Work is a funny thing, isn’t it? It consumes so much of so many of our lives, and we all have such a different experience with it. Some of us are privileged enough to be working at a job that we enjoy, others aren’t so lucky. Some of us work standard nine-to-five shifts, while others work outrageously early morning shifts or outrageously late night shifts.
When it comes to bosses, too, we have a whole range of different experiences. Maybe we are the boss. Maybe we're the lowest rung on the company ladder. Maybe one's boss is a sour-faced, corporate enforcer, like the Terminator in a shirt and tie. Maybe, on the other hand, they’re the kind of person who imposes mandatory Nerf battles on everyone in the office on Friday afternoons.
We just never know. That’s what makes this wacky ride we call life so rich. The fact is, though, we can often get an impression of how things are going to play out early on. First impressions are sometimes totally way off, but there’s usually enough there to go on — enough to get the measure of a boss or employee. What kind of relationship will the two of us have? Probably not one like this. Here are some of the most hilariously uncomfortable boss-employee exchanges ever committed to text message. Or social media. Or plain old pen and paper.
20 Having Some Toilet Trouble On The Tollway
Now, I appreciate autocorrect. I really do. Back in my day, predictive texting wasn’t really a thing. We had to laboriously type out each individual letter, hitting the same key three times to get to a C, F, I, and so on. How do you think text speak came about? Because we were all wasting literal seconds of our lives writing out phrases like see you.
You might not think you’re saving much time by replacing that six letter nonsense with C U, but on an ancient Nokia 3310, you really were.
These days, autocorrects tries to save us time and let us actually write in full sentences, but… well, sometimes this happens. Autocorrect’s hit rate isn’t bad at all, but sometimes, tollways become toilets.
19 Because Your Boss Is Lowkey A Walrus
There are some things in life we just do not question. They’re here, we’re grateful, there’s no need to look too deeply into it. How do airplanes fly? How are hot dogs made? How does autocorrect know where we’re going with this sentence?
As far as the latter’s concerned, the fact is that sometimes it clearly doesn’t. The tech in question isn’t nearly fancy enough to be able to try and predict based on context within a sentence, which is relieving for anyone who’s seen the Terminator movies, but not so helpful for texters.
Come on, autocorrect. You’re not even trying any more. How could ‘walrus’ possibly work in that sentence?
18 Taking Pictures Of Your Dog Instead Of Heading To Work
Now, see, this is something I can truly respect. So many workers, students, and pupils around the world will try and fob you off. They’ll try and hit you with any and every excuse they can think of. From that old classic "my dog ate my homework," to something a little more creative, there’s nary an excuse left that hasn’t been tried.
Meanwhile, this worker isn’t trying any of those shenanigans.
No lies, no bargaining, none of that. Just straight up truth. Yep, I was taking pictures of my dog instead of getting ready for work. I’m sure most pet owners can empathise with that feeling.
17 Sometimes The Boss Is As Late As You Are
So, as we’ve established, there are all kinds of bosses. If you’re the kind of person who has moved around from job to job over the years, you’ve probably experienced the rich tapestry of boss-ness that’s out there. The understanding ones, the empathetic ones, the "totally down to earth and one of the workers" ones...
They’ll all have their own approaches to the usual work-related dilemmas. Employees arriving late, for instance. There are bosses who will land on you like a sumo wrestler jumping from a ten-storey building onto a grape, and there are others who will casually arrive late right along with you. Needless to say, this boss is one of the latter camp.
16 They're SERIOUS About That Coffee
Now, I’m no coffee drinker, but from what I’ve seen, coffee is a serious, serious business.
If you’ve been chasing the bean for some time, you’ll know what a powerful draw it has.
Some become dependent on it. You hear things like I can’t start my day without coffee or don’t talk to me before I’ve had my morning coffee, but there are some who take that concept all too literally.
This person, quite clearly, is not kidding around. You’ve promised to bring their coffee, and you’d better dang well get on that.
Withdrawal is not a pretty thing. Not at all.
15 Scottish Bosses Are The Best Bosses
There’s something beautiful about the Scottish people. If you’re not from this proud, noble country, there’s something about their ways that you’ll never quite get. Like their English neighbours, they have a sense of humour that’s all their own, and wonderful, quirky ways that may seem quite alien to outsiders.
