The Resignation Checklist: 25 Sneaky Ways To Bleed Your Employer Dry Before Quitting

I awoke last night in a cold sweat, gripped with the sudden realization that I have an incredibly comprehensive resignation checklist… and I’ve been selfishly sitting on it, to the detriment of the millions of Americans who’ve walked away from their jobs in recent months.

I recognize that this constitutes a top ten anime betrayal.

許してくれ。

The thing is… I’ve been daydreaming about leaving my job for years. These plans have been a part of me for so long that I kinda forgot they were plans at all. Like, I don’t necessarily notice my own breathing, stretching, or constructing elaborate fantasies about leaving corporate America forever.

Planning to quit ahead of time is a great advantage, and not everyone gets it. In most states, people can be fired suddenly, for no reason. Other people need to leave their job abruptly because of absolutely untenable issues like workplace safety or harassment. Those people do not have the luxury of planning a soft landing for themselves. 

But if you’re planning to quit voluntarily, you can do what they cannot. You can be strategic. Y’know, like Light Yagami eating potato chips! And in doing so, you can extract a ton of value back from your employer and/or your government before you go.

I’m down to just one month at my job, and I’m systematically going through this list. It will save me thousands of dollars. It will also prevent a lot of logistical headaches for my future self. Because I wanna set her up with a low stress post-job lifestyle. Listening to the hold music for the COBRA continuation assistance hotline is not on my retirement vision board!

Here’s my ultimate resignation checklist…

What about hourly workers?

Before we get into it, I’ll confess that my list skews toward salaried workers. The reason for that is simply the limitations of my own experience. I’ve worked in salaried jobs for several years, and before that I was self-employed. (Which is a schmancy way of saying “chronically underemployed,” lmaooo.)

The last time I worked hourly shifts, I was slinging physical copies of Metroid: Other M for the Wii at a GameStop. (If you bought one of them, I personally apologize for my small role in your trauma.) So yeah, it’s been a while! For those of you who have more recent experience in this department, PLEASE leave some helpful comments for your hourly siblings below.

Remember, unskilled labor is a classist myth! Whether you make four figures or six figures, we’re all on the same team.

And if you thirst for more of our dirty commie hot takes guides to working together to refocus human dignity at the center of a new workplace culture, we gotcha.

• Antiwork Is the New American Dream
• How to Use Labor Shortages to Your Advantage
• How To Support a Labor Strike with 3 Simple Steps
• 1 Easy Way All Allies Can Help Close the Gender and Racial Pay Gap
• Season 1, Episode 4: “Capitalism Is Working for Me. So How Could I Hate It?”
• Why Are Poor People Poor and Rich People Rich?

Resignation checklist: Optimize your finances

#1: Get independent logins to your company-sponsored financial accounts.

My employer has an intranet that connects me seamlessly through a VPN network to all my many horribly designed benefits portals. (Seriously. Were they personally designed by Clippy himself?!)

Once I’m not with the company anymore, I’ll need external links and the passwords to go with them. You don’t want to exit with a hearty middle finger only to come crawling back six months later for help getting your 401(k) rolled over!

#2: Front load your 401(k) contributions.

At time of writing, people under 50 may contribute up to $20,500 per year to their 401(k)s. If you’re trying to maximize your contributions to this tax-advantaged retirement account (and squeeze the most out of your employer’s matching), you’d put $1,700 per month into it.

If you know you’re quitting your job early to midway through the year, consider a strategy called front loading your 401(k). This means depositing larger payments at the start of the year instead of steady drips throughout the year.

Since I’m leaving my job in April, I would have to set my monthly 401(k) contribution to $5,000 to make up for the whole year. That’s… insane. I’m not doing that. But I am getting as close to it as I comfortably can.

#3: Max out your company’s 401(k) matching.

If your company offers 401(k) matching, front loading may also extract the most value for that benefit.

However, not all plans allow this. Front loading builds your wealth faster by giving you the whole year to earn interest. It also lets you be sneaky and take more of your soon-to-be ex-employer’s money and run. For those reasons, not all matching plans honor front loading.

If maxing out the employer match is your only reason for considering front loading, check your plan details before you commit to the strategy. Not all plans support what’s called “true up” matching, which is what you need to accomplish this.

