What I Learned From My 5 Worst Work Experiences

I admit it. I’m a job-hopper. A typical, non-committal millennial, always looking for something new and interesting. Since finishing my Master’s degree in early 2016, I have worked at a magazine, a gym, a communications agency, a medtech manufacturer, and – now – at a UX startup. Plus, I worked countless odd jobs as a student.

What I learned from my 5 worst work experiences

So it’s fair to say that I’ve had my fair share of bad work experiences. But you know what? I’ve also had a lot of practise getting over those bad experiences. And I’ve found that once the initial sting has worn off, I am able to reflect upon the situation objectively, assess where I went wrong, and level up to a wiser me. That’s right! Just like Super Mario in the picture.

In this post, I decided to compile my 5 worst work experiences (that I can recall) and the valuable lessons I learned from them. You, dear reader, get all of Super Mario’s gold stars – without having to go through any of the blush- or cringeworthy moments.

#5 Having nothing to do

What I learned from my 5 worst work experiences

I once worked at an office where entire days would go by without a single email or phone call. Worse still, I was often the only person at the office so I couldn’t even offer to help a colleague with one of their projects.

Now, this may sound like a dream come true for people who work super busy jobs. But believe me, after a couple of days of watching YouTube videos, you start to pray for some huge project to stress out about. Also, I felt incredibly guilty. All the time. Like I was stealing my boss’ money for sitting there, twiddling my thumbs. But I couldn’t go home, could I? If the phone did ring, somebody needed to be there to answer it.

After weeks and weeks of guilt and boredom, I suddenly had an epiphany: if I couldn’t find anything to do (you can only organize your inbox or tidy your desk drawers so many times), I would read articles and watch videos that would help me hone my professional skills and excel at my job.

I started by checking out job postings to see what the requirements were to get more senior roles. Then, I taught myself several new, sought-after skills and began sending out applications. And sure enough, I landed a better job within a couple of months.

#4 Blindly following orders

Blindly following orders

When I was 24, I landed a job managing a gym. At first, I was thrilled. I felt like I had “made it” professionally. But then – it was my second week and I was still getting to know my team – I was informed that I needed to let a young man go. Apparently, he had been caught goofing off when he should have been doing chores such as tidying up the storage room or servicing the machines.

My gym was part of a chain so, unfortunately, I did not have the power to veto these types of decisions. I scheduled an appointment with the young man in question and asked someone from HR to accompany me since I had never had to fire anyone before and I hadn’t even been present when the missteps had occurred.

It was even worse than I had imagined it would be. The young man burst into tears and insisted that being a personal trainer was his dream job and that he couldn’t imagine working anywhere else. I felt like the most evil witch on the planet. But it wasn’t like I had a choice in the matter.

I kept thinking about that meeting for weeks afterwards. I thought about the young man’s hurt face and how I didn’t think he had deserved to be fired without warning. The more I thought about it, the angrier I got. Nobody had told me about a difficult situation with any of the employees during the hiring process. And yet, I wasn’t granted permission to decide for myself whether I wanted the young man on my team or not.

That’s when I started to realize that I really didn’t agree with the company’s principles. So I quit. And I never looked back. Fairness and honesty are important to me and I want to work for an employer who shares those values.

#3 Skipping out on my colleagues

What I learned from my 5 worst work experiences

At a different office job, times got tough when there were several changes in upper-level management. The strategy and business goals shifted and more and more people quit as a consequence. When several people in my team left, too, I thought: why exactly am I still here? I could be making a lot more someplace less hectic.

I started a secret job hunt. And, eventually, I got offered a job where the employees seemed genuinely happy and the salary significantly exceeded what I had been earning. Still, I debated about actually taking the job for a very long time. I felt guilty about leaving my remaining coworkers high and dry. Especially since I knew that I wouldn’t be replaced for a long time. Waiting to fill an open position until the team couldn’t manage the workload was a commonly employed strategy to save money.

Unable to make a decision, I turned to career advice articles. And they spelled out the cold, hard truth for me: no matter who you are, life will go on without you. Even if you’re a big fish (which I wasn’t), your absence will only cause a temporary ripple. What’s more, the company wouldn’t think twice about letting me go if they needed to cut costs.

So, eventually, after several sleepless nights, I handed in my resignation. And I felt quite sad for several weeks. But it was the right choice. You can’t stay at a job because you feel sorry about burdening your colleagues. The company that doesn’t rehire in time is the real culprit.

#2 Embarrassing myself in front of the CEO

What I learned from my 5 worst work experiences

Not long ago, I interviewed for a job in three parts. First, there was a phone interview which went very well. Then, I was invited to the office to meet the team. This part, too, went very well – until the CEO gave me a stress test. Armed solely with a blackboard and a piece of chalk, I was asked to calculate how many women were currently seven months pregnant.

I figured that the test was more about how I approach problem solving than how much random trivia I know. So I began explaining how I would calculate this and that. So far, so good. But then, for no apparent reason, I got nervous and had a total blackout: I was no longer able to do simple math in my head and ended up getting the calculation wrong by a factor of ten!

And it gets so much worse: when asked why I had guessed that 51% of the population is female, I started babbling about how I had read somewhere that sperm that creates female children survives longer in the uterus than sperm that creates male children. The CEO gave me a puzzled look and said: “Oh. Don’t you think it’s just because women live longer than men?” It was only then that I realized I had just used words like “sperm” and “uterus” in a job interview. Awkward!

When I got called back for the third part – a day at the office doing work that the role actually required – I was stunned. I thought for sure my inability to do simple math or answer questions like a normal person had eliminated me. But, embarrassed as I was, I went back, performed well, and landed the job.

#1 Getting duped by a customer

The perhaps worst thing that ever happened to me at work was when a customer deliberately tricked me into harming another customer. I was working as a personal trainer at a gym and a man called asking for his wife. He told me her name and I checked our registrations to see if she’d been in that day. Blue-eyed and trusting as I was, I told him that she’d been in in the morning and had left already. He thanked me and hung up.

Shortly afterwards, the phone rang again. A very upset woman was on the line. Apparently, her ex-husband was stalking her and I had just told him when and where to find her. I was mortified. I couldn’t believe that a) someone had lied to me so callously and that b) my stupidity had caused someone so much trouble. I apologized and the woman actually accepted my apology. She didn’t report my wrongdoing and I didn’t get fired. I didn’t even get in trouble!

That experience taught me that you never really know who you’re dealing with. Some customers seem sweet but are actually lying to your face. Others get upset and shout at you – but then they are able to forgive a gross mistake that put them behind the eight ball.

To sum up:

If you have too much time on your hands, invest that time in yourself.

  • Don’t be afraid to stand up for what you believe in – even if that means throwing in the towel.
  • You are responsible for your happiness and nobody else’s.
  • If you make an embarrassing faux pas, bite the bullet and move on.
  • Never judge a book by its cover.



How did you turn a bad work experience around? Let me know in the comments.


This has been a guest post by Tamara Marie Johnson. She is a former copywriter and journalist turned digital marketer. She currently works at a tech startup and, in her spare time, she helps restaurants and other local businesses up their online advertising game.


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