Is It Time To Quit Your Job? [TFC 113]

Is It Time To Quit Your Job?
[TFC 113]

The pandemic has fundamentally changed the way we view work. With the increased amount of time spent working from home, many of us have more time to reflect on the kind of job we want and sometimes we may wonder: is it time to leave for greener pastures? On the other hand, it does seem risky to quit during such uncertain times, doesn’t it? Get more clarity on this thorny issue in TFC 113 as Reggie describes 3 scenarios that may suggest that it’s time to quit your job. 

The idea of quitting your job can be daunting to some of us.
While everyone’s situation is different, there are some signs to look out for where it might be better to leave. In this episode, host Reggie explains each scenario and gives clear examples to support his argument. Some of these scenarios may actually surprise you!

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podcast Transcript

Reggie: Hey Coconuts! So yes, I am in Georgia… Tbilisi, Georgia and I’m recording from here today so if you hear any kind of audio discrepancies, a little bit different from the usual, bear with us. I’m going to keep tweaking and work towards it. But today we’re going to focus on the great resignation which is a thing that’s going online. Everybody’s talking about “oh, I want to quit my job” and all that, but especially common in the US. There’s no real data coming out of what is happening in Singapore, but I’m pretty sure that through this pandemic period, a lot of us are rethinking what we want in our lives.

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Do we want to do all these kinds of long working hours? Do we want to milk ourselves dry doing all the jobs that we are doing currently? Hey, if you are already in a job that you love, great. Good for you. Kudos. But for the many other people that are thinking “maybe I should change jobs?” How can I go about quitting my job? So today I’m going to share you three situations where I think it’s a good time to reconsider your job and maybe a good time to quit your job. Welcome back. 

Good morning, everyone. I welcome you to another day with The Financial Coconut. In our podcast, we will be debunking financial myths, discovering best financial practices and discussing financial strategies that fits our unique life.

You get it, ultimately empowering us to create a life we love while managing our finances well so today we’re going to spend some time to talk about when should you quit your job? I know it’s very popular. A lot of people want to know about this and yeah, we’re going to have a good time talking about it.

Okay, so let me first be clear. I’m not a big proponent of “oh yeah, everybody should quit your job, start your own business, do your own thing and join the gig economy” and all that jazz. Well, we’ll talk a little bit more about the whole gig economy, starting your own business, that whole kind of cycle and change in episodes to come. I have some thoughts and I wrote down some things especially after talking to a lot more people that are traveling around and being part of the gig economy. 

There’s a lot more to share and I may invite a few of them onto the Tuesday segment to share with us more since Andrew now takes the Thursday segment, so I’m only left with the Tuesday segments and great, I’m going to do… may do some interviews about that so if you have anything you want to know about geoarbitrage or the gig economy and what have you, just email us:, DM us on socials, join our Telegram group and all that jazz.

But the topic of quitting your job… I think for a lot of us, the cycle is clear, right? You study very hard and then you get good grades. You go into a good school, you graduate, get into a good job… whatever is defined as a good job and then you accumulate your wealth. Eventually, you buy a house and you start your family and you retire? I don’t know, it sounds very sad talking about it, but it is what it is. That’s the narrative in Singapore. A lot of people have planned their lives around that. 

Of course, I know the beauty of the millennials today is we have options, we have choices now. There’s so many things that we can do. A lot of people are exploring all these different ideas, but may not… be a little afraid to do it. I’m vibing with you on this and we will take the next few episodes to talk a little bit more about it. Getting out of the rat race, how is it going to look like? Geoarbitrage, working remotely… all that jazz, they will come, but today just focusing on when should you quit your job?

I think one of the fundamental questions… not part of the usual three points, one of the fundamental questions we gotta ask ourselves is: have we ever taken time off this cycle of work… study hard, get a good job and then build your wealth, build your family? Has anyone really taken time off to think about it and re-evaluate this whole thing… which is why I’m not very surprised a lot of people are quitting their jobs after two years of pandemic. 

Firstly, you’re not spending as much during a pandemic. You’ve definitely saved up some firepower. Also, you have a lot of time. You have a lot of time sitting around thinking about “is this what I want?” “Am I on a… what they call ‘airplane mode’ like I’m just cruising by” and “is this really the future that I want to embrace?” 

I think this is fundamental as to why there’s a resignation and I’m pretty sure a lot of you have questioned your job, questioned your life, questioned the future during this period of time so that’s great. Before that, everybody was just kind of moving and moving and chugging along and nobody really knows what they want. 

