My Worst Three Jobs

Have you ever been lying in bed, dreading getting up and driving to a job you hate? I know I have, and today, I’m going to share my experience with three different jobs that had me feeling miserable.

Job #1 – Nightmare Catalogs

I was hired as a customer service representative for a catalog company. My job was to take orders and process refunds. My company sold everything from slippers to glow-in-the-dark snowflakes you could put on your windows during Christmas time. The products we sold had stunning pictures in the catalog, but were made cheaply overseas. So customers were upset when they opened their packages and found products that looked nothing like what was advertised. As soon as they got their item, they called our phone line and demanded a full refund.

Most of the customers were senior citizens, which meant most people I spoke with were hard of hearing. It was rare to make it through a call without having to repeat myself multiple times. The most common words I heard all day were “What?” “Say that again, please,” and “I didn’t hear you.” I grew up taking care of my grandparents, so I was used to speaking loudly, but with these customers, I constantly had to raise my voice. After working there for a while, I even started talking loudly outside of work.

I’d be having a conversation with a friend, and they’d say, “Daniel, why are you yelling?” I’d lower my voice and explain that I spoke loudly because the clients I worked with had hearing problems. Eventually, I began making a conscious effort to speak at a normal volume when I wasn’t working.

Despite the communication barrier, working with elderly people could be entertaining. Most of our customers had a great sense of humor about the crappy products we sold. One customer told me he received his glow-in-the-dark snowflakes but wanted to know why they didn’t glow. Another client proclaimed that the slippers he got in the mail were “made of plastic.” My supervisor showed me the slippers he ordered, and I almost died of laughter when I saw how poorly they were made. In the catalog, they looked like something you’d find in Nordstrom, but the actual product looked more like something you’d see at the 99 Cent Store.

After working for a catalog company, I’d never order from one. Why’d you even want to these days, since you can order pretty much anything from Amazon faster and cheaper? Catalog companies target older people because they’re more susceptible to attractive pictures and bold product claims. If your parents or grandparents decide to order from a catalog company, make sure you research the company before placing an order. When I eventually checked out the reviews for my company, they were all terrible – shocker. People could’ve saved their time and money by doing a quick Google search, and I could’ve saved myself a year-long headache.

Job #2 – Cable Company

Next on the list was working as an inbound sales representative for a major cable company. I sold cable, internet, and home phone services.

Before I started selling, I had to complete three weeks of group training. Our class covered the company’s services, and our instructors taught us how to use the software. The services were easy to understand, but the CRM was complex. Most of my class struggled to learn it. Thankfully, when it was time to take the final, we all passed and were transferred to the call center.

The trainers told us we’d be answering live calls under supervision for the next few weeks. If we showed competence, we’d be given a seat on the sales floor. Everyone was nervous and constantly needed help, but ultimately, we all made it. By then, I realized this job would be way more difficult than I had anticipated.

When I applied for the sales position, I knew selling internet service would be easy, but I hadn’t considered that the world was moving away from cable and home phone service. Most people started the conversation by saying, ‘Hi Daniel, I’m calling in today to get internet service only and no cable or home phone.’ I could sell customers internet service on its own, but I was graded on my ability to sell bundled packages rather than standalone services. Every call was monitored to ensure I pitched all three products to customers.

Selling cable and home phone service was tough. On top of that, the company didn’t make things easy on us with their clunky systems. I’ll give you a breakdown of all the challenges I faced on the job.

Challenge #1 – Selling Cable Service

When people started using streaming services like Netflix and Hulu, they realized they could watch their favorite shows on demand for less money. They didn’t need to have a technician drill holes in the wall and deal with an expensive cable bill. When I spoke to customers and they brought up the benefits of streaming, it was hard to rebut them because, deep down, I knew they were right. They were getting a superior product that was cheaper and more convenient.

My success in selling cable usually depended on the customer’s age. If I answered the phone and the client sounded young, they usually had no interest in cable. More likely than not, they were tech-savvy and knew all about streaming. On the contrary, if I spoke to an adult who’d been using cable their whole life, my chances of selling it increased. They were familiar with the service and not ready to try streaming… at least not yet.

Challenge #2 – Selling Home Phone Service

I felt like a clown when I spoke with customers and brought up home phone service. It was hard to sell a product I knew most people didn’t want. Before I could finish saying “Home Phone,” customers would interrupt me and tell me they weren’t interested. You’d think I insulted their mother the way they responded.

