Think it’s Time to Leave Your Job? 4 Questions to Ask Yourself Before You Tender Your Resignation.

Death to Stock Image and Mumsy

“The grass is greener on the other side” and it most certainly can be, but I’m also a strong believer in this other saying, “The grass is greener where you water it”. Not always, but in many situations.

Millennials, like you and me, are often painted with the same broad strokes of being characteristically innovative, but lazy, unmotivated, and sorely lacking in loyalty; the sort of people who would always believe in the former grass situation rather than latter. I’m not going to debate that stereotype today (there’s no point in that, people believe what they want to), but I am going to write about what happens when the grass does appear much greener and you’re tempted to leave your job. This piece lists some things to consider before you type out that resignation letter and submit it.

For the Gen X or Baby Boomer Bosses

On the flip side, if you’re a Gen X or Baby Boomer boss (or HR personnel) still trying to wrap your head around us strange, unfamiliar creatures, read Kenneth’s #CareerLaunch piece on Why Millennials in Singapore Leave their Jobs. The rest is kinda up to you… and your HR policies.

1. Are You Burnt Out?

The big follow-up question is, “Is it by work, lifestyle or both?”

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Come on, I’m a millennial, I know how it is. I suffer from FOMO or Fear of Missing Out (When is this actually gonna be a medical condition?) all the time.

The pressure of being “on par” with the rest of our social circle’s social media life is real and a 24/7 thing, be it on LinkedIn (“Bloody hell, she’s already a Manager?!”) or Instagram (“I can’t believe they’re at another awesome new top restaurant! How do they find the time?”).

If you’re thinking of leaving because you’re exhausted and feel that you’re burning out, have you really gotten honest on why you’re in need of a break?

Are you subconsciously doing the following and blaming yourself for not getting there because “everyone seems to juggle that just fine!”:

  • Relentlessly chasing a social life or lifestyle that is out of reach? (Extreme fitness regimes and late night expensive parties, we’re looking at you!)
  • Putting in excessive hours into work (to the point it affects your rest) in order to meet goals set to accelerate your career progression?

There is absolutely nothing “wrong” with the above two scenarios, but like I always remind myself, it’s important to be honest with myself on what I am doing and what objectives are so that I can get real with myself when I am just “doing things for the sake of doing them”. Sometimes I fall into the trap of thinking that it will reap the result I want because I am doing “more” and working myself harder, instead of actually observing when something may not be productive and changing the way I do it. (See point 3.)

Anyhow, there are instances, your (dead end) job requires so much and you may feel trapped in a situation where you’re not able to manage your bosses or get the help you need to work effectively (even after various personal adjustments).

A tell-tale sign that it’s time to go is if you hit a wall and find yourself unable to get out of hitting walls over and over again on the same issue even after sharing with your superior  or upper management on the issues faced AND proactively finding new ways to avoid it. Also, if you’re constantly stuck in the same ‘ol massive time suck and no one seems to mind that you are even after raise it one too many times. If that’s the case, you’ll know it’s time to find some place new where YOU can work out a realistic and reasonable balance (keyword is reasonable) to produce work that makes you feel some achievement and satisfaction.

2. Have You Outgrown Your Job?

If you’re thinking yes, are you clear on your own personal development?


As a millennial employee, many of us desire growth even when we don’t realise it. Whether or not we chase it, that’s another thing, but for that group of us who feel a little uncomfortable in comfort and who find status quo of doing the same thing over and over again stale and unsatisfying, yes, here’s the deal: You’re feeling that way because you’re not growing.

Still, it’s convenient to say, let me do a job switch, because that will always present a new challenge, especially in the early days when there are adjustments to be made, new ways of working and fresh environment to figure out. While that’s awesome, that’s still just super… superficial. What happens when the new job, isn’t new anymore?

Something I found helpful was to ensure my own growth no matter where I am by figuring out what personally brings me achievement and satisfaction along with what areas I’d want to be challenged. But first, do I know what I want in my career?

When you’re new to the working world, it’s totally okay to not know and take on a junior role to get started and learn a whole bunch of new skills and see what really compels you, but if you’re bored at work and thinking it’s time for a new job, it’s important to ask yourself, “What have I learnt? What do I need to learn that I haven’t?”

By this time though, you’ll somehow need to figure out in which direction you’d want to develop in. Are you hoping to be a Marketing Communications professional or would you rather pursue something more niche in Digital Marketing? You’ll need some sort of goal at the very least because that’s how you hunt down ways to learn how to get better at work in those skill sets you require to move on… and up. Then speak to your boss or manager in a similar field to seek advice on what is needed to get there. Which brings me to the next point.

3. Do You Have a Good Mentor?

And are you actually listening and willing to work to get where you want to be with that insight?


