How To Take A Career Break Without Worrying About Money

This is a sharing post, taken from One of the top blogs that I frequently visit.


What do people remember Mr 15HWW for?

This question got me thinking and other than being the only weirdo on the blogosphere to track and publish monthly expenses for the best part of 3 years, I was surprised to find out that taking a 6-month sabbatical left a deep impression on many. 

So deeeeep that Lionel from Cheerful Egg actually approached me to find out more about it and he even decided to do this guest post!

Besides being popular, successful and of course handsome, one of Lionel’s most important contribution to mankind has to be inspiring yours truly to start blogging.

I stumbled on Cheerful Egg about 4 years ago and I have been an avid reader since then. Yes, I want to hatch a rich life!

And if not for his advice on how to outsource and automate some of our daily tasks to save time, you can probably still spot me queuing up to top-up my EZ-Link Card at MRT stations. (Please get on EZ-Reload if you have not done so!)

So if you’ve ever thought about taking a career break but haven’t had the courage to take the plunge yet, you will find this post VERY VERY useful!

Featured imageI have a friend who loves climbing mountains. Last year, he climbed to Everest base camp. And just last month, he scaled Mount Elbrus – the highest mountain in Europe.

One day, as he was reflecting about his career, he realised that he’d been working full-time for 10 years without a break. Knowing that there were a few more mountains he wanted to climb, he decided:

He’s going to take a 6-month career break. 

During his career break, he plans to pause, rejuvenate and pursue a couple of personal projects. Oh, and he’s also going to scale Mount Kilimanjaro in Africa.

As our jobs become more and more demanding, career breaks are becoming increasingly popular:

  • One of my college friends is on a 6-month sabbatical travelling through Asia and studying data science
  • An ex-colleague decided to quit his job to pursue his childhood dream of becoming a pilot.
  • And as we all know, Mr 15HWW himself went on a 6-month career break to focus on reading, writing, fitness, and moving closer to his dream of a 15-hour work week

Clearly, career breaks can be good for the soul. So why are so few of us willing to take the plunge?

The #1 Barrier Holding Us Back

Many of us desperately want a break from our careers, but we feel stuck. Why? Because every time we consider taking one, we start to feel a mix of three different emotions:

  • Uncertainty: How much will this crazy adventure actually cost?
  • Fear: What if I run out of money? What if I can’t find another job when I get back?
  • Guilt: Aren’t I just being irresponsible? Shouldn’t I be saving more for my retirement?

And so every day, we sit at our cubicles, torn between these crippling emotions and our desire for adventure. However, notice how most of these barriers stem from a single source: Money.


Yet, people like Mr 15HWW and my friend aren’t dumb. They’re not the kind of people who would do something completely insane without worrying about the financial consequences.

How did they decide that they were truly ready for a career break? What sort of planning did they do?  How can we confidently take a career break without worrying about the money?

I chatted with them, and here’s what I found out:

Step 1: Get Ultra-Specific 

It’s not enough to simply say, “I just want to relax for 6 months”. Smart people know that if they really want to turn this dream into reality, they’ll have to dig deeper into the details.

In the case of my friend, he knew that he was going to do 2 things:

  • Climb Mt Kilimanjaro
  • Live in Bangkok for 3 months

It was then a matter of breaking it down into the specific individual activities, calculating the costs, and arriving at a final number.

Now, I don’t know what my friend’s exact expenses are, but I did some simple, back-of-envelope calculations:

  • Return flight from SIN-JRO: $1,498 (from Expedia)
  • Climbing expedition: $4,038 (approx cost from here)
  • Return flight from SIN-BKK: $139 (from Expedia)
  • 90-days Airbnb private room in Bangkok: $2,422 (from here)
  • 180 days of living expenses at $20 a day: $3,600
  • TOTAL: $11,697 SGD

Yes, it’s a huge sum. But it’s definitely not impossible.

With the right methods, you could easily save that amount within a year. (Check out my free ebook Small Tweaks to learn the system I used to save an additional $300 a month over and above my current savings)


If you really want to take a career break, get ultra-specific and compute the expenses. Don’t forget to include the recurring non-travel expenses too: Phone bills, parents’ allowances, insurance premiums, etc.

