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6 Better Questions To Ask Yourself Than "Should I Quit My Job?"

There's no one reason to quit a job you aren't happy with, but some may be better than others.

[Photo: Flickr user Florian .]

As you already know, making decisions can be hard—especially when they feel like the kind that can permanently alter the direction of your life. As a decision coach, I’ve heard it all. And what I get asked often are questions related to careers. In fact, it probably won’t come as a surprise to you that one of the most common decisions people struggle with is whether—and when—to quit a job.

There are plenty of reasons you might be motivated to leave, some good and some very, very bad. Whatever boat you’re in, you’re probably wishing someone else would just make the call for you. While I can’t do that, I can provide a guide for deciding whether or not to jump ship based on six common scenarios.

1. Should I Quit My Job If I Don't Have Anything Lined Up?

The short answer? Probably not. If it takes you a lot longer than expected to find something else, you could end up taking something that you dislike even more—or that pulls you off the track you’ve been working toward—just to pay the bills.

However, sometimes a job is taking such a toll on your mental health that you have to get out. If you’re desperate to leave and don’t have somewhere else to go, do these three things first.

First, figure out how long it will take you to save enough money to live for up to six months without a paycheck.

Second, pick a "quitting date" in your head: This is the day you’ll hand in your notice. (Don’t tell your boss yet; but having that date set, even if you’re the only one who knows it, will make it easier to get through the workday.)

Third, save like crazy! Cut all unnecessary spending. Sock away every penny you have in what you can now call your "get out of hell" fund. Then, when you’ve hit your monetary target, give notice and start looking for something new.

Related: 4 Lessons I Learned From Quitting My Job With No Backup Plan

2. Should I Quit My Job To Go Back To School?

Many people who are considering going back to school aren’t happy with their current job—and they’re just not sure what to do next. Going back to school means they can put off making job-related decisions, at least for a couple of years. So if you’re in that boat, ask yourself what I ask my clients: "If I had a job that I loved, would I still want to go back to school?"

If the answer is no, then your next steps should be focused on finding a better position and developing the skills and experience that’ll get you one. In too many cases, going back to school’s just an expensive method of procrastination, resulting in a not-very-useful degree, tens of thousands of dollars worth of debt—and still no idea what you want to do next.

On the other hand, if you know exactly what you want to study, have a solid (that means detailed) plan for paying off the debt you’ll incur, and know that having this degree will make a quantifiable, guaranteed difference in the salary and/or prestige level of the jobs you’ll be able to get afterwards, then go for it.

Related: Should I Go To Grad School? 5 Questions To Make Sure It’s The Right Move

3. Should I Quit My Job To Freelance?

Before you decide if you’re ready to become a full-time freelancer, ask yourself: How many clients can I count on right now? Not potential clients, but people I know will pay me money to do work for them? And how much can I be sure I’ll take in each month?

Unless you can make rent with that number, stay at your job a while longer. Work on your freelance business on the side, grow your clients, and put out feelers for new ones. There are few things more stressful than trying to scrape together enough work to pay your bills, and you might find yourself dreaming of the regular paycheck you left behind.

Related: Every Resource A Full-Time Freelancer Could Ever Need (Plus Some)

4. Should I Quit My Job And Take a Lower-Paid One In My Dream Field?

Be really honest with yourself: Can you can get by on the lower salary—and not feel taken advantage of? Are the adjustments you’d have to make on the smaller side (packing your lunch each day) or larger (moving to a different apartment with two roommates)?

Next, consider how short-term (or long-term) this more frugal lifestyle would be. Is there going to be room for advancement in your new field? Can you see a clear path from the new job to your dream job? If so, I’d say go for it. But if it’s going to be five years before you make half of what you’re making now, see if there aren’t smaller steps you can take to incorporate more of what you love into your current role, as opposed to taking the leap right now.

Related: A Career Changer’s Guide To Switching Industries Without Going Broke

5. Should I Quit My Job And Go Work At A Brand New Startup?

It’s common thinking that taking a job at a startup is inherently risky, but it’s worth remembering that no job’s guaranteed. You could be laid off tomorrow—from anywhere. The key, though, isn’t just to join one for the sake of doing it. Do your research to see if the company has a viable business plan (and if you’ll still be employed down the road).

Additionally, lean startups can offer more responsibilities and a shorter ladder to advancement. That means you’ll learn new skills (fast!) and be trusted with more than you’re doing right now. You could leapfrog over a bunch of intermediary levels and go straight from a low-level position to one more senior than you’d qualify for in the same time in a more traditional field.

If you’re the type of person who’s willing to put in lots of hours, who’ll do work that might not appear in your job description, and who thrives in an unstable environment (which are all common startup scenarios), then working at one could be a smart move for you.

Related: 5 Ways To Know If Joining A Startup Is Worth The Risk

6. Should I Quit My Job And Travel the World?

If you’re at a point in your life where you don’t have kids, a mortgage, or elderly parents who need lots of help from you, there will probably never be a better time for you to quit your job and travel. Just be realistic, and remember that the longer you’re away from the workforce, the longer it’ll take you to get where you want to go on your career path. But once you’ve got the basics in place (enough money saved, a realistic idea of how much plane tickets, accommodations, and a plan for restarting your career once you get back), do it!

Plus, there are a couple of things you can do now to make life easier on your return. First, don’t burn any bridges at your job. Give plenty of notice and prepare everything you can for your replacement. You might not want to work there again, but you should leave with your reputation intact. (It’ll help you get a good reference later.) Second, if you love your job and have a good relationship with your boss, consider that maybe you don’t have to leave permanently. Could you arrange for a sabbatical? Might there be an opportunity for you to freelance for the organization when you get back? Bring these options up and see what your manager says before you give notice.

Additionally, when your return date is a month or so away, start sending out emails to your network. Let them know you’re going to be back in town and that you’ll be looking for work. Having a handful of coffee dates and informational interviews already set up for the week you get back is going to feel a lot better than staring at your empty bank account and applying for sketchy jobs because you’re panicking upon your return.

Related: I Quit My Job To Travel The World And I Don’t Regret It For One Second

Quitting can seem hugely risky, but if you take steps to mitigate that risk (building up your savings, establishing a good network, developing valuable skills), then making the decision to try something new can be the best thing you ever did.

This article originally appeared on The Daily Muse and is reprinted with permission.

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