#4: Check your vesting schedule on “extra” money like retirement matching, bonuses, or stock options.

Perks like these became fairly rare in the last twenty years. But I suspect they’ll see a resurgence in popularity if labor continues to strengthen.

Vesting can be a little confusing. Luckily, we just did a deep-dive on how vested funds work. You can read that here…

• Ask the Bitches: “Can I Quit With Unvested Funds? Or Am I Walking Away From Too Much Money?”

But the tl;dr is that some financial benefits don’t truly become yours until you’ve worked at the company for an arbitrary amount of time. So before you quit, you need to know if the money that appears to be yours will actually go poof! because you were three months shy of its vestment date.

Not that you asked, but I personally think deferred compensation is denied compensation. I never count on vesting funds, because I want the psychological freedom to walk away from jobs that don’t work for me. (Leaving money on the table causes me psychic damage—and they know it.)

#5: Secure loans for major purchases now.

Six years ago, I closed on a house the same week I started a brand new job. My bank was surprisingly chill about it. They accepted a copy of my formal offer letter as proof of income.

If I were trying to do that now, I don’t know if it would be so easy. Inflation and interest rates are rising. Money won’t shoot out of banks quite like it did in the good old days—like a greased pig on a Slip ‘N Slide. So if you’re thinking about major purchases like a home, car, or educational degree, secure those loans before you quit your job.

There is an exception. If you expect a large pay bump in your next role, hold off. You may qualify with more lenders and better terms with a higher income.

Resignation checklist: Choose the right time to quit

#6: Plan to quit in the first few days of a new month to extend your healthcare coverage an extra month.

Employer sponsored healthcare benefits are one of my least favorite features of this timeline. But that’s all the more reason to exploit them where we can.

At most companies, your healthcare benefits remain active through your last month of employment. For example: if you quit on January 2nd, you have 29 days before you need to get a new plan. But if you quit on January 27th, you have only 4 days. For that reason, I highly recommend quitting in the first few days of a month. It saves you money and buys you time.

But do your homework first, because although that’s what’s most common, it’s not the only possibility. Some businesses offer a flat four-week continuation, and some stop cold on your last day. Bastards.

#7: Plan to quit after January to collect a full year’s paid vacation time.

If you get paid vacation time and you live in a state that considers vacation time to be wages, you’re in luck. If you quit after January 1st, you’ll get a fat final paycheck for all those unused vacation days.

Unfortunately, our useless representatives don’t set this policy at the federal level. So you need to look up your state’s laws to know if it applies. Here’s a handy chart where you can look your state up.

#8: Cover an employment gap by quitting just after the new year.

There’s another good reason to quit early in the year. It’s much easier to hide an employment gap if you quit in the new year.

Now, employment gaps should be normal. For those of you who will one day sit in an interviewer’s chair, I beg you—don’t ask people to explain gaps. The company doesn’t need an explanation for how a candidate spent their time when they weren’t even employed there! It’s almost always some incredibly personal bummer shit—caregiving, illness, unemployment—that neither of you want to talk about.

#9: Plan to quit only after getting the most out of your benefits.

I get an annual bonus. It comes every year during the last week of March.

Don’t you just find it so weird and incredibly coincidental that I’m leaving the very next week?

If you have good benefits, make the most of them before you leave.

• Do you get an annual or quarterly bonus? Make your exit after that delicious extra money lands in your account.
• Are you planning for children? Suck their parental leave dry before you go! (If you’re a lady, you’ve already preemptively been punished for it, so ya might as well do it!)
• Are you considering getting a new degree? If your company offers tuition reimbursement, make use of it before you bounce.
• Do you need specialized medical care like gender transition support or fertility treatments? Those can be extraordinarily expensive, and not every plan includes them. So if you have good access now, use it before you go.
• Do you get ANY other cool perks? I’m thinking employee discounts, gym memberships, home office stipends, vehicle usage reimbursements, personal development budgets, or free tickets to sponsored events? Those are sweet perks! Vacuum that free money up. And check your employee handbook, sometimes these perks are intentionally under-advertised.

#10: Use every single sick day and vacation day that won’t be paid out.

I’m super lucky. My state compels my company pay out my vacation time. And I have a good boss, so I don’t need to lie about how I use my sick leave.