First, figure out exactly how much your career break will cost. Then, take steps to save up for it. This method has 2 huge advantages:

  1. Your brain automatically gets to work figuring out how to achieve it
  2. By saving up for the break from scratch, you avoid dipping into your existing savings

Do you see how much better this approach is, compared to sitting at home and complaining about your job?

Step 2: Cover Your Liabilities

Unless you’re lucky enough to still be living with your parents, you probably have a housing loan to service. That’s not going away, even if you’re on a career break.

Now, if you’ve been working for several years and bought a house you can truly afford, your CPF account should be sufficient to cover your mortgage for at least a few months.

Of course, the larger your CPF balance, the more prepared you’ll be. Mr 15HWW said that when he quit his job, his CPF account was enough to cover his mortgage for severalyears before running out!


So how much should you have before taking the leap?

You don’t need a huuuuge balance like Mr 15HWW, but ensure that you have enough to cover your mortgage for at least twice the length of your career break.

So if you’re planning to go for a 3-month break, your CPF balance should cover your mortgage for 6 months. If you’re planning on taking a 6-month break, your CPF should have enough to cover your mortgage for a year, and so on.

If you don’t have enough right now, be patient – you can usually get there within a year or two. Remember that the first $20,000 of your CPF earns an additional 1% in interest, so topping up your CPF account with cash could help you get there a little faster.

Take a couple of minutes to check your balance now – What you find might surprise you.

Step 3: Take Care Of The Long-Term

Okay, you’ve computed the costs, you’ve taken care of your liabilities… do you start writing your resignation letter now?

Well, you could, but I suspect that you’re still feeling slightly uncomfortable.

Why? Because you can’t help but worry that you’re being “irresponsible” and “throwing away your future”. Never underestimate the power of these self-limiting beliefs that will inevitably creep in. Especially when you try to explain your decision to your parents.

So how do you deal with that? Take care of the future first.

You don’t need to have millions of dollars in a trust fund before going on a career break. But imagine how much better it would feel knowing that your money is still working hard for you in the background, even if you aren’t.

Growing money

That’s right – I’m talking about investments.

In fact, as this blogpost shows, taking a gap year would hardly make a dent in your Financial Independence dreams… but only if you have an investment portfolio.

Think about the message you send to yourself when you have an investment portfolio – even if it’s just a small one: “I’m the kind of person who plans for the future.

And to all the naysayers who think that you’re financially irresponsible, you can smile and ask them, “Have YOU set up a portfolio? Because I have.”

Not only will an investment portfolio provide psychological assurance, it’ll also serve as an additional safety net. If your savings and CPF do happen to run out, you’ll still have something else to fall back on.

Safety net

At the very minimum, aim to accumulate a portfolio that’s at least equivalent to your career break costs. So if you calculated that you’ll spend $12,000 during your career break, make sure you have a separate pool of at least $12,000 invested before you quit your job.

Of course, the bigger your portfolio, the better. If you’ve just started working and plan to take a career break in 2-3 years, NOW is the time to start building your investments.

But wait – how do you even start investing? 

Personally, I prefer to keep it simple. Don’t go for some stressful, high-risk strategy that will suck up all your time and energy.

Instead, I prefer the lowest-maintenance strategy out there: Index investing. Invest your money into a simple, low-cost investment like the STI ETF. (Mr 15HWW invests part of his money in that too!)

Index investing is heckuva easy to set up. You don’t need to know complicated investment terms like “alpha” or “mean-variance frontier” to do it.

If you’re interested to start implementing this for yourself, check out my free ebook on How to Start Investing in 3 Days. And don’t worry, it’s not one of those “free” ebooks that upsells you to a more expensive course at the end. I hate crap like that.

In Short…

Many of us could use at least one career break to recharge after several years of hard work. However, it can be terrifying to go for several months without an income.

But as my friend and Mr 15HWW have shown, you’ll know you’re ready for a career break when you:

  • Get ultra-specific
  • Cover your liabilities
  • Take care of the future

Life is more than just about going to work, paying the bills, and dying.

Take your time to plan it right, get your finances in order, and confidently take your career break. You deserve it.


Lionel Yeo is a ramen-slurper, bathroom dancer and financial hacker behind, a personal finance blog for young executives. His material has been featured on the Sunday Times, Yahoo!, KISS 92 and more. He also secretly dances in his room. Subscribe to his VIP list for more smart hacks on hatching a rich life.

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