Upworthy’s book GOOD PEOPLE is coming this year — pre-order now!

Shop
 Explore 

mistakes

Joy

People share their biggest job 'oopsies' and it's a celebration of human imperfection at work

Always nice to know we're not the only ones to mess up royally.

Antoni Shkraba/Canva

So many of us have had "oops" moments in our jobs.

Nobody wants to mess up in their jobs, especially in a way that's highly visible or embarrassing, but it happens even to the best of us.

And while it may not take away the red-faced embarrassment that inevitably follows a major mistake, it is always good to hear that other people have royally screwed up at work, too.

That's why a 2021 tweet from HBO Max's helpdesk about an intern sending a blank test email prompted a celebration of human imperfection as people shared their own biggest work "oopsies."

The original post on X read, "We mistakenly sent out an empty test email to a portion of our HBO Max mailing list this evening. We apologize for the inconvenience, and as the jokes pile in, yes, it was the intern. No, really. And we’re helping them through it." The ended their message with a heart emoji.

Responses to the tweet included a flood of "Dear intern," messages with people sharing encouraging words and personal faux pas, such as the 37-year-old woman who realized she'd accidentally been putting her menstrual cycle start on the company's work calendar.

Swipe through for more:

See on Instagram

The share of the MaxHelp thread on Upworthy's Instagram inspired even more people to share their work mistakes.

Here's a sampling of the oh-so-very-human stories people shared:

"Sent a press release with Pittsburgh Pubic Schools in the headline."

"I was in charge of creating tags for a local grocery chain. I proudly typed up 'Colgate Cum Comfort Toothbrush.' It should’ve said 'gum comfort.' This tag went to 200+ stores. I came in late the day after they hit stores and couldn’t figure out why I had roughly 80 emails. After dying inside at least 3x, I finally went to my boss to apologize. She was laughing harder than I expected. I was 30. I had been there for 5yrs. This tag is now framed in my living room."

"I once worked for a large, very high quality (and high fees) childcare company…many of our parents were high profile people. I sent an email to an entire centre with over 700 families telling them about some new activities we had planned for the Tiny Tits room…instead of the Tiny Tots room. Thankfully most the parents had a sense of humor about it 😂😂"

"I made a huge mistake at work yesterday and informed my boss via email. He never responded, and I was nervous all night. This morning, he sent me a quick email in response: 'Do not worry about this… we will fix it together when I come in.' Not only did his kind response make me feel much better, but he ended up screwing up even worse than I had lol it was great."

N"ot an electronic mistake but - my first night as a waitress I dropped a hot fudge sundae on a man's lap and proceeded to grab a rag and wipe his crotch to get the whip cream off. It took me a few seconds to realize what I was doing and the whole table was laughing at me but I thought I would die. I did get a decent tip out of it, though. 😂"

"I once worked for a visitor’s center in a small town. I was in charge of mailing out a monthly calendar to the community of the different groups in town. I put that 'Bikers Against Child Support' we’re in town for a weekend rally. The name of the group is 'Bikers Against Child Abuse.' I found out when a couple of big names in the community got their calendar and called my boss. Everyone laughed at the mistake and the biker group got a kick out of it. I haven’t worked there in 15 years and it is still brought up each year at their rally."

"I work for a rock radio station in Canada and once deleted ALL of the Canadian music out of the system. On a Friday. At 4:30. Good times. Still employed though!"

"Dear Intern, I did a search and delete for soft returns in a word doc and when I reviewed it with the lead engineers at Hewlett-Packard they noted 17 instances of the word penis inserted, where it should have been pen is inserted."

"Dear Intern, I once sent out a confidential email about an upcoming stock plan to all our European employees. I was a 33 year old lawyer. We all survived and you will too. 😘"

"Dear Intern, I used to type retail ads for our local newspaper. One ad was for part-time work, and I didn't find out until it was published in the paper that I had typed the heading as 'Fart Time'. A local radio DJ took it upon himself to shout that out far and wide. He thought it was hilarious. I was mortified. However... no one actually knew I made the typo except my immediate co-workers. (Thank God.) But afterward, the owner of the advertising agency withdrew all of her commercial time from the radio station because of it, so, he lost out, and I was vindicated. 😏 🙌"

People loved reading through all the examples of humans not being perfect and others being understanding and compassionate about it:

"I ❤️❤️❤️ this. Let’s normalize making mistakes. We all do it. So nice to see humans uplifting other humans dealing with their human-ness."

"Without the mistake, all these very genuine human connections would not be possible."