The only thing that helped me sell the home phone service was a promotion my company offered, which allowed customers to bundle it with internet service and receive a discount. Their wireless router had a port on the back for customers to plug in a landline. Most people I spoke to didn’t have a home phone but wanted the discount, so they agreed. When clients requested home phone service, it was usually for their parents, not themselves.

Challenge #3 – Phone Que

When I started answering calls, I assumed I’d only be speaking with new customers, but boy, was I wrong. Most calls I took were from existing clients who wanted customer service or technical support. The worst part? Before transferring them, I had to look through their account for services they weren’t subscribed to and try to upsell them.

This led to frequent arguments with clients who just wanted to be transferred and didn’t want to discuss adding home phone service when their cable box wasn’t working. It was awkward, and if I didn’t convince them to add additional service, it counted against me on the sales report.

Challenge #4 – The CRM

The company’s software was terrible. Even for straightforward orders, you had to navigate multiple screens and enter a ridiculous number of codes, like you were trying to solve a calculus equation. It was also riddled with bugs that forced you to restart your computer mid-call or left you guessing which codes to enter while customers waited impatiently on hold. One time, while I was setting up service for a customer, he told me, “I had no idea getting internet took this long.”

It was so broken it felt criminal that the company was making us use it.

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Before taking this job, I was unaware that cable companies were hated by consumers, but after working for one, I understand why. The long wait times, misleading advertising, and frequent price hikes make service providers infuriating to deal with. As a result, every day was draining because most people I spoke with were mad.

I felt like a firefighter as customers brought up a barrage of complaints. Not to mention, I had to sell them services that were on the verge of becoming extinct.

There’s no way to beat around the bush – this job sucked.

Job #3 – Telemarketing

My worst job ever was working as an appointment setter for a home improvement company.

I ended up working as a telemarketer because I quit my job one day and needed to quickly find another gig. I saw an advertisement on Craigslist for a local sales position and called to set up an interview. When I went in to speak with the sales manager, we had a great conversation, and he hired me on the spot. I showed up on the first day and walked into the main room, where there were about 40-50 people. There was clearly no dress code, and the office was mixed with both young and old people. The room was filled with rows of computers, and everyone was talking on the phone. My manager was assisting someone, so I had to wait a few minutes. Once he was done, he walked me to my desk at the back of the room.

I sat down, and my manager grabbed a co-worker to train me. My colleague came over and explained that my job was to book appointments for people interested in home improvements. He gave me a script and showed me how to use the computer’s dialing system. Everything seemed easy enough, and I confidently told my trainer I was ready to start making calls.

I began dialing, and as soon as someone answered, I started my introduction.

Me: Hi, this is…

Client: Click

Before I even said my name, the person hung up on me. The dialer quickly connected me to someone else, and my next call ended the same way. As soon as the person realized I was a telemarketer and not a family member or friend, they immediately ended the call. I spent the rest of the day trying to book appointments, but I had no success. I went home that day feeling beat up and brain dead from all the rejection.

I got to work early the next day and grabbed some coffee before returning to the battlefield. I studied a few of the top performers in the room and noticed they all had charisma on the phone. One guy sounded like he was an actual licensed contractor, and one girl was damn near yelling at people and demanding they book a free estimate. I don’t know how she did it, but she was booking appointments all day. I wasn’t about to take her yelling approach, but I knew I needed to adjust my pitch.

I started reading my script more passionately and researched home improvement outside of work, so I was more knowledgeable. I learned over time that as long as I kept my energy high throughout the day, I would speak to at least a few people interested in booking an appointment. I never knew when they’d show up, so I answered every call enthusiastically. Even the ones that came in towards the end of the day, when I was tired from answering hundreds of calls.

It wasn’t easy spending most of the day getting hung up on, but since I had cool co-workers, it was bearable. Our office was like a circus, filled with all sorts of characters. There was no background check or drug test at this company, and as long as you could talk, you were eligible for hire. We had musicians, actors, drug addicts, and even felons. Fights would break out in the office, and people frequently got caught using drugs in the bathroom.

You never knew what to expect when you came into work.

The most memorable part of this job was the manager, who was a guy we’ll call Fred. Fred was a bulky guy who wore black sunglasses and the same outfit every day. He was an odd but funny guy, and his sales meetings were unlike anything I’d experienced before. We’d meet in the center of the room, the normal lights would go off, and a disco light would come on. Then our supervisor beat a drum while everyone stomped their feet and banged their hands on the wall. After hearing the commotion, he’d come out of his office and make the type of entrance you’d expect from a Roman emperor or celebrity.