The Scots have a unique way of making absolutely everything hilarious. Here we see a worker trying to cadge themselves a day off work. Nothing unusual there, but because we’re dealing with a Scottish worker and Scottish boss, things instantly took a turn for hilarity.
So you want a day off because you supposedly have diarrhoea? It’s Sunday, friend.
14 And Scottish Resignation Letters Are The Best Too
Speaking of our friends in Scotland, what happens when they resign from a job? That’s right, hilarity ensues. As we all know, this is never a decision to take likely, and can often be the result of weeks and months of painful soul-searching. It’s like a break-up, only… you know, from a job.
Unless, as I say, you’re Scottish, in which case it’s just another opportunity to be effortlessly funny.
I’m not sure how they do it, I’m really not. All I can tell you is that this letter started off with such a professional tone (that header was bolded and underlined), before careening off into pure savagery. That sign-off, Yee Ha, is definitely the greatest thing I’ve seen today.
13 At Least Tom Is Okay With It
So, yes. This one, I’m totally on board with. Good old Tom. We could all use bosses like Tom in our lives. See that, how he takes the time to help his employees out and accommodate them? That’s what leadership is all about. You don’t take crapola, sure, but you don’t dump it all over everyone either.
He rolls with the punches and he makes things work, that’s Tom. You want your shift swapped? There you go. You want to inadvertently call him "baba" and send him kissy emojis? He’s fine with that too. He is Tom, and he knows that cell phones just love embarrassing the heck out of us at times. We could all stand to be a little more like Tom.
12 Why You Don't Lie On Your Resume
Do you remember that Friends episode where Joey attempts to speak French? Predictably, everything goes to crapola around him, and he’s left with no choice but to review his resume and remove all of the lies from it. Horseback riding? Nope. Tap dancing? Nope. Archery? Nope. Drinking a gallon of milk in 10 seconds? Well, also nope, but his attempt was hilarious.
Now, it’s not often that Joey Tribbiani teaches us valuable life lessons, but this was definitely one of them: don’t lie on your resume.
If you say you can speak fluent French, you’d better be sure that you can.
If you say you’re a keen swimmer, then heck, you’d better be prepared to swim on over to work, whatever the conditions. Apparently.
11 The Greatest Excuse EVER Isn't Going To Save You
Oh. Oh dear. Now, sure, modern technology enables us to get in touch with just about everybody we know, knew or want to get to know, wherever they may be. That’s what social media is all about, really. Connecting people. Well, connecting people and stealing jokes for the likes and retweets, but still, that counts as connecting, too.
This is all well and good, but there’s something incredibly dangerous about having all of our contacts in one convenient place like that. When you’ve got bosses and BFFs right next to each, this can so easily happen. It can never be taken back, either (does anybody believe the sorry, my friend did it thing anymore?).
There’s a simple moral to this story: don’t ditch work to lay on a beach drinking pina coladas.
10 When The Boss's Lincoln Park Snark Is On Point
See, this is exactly what happens. In this age of cyber-theft, hacking and all kinds of other shenanigans, you’ve got to be super, super careful what you put out there.
If you’re just joking along with friends in a group chat, then have at it.
If you’re dealing with sensitive information or just plain dirty lies, you’re really going to at least want to take a quick look who you’re sending this stuff to.
Come on, Ken, get with the program here.
When you’re dealing with a boss capable of this sort of razor-sharp snark, you’ve got to be extra careful.
9 The Boss Who's Always There For You... Or Not
Again, getting back to the subject of bosses, and the many colourful varieties of them that have been discovered. Some bosses are content to sit way up there in the highest tower, completely unapproachable, protected by electric fences, guard dogs, and a couple of those big old fiery eyeballs from Lord of the Rings. Others are not about that life at all.
The truly great bosses are the ones who are down there in the trenches with the rest of the staff, leading by example and toiling right along with them. This boss may not be quite there, but they’re offering support and helpful suggestions. So that’s something.
8 When They Take Your Peanut Allergy Dang Seriously
Why does it matter? Because there’s a certain give and take here... A relationship that has to be fostered. For companies to work well with clients, the management have to work well with the rest of the staff. That’s what business is all about.
