My First Job in Florida

The day I met Jackie Cain I was desperate. I’d moved to West Palm Beach two months earlier and still didn’t have a job. My roommates weren’t hassling me, but I felt like a burden.

I was ushered back to her office by a teenager that I later found out was her daughter.

Her desk took up a sizable portion of the office and she sat behind it in an enormous office chair that dwarfed her petite stature. She wore a tight white sleeveless dress and matching jacket, and her brown hair was thin but shaped into modern bouffant with an extraordinary amount of hairspray. A large ornamental necklace rested above her décolletage.

Jackie rose to her full five feet and extended a manicured hand. She smelled expensive.

Her voice was breathy, and I noticed the lines around her eyes and mouth despite the attempt to hide them with makeup. She asked me a variety of questions about my education and background. At 24, I had some solid experience that more than qualified me for the administrative assistant position available in her ad agency.

The next day I got a call from a woman named Claire, who told me I was hired.

There was no orientation, just introductions to Claire – the CFO, Tony – the art director, and the daughter I’d met the day before, Rachel, who evidently came in after school to help. That was it. The entire company.

Claire, in her early 40s and always impeccably dressed, and the heavy gold chains worn around her wrist jangled when she walked. Her blond hair was always neatly trimmed in a short bob, and she was perpetually tan. This woman had a way of handling the clients, especially when invoices were overdue, that was both sultry and stern. She always got the bill paid.

Tony was in his 50s, a tall thin man who wore jeans and plaid shirts every day. He had a full head of grey hair and bushy mustache and spoke with a midwestern accent. He kept to himself in his office, a large room with drafting tables and art supplies, although we occasionally shared lunch together in the break room. This is where I learned he’d been working for Jackie for five years, after moving to West Palm Beach from Illinois.

For the next three months, I sat at the front desk answering phones, typing letters and contracts, and escorting clients, mostly men, back to Jackie’s office. She always shut the door when it was a man, which I found unusual, but I’d already learned not to ask too many questions because none of the answers every satisfied me.

I was also the errand girl, running documents to clients, picking up lunches and dry cleaning and occasionally taking Jackie’s Porsche 911 to the dealer for an oil change or new windshield wipers. At least I got to drive a Porsche even though I often waited more than two hours without the benefit of a smart phone. It was after all, it was 1987.

Jackie had two other daughters who occasionally showed up with Rachel, the oldest, and they would huddle in the conference room to do their homework. Sometimes when they finished before Jackie was ready to leave, she had them dust and vacuum the office.

There were often clandestine meetings between Jackie and Claire, which I thought were just about business at first. But when I’d walk past Claire’s office, I’d hear them giggling like schoolgirls from outside the closed door where they would sometimes be for over an hour. I wondered what in the world could be so funny.

It was all imagination and hypotheses until I found out part of the reason why my Spidey senses tingled all the time.  

The break room was huge and also used for storage – reams of paper, office supplies and old files. One day while making a cup of tea, I rooted around in the cupboard for a sweetener and stumbled on a stash of cans. SpaghettiOs, chili, and soup, along with boxes of Pop Tarts and cookies. I figured someone liked to have lunch options available and took my Earl Grey back to my desk.

A few weeks later, while searching for paper clips, I found two pillows and blanket stashed behind a large box of old files in a cabinet. Again, I convinced myself it was fine. Maybe they were there in case one of the kids wanted to take a nap.

But I kept noticing strange things. Like the morning I found Tony in the break room with remnants of shaving cream on his face. Or the time I saw him walk out the back door and duck into the stairwell as I unlocked the front door only for him to stroll past my desk minutes later as if he had just arrived.

Then I found a letter abandoned on the copy machine. It was to Jackie from Tony. In the missive, he pleaded with her to cancel the contract he’d signed to take over her lease for a Sebring convertible after she purchased the Porsche. He explained that the $400 per month lease plus the $75 fee she charged him to process his payment, were a strain.

He also reminded her business had been slow in the art department as most clients were focused on buying television and radio ads recently. Tony asked her to reconsider their arrangement and pay him a salary instead of only for the actual hours he worked. He mentioned he was willing to do other tasks around the office if that would help sway her decision because he had run through his savings and could no longer afford rent.

The pillows weren’t for Rachel’s sisters. He was actually sleeping in the office.

I was at a loss for what to do with this information. Should I tell Jackie? Claire? What might the blowback be? I would, after all, be the messenger.

In the end, I decided to keep quiet. It was just so… messy. Her kids being ordered to clean the office when their homework was finished. The secret meetings, which I later learned were to share their dating and sexual escapades since both of them were evidently single. And an employee sleeping in the office.

By this time, my roommates and I had started our cleaning business so I decided to stay while our company got off the ground and could hopefully earn enough for me to quit. Jackie didn’t disappoint and there were plenty of other bizarre experiences during that time. Stay tuned…