rest of your money independently. This approach gives you greater flexibility, lower costs, and better liquidity to adapt as your circumstances change.

Action Step: Review your current insurance products for hidden fees (our salaried insurance specialists can help with that).

Which of these insights resonates most with your career journey? Share your thoughts below.