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A Gentleman’s Guide to Stepping Down at the Right Time

How to know when it’s time to quit your job, and how best to do it

Maybe things have been stale at work for a while now. Maybe you have a new micromanaging boss that you’re positive you can’t work with. Maybe you’re just DONE with those fucking fuckers and you need to tell everyone to go fuck themselves. No matter the situation, knowing exactly when to quit a job isn’t easy, so consider which of the following situations apply before flipping your desk and storming out the front door.

The Stale Job

You’ve been at your job for a while now and the same old duties bore the shit out of you. Regardless, you may not want to leave your job just yet — at least, not before you try a few things first. HR recruiter Holly Oths recommends that you have a talk with your supervisor and see if there may be a special project or new duties you can take on to shake up some of the monotony in your routine.

If your supervisor isn’t supportive in this effort, it may be wise to look at your organization’s internal postings, as most companies like to hire from within. If there are no appealing opportunities, or if your company is too small to offer much diversity in what you’re doing, then yeah, it’s time for you to step down from this boring ass job and head somewhere that challenges you more.

The ‘I Can’t Advance Any Further at This Company’ Job

Before you abandon a dead-end job, you want to be sure that you actually don’t have any prospects there. “Unless you’re with a big corporate company that handles your career track, no one is going to do this for you,” points out human resources manager Vaness Wiley. She recommends bringing up the subject with a manager during a performance evaluation or some similar meeting. Let them know your desire to advance, and they should appreciate that you’re interested.

If they don’t seem supportive, that’s a red flag. “Sometimes people like the person in the role they have now,” says Wiley. “That role may be hard to fill, so perhaps they don’t want to risk losing you.” A good, supportive manager should support your career growth, though, especially if you’re at a company where there’s enough room and different departments to move up. Just be careful how you frame the conversation: Wiley says to present the subject as though you want to “contribute more to the organization,” instead of looking like you just want a promotion or you’re going to jump ship.

But perhaps you feel like you’re ineligible for a promotion because you’re being blackballed, or that someone doesn’t want you to move up. You’ll be able to tell if this is the case by looking at internal postings and expressing an interest. If you get an, “I don’t think you’re a fit for that” from a supervisor or higher up, it’s a good sign that they prefer you right where you are and have no desire to promote you, maybe ever. So start steppin’.

The ‘I’ve Accomplished All I Can Here’ Job

Nothing left for you to accomplish at your current employer? Well, before you decide that’s the case, “you should pressure test that,” says Josh Miller, executive coach and author of I Call Bullshit: Live Your Life, Not Someone Else’s. Like the previous scenarios, you should see if there are special projects to take on or if your company has internal opportunities that you’re interested in. “If you like the company and the culture, assess your options before you throw out the baby with the bathwater,” says Miller. If you’ve explored everything and you still come to the same conclusion, you may very well have outgrown the organization. Byeee!

The ‘Being-a-Manager-Sucks’ Job

“Most managers don’t get any formal managerial training,” says Miller. Because of this, they may not be ready to lead others; they may have bad habits; or perhaps they felt like they had to become a supervisor to get the pay they wanted. If you’re a manager and don’t like it, Miller says to take a hard look at whether it’s being a manager you dislike, or if you feel like it’s the organization that’s not supporting you.

If you like developing people and teaching others but you still don’t like the position, it may be that the organization doesn’t support their middle managers. However, if you blow your lid every time you have to show that moronic junior how to use the Outlook calendar, you may not be patient enough to be in charge of anyone.

Either way, you probably will have to find a new place to work. Taking a step away from a managerial position won’t look good and would probably come with a pay cut, so when looking for that new job, just remember what you did and didn’t like about your last leadership position to help decide if you want to be a supervisor again.

The ‘I Want a Whole New Career’ Job

For those who want to move on from their current field completely, Miller says to find a friend who you can trust to be honest with you and lay out your situation. Refrain from using parents for this, as they may try too hard to protect you instead of telling you what you may need to hear. An objective, truth-telling friend may be just what you need to see if you need to stick out your present situation, or if you should give it all up to pursue your dream of viral farting.

The ‘Office-Relationship-Ended-Badly’ Job

“Don’t, don’t, don’t” is Wiley’s career advice on office romances, but if you already did, did, did, then you may have to put up with an uncomfortable period before things level out. If a fresh breakup makes work unbearable, Oths says it may be wise to take a vacation or a leave of absence and see if things blow over. If you come back and still can’t work around this person, it may be wise to look into a transfer or simply a change of your office or desk location.

If your illicit affair ends up being the favorite topic of the office rumor mill, it’s probably best to weather the storm until a new fixation comes about. If it doesn’t dissipate quickly enough, going to HR can help sometimes, but Wiley explains that all they can do is meet with people and say, “Please don’t talk about other people.” Outside of that, they can’t really control whether or not people talk about how sad you get after sex.

If all this discomfort doesn’t blow over after a few months, it may make sense to move on from this job and start fresh someplace else. Just remember to refrain from shitting where you eat, again.

The ‘They’re Downsizing, and I’m Next’ Job

This is a hard one to peg. Wiley says that unless you’re close with your supervisor on a personal level, you probably can’t be sure if your job may be made redundant by the powers-that-be. For Don Gorman, for example, who was laid off from a online clothing company in 2010, he says his only real warning beforehand was that people stopped replying to his emails a couple of weeks before he got the axe.