"So much humanity and compassion…Am i living in a parallel world? I even smiled sincerely."

Here's to us all being being human, in all our embarrassingly imperfect glory.

From Your Site Articles

humanity

One mom's strong case for letting your kid make lots of mistakes.

There was a kid running at the neighborhood pool the other day.

Photo via iStock.

The pool attendant asked him to walk , as pool attendants have done since pools existed. Then the boy’s dad (a big-chested, serious kind of guy ) came over to the attendant and told him that as the child’s father, he was the only one who could tell his kid what to do. He said that if the attendant has something to say, it should be directed at him.

Basically, don’t talk to his kid, and this dad will decide if his kid needs direction.

The attendant kept his cool and replied — carefully — that it was his job to make sure that people follow the pool rules.

He explained that "no running" is pretty much the universal pool rule. The dad pushed back and added some aggressive posturing to intimidate the pool guy, saying that he didn’t see anything wrong with what his kid was doing. As far as he was concerned, the pool guy needed to back off.

In summary: The kid was free to run at the pool because the dad said so, screw the pool rules (this is America!), nobody tells my kid what to do except me.

There’s a weird sort of fear spreading among reasonable grown-ups.

My sister’s family had some friends over, and one of the adults gave one of my sister’s kids some polite direction about sharing. Then the grown-up realized the grave error in 21st century feedback rules concerning kids who aren’t yours and apologized to my sister for shamefully overstepping.

"Are you KIDDING?" my sister said. "I absolutely want you to tell my kids if they’re doing something you don’t think they should be doing! In fact, do more of it! They need to learn to hear things from people other than me."

If I’m the only one who can tell my kids what to do, I’ve failed them in every possible way by making sure they have completely unrealistic expectations of the world.

Also, I can’t ever die because my kids won’t be able to take care of themselves. Following Big-Chested Dad at the Pool’s logic, a lifeguard can’t lifeguard, teachers can’t teach, coaches can’t coach and, later in life, managers can’t manage ... you see where this is going, right?

Is cushiony perfection for our kids a new national obsession?

We all know That Mom in the neighborhood, who is literally at the school every day, escalating everything to make sure her kid gets an A, is chosen for student council, or gets placed in the gifted program. Later, when her kid is in college, professors will hang up on her and laugh behind her back because she’ll call about something that’s none of her business.

You know this kid. We all know this kid. Photo via iStock.

My middle-schooler and his project partner failed to turn an assignment in on time after many reminders of the deadline. The other kid’s mom (who I met once, briefly) came to my house and wouldn’t leave until I talked with her for nearly an hour about the injustice of it.

She was heartbroken for the disappointment her kid must be feeling at the failure and wanted to fix it somehow. She left, but I think it was only because I told her I had no idea how to reverse the course of what happened and suggested she escalate to a school administrator if she believed the teacher could be convinced to reverse his decision. I haven’t heard back from her.

I don’t mean to brag, but my high schooler fails at quite a few things, too.

None of them too epic, but there’s still time. We talked about it recently. I told him it’s my job to let him fail while he’s still at home with me because he needs to learn how to lose his shit and then pick it up and move forward.

That’s the most major of life skills — in my experience anyway — and I’ll be damned if any kid of mine is going to fall to pieces his first semester in college because I’m not there to fix life for him.

You remember that person from your dorm days precisely because that person became an utterly forgettable shadow.

This is an open notice to people who know my kids: You can tell them what to do.

It’s really, really OK. Tell them not to put their feet up on your coffee table. Tell them to stop running, not to play with that knife, or not to touch your things.

Actually, now that they’re older, you’ll likely be telling them not to eat all of your potato chips and beef jerky and not to take that drink onto your freshly cleaned carpet.

Whatever the rules are at your place, tell my kid to fall in. I have a selfish motive.

Maybe the road to success is paved with mistakes.

You can’t achieve perfection. You can’t even fool the rest of the world into thinking you have.

Instead, getting somewhere — getting anywhere — in life is about going through a process of experimenting, making mistakes, learning, and improving.

If you try to get around that process, the only thing that happens is you become completely wound up in yourself and you fail to improve your work, your product, or your creative skills.

I’ve learned over the last 15 years that success in life isn’t best measured by what you achieve. It’s measured by what you overcome. For me, that has meant overcoming the sheer weight of my own mistakes.

If you pretend that you don’t make mistakes, you lose the chance to do remarkable things.