But on this basis, it becomes a little bit scary of… okay, so now I kind of know that maybe this is not what I want, at least not in the next near future, then how do I go about doing this? What can I do? What should I consider? There are many things to consider and I think we’ve covered a lot of them. A lot of people out there have talked about your financial resources, you have a financial plan, blah, blah, blah… all that jazz. 

All that aside, I think there are three scenarios that I will strongly advocate people to take a break, quit your job, take a sabbatical, whatever you want to call it. There are three scenarios that I feel is something that… it’s like if you’re in this situation, then you really should consider it. Under all other situations, then it’s a little bit more tinkering, a little bit more like a balance of different options and what have you. 

I’m going to give you my first situation as to when you should quit your job. I don’t know, man. I think employers will hate me for this but okay. First point is after you survive restructuring. Yes, I know a lot of people take pride in like “oh yeah! You know I survived restructuring? I didn’t get fired although my company is cutting resources, cutting corners, cutting costs and trying to make the business work and I survived. I am important in this company.” a lot of people take pride in this. I survived restructuring, especially our friends in engineering and finance. We have been through cycles of restructuring in this spaces and people are like “yeah!!! You know, it’s my thing.” 

I really think if you survive restructuring, this is your best time to quit your job. Of course, I’m not in the idea of immediately drop your letter and say “I’m going to quit”, but this is your best situation to change a job, find something else, go out there and put yourself out there in the job market. Because… a few sub pointers. Number one is you have been evaluated as a valuable member of a dying or shrinking company… not dying, a shrinking company which means you are evaluated as vital at some level, right? At some level, the price you are being paid for and the quality of what is coming out from you is good enough to keep you on this ship that is not as luxe anymore, not as big and not as… with more resources anymore. 

That is great lever. You can go to your competitor companies or you can go to other sectors and say “I survived a restructuring. This is the kind of job that I’m looking for.” Put yourself on the job market right after that. I think that’s important. 

Number two, of course you have leveraging power, which is why I say employers will hate me after they listen to this. Right after I sack 40% of the department, you are the remaining few that I think… valuable, good, should keep in the company. Now you come and tell me “boss, I got another job offer and I want to negotiate higher.” But actually, if you think about it, that is the best situation because the company just fired people. They have evaluated that you should be part of the team. This is your best chance to go and negotiate if you have a counter offer.

If you have a third party, put yourself up on the job market and you got an offer, you can come back to the company say “hey boss, I got an offer elsewhere and I want to negotiate higher.” I want to negotiate maybe a higher position in a company or to negotiate with you based on the offer that you got. 

This is your best time to put yourself out there in a job market and maybe quit your job, not to be there and like “yeah, I survived”. Because I think that’s what a lot of people think about. It was like “oh my god, I survived multiple rounds of restructuring.” I know of a friend who went through three rounds of restructuring at one of these huge, old company and they take pride in it. I’m like “guys, really. This is your best time to go out.”

Also, another thing under this situation is that you need to realize the growth trajectory of a company. When a company first started, there’s nothing. It’s an idea that’s growing. They are defining themselves. But after a while, they get to a stage where we have a business, we have a model here. Let’s scale. So they start hiring a lot of people and they bring in money, they bring in capital. 

During this process of hiring, they tend not to be very efficient. They tend to be like “okay, we can pay you a little bit more. We can do this a little bit more for you” provided they have money to begin with. Not like young startup but the scale-ups: the guys that are growing fast… 30, 40, 50, 100 men team. They’re trying to take a bigger market share which are all your big tech companies that are paying a lot because the particular things that are looking for, the particular people that are looking for is firstly rare. Secondly, they want to grow fast so they want to make sure they give very good compensation that can get you in. 

I’m sure many of you Singaporeans remember a time when people say “fly SQ (Singapore Airlines).” SQ girls, SQ guys is like premium, but that was long ago because at that point in time, Singapore was trying to grow its airline sector, so they were hiring all the best. They were paying the premium, paying all these good-looking people to come in and just be air stewardess. 

Okay, shout out to all you air stewardesses listening. I’m not saying you are not doing an important job, but you get idea, but eventually SIA and SQ struggled to keep growing and maintain its margin. It had to cut back a lot of the perks. As it cut back a lot of these perks, then the job becomes not as sexy, not as viable and so a lot of people will start to change out of the sector or they get restructured out. 

It’s the same cycle for all businesses. After they found their business, they grow, they scale. They want to get all these best people. They will pay. There’ll be a lot of “wastage” during this period. They’ll pay you more. They give you more perks, more offs, more things but eventually when the business start to plateau and the business start to become what we call matured business, then all these things get cut back. All these things get reduced and people start to have to live with it. All the perks are being removed.

