Skip to main content
Updated date:

8 Binary Questions You Should Ask Yourself Before You Resign

Before you quit your job, try to ask yourself these important questions.

Before you quit your job, try to ask yourself these important questions.

Thinking about quitting your job is no fun at all when you don’t have a transition plan. It becomes easier if you’ve already secured a job offer, or if you happen to have multiple options open that can land you your next role. And for some lucky few, quitting a job means giving up a life being under the employ of someone who has control over your time and energy, moving on to independent living and unbridled autonomy.

If you happened to stumble upon this article, you’re probably not the latter example, but are instead more likely to be at a stage of second-guessing your decision to leave your current job. At the time that this was first written, the Great Resignation was in full swing in the United States, with millions of Americans deciding to leave their jobs because of any or a combination of the following factors:

  • Their company is mandating a return to the office (RTO), but they want to continue working remotely;
  • They want to stay for good at their new residence, but with RTO mandates, living near the workplace becomes a given;
  • They feel burned out because of the working conditions and/or demands during the pandemic;
  • They feel micromanaged because of the employee tracking that goes on for remote workers;
  • They’re unable to see a clear path for how their career will progress, especially with the uncertain times and volatile conditions;
  • They feel disengaged with their co-workers and/or manager;
  • They feel underappreciated while at the same time feel overloaded with work.

These are just seven of the reasons for employee attrition that I could think of, that I feel are closely tied with the Great Resignation. And there are surely checklists out there worth reading, to see if you’re prepared to join the millions who have already turned in their resignation notices. Instead of going wide and covering all bases (finances, healthcare coverage, etc.) what we will do here is far simpler – a list of eight Yes-or-No questions, inward and reflective in nature, to ask yourself before you leave:

1. Is the grass truly greener on the other side?

It’s hard to tell if conditions, compensation, and career outlook are truly better on the company you are considering joining. Perhaps compensation would be the easiest to tell, since during a job offer that information is normally provided – but even then, it may not be readily apparent that your salary would be commensurate with your workload and responsibilities.

It’s also easy to get enamored when you find a job elsewhere that provides better pay with less responsibilities and accompanying workload. It’s an opportunity to discover if you’re being taken advantage of to near-exploitation territory, but it’s also a timely self-check to understand better just how much your current employer values your work.

If you answer YES: it’s good to compare your current workload with the expected workload on your next job. And good to connect with current employees of your prospective employer and see what they think.

If you answer NO: then you must have some renewed appreciation for your job, or whichever reason it might be.

2. Have I thought through the possibility of returning?

“Don’t burn your bridges,” the old adage says. If your cause for resigning is not interpersonal in nature, then it’s highly important that you transition in a positive note. And even if it’s on a highly positive way that you are heading out, you always try to think of the possibility of coming back. There are known benefits to coming back to your old employer – some have reported significant salary increases, a positive change in the company’s perception of you, better working conditions, and much else. While it’s an obvious sign of loyalty towards your employer when you eventually turn back around and beg for your old job, it also gives the employer confidence of its market edge against others. Things could also take a turn for the worse on your next job, so having a path to return would come in handy.

If you answer YES: it might mean your company is worth returning to – and, staying at, in the first place.

If you answer NO: it’s probably not too bad to entertain your chance of coming back. It must really suck as a workplace if you’d never want to return at all costs.

3. Do I have enough backup strategies in case my next job doesn’t work out as expected?

You might find it handy to keep in contact with other job prospects while you’re still starting out on your next role. If you haven’t transitioned yet, then it might be helpful to think of backup strategies in case you’d later on realize that moving out was a big mistake. It’s completely normal for things not to go as planned, and you shouldn’t be embarrassed about this. What will help you is to think of other options you can take – a part-time job here, a short study leave to cultivate your skills, volunteering, etc.

If you answer YES: then you are going about your transition practically – not too high, not too low.

If you answer NO: then you must be extremely confident that everything will work out well on your next stop.

The universe is unpredictable. Backup strategies always come in handy.

The universe is unpredictable. Backup strategies always come in handy.

