'She's one of those super aggressive types that wants to be CEO before she is 45': Gen X employee gets revenge on overbearing boss by scheduling emails to send all throughout the night

Author image for Isabella Penn
Isabella Penn
Aug 24, 2024 11:00 PM EDT

To be fair, this boss had it coming. The concept of 'work-life balance' is becoming increasingly normalized throughout the workforce, as it should. No one wants to spend their entire lives planning around their jobs. And although that used to be the case in generations past, nowadays, employees don't stand for mistreatment; instead, they just leave. 

Well, this Gen X employee can't really leave the company. He's been there for years and is nearing his retirement. So, instead of up and quitting, he decided to get the best petty revenge he could think of. And played his cards just right. This entitled boss is newish to the company, and she's a workaholic. The Original Poster (OP) even described her as "one of those super aggressive types that want to be CEO before she is 45". You get the picture. After getting fed up with her constant emails from 7 am to 12 am that demanded an immediate response, the OP decided to schedule urgent emails to send to her from midnight to 7 am, right during her sleeping hours. And the best part is, it actually worked. 

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  • 01
    r/antiwork ⚫2 hr. ago virginia-gunner I broke my Boss using Microsoft Outlook Delayed Email
    via u/virginia-gunner
  • 02
    Longish story so I will try to keep it short. New job, new boss, old problems. She's one of those super aggressive types that wants to be CEO before she is 45 so she's doing it on the backs of the entire team. I'm close to retirement. I give zero
    via u/virginia-gunner
  • 03
    phucks. Her MO is to send emails all day asking & expecting an immediate response. She sometimes emails up until midnight, and starts again always after 7AM. So I figured she is a Midnight to 7AM sleeper. She has three kids, a 9 year
    via u/virginia-gunner
  • 04
    old, a 12, and a 17. The 17 year old kid has most of her attention her right now because of 17 year old girl drama. No further explanation needed. So Outlook has a function when you can delay sending an email to a set time. So
    via u/virginia-gunner
  • 05
    for the last month I have been selecting certain emails to be delayed-sent at set times, beginning at 11:30PM, 11:47 PM, 11:58PM, 12:01AM, 12:07AM, 12:15AM, 1AM, 2:30AM, so on a so forth. I am bracketing the time I know she is winding down getting ready for bed and trying to fall asleep. My goal is to spin her
    via u/virginia-gunner
  • 06
    up on random days via email so she can't get to sleep easily. I don't do it to all of my emails, just the random emails I need to send her during the day when I am the topic starter, and usually random subjects like: "Hey I noticed we are overspending New
    via u/virginia-gunner
  • 07
    Business Funds by 17% on this project, but we could reduce that spend by 3% by switching to using one of the interns who get paid less than Barbara, who is paid more." These emails trigger her because I know she is super sensitive about budget
    via u/virginia-gunner
  • 08
    overspend and also older workers who cost her more to use. She usually can't not answer. And I know she leaves her smartphone on next to her bed, and won't silence it. My goal is to deny her sleep and to spin her up all night long so she can't get back to sleep. I know her husband
    via u/virginia-gunner
  • 09
    (informally via a co-worker) and he told him that he's been sleeping in a spare bedroom because she won't silence her phone and it "dings" all night with emails. That's me.
    via u/virginia-gunner
  • 10
    So, these delayed emails I am sending, she can't figure out if I am using delayed send or not (The IT team works for me, so they aren't helping her) but the lack of sleep is starting to make her crack. She asked me last week if I am working all night. I told
    via u/virginia-gunner
  • 11
    her the wife and I are getting a divorce so I am so depressed that I bury myself in work all night and doze in my office chair at home. I don't actually. I'm in bed hugging the wife and sleeping like a baby from 10PM to 7AM. Except for certain
    via u/virginia-gunner
  • 12
    days when I like to awake at 4-5AM and go for a walk or jog in the early morning. Yesterday during a staff meeting she dozed off right in the middle of the meeting. She just nodded off almost in mid sentence. All of us in the room
    via u/virginia-gunner
  • 13
    stopped talking while she snored softly for about 4 minutes and then popped awake. Nobody said a word. While she was dozing I sent her a delayed email set to arrive at 12:05 AM tonight. I'm awake right now. It's 5AM. I've been sending her live emails for the last hour.
    via u/virginia-gunner
  • 14
    She's responding. She's losing her mind right now, I can tell from the tone of her emails. Happy Friday Gwen "Whatsoever a man soweth, that shall he also reap." Galatians VI. One of my favorite bible passages.
    via u/virginia-gunner
  • 15
    Transmutagen 9h ago The best part of this is that all she has to do to not be affected is just ignore her work email when she's not at work like a normal human being.
    via u/Transmutagen
  • 16
    rexel99 • 9h ago Sad, petty man, keep it up.
    via u/rexel99
  • 17
    sing_4_theday • 8h ago I had a boss that loved suspense times. I need that by 5pm, get it to me by 3:45, no later than the end of today. It didn't matter how big or small a task, it always came with a due date and time. And I would use the delay send to email the suspense at 4:59, 3:44, 11:59. We didn't get along before and delaying the email didn't help any. But just like most bosses, he left before he could do anything to stop me.
    via u/sing_4_theday
  • 18
    sevbenup . 8h ago "While she was dozing I sent a delayed email" I hope this is real I am loving this whole story
    via u/sevbenup
  • 19
    . HootenannyNinja • 8h ago Why does this read like a 5th episode twist in a true crime podcast about a manager snapping and going on a rampage with an AR-15. Career woman, wife, loving mother, mass murder... the Gwen Story.
    via u/HootenannyNinja
  • 20
    Euphoric-Elk-940 . 9h ago Thank you for such a wonderful post to start my Friday morning. You have made my day.
    via u/Euphoric-Elk-940
  • 21
    SOS 8986
    via fauxels

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boss employee drama job work petty revenge ceo Office gen x Horrible Bosses Reddit karma
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