You see it even in Grab drivers when there was a period of time when Grab was trying to get market share. They were just giving out all those stuff. Eventually, they moved on. Eventually, all these perks come down. So same idea. Once you survive a restructuring, this is your best time to quit and go and put yourself out there in the job market and see what is out there.

To me, that is your best opportunity. Okay, all your sponsors that are on the sidelines, I still love you guys. You can still come and sponsor us… that’s that, after you survive restructuring. Point number two is a little bit cheesy… is that when you’re feeling like you’re empty and you should recalibrate your incentive system but I’m not coming from the angle of full, full, feel, feel all that stuff. I do have some thought process on this and I will talk to you a little bit more about point number two after a word from our sponsor. 

When you feel empty… I know this is very hard to talk about. It’s a little bit all over in the air. A lot of people are talking about it. You don’t feel fulfilled blah, blah, blah… Let me give you a clearer anchor to anchor on. When we first graduate, when we first… okay, I never graduated but anyway. When we first graduate and we get our job and what have you, what were we? We were broke kids, right? We didn’t have money, we didn’t have resources and we didn’t have experiences. We don’t know much about what is out there so when we are at that situation, a lot of things will fascinate us. 

$3000 starting pay is amazing, $5000. starting pay is like whoa, amazing, man! Promote to become supervisor is cool, become a manager is even better. We got all these extra perks. All these things were fascinating at first. For a kid, for someone that just came out, a millennial or graduate that just came out of university, having nothing in their bank account… in fact, having $20 000 in debt, $3000, $5000 pay is amazing.

But after a few years in the workspace, after your first few years of playing around and spending… buying bags and partying and all that jazz, which is very normal because when you don’t have the resources to begin with, you won’t do all this. Once you have it, you want to do it, right? Fair.

Eventually, I hope after listening to the podcast or eventually… you’ll fade out this phase of just having fun and YOLO (You Only Live Once), you start to accumulate wealth. For whatever reason, it can be a plan accumulation or it could be like “I’m a little bit sian (bored) of YOLO and partying” or your body just cannot keep up.

I mean guys, really. By 30 years old, you still want to [makes club sounds] every weekend? It doesn’t work that way. Eventually, you fade out the phase and you start to accumulate. As you start to accumulate wealth, from that dude that has $0 in the bank account and $20 000 in debt to $50 000, $60 000, $100 000 savings sitting around. Or maybe if you marry early, you have a house going on and you start to have all these accumulation of wealth and you also accumulate experience. As you also accumulate resources out there with relationship and what have you, you are really in a different incentive situation now so you cannot blame yourself for feeling like this is not for me anymore, of course. 

Because three years ago or five years ago, when you joined the company, you were in a different situation. But now five years later, if you are still in the same company or still in the same sector and you don’t feel as excited… hey dude, it’s normal because you are in a different financial situation. You have a different set of resources. You are just incentivized differently which is why for the longest time ever, a lot of the first world economy, we’re pushing a lot of job fulfillment, actualization, build good relationships at work and all that. 

If you think about it, it’s because they have moved away from the material level. Essentially, their whole workforce have made money through the process of the growth of the company or the sector or the country. They have elevated away from material wealth and they reached a point where they want the whole spirituality. They want the inner world. They want to feel fulfilled and all that such that in order to keep these guys in the job, the company has to create that great environment for friendship, great space for you to try new things and all that, right? 

So it is really just companies trying to help the employees to actualize at a higher order to keep them at the workplace so that they will continue to come. But if you feel that your company is giving you all that: the great workplace, great understanding boss, good friendship, a lot of opportunity to try new things, then actually all these things which is all in the discussion out there today can really be done on your own. You can do it at home. You can do it with your hobby. You can start an interest group. You can join an NGO. There are many things that you could have already done it on your own. 

But for the longest time, companies were trying to internalize this need of yours so that you continue to work for the company and I want to clarify that I don’t think companies are evil. They just want to pursue their company’s interests. In that sense, you get the idea of why things are like this. If you feel like the company is not giving you that higher order fulfillment, which… that means the company passé already, old school, they don’t understand this, there are two ways that you can go about doing this. 

One, of course, is to go find the other environment that can give you all these higher actualized needs that you want to go about. For all of you that don’t know, you can go and read Maslow’s hierarchy of needs. I think that is one of the easiest presentation of needs so far, human’s order of needs but I recognize the counter argument.