But if you aren’t that lucky and can’t look forward to getting that money back, use those days up. Use them with wanton brutality.

If I worked for a crappy company in a crappy state, I would feel no shame whatsoever in faking sick or taking staycation days. In my opinion, the easiest way to fake sick for a good chunk of time without straining your ~*acting abilities*~ is to announce that you’ve scheduled a minor surgery and will be out to recover.

(I’ve devoted many shower thoughts to this. I think the best fake surgery is a pilonidal cyst excision. It’s common, so you won’t diminish the experiences of the truly sick. It’s minor, so you won’t worry the nice people at work. Since it’s on your tailbone, you can’t really do anything but lay on your stomach for several weeks—no standing or sitting allowed. You don’t have to fake coughing or fatigue. Plus people don’t pry once they learn it’s within six inches of your bunghole. It’s the perfect crime. And you can always mention a “ripped stitch” or “infection” to prolong your paid time off. YOU’RE WELCOME.)

Resignation checklist: Get the most out of your existing healthcare

#11: Schedule your annual physical.

Thanks to the Affordable Care Act, lots of routine preventative medical procedures are now free.

Actually, it’s more accurate to say that you’ve already paid for them. So if you don’t use it, you’re wasting the money you’ve already spent on it when you paid your first insurance premium.

The first, most critical step is to schedule an annual physical exam with your general practitioner. Do it to renew outstanding prescriptions, address any health concerns, and avoid unpleasant surprises while you’re transitioning between healthcare plans.

#12: Get your vaccinations, including the flu shot.

I’m not a doctor. But I watched a lot of Scrubs, so I’ve got this.

Everyone’s lifestyles, risks, and needs are different. Talk to your doctor, ya dirty step skipper! But in general, adults need the following vaccines:

• COVID-19 vaccine and booster
• Seasonal flu shot every year to prevent influenza
• Tdap booster every 10 years to prevent tetanus, diphtheria, and pertussis
• HPV before age 26 to prevent genital warts and cancers
• And you may need more if you’re…
  • Over 50
  • Pregnant
  • Working in healthcare
  • Traveling internationally
  • Missed critical vaccines during childhood

Piggy and I have a friend who almost died in their 20s from regular ol’ influenza. It’s not just a bad cold—it’s a serious disease that claims tens of thousands of lives every year in America. So we were ferociously passionate about this even before the pandemic made it all trendy! Get your shots before you need them.

#13: Have your teeth cleaned and x-rayed, and any cavities filled.

Tooth pain is proof that god exists. And he hates you.

I barely remember orientation week of college because I was in so much pain from a tooth abscess. I even met my future coblogger during this time! (And Piggy thought I was preppy. Her bad judgment? Or my good Vicodin? You decide!*)

Most plans cover 1-2 annual cleanings and a set of x-rays. If you have a cavity or something more serious, you want it taken care of now. You don’t wanna be interviewing for new jobs with a toothache so bad you can’t think straight.

*Editor’s Note: Piggy here to set the record straight. Bitch showed up to move-in day in an A-line skirt and kitten heels.** What the hell was I supposed to think?

**Author’s Note: THEY WERE 2.5 INCH MULES, NOT KITTEN HEELS, GET IT RIGHT. I HAVE LOW ARCHES AND AN INDOMITABLE SPIRIT.

#14: Get new glasses and/or contact lenses.

Most plans cover an annual eye exam, plus a set amount reimbursed for new lenses every year and new frames every-other year.

Again, you’ve really already paid for it. When you switch to a new insurance, you can get even more! So get a fresh prescription. If you don’t need anything, use your imagination. Get a second pair, higher quality contacts, or prescription sunglasses. Just get something. Why waste it?

#15: Stockpile extras of your most necessary prescriptions.

If you’re leaving your job voluntarily, hopefully you already have a plan to move to a new insurance provider. But if that plan falls through, you don’t want to be without the medications you most need. You may need extra time to find a new provider if your current doctors don’t take your new insurance.

I remember running out of birth control pills during a job transition. Gotta tell you: not an ideal time to experiment with your hormones. My body became 1,000% convinced it was pregnant—sitcom cliché pregnant. I made my partner go to a convenience store after midnight for poofy-style Cheetos because the idea of not having them nearly brought me to tears.

