“I wish I could quit my job” are words that most of you reading this have probably uttered before. I know what you might also be thinking: such typical first-world millennial problems! But it happens to the best of us, whether it’s because we’re simply burnt out, or because we’re stuck in jobs that we aren’t truly passionate about.
Wishing to quit and doing it are 2 completely different things. And when I did it at my previous job, pretty much all of my friends applauded me for doing something they’d always dreamt of. The only thing was, there was a lot more to the romanticised notion of “following your heart”. Here’s what really went down:
Note: All this is based on my personal experience, and the situation may differ for different people.
So, before keyboard warriors start hurling words like “entitled millennial” about, let’s clear some things up.
I had previously left a comfy career in the media industry in Kuala Lumpur to become a cabin crew for Singapore Airlines. This was in a bid to travel the world, earn more money, and have a quarter-life YOLO stint before I settled down. Prior to this, I had always taken calculated moves with my career – only leaving a job should I have a good backup in place.
Now don’t get me wrong, being a cabin crew was a once-in-a-lifetime experience I’ve never regretted. But 2.5 years in and I was perpetually riddled with terrible anxiety. I hated not knowing if my next flight was a lion’s den with a particularly nasty crew member or passenger. Plus, behind a facade of glamorous hair and makeup, work was physically taxing. 
Painful days aside, I had amazing experiences onboard that I’ll always cherish. Needless to say I have mad respect for crew who make a career out of this – but this job just wasn’t for me.
Image credit: Jessica Fang
On top of that, this job caused me to always be M.I.A. when it came to spending time with loved ones. I was always either abroad, or recuperating in bed completely knackered from flights. Worst still, I dragged myself through all this knowing I was “stuck” in a career I wasn’t truly passionate about, but was too exhausted to find another job.
It got to a point where just waking up each day felt unbearable, and I could no longer cope with feeling frustrated and hopeless all the time. So without a second thought, I resigned without securing another job, and finally waved goodbye to life in the skies. 
My last flight was filled with crew who were arguing with each other throughout – needless to say, the look of joy on my face after I stepped out of the terminal was legit.
Image credit: Jessica Fang
When I did that, a lot of friends gushed about how they wished they no longer had to deal with the daily struggles they faced at work. That, and take a break without worrying about their next gig. It all seemed like a dream come true from the outside, but I wasn’t prepared for the harsh reality that followed: unemployment for nearly half a year.
Below is what I went through, with tips on how to “survive” joblessness post-YOLO-resignation.
Needless to say, not having to wake up to a job that shrouded me in anxiety was initially extremely liberating. I no longer had to bid for annual leave or tediously swap flights for days off. And I didn’t have to paint my nails or put a full face of makeup on for work. That – plus no more obligation to be constantly courteous and make nice with hundreds of strangers each day.
Not having a care in the world was exactly what I needed to recuperate from never having taken a proper break from work for some 7 years prior. 
By my 2nd month of funemployment, I fell into the habit of waking up at 2PM and sleeping at 4AM, and lounging in front of the TV all day.
Image credit: Jessica Fang
But after about a month or so, “funemployment” lost its charm on me. I had planned to use my free time to brush up on my hobbies and take language and art classes. Instead, I fell into a cycle of watching Netflix and indulging my video game habit all day long.
And I wasn’t alone on this – many of my friends who’d taken significant time off work have also experienced this trap of unproductivity.
There was one particular day where I paid my rent and realised my bank account balance had dwindled more than I expected it to – and I had nothing to show for it. No new skills or experiences, just the after-effects of constantly ordering from food deliveries and buying PS4 games.
My laziness eventually backfired on me. Should I have used up this time to start focusing on upskilling or looking for a job, the few months that followed might’ve been less painful.
Tip: If you’re planning to quit your job but don’t have a backup yet, prepare a schedule of to-dos. Set personal goals to hit by specific dates, and send yourself reminders if you tend to procrastinate. Check out these free productivity apps if you need a boost.
Having a plan may not sound as YOLO as the idea of quitting your job, but it will help alleviate any productivity funk you may fall into.
The thing about quitting your job without a backup is…well, you don’t have a backup. There are people who are lucky and coveted enough to be able to find another position as soon as they’re ready to kick back into action. Others like me? Not so much.
I could list down a myriad of reasons – or excuses – as to why it was so difficult for me to find a job, but none of it changes the fact that Singapore’s job market is extremely competitive. It also didn’t help my case that the only experience I had working in Singapore was with SIA. Plus, I wasn’t qualified enough for the media jobs that I was ambitiously eyeing.
Many companies tend to ghost candidates who don’t get the job, so prepare to wait…and then wait some more.
After 2 months of slacking, it took another 3 months for me to finally snag a small handful of job offers. 3 months wasn’t long per se, but after you send out a hundred applications and only receive 10 replies, job hunting can get extremely demoralising. It didn’t help that some companies required several rounds of interviews which stretched over a couple of months.