For all of you there are super deep in sociology, psychology, Maslow’s and what have you, don’t flame me but for everyone that has no idea, please go and search “Maslow’s hierarchy of needs”. This gives you a clearer idea why at certain level, you feel like there’s nothing much here because you have already covered your house, you already have your wealth. You have some sort of savings sitting around that you ask yourself “maybe I can stay in Portugal for a while or stay in Malaysia for a while and I’ll be fine.” You have optionality. Things have changed. You want the higher order, the actualization, the love, the relationship and all that.

Like I said, two ways, right? One is you go find a new place that can give you all these things in a package of work. The other is you totally split it out of work. That means you take all these other needs of yours another way, you go on a date. Go make some friends and hang out with some people or go and help out in society, do some care work and all that.

There are many things that are going on. I think Singapore government is also trying to do a lot of these things: getting people to go back to society, put more money in a lot of these NGOs, a lot of these initiatives. I know there are a few guys that are running this whole engineering thing where you can go and help to fix things. I can’t remember the name, but if any of you NGOs listening and you want to propagate all these extra stuff that you’re doing… okay, not say extra, but all these things that you’re doing and you think our community could send some people over, let us know. We could give you a shoutout. 

But, yeah. That is the idea. When your incentive system change, you will feel empty. You will need to meet your higher order needs. In this situation, you can either quit your job or you can fulfill all these needs elsewhere. I hope this gives you a clearer idea because I know a lot of people, when they talk about this… “aww you feel empty” blah, blah, blah, it’s very spiritual, very voovoo. I hate those. I hate those voovoo kind of thing so I hope I have anchored this in a clearer idea why your incentive system has changed over time, why you’re in such a situation and what can you go about doing. Hopefully, it helps you to get a clearer idea: should you quit your job or should you just fulfill your needs elsewhere? 

Of course the third situation where I think you should quit your job is what I call when you have an opportunity of a lifetime. Opportunity is also one of those words that’s being thrown around every day. “This is a new opportunity” blah, blah, blah and all that jazz. Generally, I am a hype averse and I’m learning why I am so over time, I will share with you guys more as I recalibrate what is hype and all because I think the world is moving slightly different so I need to recalibrate this idea of maybe I shouldn’t be so afraid of hype and I should join in a little bit more. I just need to cover my base so I will talk a little bit more about that another time.

But I want to point out this thing called opportunity. Opportunity is a word that’s being thrown around a lot. A situation where under normal circumstances, you will never get this. Opportunity, to me, is defined as under normal circumstances, you will never get this. Let’s say you are born into an average family like myself. Under normal circumstances, you will never go into the best schools. You will never get a scholarship. That is normal circumstances, right? 

Because you are born into an average family, you really think you can become a dragon and a phoenix? It’s a bit hard which is why, if you break through, that is an opportunity. If you got a scholarship, that is an opportunity. You should take it. Same for when it comes to career. Under normal circumstances, you may never get promoted. You may be quite good and middle management, but you will never move up because let’s say nothing happens in a company or you’re not being spotted. 

Let’s say somebody in the higher wrung, something happened to them, they couldn’t fill the role and in the short period of time, they needed to fill someone and they want to promote you, this non-scholar guy that grind up from the ground and they want to promote you. What you should do? You should take it! Because that’s the opportunity of a lifetime. Under normal circumstances, you will never get it. 

This is the reality that I think a lot of people need to recognize because a lot of us want to believe that all we are special, we are exceptional and blah, blah, blah… which I don’t deny that we may be exceptional, but if we were born into a different situation or if we grew up in a different environment, we could be even more exceptional. I totally hear you on that. I’m not doubting the individual but I’m just recognizing that where are you, how are you born into, how are you educated, what is your social status at this point in time, there is a normal trajectory for that. 

Only when something exceptional happens will you be able to break through and under those situations, you must take the opportunity. I think you must take the opportunity. Let’s say you have a bunch of great friends. They started a company and when they first start, it’s a bit cock and they’re like “hmm I don’t know whether I can do this. It’s a bit weird” but they are starting this whole new, interesting technology which you actually have some sort of fascination for. You are in a relevant space and they wanted to recruit you. 

At first, you will be like “hmm, I don’t know”. Of course, because when they have nothing, you are their opportunity. They are not your opportunity because under normal circumstances, you can easily get work in a startup, but after they grow and they become much bigger, more dominant in their funding and all that jazz… now, if they come back to you and say “hey brother, you want to be our CTO because you have relevant tech experience in this space”… whether is it engineering, whatever. 

Under this situation now, what does that mean? It means in normal circumstances, you cannot get it ever, right? So okay, time to jump. That is my view of things so always remember that if anything that comes to you and wrapped as an opportunity, but under normal circumstances, you can easily do that, then you are the other person’s opportunity or you are the company’s opportunity. It is not your opportunity. Hear me? 