Honestly, a good mentor is far and few between even though successful people can be found in every organisation. Here are a list of nine characteristics a good mentor will have, which I find pretty spot on.

Just a gentle reminder: If you’re not speaking to people in your company outside of the “comfort group” of peers like people in managerial positions, how are you going to identify a mentor anyway? In order to do so, you’ll need to be willing to take risks in meeting and having heartfelt conversations with different people and sharing your aspirations without fear of judgement.

Once you have found someone you feel you can learn from, the important thing, aside from openly sharing your career goals, is to really ask questions on how to get there and really listen to the answers given!

Before that, don’t forget to Google and read up on those fields. Having SOME knowledge and a humble desire to learn more from the person you speak to (and not debate with them on your opinion of what you think is needed) is more important that you’d imagine. No one wants to guide a know-it-all and it is not an easy task to guide someone who doesn’t seem to care enough to do prior research before asking questions.

When tasks are given they all serve a purpose. If you’re interested in understanding the work you do, you’ll ask yourself:

  • Why is it important? What role does it have in the big scheme of things?
  • How can I bring value to the process of doing my task?
  • When are these tasks assigned to me and when can I proactively do these tasks?

Even the most trivial of tasks are building blocks to something bigger. Go do it, do it well and as you’re doing so, find ways to do it faster, then with the additional capacity, ask your mentor for more challenging tasks or hunt down projects YOU know you’ll be able to execute well.

On occasion, I notice myself getting a bit impatient or a negative thought about the task I’m assigned creeps in, and I ask myself, am I having the right appreciation for my mentors time and the right attitude towards feedback? If I’m given feedback:

  • Am I stubborn and refuse to look at it as a different perspective?
  • Do I treat the feedback on how to do something differently negatively?

It’s okay. We’re all human. We experience that defensiveness, especially as we get better at doing what we do. We just need to know when to shift out of that frame of mind when we’ve had our chance to digest it all. If I really don’t think something works, I pose questions to my mentor and share clearly my thought process. If he or she trusts me to do it the way I propose, good for me, if not, I’ve made my case and this “different way” is a learning experience.

The thing here is, when you’re making headway with your work and your working attitude is stellar, no good mentor in their right mind will refuse to give you more challenging work. In fact, it’s a relief because they have groomed someone they can rely on to deliver even with light touch guidance and they will be happy for your achievements!

4. Are You Really Tempted to Leave Because of Salary?

Or are you really leaving because of other factors and salary is just one of it?

Photograph 070 by Ashley Schweitzer found on

I kept the best for last. Salary. The thing is money is it will never really be enough and our salaries can never get “too high”.

It’s really debatable (don’t we all know that there are so many conflicting schools of thoughts on the internet), but it’s been found that while fair renumeration is important, studies have found that employee engagement is not tied to higher salaries. (Read this Harvard Business Review article “Does Money Really Affect Motivation? A Review of the Research”.)

Which begs the question, are you REALLY motivated by a higher pay check even though you wouldn’t mind it?

It probably is important, but it is unlikely the only one that takes precedence over others, unless you really have personal needs that your existing monthly salary seriously can’t support. We’re not talking wants here, by the way. We’re referring to serious medical reasons, financial commitments or family related responsibilities.

It’s always great to look at your relationship with money and what it means to you. What are your beliefs about money? That’s a good place to start. Different people have different attitudes towards it so that affects how you react to a raise and even a job offer with a higher salary.

At the end of the day, you’ll need to be satisfied with what you get and you’ll just have to honestly review your experience, the value you can bring to your company and the job market (other than just comparing with peers, especially if they are not even from the same industry) on what you could get in return that makes sense for you and doesn’t leave you resentful.

Say no to a salary that disrespects your value, but if you’ve said yes, you have to realise you’ve made your bed and you’ll have to lie in it. You don’t have to resent the decision or the company. You’ll just have to find your way out and plan your next steps.

When all’s said and done and you’re just not that into your job anymore, you’ll know what you’ll have to do. It’s whether you’re ready to do it! And if it’s time, you have to just got to go for it.

About the #CareerLaunch series

#CareerLaunch is a series of articles aimed at the millennial reader by millennials, helping them make career decisions. It is written in collaboration with Kenneth of Join the #CareerLaunch conversation! Email contact[at] and kenneth.lee.rj[at] to collaborate on future articles.

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  1. #CareerLaunch: Why Millennials in Singapore leave their jobs - - April 13, 2016

    […] I often ask people this question, more as a lead-in to self-reflection. Firstly, it helps them understand in clear terms what they define as a “need”, then allows them to list their litany of needs. By the end of that thought process (which can take an entire night), they’ll probably be able to know if this is a real problem or not. If it is, they’ll probably also figure out how much more they need. That’s highly important. Carrie’s perspective on this issue is also worth looking at, mostly because she’s asking the question of when money quits being fulfilling. […]

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