If your doctor is cool, ask if they can write you a prescription for a longer period of time. If they aren’t—or if your medication is a controlled substance, so they can’t—just be savvy and stock up some extras in whatever way you have to, so long as you’re not endangering yourself.

#16: Pursue any necessary medical diagnoses before you quit.

If you have a niggling feeling that your weird mole has become a Weird Mole, it’s better to get it looked at now. You don’t have to solve every issue. It’s enough to seek the clarity of a diagnosis and familiarize yourself with treatment plans.

When you start your next job, you’ll likely be offered tiers of healthcare plans. If you know you have a condition that requires expensive procedures, like surgery or physical therapy, you can strategically choose a higher tier to offset the damage.

My only caveat is mental health. I would not recommend starting therapy just before quitting your job. Finding a good therapist and building a relationship with them is exhausting. I’d hate to see you throw that work away because your therapist doesn’t accept your new insurance plan. But you know best, so trust your own judgement about what you need.

Resignation checklist: Get the data you’ll need in the future

#17: Make personal copies of critical files

Make sure you walk away with everything you need to secure another job in the future. Some companies frown on you making personal copies of your work. Some outright forbid it. But personally, I take what I want and don’t even bother to ask permission.

That’s because I work as a graphic designer. It would be impossible for me to demonstrate my skills without examples of my past work. So any time I make something great for any employer, it goes right in my (password-protected, hidden from search engines) personal portfolio. If it contained proprietary information, I redacted it or replaced key parts with dummy text before using it.

You’re all smart people. I think you know the difference between some portfolio pieces or supportive analytics reports and, uh, trade secrets that will send your cheeks to federal prison.

#18: Copy important emails to your personal account

Whenever I get a really important email, I put it in a folder called “useful.” And when I’m ready to leave a job, I download those emails or forward them to my personal address.

This is especially important if you’re leaving your employer on bad terms. We pray at the Holy Church of Document Everything. If you’ve been harassed or treated badly, make sure your future self has the proof they need to pursue justice. Check out this guide for more specific steps to take if you’re in this situation…

• Sexual Harassment: How to Identify and Fight It in the Workplace

#19: Switch any account logins that use your work email address

Your work email will likely be deleted or passed on to someone else. Check your password manager for non-work-related accounts linked to it, and switch them over now. It’ll be a lot harder—or even impossible—to do so after you’ve lost access to your work email forever.

Resignation checklist: Solidify relationships

#20: Save coworkers you like

LinkedIn is the easiest way to stay in touch on a neutral, professional level. Whenever I leave a job, I invite everyone to add me as part of my final farewell email.

If you found someone who’s more like a friend, add them on whatever social platforms you use.

#21: Delete coworkers you hate

When I announced my impending retirement on my private Instagram, I got a lot of positive comments from friends and acquaintances.

I also got one snarky comment from a former manager. “Aw, just when I was about to call you about a job!” Cue stink face. This dude and I haven’t spoken in years. And when I was in his department, he criminally underpaid me based on my age. I’d rather eat ass 40 hours a week than work for him again. So ew! So no!

I deleted him. It’s the perfect time to clean house! You’ll be so much happier if these tools aren’t living rent-free in your feeds.

#22: Ask for LinkedIn recommendations

For a variety of reasons, professional references don’t carry the weight in the hiring process they once did. Which is a shame, because I think they’re very illuminating. (And a pretty great way to screen out high-purity whackadoos.)

One of my core strengths in the workplace is building trust and relationships. So I need another way to express that, y’know, people like me and enjoy working with me?

Public LinkedIn recommendations have been great for this reason. When I leave a job, I usually ask several people to write one for me. Since it lives on my profile, future recruiters can see what I’m like to work with before they ever interview me. I only ask people I know I can trust, and in a clear “no pressure” way. And I try to include a spread of coworkers, managers, and mentors to showcase my ~*social adaptability.*~

Resignation checklist: Miscellaneous

#23. Steal office supplies

I haven’t been to my office since the pandemic started, so I don’t even know what’s in there anymore. Pens? Awkwardly sized notebooks? Maybe a cardigan, at the most. Nothing I’ve missed. So I don’t think I’ll go back.