Only quit your job… actually, I’m quite a big proponent of this because I believe that… what is the worst? Just go back. Continue to do your work and continue to offer your service in exchange for money and all that. It’s fine. Under a situation where it is an opportunity, ask yourself: normally, can I get this? Can I get this kind of jump? Can I get this kind of new tech growth? Can I get this… join this space? If under normal circumstances, you canot, this is an opportunity. You should grab it. 

If it’s like “join something, sell something” blah, blah, blah… I don’t want to name names, but you get the idea. Everybody calls it opportunity, right? Dropshipping, blah, blah, blah. But everyone is doing it and you can do it at any time. How is that an opportunity? You can ride something. Eventually, it may become an opportunity, but it shouldn’t be mesmerized as an opportunity right from the start. It could be “oh, I’m trying this side thing. I’ve been trying this e-commerce thing” and all that, but always remember: under normal circumstances, do you get such a thing? If it is, then it is not an opportunity for you. You are the opportunity for the other party. If it’s not, then it’s an opportunity for you.

So, yeah. I hope you will learn something useful. I know a lot of discussion can be deeper and we can continue chatting on all of this as we go along on the next few episodes. We’re going to spend more time to talk about work and the rat race. 

So yes, I’m going to sum up today’s episode on the three points of when should you quit your job? I know I have moved away from the full, full, feel, feel kind of things, because to me, those things are important. I’m not saying they’re not, you must recognize how you feel, recognize whether you’re feeling fulfilled and all that. Yes, all these are great, but there’s absence of discussion of what situation should I quit? Think about this as some of the best situations to quit your job in my view, okay? 

Number one is when your sector is shrinking and you survive restructuring. If you survive restructuring, you’re validated as good quality. You should go out there and try to find another job and get a better job and come in and negotiate with your boss and what have you. You are defined as someone that is of quality and you shouldn’t feel great that you know… “I survived restructuring” because the resources are going to keep shrinking. The company may have shrinking margins. It’s not a great place to be any more. 

Number two is when you feel empty. Your incentive structures have recalibrated overtime. When you first started, you were young, broke and what have you but now you have some sort of, house, you have some sort of wealth together and all that jazz. You have a life partner that can support each other so you have a lot more things and you have more options, more things to choose. You can recalibrate this incentive system of yours going into higher order needs.

You can either get that from another company or you can fulfill all these higher order needs elsewhere. If you feel like I don’t want to fulfill anywhere. I just want to quit my job and take a break. Why not? Just go for it. 

Number three is when you have an opportunity of a lifetime. When you have an opportunity of a lifetime, you should grab on it, whether your competitor poach you to take a higher role or whether internally there’s a promotion and you gotta go for it, your friends start a thriving company and you want to jump in. There’s a new sector out there that you think you have relevant space and they’re growing super fast, 200, 300% every year, maybe it’s time to go for it. 

Some of these situations are opportunity of a lifetime where under normal trajectory of yours, you will never meet so those are best times to take. Under all other times, most of the time, you are the opportunity. So yes, I hope you learnt something useful today. See ya!

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Hey, I hope you learnt some good stuff and I am learning how to record here remotely and all that jazz so if you have any questions about remote working, about the gig economy, about geoarbitrage, I think it’s a great time to ask me. I have a lot of people that I can talk to and I will bring on some good friends to interview.

Of course, following on today’s topic. I’m not saying that you definitely should quit your job but I’m saying that we’ve taken two years to rethink about what is life and all that. I do think in our generation, the relationship with work is very different. The relationship with money, work and all these things are changing, which is amazing, right? Because empowered by technology… if you think about it, we today can really just not work anymore. We can nationalize all the machines if we want to and we could produce enough just on machines alone and that’s amazing.

Never in human history can machines do everything for us such that we can survive and do our own thing and have fun and do our own jazz so I think it is a good time for us to recalibrate. But of course, like I said, out of these three situations is a lot more about choices and measuring and all that.

If you have a family, your fixed expenses, maybe you want to look at sizing down your expenses so you have more options. All that stuff, we can talk about another time. But these three situations are what I think is definitely a good time to quit, but this is a personal viewpoint, not saying that you must take it.

If you have any other things that you want to clarify, join our Telegram group, have some fun and yeah, we’ll learn as we go along. Next week, we’re going to talk a little bit about remote working and geoarbitrage. I know a lot of people are thinking about it. “I’m going to be a digital nomad” and all that jazz. So yeah, I will share with you a little bit more next week about remote working and geoarbitrage. See ya guys.

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