If your workers don’t like or respect you, they’re not going to be giving their best, are they?
"A happy worker is a busy worker," as The Simpsons’ miserly old Mr. Burns once said. Co-operation is the key. Everyone’s got to care about each other.
What if they didn’t? What if Patrick didn’t leave his super helpful note about the peanuts?
7 When You're A Real-Life Grown Up Now
Honestly, I’m a little conflicted here. I can’t quite tell who’s to blame with this.
On the one hand, we’ve got a ruthless draconian boss, refusing to let a little thing like illness stand in the way of a work day unless it really, really has to. I’ve dealt with a few of those in my time, and you may well have done, too.
Is it that or is it employees with a history of weaseling out of work that has driven the boss to it? I wouldn’t be surprised either way, if I’m honest. I’m definitely getting a "...but you’re still coming into work, right?" meme vibe from this.
6 When The Prune Isn't Going To Take Any Of Your Crapola
Oh very dear. People never do seem to learn, do they?
As much as we all enjoy social media, it should probably come with some kind of warning.
You know, just to be sure. Something like a confirmation screen that reads, “Are you sure you want to post this? Remember, people can dang well read it. Think about it for a while. Maybe lay down in a darkened room for a moment before continuing.”
People will still insist on it, though. On dropping public posts for the entire dang world to see, and then wondering how they got into such trouble. Now this one was brutal.
5 When You're Just Not A Morning Person
Maybe it’s me. Maybe I’ve become a miserable old cynic (I’m just entering the last month of my 20's, and I’m considering buying a Harley and dyeing my hair jet black at the very thought of turning 30). Maybe I’ve just read too many of these disastrous posts over the course of researching this article. But… what? How do these things possibly happen?
We do understand what happens when we post to social media, right?
There’s no really any acceptable excuse for this sort of thing, unless you’re an OAP who’s just joining the internet age for the first time. I’m certainly no fan of mornings, so I can somewhat empathise, but still, stop with the public posts.
4 Promoting A Healthy Body Image
This is more like it, right here. This is super uplifting; the sort of message that we just don’t hear often enough these days.
Here we see a boss doing the whole boss-ing thing the right way.
We don't see some distant, unapproachable ogre, but a person. An actual human being, with a sense of humour and emotions and everything. They are out there, and they’re dang precious things.
A simple typo in a message becomes a great hunk of body positivity. That’s something I’ll always be on board with. Nope, there are no big bellies or behinds here, just totally content people who are fine exactly the way they are.
3 Lynn Is Not Impressed By Your Week At The Beach
So, yes. There are wonderful bosses out there. Understanding, friendly, supportive people, who are a pleasure to work for. The sad thing is, with a lot of such people, these traits are undervalued, or downright taken advantage of.
Give people an inch and they’ll take a mile, as they say.
The important thing is not to let anybody walk all over you. If you’re too nice, you’ll be devoured like a one-legged gazelle on a David Attenborough show. The key is to be reasonable; empathetic while still capable of dropping the ruthlessness where it’s necessary. It was definitely necessary here, and Lynn dropped it with absolutely zero remorse. There was a little smiley face, though.
2 When You Just Can't Hide Your Feelings Any More
So, over the course of this rundown, we’ve seen a lot of very different management from a lot of very different bosses. Some have been just plain vicious, some have taken the joke in their stride — there's been all sorts of varying approaches. That’s the way it’ll always be, because people are different and have different priorities when it comes to the image they want to project.
This boss right here, for instance, is the very essence of chill.
He’s cooler than those polar bears that used to cavort on the ice with Coca Cola bottles in the old commercials. This is how you defuse a possible professional disaster.
1 An IT Problem Of The Snarkiest Kind
When you get right down to the nitty-gritty, though, it’s a sad fact that things just don’t go the way you want them to sometimes. You might have an absolute nightmare of a boss or the greatest one ever, but in the end, you never really know what’s in store. A better opportunity, perhaps, career advancement, all these sorts of things.
You never quite know when you might need to leave a job, as difficult as it can be.
This is the last communication you’ll have with your boss, and you’ve got to carefully consider how you’re going to manage it. This designer left an oh-so-slightly extra message on his screen, for everybody to see.