Career

The Biggest Mistakes We Made During Our First 9-to-5 Jobs

You probably won’t forget your first kiss, but you’ll never forget the first time you hit ‘reply all’ on that snarky email about your boss. The mistakes we make in the early days of employment can be mortifying – but they also teach us how to survive in the wild jungle of the workplace.

Silly mistakes 

Some mistakes are simple accidents that perhaps can’t be avoided. You remember the first one, but the reality is you’ll probably make similar mistakes again. At least you can get a funny story out of them!

Holiday jobs in retail and hospitality are an adolescent rite of passage. “I worked at a snack bar on a Wynyard Station (in Sydney) ramp during my high school holidays,” recalls Stella. “I was asked by a customer for ‘senior service’ and so I went and got an older woman to serve him. Apparently it was a brand of cigarettes.” These days, Stella makes sure she knows all the necessary jargon in her role in public health.

Katie has a flourishing career in Events Management and Marketing, but some mistakes early on nearly threw her off course. “There was the time I did serious damage to my manager’s car the first time I took it out. Or the time that I possibly got a speeding fine that my manager got stuck paying because no one could be sure who was driving at the time.” Katie kept quiet about her indiscretion, a lesson some people learn a little too late.

Learning when to keep your mouth shut

Lauren, a journalist, learnt the hard way that “my door is always open” isn’t always as simple a statement as it seems. “There was an organisational restructure going on, and a lot of people were scared they were going to lose their jobs. I sent an email to the CEO (who had reiterated in all communication that she was available for any concerns people had about the process) saying that people weren’t clear on what was happening. I got pulled into her office and yelled at. I was trying to embarrass her, it wasn’t my place to say anything, who did I think I was? I was then told my contract was being cut.”

Jen, who now works in publishing, learned her lesson when another colleague made an email blunder. “I told too many people how I felt about other people and situations. I thought I could vent as much as I liked, but I underestimated the relationships all these people had that went back way further than their acquaintance with me. I shared an inbox with a colleague at my first office job and came in one day to a reply from a friend of hers to an email she’d sent absolutely roasting me. From my own email account. That was her mistake but it was pretty extreme and taught me a lot,” says Jen.

But Jen used this stuff up as an opportunity for personal development. “I became a better colleague from actually taking some of the nasty things she said about me on board. For example, I’d been sending long verbose emails to everyone in the company when I just needed to be sending basic alerts, basically begging for attention and praise. If you’ve got a job, you have to be able to do that job before someone is going to let you do a fancier job. This is a huge issue for entry-level people. You think you can do your supervisor’s job; it looks like they’re not doing it as well as you would do it, you think you just have to show them you can do it and they’ll recognise your brilliance and promote you. But you do that at the expense of the job they hired you to do, and then nobody is happy.”

Mixing business with pleasure

“[I had] a night of passion at the gym I worked at, all caught on camera and watched live by security,” confesses Kim, who now runs his own IT business. “I would’ve been sacked but the manager was having her way with a Personal Trainer in the pool and she destroyed the tapes. Or so she said…”

Kim made it through his office romance unscathed but not everyone is quite so lucky. Office affairs are great fodder for romantic comedies, but they often aren’t worth the drama they can cause, as Jo found out at her first job working for a local council.

“The worst thing about sleeping with your boss is that they still have to sign off on your performance agreement and time sheets,” says Jo. “The power thing is sexy until it isn’t. You have sex in place you shouldn’t and that is fun at first but then it is dirty, desperate and sordid. I had to leave my job because of it. I would have taken leave without pay because I was going overseas, but she talked me out of my entitlement because we were breaking up and she didn’t want me to come back. What I learnt through this experience is that there are other more financially secure ways to get that power dynamic in the bedroom. You don’t need to screw the boss for it.”

Workplace romance didn’t go quite so badly for Sasha, who now runs her family’s holiday homestead in rural NSW but spent her 20s managing crews for theatre and events companies. “I slept with people I was the boss of several times. But perhaps it wasn’t a mistake because I once slept with one of my crew, Brian. He is now my husband and I am more the boss of him than ever.”

Knowing your rights

Not every workplace mistake involves clumsiness, unchecked passion or unflattering emails. Hindsight often reveals that young employees are unaware of their workplace rights, leaving them open to becoming the victim of workplace bullying or ill treatment.

Jesse, now an academic, skipped her Schoolies trip to work in a Sydney bookshop where she was responsible for counting cash at the end of the day. “The boss was this nasty piece-of-work called Wolfgang. One day, I noticed that the cash looked oddly low in the till so I did a quick count and we were $200 short. I immediately let one of the lower-level managers know. She passed on the info and the search commenced. Another cashier and I both offered our bags up to be searched, which management refused to do. We looked everywhere, no luck. The biggest mistake was noticing the $200 in the first place because they docked my pay by $200! Wolfgang said, ‘well the money has to come from somewhere’. Second biggest mistake was not joining a union and fighting it, I suppose.”

Yvette now has a job she enjoys working for the State Government, but her first role working for a touring festival was a harsh lesson in toxic work environments. “Possibly the biggest mistake I made was taking the job in the first place,” she says. “But how about putting up with an abusive, bullying culture, run by a megalomaniac and his cronies? I wish I had known my rights, or spoken up for myself and others about bullying or exploitation. I have since worked in another workplace that had entrenched bullying issues, and didn’t hesitate to speak up. I learned my lesson.”

The best way to cope with those early days of full time employment is to think before you speak, never send personal emails from the work account and learn from your mistakes when they happen. Everyone’s got a tale of remorse from when they transitioned from study to the workplace. What’s yours?


Maeve Marsden is a freelance writer, director, producer and performer, and the creator of Sydney cabaret act, Lady Sings it Better. You can find her on Twitter here.