July 21

Courage to quit job (when you have no income certainty)


In October 2021, I quit my job with nothing lined up. For 6 months, I had been searching for a job whilst still in my previous role. But now, that role had ended. My contract came to an end, and whilst there were initial discussions to extend it, I didn’t want it.

I wasn’t happy, and my hair wasn’t happy. I’m not joking. I was balding faster than I ever saw. My clothes hung loosely on my shoulders.

This is not an article that encourages you to pump your chest like Tony Robbins, to visualise yourself having a job like Rhonda Bryne’s visualisation techniques, or to make you feel worse about yourself by sharing my success story.

courage to quit job
It doesn’t have to be like this in the office

Rather, I hope to share with you the realities of what it’s like to quit your job, especially when you have no income certainty.

The truth?

It is very hard to even find a place to work after quitting

Don’t underestimate how difficult it is. I never used to appreciate my office, until I started to work without an official office. Now, I work wherever I can find air-conditioning. In Singapore, working without air-conditioning is a guaranteed way for you to perspire in the 34 degrees heat.

Staying at home wasn’t an option, especially when I saw how working in my room affected my sleep by associating a place of rest with work. For 15 months, I stopped being able to sleep through the night.

The hardest thing isn’t finding a place to work. It’s finding a place where you won’t be disturbed. Working across different places in Singapore, I’ve been regularly accosted by security guards asking me what’s my purpose or if I have any reason to sit in the spaces.

Perhaps what’s even more difficult is the sheer lack of dignity and respect people give you. They treat you like dirt. Or worse than dirt. Often after these interactions, I feel as if working is wrong.

I don’t know how to describe it. It’s not a nice feeling to have people constantly looking down on you, thinking that you’re leeching onto their space.

And you might say,

Well, John, it just isn’t your place, is it?

That’s true. But what’s also true is the difficult experience of finding a place to work on something that matters to you.

I want you to know that things you took for granted in the office, like

  • hot water
  • chairs
  • desk
  • electricity
  • WIFI

All these logistical issues need to be thought about.

Working in a cafe may be an option, but you don’t want to be spending $5 a day just to get to work. You shouldn’t have to pay to work.

I want to dissuade you because it is difficult and anyone who says “Just quit!” Is probably someone who hasn’t personally quit themselves.

You need to know how you’re going to make money

If you have never earned a single cent outside of a formal contracted job, you should not quit.

courage to quit job
Do you know where the money is going to come from?

Please don’t send that resignation letter yet. Before I quitted my job, whilst I didn’t have a big income, I had paying gigs, that I needed to fulfil.

I had closed a deal with a local education institute to produce videos. There were also 4 other regular clients who were paying me to write. Whilst I started with about $600 a month, it was enough to pay some of the bills whilst drawing down on some of my savings.

You need to have some form of skill that is freelance-able. This means that it’s usual for this market to hire external help, rather than keeping the work within their staff. Usual ways I’ve seen others earn is:

  1. Yoga
  2. Fitness classes
  3. Personal fitness training
  4. Writing
  5. Design work
  6. Training
  7. Speaking

On the other hand, I think some jobs are definitely not freelance-able. If you’re in these jobs, you should think harder before you quit.

  1. Administrative work
  2. Bureaucracies
  3. Defence

You need to live on less

For the past 9 months, I eat out once a month. In Singapore, there are two forms of eating out – at hawker centres or at restaurants. Hawker centres are very affordable, at perhaps $4 per meal, rather than the typical $19 you will see in a restaurant.

I hardly even eat at hawker centres.

courage to quit job
What are the lengths you’re willing to go to just to quit your job?

Earning less means living on less.

This was made clear to me when I was unwilling to throw away a banana, even when there were maggots crawling in it.

I picked out the maggots and continued eating the banana.


Don’t scream. This isn’t living like a beggar. It’s just testing the limits of what I can tolerate.

You need to be willing to test the limits of some conventions

If you’re not willing to test some conventions, you shouldn’t quit your job. At least, not yet.

Take the example I shared just now of finding a place to work. Usually, people don’t go to places looking for sockets and places to sit. Nor do they see card access areas and try getting in, just so that they can find a place where they won’t be disturbed.

Having a healthy ability to test conventions is really important, because ultimately, quitting your job is going to make some people (like your parents) very upset. They may throw the ketchup bottle at you if you tell you’ve quitted your job.

They would ask you how sustainable your income is.

These are conventions.

Those who quit jobs to do something on their own, need high tolerances for pain

Don’t quit if you want a comfortable life. If you’re quitting to start a business, that’s even more painful.

I hear many people talk about starting businesses, but they are more attracted to the glory than the gory pain of businesses.

Come on. To start a business, you’ve to be so thick-skinned to accept rejection after rejection, people chasing you away, people not even wanting you there, but you still continue showing up everyday, knowing that you’re on a mission.

courage to quit job
you need to be willing to accept nonsense from the people around you everyday.

You need a very high tolerance for pain and suffering. Because the upside is perhaps in 10 years, not in 10 days.

Breakthrough businesses just don’t happen. Even Bezos was shipping Amazon books out of his garage.

Come on. Get real.

Forget the glory. Get stuck in.

So why quit?

Because you’re choosing not to settle.

I’ve seen many people unhappily dragging their feet to work and very early on, I realised these people had lost the spark within them to do something meaningful. They were content with life as it is, getting their comfortable salary, going on the occasional holiday, and spending on the occasional treat.

I would rather be sailing the seas as the captain than seated in a comfortable luxury liner.

To me, life is an adventure. But it may not be for you.

Secondly, there’s an opportunity, especially in your 20s to do something. Despite all the nonsense I get from people, I stayed quitted because I believe that there’s a limited time for me to start a business. I’ve no responsibilities with children or a wife, and I can go at this for as long as it takes to be successful.

What made you quit, isn’t going to make you stay quitted

You can have your own reasons for quitting, but what got you to quit, isn’t going to make you stay quitted.

Finding courage to quit, is the wrong thing to find. You shouldn’t even try finding that. You should find something worthwhile to do after quitting.

There’s the push factor that can push you to quit, but what’s the pull factor? Have you ever thought through that? If you haven’t, then quitting is not going to solve your unhappiness with your boss or your job.

It will probably make you unhappier.

When I quitted, I knew that I had worthwhile projects to work on like writing a book, speaking, and training others.

How do you find courage to quit?

Stop reading this article.

Go do something.

Then come back and tell me what you found.

Seriously. I’m not kidding. If you’re just another info-tourist hoping to be inspired by this article to go change the world, that’s not going to happen. Motivation just doesn’t last.

Commitment does. If you have the balls to quit and make something you really want happen, go do it. There’s no recipe book.


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