Wiley says that you also want to look out for your supervisor suddenly asking you to document your processes. If you’ve been doing the same job for a decade and suddenly someone whats to know how you do it, that’s probably a warning sign.

Wiley cautions that you should probably ignore too much water-cooler talk around layoffs, as speculation will run rampant. The best you can do is, if you begin to see layoffs in your company and you fear that your job may be one that’s cut, start looking for jobs right away. The difficulty, of course, may be that your job is never cut, so the goal would be to find a new job that you’re okay with taking even if you aren’t going to be laid off.

The ‘I Don’t Like Where This Company’s Heading’ Job

This is another tough one, because things probably haven’t gone bad yet, but the way your company is going is giving you pause. It may be that they’re making poor decisions and you can see that the business is deteriorating, or maybe you feel the company has become unethical and you don’t fit into the culture anymore. Whatever it is, you know that where the company is going isn’t where you want to go.

In this case, it probably makes little sense to confide in a supervisor because they may be part of the problem. Instead, “Save yourself time and start looking for a company with a better culture fit,” says Miller. “Thinking your organization may come back to where it used to be isn’t realistic.” If you stick around, Miller says that you can expect to become disgruntled, which will likely lead to a performance dip, making leaving on a good note harder to do.

When looking for a new job, never complain about the old one, Miller cautions. They’ll immediately peg you as someone who can’t conform, and they’ll probably skip over you in favor of someone with more of a “team-player” mentality.

The ‘My New Boss is a Dick’ Job

Things were fine at work until he showed up. Now you spend your work day trying to dodge that fucker and spend your nights blowing off steam by being an asshole to your family.

Wiley says that you can try to nip the mistreatment in the bud by meeting with your boss and letting them know that their particular brand of dickery doesn’t fly with you. If that doesn’t work, you may want to go to HR and have them mediate between you two. More than likely though, unless you move departments, it’s hard to work with an asshole boss, so it’s probably best to get out of there.

The ‘My Ass is About to Get Canned’ Job

“When you work at a place long enough, you can see how they treat other individuals on the firing line and you start to recognize those traits when they’re being directed toward you,” says Christopher Wallace, who narrowly dodged being fired from his job in 2016. In his case, Wallace found his role unexpectedly changed and a massive increase in the scrutiny of his work. “My supervisor even moved his desk right behind mine, less than three feet away,” Wallace shares. “Also, watch out for them moving the goalposts on you,” he says, explaining that if their expectations of you suddenly shift, they may be trying to set you up to fail.

Building a paper trail is another clue that you’re about to be canned. So if your supervisor is suddenly emailing you with “concerns” they have while copying their boss, that should worry you. Getting a write-up for something stupid may be another sign. The idea here is to build a case against you so that you can be fired without dispute. “Also, watch out if your boss suddenly becomes less friendly with you,” Wiley warns. “It’s never easy to fire someone, and people know that people have bills and families and that they’re going to be affecting your life in a major way.” By being less personable with you, they’re trying to make things easier on themselves when they finally do get rid of you.

In this situation, try your best to buy yourself some time. For Wallace, he used an old back injury to his advantage. “I went to the doctor to see if I could could get some time off, and as it turned out, I really did have something wrong with my back.” With a healthy bank of sick time and vacation time, Wallace spent the next two months looking for a job and never returned to his work, dodging a bullet clearly marked for him.

Next Steps

Whichever reason applies to you, you want to try to set yourself up with a new job before departing the old one. “You don’t go to the airport and just hop on an airplane,” says Miller. “You do your research first.” Make sure you know where you’re going before you leave where you are and be especially careful of making rash, emotional decisions that can have huge impacts on your future.

Wiley stresses the importance of the customary standard of giving two weeks notice, saying that it can burn a bridge pretty bad if you don’t. Trying to jump too quickly to the next thing might actually hurt you with the new job, too. “If you say you can start tomorrow, that can be a warning sign to your new employer. They may end up thinking that you can’t handle things appropriately if you ever left them,” Wiley explains.

Do what you can to not burn things down as you leave. It’s nice to have a safety net out there, and even if you never go back, Miller cautions that “it’s a small world,” and you never know who knows who: A burnt bridge may haunt you for a while.

Unless of course, you find a pretty fucking awesome way to burn that bridge! For example: After years of mistreatment at the hands of a Rhode Island hotel, Joey La Neve DeFrancesco had enough. He and his coworkers had endured crazy shift schedules, managers who stole their tips and constant disrespect, so after trying to fix things by forming a union for service-sector employees, Joey needed to move on and did so by concocting the most obnoxious plan possible.

After working a double shift while sick, Joey finally decided that he’d had enough and reached out to a street band he used to play in. Once they arrived, he entered the hotel with the band, waited for the douchiest of his bosses and handed him a resignation letter. Then the band burst into song and lead Joey triumphantly from the building.

While Joey says that he still thinks the best thing to do is try to fix things the right way, if that fails, try to find a way to “put the power in your own hands,” even if it’s only for one glorious minute.

Sweet revenge indeed.