4. Am I just having a bad stretch?

How long a bad stretch exactly is, depends from person-to-person and on what the surrounding circumstances are. Sometimes, our bad stretches are caused by things completely outside of our control and we fail to realize this, at worst cases only after we’d already turned in our resignation.

The prominent organizational psychologist Adam Grant emphasizes that you shouldn’t quit on a bad day. By the same reasoning, try to contemplate if the reason you are planning to resign is because of a period of time that’s going unusually negative for you. Point out both the professional and personal circumstances that might have something to do with your bad stretch.

If you answer YES: take time to regroup. Whether it’s burnout, poor health, family events, or whatever reason – taking time to regain your footing is important.

If you answer NO: then you probably have already compared your bad stretch to some of your ‘best’ stretches in your current role.

5. Will I eventually fall into the same pattern of discontent?

There are a lot of factors that go into becoming a discontented employee. Typically, interpersonal relationships at work have something to do with it – not being appreciated by your boss enough, not ‘fitting in’ with your team’s culture, not being motivated with what you’re being asked to do, etc.

If you have enough wisdom and foresight to answer this question, then good for you. Otherwise, try to look for the path that transformed you into a discontented employee, if you are one. Was it something your boss said to you? Was it because of organizational changes that the company made? Answering this question is tricky, but at the same time it’s good to be self-aware of the things that trigger you or bring you to discontent at work.

If you answer YES: maybe your current job or employer isn’t exactly the problem. Maybe a career shift would help alleviate the discontent you are feeling.

If you answer NO: then perhaps there’s something about the work culture in your prospective company that’s clearly missing in your current one.

6. Are my co-workers or teammates helping me cope with the demands of my current job?

There’s something extremely underrated about having teammates or co-workers who genuinely care about. Not only will having ones who care help you stay at your job, but it shows that you are in a culture where being in a team has more depth in meaning. In some work cultures, being in a team doesn’t mean much – you go about each of your works robotically, you try not to step into someone’s toes, and there’s apathy when it comes to helping someone out.

If you answer YES: then you are quite lucky. With the heavy competition for promotions and raises that goes on inside organizations, having co-workers who deliberately carve out time to help you out means everything.

If you answer NO: you probably need to ask yourself more questions – am I in the wrong team? Is my company’s culture the problem? Am I intimidating others? And more. Get deeper into why you aren’t getting any help.

7. Am I ready for the workload in store for me at my next job?

In most cases, the workload that’s advertised on the job description is NOT the full story. If you are determined to leave your current job, it’s practical to expect that the lightness of the workload at your next stop is actually undersold. Try to ask people from that company how they are handling their workload, and employee reviews are also available online in websites like Glassdoor and Jobstreet.

If you answer YES: then you must be confident about your ability to adjust and adapt.

If you answer NO: maybe try to talk to your manager about your existing workload. Maybe some changes can be made that will make you work for effectively, with a lot less stress involved.

8. Will my current skills still add value in the next few years?

This last binary question to ask yourself is probably the most important one – and it’s not limited to the short-term future. With a rapidly changing labor industry, some skills become outdated too quickly. For example, jobs in tech that are too dependent on the mastery of specific tools, are probably ones you should be wary about. That is why in most disciplines, they emphasize the importance of ‘mastering the skill, not the tool’ or ‘knowing the principle, not the action.’

While you are in a phase of transition, it is very timely for you to take a look at yourself and evaluate whether you still have skills that will add value to businesses or industries in the next few years. Your skills may add value now, but what if there’s a significant technological development and your specialties are no longer relevant?

If you answer YES: way to go! You are clearly a person who never stops learning.

If you answer NO: your transition time is a way to add or cultivate upon your skills. Dedicate significant time in rebranding yourself as a worker.

Good luck to you!

I’m not sure how you answered these eight questions – surely there are more important questions to ask yourself aside from the ones I pointed out. Feel free to let me know via email or the Comments if you feel like these eight questions have any relevance to what you’re going through. With my experience of having gone jobless multiple times, I wish I’d been able to ask myself these questions before I decided on anything. Good luck!

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

Related Articles