… Oh god. I just considered… What if I left snacks in my desk?

Do you think they’re so covered in mold they’re technically, legally alive?

Will I have to send a team in hazmat suits to establish diplomatic relations with them?!

Regardless, I sanction the theft of office supplies. You gave them the best years of your life. PLUNDER THEM OF THEIR PRECIOUS POST-IT NOTES AND UGLY TEAM T-SHIRTS LEFTOVER FROM LAST YEAR’S FUNDRAISER!

Personally, my modus operandi is mugs. I steal a mug from the last workplace and use it at the next one. Drinking from it reminds me of all the lessons I learned in the past. And when it’s time to move on, I leave the old one behind for someone else to steal anew.

#24. Take time off for yourself

This is a luxury. It shouldn’t be! But it is, because you need money, time, and support to do it properly. So if you can, please consider taking a few days or weeks to enjoy being your autonomous, uncommodified self.

For one reason or another, I’ve never been able to take time off between jobs. I’ve always had to rush into the next thing. And now that I’m at the end of my career, I realize how much I regret that. Everyone deserves time to rest and reflect after a major life change, and prepare for what comes next.

#25. Go out as a legend

I don’t know what it is. Maybe I just love a dramatic ending. But I often find myself honoring the ends of eras with a bit of harmless devilry.

When my beloved first dormitory was sold, I said goodbye to the building by instigating a massive multi-floor water gun brawl. My memory is awful—I have a Bad Brain™—but I will never forget streaking down her hallways and coursing up her staircases, fingers blistered from the cheap pump-action knock-off Super Soakers we’d found for $1 in Chinatown. It was the first place I’d lived where I truly felt I belonged. And it was the send-off she deserved before being torn down to the studs to make more apartments for millionaires.

This spirit has carried through to my jobs as well.

The last time I quit a job (not my current job, but the one before), it was to escape a truly terrible workplace. It was toxic and oppressive, with an omnipresent tension in the air. There were good people on my team, and I hated to leave them behind to suffer without me.

I wanted to make sure I left like a legend. So I set off two (figurative) bombs.

First, I detonated an immediate accountability bomb. I hadn’t been the victim of the racism, the nepotism, the bullying, and the sexism… but I’d seen it happening to others. People with families and obligations that made it difficult to speak up or walk away. I did my best to speak for them, leaving an anonymized molten hot dossier with HR. My CMO left our exit interview feeling “humiliated” by the way I characterized my time there. (Good for you, Barbara! You should be!)

Second, I detonated a time-delayed comedy bomb. I hid photos of hairless cats shellacked in Geocities-era sparkle gifs throughout our team’s project folders. Each one was annotated, in lime green Comic Sans font, with different callbacks and inside jokes. My team was still finding them months after I left, and sent me texts howling with laughter when one appeared in a hidden layer or device wallpaper.

I felt gutted to leave the good, kind people on my team behind. I knew that despite my best struggles, HR and leadership wouldn’t do a damn thing to make real change. It made me feel so powerless. Leaving subversive little gifts of laughter felt like the right way to stay connected to them, and give them hope that they’d soon escape too. Which they all did, in their own time.

For the rest, I channeled a lot of that anguish into words. First for catharsis; then, hoping to guide others to be more effective change-makers than I was. I teamed up with Piggy, whose different experiences somehow brought her to the exact same place. And eventually we published everything. That’s the blog you’re reading today, and the calling I’ll continue to pursue into retirement.

That’s why my final piece of advice is to go out like a legend. I think we’ve been far too conditioned to hide our true selves while at work, to act like perfect commodified automatons. Whether quitting your job leaves you feeling sad, angry, conflicted, or joyful, find a way to let those feelings live in the way you choose to quit.

Give us your tips

Readers, what do you think? Did I miss anything? I would love to hear more tips from you, especially for hourly workers or people in unique industries. Please add your thoughts to the comments below!

Piggy and I are seeking fair compensation for our writing. (Writers? Being paid?! Whatever will we think of next???) So if you liked this and would like to see more, get in on our whole Patreon situation! If this resignation checklist was helpful to you, the best way to tell us is by supporting our work.

And happy quitting! <3