Instead, you’ll spend your time doing safe things. So celebrate your mistakes. Don’t glorify them — but look at them as chips that can be cashed in for future success.

All photos via Redd Angelo, used with permission.

Here are six mistakes I think you almost have to make to be successful and fulfilled in life:

1. Trust the wrong people.

When you’re starting out, you want to be a trusting person. Start out optimistic, open-minded, and free. Don’t be too quick to judge because you’ll be basing that judgment on zero data.

By trusting everyone, you’re going to end up trusting the wrong people. This just happens, because the world is full of crappy types who want to screw you over and take everything you’ve got.

This is going to teach you who is actually worth trusting in the future. It will give you the information you need to make informed and valuable choices around who is worth trusting and who is not worth your time. Trust the wrong people because it’s one of the only ways to end up trusting the right ones.

2. Screw up your finances.

Everyone should make at least one bad financial decision. This is something I truly believe. There’s just something about that moment of realization, when it hits you that you’ve made a truly terrible mistake with your money, that can sober you up for life.

My mistake? Debt. $10,000 worth of credit card debt, racked up funding software development. That’s something you can’t just shrug off or think away with positive thoughts. That’s something that wakes you up sweating and panicking.

I’m on my way out of that. Well on my way. It’s a mistake I can’t see myself making again, and it’s a mistake I know I’ve learned from.

3. Choose a bad career path.

I love it when people tell me they started out on a career, founded a company, designed something, and then quit when they realized it wasn’t for them. How brave is that? To be able to admit that you walked the wrong path and take the time to switch?

I think one of the only ways to know what you really want to do is to try a whole bunch of things and learn what it feels like when you’re doing the right one. That gives you the knowledge you need to make a better choice.

Choosing a bad career path sucks, and it can feel like a huge setback. I’ve done it enough times to know that when you’re right in the middle of it, you will feel like a failure. Don’t look on it as a waste of time. Trust me, it’s not.

4. Make selfish decisions.

When you’re young, you’re selfish. This isn’t an indictment of millennials — I am one. The fact is, we are taught empathy throughout our formative years, but it’s not a skill that can be learned in the abstract. Empathy is something that can only be picked up with hands-on experience.

And that means you’re going to make selfish decisions. Maybe you’ll screw over the co-founder of your start-up. Choose money over your family. Break up with a person who trusted you, in the worst possible way. I’ve done all of that.

Seeing the impact of those selfish choices breaks you. In little ways, in big ways. It changes the way you see other people. If you’re lucky, it stops you from being able to pretend that everyone else in the world is a non-player-character in a game.

5. Take the easy way out.

It’s so hard not to do this. It’s so hard not to take the easy way out when you know how much simpler it will make your life. And when you haven’t been burned, it’s hard to see a reason why you shouldn’t try to shift the blame or do a half-assed job.

But do it once, and you should learn something: Taking the easy way out will often come back to bite you. You will likely regret it. Quality will suffer, your reputation will suffer, and your own experience of it may even be terrible.

“Don’t do anything by half. If you love someone, love them with all your soul. When you go to work, work your ass off. When you hate someone, hate them until it hurts.” — Henry Rollins

6. Work too hard.

I see this from would-be start-up founders and artists and writers every day. They talk about hustling 18 hours a day. They tell you they’ve worked every weekend, every night. They buy into the fallacy that letting your work rule every waking moment is the only way to be successful.

“I’ll sleep when I’m dead.”

“It’s all part of the hustle.”

“You can start up or rest. You can’t do both.”

This is all a complete fabrication. It’s been propagated by the insane work schedules of a small percentage of billionaire founders and visionary creatives who were able to function on a fraction of sleep every night.

They are the exception. You are the rule. If you choose to work too hard once and you burn out, that’s an awesome opportunity to learn. But you have to learn from it. You have to learn that trying to maintain that level of skewed work-life balance is rarely going to work for you.

One of the guiding forces in my life has been my ability to screw up completely, get back on my feet, and keep on swinging.

Did I shut down a creative services agency because I had zero idea of how to run a business? Absolutely. Did I get completely ripped off by a former business partner and end up massively in debt? I won’t deny it.

Did I drop out of law school and fail to accomplish anything more meaningful than binge-watching TV for seven months? That checks out.

But the unifying theme behind every mistake I’ve made is that no matter how long it took, I learned something. I took something home. I gained valuable information about myself, my challenges, and my path.

So screw up once in a while. Hell, screw up every day! And take something from those mistakes, because in my book, messing up is a quicker road to success and satisfaction than being perfect every day of the week.