During the meeting, Fred reviewed the company’s recent sales. Whenever one of our estimates turned into a signed contract, he’d announce the salesperson’s name along with the value of the deal. We all kept our fingers crossed, hoping to hear our names and praying the number would be a big one. My largest sale was worth around $200,000. When Fred announced it, I felt like a king. The room erupted in applause as I walked to the center, struck the gong, and exchanged daps with my coworkers as they congratulated me.

We had a blast at these meetings, and they were the best part of our day.

Compensation-wise, we got paid close to minimum wage, but they were supposed to give us a “bonus” for the deals we helped close. If the customer’s project cost under $10,000, they gave us $10; if it was over $100,000, they gave us $100. It was a pretty pathetic commission plan, and collecting our bonus was challenging because of the lengthy sales process and shady management team. You didn’t get paid until the project was complete, which could take months, and there was no way to track the status of your deal. You had to trust management to be honest about paying your commission, which my co-worker Oscar explained was a bad idea.

He told me that one time, he went to management to check on one of his commissions. They told him that one of his clients backed out of the deal, and he wouldn’t get his bonus. He had a hunch they were lying, so he called his client to verify the story. It turned out they hadn’t canceled the deal and had recently finished construction at their house. After he found out, he made a big scene and got paid, but he never trusted them again.

I had my own struggles collecting commissions during my tenure, but eventually, I stopped fighting with management over it. Every time I discussed my bonus with my manager, he got angry and pointed out the times I hadn’t met my sales quota. Then he reminded me they could fire me, but since they liked me, they let it slide. I had to accept defeat and come to terms with the fact that I could only count on them for my hourly pay, not a penny more.

Once I became a top producer, he’d constantly promise me a promotion but never follow through. One day, I overheard him talking about his employees, calling us losers when he thought no one was listening. That was the moment I realized he didn’t care about any of us. It was just a boiler room designed to make him and his friends as much money as possible.

Here’s a story that shows how much they valued us.

One day, the company had us step away from the phones for a brief meeting. The management team told us they appreciated our hard work and wanted to throw a company picnic. The plan was to work a half-day on Friday and then go to a local park to play games and eat. It sounded great. We left the meeting pleasantly surprised and couldn’t wait.

On the day of the picnic, we clocked out early and headed to the park. We hung out, ate food, and had a good time. The following Friday, our supervisor was passing out paychecks, and I overheard people complaining that their checks were short. When I got mine, I was short a few hours, exactly the length of our picnic.

The whole room started demanding answers. Our supervisor came to the center of the room as things erupted around him. He looked nervous and explained that the company had clocked everyone out when we left for the picnic and stopped paying us for the day. The money they saved was used to pay for the event. They made it seem like they were throwing the picnic out of the goodness of their hearts. The reality was that we paid for it ourselves.

People in the room started yelling — ‘I have rent due,’ ‘I needed that money for my kids.’ One of my coworkers said that if he had known his check was getting cut short, he would’ve rather worked the whole day. I was about to speak up, but I looked around and saw so many people yelling that I realized my voice wouldn’t have made a difference. Our supervisor apologized and admitted he should’ve told us we wouldn’t be paid for clocking out early. People wanted their money, and some got hostile. Everybody left furious.

The next day, Fred was at the office in the morning, which was odd because he usually came in the afternoon. He called a meeting and told us everyone would get paid for the missing hours. Our supervisor handed him a list of people who’d yelled at him the day before, and they were sent home and suspended. We got our money back, but nobody forgot what they did.

After that, I’d had enough and started looking for another job.

I had fun the first few months, but over time, it got old. Getting hung up on hundreds of times a day wears you down. It didn’t help that I was working in a gloomy office with outdated computers, dirty carpets, and old desks. I had great co-workers, but for every quality person they brought in, they hired three weirdos. One of the guys sitting near me had been convicted of touching a minor. It was apparent that this company targeted the dregs of society.

I knew that wasn’t me, and it was time to go.

It took a couple of months, but I finally found another job and quit. Years later, I heard from a coworker that the building we worked in had burned down. I can’t say I was surprised. By the end of my time there, I felt like I was walking into hell every morning.