Tip: Prep your CV and portfolio before you leave your company, while your achievements are still fresh. It may seem like a difficult step when you’re already exhausted at work. But it’ll be all ready for you to send out once you start applying for jobs.
While you’re enjoying your life of freedom, don’t alienate yourself from your work-related acquaintances. Add them on platforms like LinkedIn or even Facebook. These connections could potentially help you score that new job, or even provide alternative forms of work for you.
I’d always kept in touch with my former colleagues in the magazine industry in KL. This was how I managed to continue writing freelance while I was unemployed.
Check out these job-hunting tips and LinkedIn profile tips if you don’t know where to start.
I was about 4 months into unemployment when I really began to get desperate. My small freelance gigs were not able to financially tide me through. I was barely getting responses from media companies. So I began applying for jobs in sales that I knew I could get thanks to my experience with SIA.
By doing so, I was immediately offered a job as an insurance agent. Now here’s where you can say I got a little entitled: I decided to turn it down because taking up this job was as good as me staying in SIA – I would’ve been doing something I knew I wasn’t passionate about, and dread heading to work each day. 
My friends meant well – especially since some of them had been in the same boat before. But no one really saw the struggle that happened behind-the-scenes.
Image credit: Jessica Fang
Tip: You quit your last job for a reason. Don’t bother applying for jobs that will devalue your experience. That, or place you in a similar situation you wanted to get out of in the first place.
Also, don’t wait too long to start sending out your resume. A good buffer is about 1 month post-resignation so you can avoid awkward answers when potential employers ask you about your “break”.
As soon as you see a position that’s suitable for you, apply immediately. If you get the job, you can let your employer know that can only start in 1-2 months time.
Let’s backtrack to before you hand in that resignation, and talk about money. I was pretty frugal with my cash while I was flying, and managed to amass quite a lot of savings over 2.5 years. But if you’re living on several months on savings alone, it’ll run out fast, especially when you can’t help but splurge on those cups of BBT to kill time. 
Tip: Have savings equal to 6 months of your salary to tide you through at least 6 months of unemployment. Avoid splurging on luxuries like a 3-month-long Eurotrip, in favour of more affordable holidays to nearby countries. My R&R breaks were spent in Kuala Lumpur, where I could take advantage of the favourable exchange rate.
Budgeting is also important so you don’t deplete your savings too quickly. Prioritise necessities like utility bills and food, and try not to spend excessively on luxuries like shopping and partying. It’s easier said than done, of course, given the amount of free time you have.
It does help if your family is able to cushion the blow, but don’t expect them to readily help you. After all, money issues tend to cause friction. Always be open and talk to them about your to-be financial situation if you’re thinking of quitting your job.
If you’ve been reading this far, you can already tell that my situation was filled with irony. I had quit my job in order to find solace for my mental health, but by being unprepared, it ended up backfiring on me.
That said, my mental health did not take months of joblessness and uncertainty very well. Think 4am anxiety attacks and extremely dark thoughts of worthlessness wondering if I simply wasn’t good enough for Singapore’s workforce.
Tip: Never shut off. Be honest with people you can trust or consider counselling if you have frequent bouts of spiralling negative thoughts. It also helps to detox from social media – during this time, I deleted my Instagram and Facebook account as I found myself constantly comparing my desolate situation with my friends’ happy lives and successful careers.
Most importantly, ask for help or accept help when it’s offered. I had wanted to “do it all” on my own. But when you’re in a pit of disparity, sometimes a helping hand can make all the difference.
In a twist of fate, a friend offered to refer me to TheSmartLocal. Although I was throughly exhausted from the string of companies ghosting and rejecting me, I forced myself to write in. Needless to say, pushing forth got me out of the jobless funk, and now here I am…writing this!
From then, I realised that it’s always going to be a “no” if you don’t bother trying. And even when it doesn’t feel like it, the stars will align and job opportunities will come if you put in the work, like tailoring your resume and cover letter for the roles you’re applying for.
Check out these job search mistakes to avoid and online interview tips to brush up on job-hunting. Also, read these tips on mental health and mental health support workshops if you’re experiencing feelings of hopelessness and depression.
And if you’re looking for a job, check out openings at TheSmartLocal – sorry, couldn’t help it.
Quitting a job without a backup has probably worked for some of you reading this. But for me, it was a whole new ballgame I wasn’t prepared for.
Don’t get me wrong – I have zero regrets on leaving a workplace that I didn’t see a future at. But the glamorised idea of marching out of your workplace to finally “live your best life”, is simply overrated. Unless you have zero commitments – and tons of cash to fall back on – it can be an uphill struggle to get back on your feet.
So if you’re currently in the same shoes as I was, it’s best to really prepare before taking the leap. It could be the best decision you’ve ever made in your life. But it also comes with a reality check that not everyone would be willing to face.
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