With the amount of jobs I’ve had in my lifetime so far, you’d think that I was either a workaholic or owed a lot of people some child support. (Neither is true.)

Working, to me, meant more financial independence to buy and save for the future, so I entered the workforce a little earlier than normal. And often times, I’d hold multiple jobs at once.

I didn’t think anything of it. That was normal for me. But as I thought about the jobs I’ve had, I realized that every single one of them—except my current one—had either an unusual working environment, boss, clientele or combination of the three.

---

Babysitting (Age 12-16)

While most teens were just building their babysitting clientele at the age of 14, I was already a vet in the game. Thanks to my sister, I built my babysitting empire at the age of 12.

Who would trust a 12-year-old with their children, you ask? Exactly. But I was able to sneak into the industry on the back of my sister Grace.

She started working at the church when she was about 14 for all those “childcare is provided” events. The church crew liked her, so they started letting me work as a care provider too. I remember thinking it was too cool to manually punch in and punch out of my timecard because it meant I’m a working woman. HA!

Like everything she does, my sister rose to the top of the pack. And later on, the church members liked her so much that they started hiring her to be their personal babysitter.

She did a few gigs by herself, but I started tagging along pro bono to keep her company. Plus, my mom didn’t like the fact that she was at someone’s house by herself.

Grace and Hope Incorporated was a hot commodity, and the requests kept rolling in.

“Are you guys free this Friday?”

“Can you guys work tomorrow?”

“How about tonight? Will you guys be busy?”

Word of mouth was traveling fast. Two sitters for the price of one? And our rates were ridiculously too low affordable.

(Side note: We tried to raise our price multiple times, but my mom always guilted us into not doing that because our “reward would be in heaven.” Well, I want a piece of the down payment on earth too, Ma.)

There was never a free weekend, and they even called to hire us during the weekday. That’s when Grace had reached the end of her rope. She cared more about her free time and sanity.

The dynamic duo daycare was about to dissolve for good, and I was about to be out of work—or was I? 🧐

“Hello? Hope? This is Mrs. Ryans. I was wondering if you and Grace would like to babysit this Friday for me.”

“I’m sorry. Grace no longer babysits.”

“(Pause) Oh. Geesh. Ummm. Wow. I’m sorry. I wasn’t expecting that. Ummm… alright, well tell her I said we’ll miss her and that we wish her the best in…”

“Grace doesn’t babysit anymore, but if you’d like, I can still do it.”

“Oh. That’s so nice of you, Hope. But, how old are you again?”

“12-and-a-half.” (False. I was way closer to 12 than 13, but I added that to sound older.)

“Hold on, Hope.”

She murmured some things to her husband during a time in which the mute button didn’t exist, so I roughly heard them deliberating.

“That’s the younger one? 12? I don’t know. But she’s been doing it anyways. She’ll just be alone this time. The kids already know her.”

Mrs. Ryans put the phone back to her ear.

“Hope? What time can you come?”

Business kept booming. I was booked to capacity as a 12-year-old solo babysitter. Even though my rates were cheap, I learned to compensate by eating all the snacks I want, calling friends on their phone when the kids were asleep, and watching different cable shows that I didn’t have at home.

The craziness began when I was about to turn 15 years old. The church members started meeting up as a small group and having me watching all of their kids.

I was babysitting anywhere from eight to 13 children at a time for the same dirt-cheap, one-kid rate. Lord, you still have my treasure up there, right? Because I’m getting robbed down here.

Babysitting was officially not fun anymore. I still said yes because I wanted the chump change, but I was counting down until my 16th birthday so that I could get a more corporate-like job.

---

Chuck E. Cheese’s (Age 16-18)

Apparently, God and I have a different meaning of “corporate.”

When I turned 16, I dumped my babysitting gigs and started looking for openings at different companies. Experience was my arch nemesis.

I wanted to be a receptionist, but I would be in school during peak hours. I didn’t want to be a waitress because people start to get real ugly when it comes to their food. So, I searched for cashier jobs in non-retail industries because retail sounded like a hassle.

I searched the internet on a now-defunct online job search website for teens, and saw a job that caught my eye. It was a cashier position at Chuck E. Cheese’s starting at minimum wage. Sold!

I applied, received a call to interview, came way too dressed up for the interview, answered some simple questions and left with the job in hand.

I had no clue what I was getting myself into.

First of all, our Chuck E. Cheese’s location made the most revenue, so it was usually packed.

Second of all, our store was the most hood Chuck E. Cheese’s I’ve seen. We got robbed multiple times, parents would pop trunk in the parking lot over toys, and drug dealers would drop $1,000 to make sure their baby girl had a special day. But for some reason, people kept coming back for more.

