What my sociopath boss taught me at 22

When I was 22, a year after working my first after-college job as a market research analyst, I moved to live with my serious boyfriend.

For six months I scanned the paper looking for jobs in marketing or marketing research. Eventually I found a listing for a “marketing assistant” to sell seasonal plants out of an empty greenhouse in a farming town an hour north of my house.

The first red flag was that my soon-to-be boss interviewed me at a Mcdonald’s, and that he didn’t have a car or his own place. 

Gray looked to be in his mid to late fifties, and I later learned when I had to drive him home a few times, that he lived with his mother.

He was tall and distinguished-looking with thick salt and pepper hair, dark-rimmed glasses and a resting smug-face. He told me that he’d been a former NYC Madison Ave advertising exec who in his heyday was in high demand.

My sense was that he’d wreaked havoc in his career and was run out of the industry. Gray insisted that after he quit drinking it was he who decided to quit the NYC scene. He also claimed he made and lost millions and was starting over as an entrepreneur. 

His plan was to buy wholesale inventory of Florida seasonal plants to sell directly to customers via direct mail, newspaper, television and radio.

The dangling carrot was that while he couldn’t pay much, the money would inevitably come rolling in, and that I’d be mentored by marketing greatness.

My 20-minute interview consisted of “Do you want the job?” and a rundown of the position. We would market seasonal orchids and Neanthe bella palms out of an empty greenhouse where he’d rented space. Just the two of us until he hired a salesperson (he eventually did).

Gray spent a great deal of time telling me how brilliant he was, insisting that he knew more than most in the industry. He was loud, intimidating and incessantly braggadocio.

It was clear he sensed my naivety, ambition and desperation to work in marketing. 

One day during lunch with a potential client, the client offered to pay for our meal. Gray said thank you but I said, “Oh that’s okay, you’re the customer, we should pay.”

When we got back to the office Gray lost it.

“DON’T YOU EVER SECOND GUESS ME IN FRONT OF A CUSTOMER AGAIN!” then he threw his coffee mug on the carpet. YOU EMBARRASSED ME! LET THE GODDAMN CLIENT PAY IF HE WANTS TO PAY!”

As awkward and insecure as I was at 22, I knew despite my mistake, his behavior was out of line. I apologized then told him, “I thought I was being professional!”

Then to match his anger I threw my coffee cup on the carpet. He didn’t fire me. 

One afternoon out of nowhere Gray told me, “You know, I used to have a secretary who came to work without any underwear.”

“Uh Gray, you do know it’s inappropriate to tell me that?” 

For the next couple minutes he proceeded to yell and gaslight.

“I’M TELLING YOU THIS FOR YOUR OWN GODDAMN GOOD!!! IF YOU PLAN TO MAKE IT IN CORPORATE AMERICA YOU’LL NEED TO KNOW HOW TO DEAL WITH MEN THAT WILL SAY SHIT LIKE THAT TO YOU!”

I was stunned and disgusted that my boss not only sexually harassed me but tried to convince me that this was a teaching moment.

A conversation with my father flashed from when I was around 19.

“Has any guy ever been inappropriate with you?”

Besides a drunk college guy screaming “c…..t!” out his dorm window because I wouldn’t go out with him, and a much older yoga instructor during college who offered to trade private lessons for “massage,” no.

“Well, don’t ever let a man mistreat you under any circumstances. Pay attention to how he makes you feel.”

I told Gray that an underwearless secretary story wasn’t a “lesson” to help me navigate men in corporate America. It was gross and inappropriate.

“You just don’t get it,” he said then walked out of the room.

Gray had a former girlfriend who sometimes used our copier and fax. During one visit she pulled me aside and whispered, “Be careful with Gray. When we dated my mom thought something was seriously wrong with him. At one point she told him, ‘Listen, if you’re going to keep dating my daughter I insist you take this psychological assessment.’ I agreed with her concerns so I made Gray take the test.”

Apparently he scored off the charts on “sociopath” traits. 

The last straw was after an advertising shoot.

One morning we drove to a studio to film a 60-second ad. While he was working with the cameraman and setting up props he told me, “I need you to do the ad.” Clearly he didn’t want to spend the money to hire a professional actor and figured he could last-minute bully me into doing something that wasn’t in my job description. 
 
“Gray I have zero experience. I’m too nervous.”

“Listen, it’s only 60 seconds. It’s not hard. I’ll coach you and anyway, we don’t have anyone else. I’ve already paid for the cameraman. You have to do it. You’re my marketing assistant.” 
 
So I sat on the stool, awkwardly held the orchid, waited for the cameraman’s signal then started reading the cue cards. My hands and voice shook. I flubbed lines during every take.

Gray yelled repeatedly for me to slow down, relax and just “act natural.” At some point I was close to tears but blinked them back. 

Eventually he got frustrated, gave up and told the cameraman he’d do the ad himself because I “couldn’t handle the job, but that it would be much better if a woman was selling the orchids.” 

Fortunately no other boss I ever worked with came close to being the narcissistic bully Gray was.

In the beginning I saw him as a hard-knock, seasoned marketing professional. Smart. Creative. Resilient. Fearless. 

But he was just a pig and a fraud. 

Thank God despite my fragile confidence, my father, mother and stepmother instilled me with a strong sense of self-protection.

If it feels wrong, it is. 

Fortunately I was in a financial position to quit. I didn’t have dependents and I knew my boyfriend (now husband) and parents were there for me if I needed help. 

I can’t remember the details the day I quit, only that it took three months. I don’t remember what Gray said as I packed my stuff and walked out of the greenhouse.

I only remember I was shocked that he wasn’t mad and relieved he didn’t have a tantrum.

Maybe he ran out of money. Or maybe he realized we’d never work out because I wasn’t his naive little puppet or underwear-free secretary he secretly envisioned that day at McDonald’s.

When even the smallest red flags show up, run.