Third of all, we had to wear many hats. Although I was “cashier,” I was also a hostess, door checker, game technician and Chuck himself. (If Chuck E. Cheese’s went from 6’2” to 5’2”, then I was probably in that musty crusty costume.)

That brings me to my final point. The costume was musty and crusty because our general manager reminded me of Mr. Krabs from Spongebob Squarepants—extremely cheap. We never dry cleaned the costume. All we had was a bottle of Febreze to use prior to putting it on.

He had us pick up unused napkins and put it back in the tins, he had us pick up a customer’s unused cups and put it back in the dispensers—anything to save a penny. And we later learned that those pennies would come back to him 100 fold during his bonus time.

Yes, the general manager was cheap; but he was funny to me. He played obvious favorites, didn’t believe that the customer was always right (because that could lead to too many free giveaways, and we can’t have that), and he would sit back in his office and watch us on the security cameras to see if we’re making magical experiences for the guests.

“Tasha, come here. Did I just see you roll your eyes? It better had been because your fake lashes are too long and your light blue eye shadow is too heavy!”

I was later promoted to the semi-leadership team, and he called me the head cashier. I don’t think he factored in that I’d be going to college, though.

“Hope, I see you in a managerial role real soon.”

“Thanks, sir. But you know I graduate high school in May, right? I’m going off to college in August.”

“What? Wait. Hope, Hope, Hope, Hope, Hope. You can go to a community college that’s close by! Better yet, you can still come back here on the weekends even if you do go off to a university.”

Nope. I was leaving and living in the dorms. The goodbye was definitely harder on him than me. I enjoyed my time there, though. 👍🏾

---

Soliciting for Donations (College Years)

Once I got to college, the grind did not stop. I immediately started searching to see what student jobs were available.

Without knowing fully what the job entailed, I applied to a vague position that was offering more than I was making at Chuck E. Cheese’s (which was not hard to do).

The strange thing is that even in the interview, I didn’t understand what the job was about. I just knew that they wanted me on the phone to call alumni and would give me the script. Sounds easy enough. 👌🏾

The call center held about 20 of us who were tasked with calling alumni. I was given the script and glanced it over before I began a real call.

“Hi! This is (insert name) from (insert school). We’re calling graduates from (insert field of study).”

Seemed harmless enough. I jumped to the bottom of the script and felt the awkwardness set in.

“So, would you like to pledge a small donation of $25? How about $15? Any dollar amount helps.”

I turned into the telemarketer that I would hang up on. And boy, did they hang up.

“You guys did NOTHING to support me financially while I was there, so why would I give back to you?”

“Ma’am, I don’t want to waste your time with this script. Please take me off the calling list.”

That’s also when I learned which professions don’t make a lot of money. The social work graduates would always comment about not making enough money while having to pay off large amounts of college loans.

Turnover at the center was crazy because we realized fairly quickly that we’re basically telemarketers, and there’s a higher chance of receiving more hate than love on the other side of the phone.

I was only at the soliciting job for a few months before moving on to greener pastures.

---

Security Golf Cart Driver (College Years)

In a leap of a whopping $3 more per hour, I started working for the university’s police department.

I was the one who’d come in a golf cart to take you all over the campus after dark. My hours were 7 p.m. to 1 a.m.

The hours actually worked with my schedule, though. I took morning classes, did my homework, took a nap if needed, chilled and then went into work.

And you’d always meet the most interesting people. I was the only female on the crew, so there were creepster riders for sure, but I would counter that by having a male friend accompany me for as long as possible on any given night. (Fun fact: my now-husband was one of the people who started riding with me during my shift just because.)

The policemen were cool too. Any time I had a stalker-like person, they would come to the rescue. One time, I got pulled over in my car by one of the officers, and he just laughed and let me go.

Also, my skills were unmatched. As Paul Wall would say, I was grippin’ the grain in my golf cart! Unfortunately, grain-grippin’ caused my cart to break down on three separate occasions. Who knew that an axel couldn’t stand a little bump from a pole?

I would have stayed at that job for my whole college career. However, I somehow got the urge to work multiple jobs at once, and I couldn’t keep up with the cart job’s hours. The earliest I could come in was 9 p.m. instead of 7 p.m., which I knew couldn’t last.

I had to make a decision. The other jobs were paying more, so I had to turn in my keys to the carts and move on.

I went from having one job to three jobs by my sophomore year in college. That’s when my positions and coworkers really started getting interesting…

---

I didn’t realize that talking through my first four jobs would take this long, so I guess I’m making this a two- or three-parter. Geesh. 🤓

Check out my podcast for the week to hear more details about the hood conditions of my Chuck E. Cheese’s, the creepsters on the carts, and more. LOL!