IT HAPPENED TO ME: I Had a Male Career Mentor And Then Things Got Physical

I was discovered as a copywriter by a talented handsome ad man while on secretarial duties.
Publish date:
December 5, 2014
advertising, mad men, Don Draper, marketing, Peggy Olson

I quit my job last week.

On paper, it doesn’t make a lot of sense. I’m well respected. Paid decently. It’s creative. And for what it’s worth, it’s a “cool job” at a “cool company.”

But forgetting the “cool,” it was really special because of how I got it. As many people like to point out, it’s all very “Peggy Olson.” My narrative doppleganger and I have similar career origin stories. And for two plus years, I took pride in this.

I love Peggy. She’s smart, resourceful, and incredibly special to her creative director. They share an emotional intimacy that bolster their work, never tarnished by Don Draper’s womanizing tendencies. And this was the same as Max and I. Until it wasn’t.

I met Maxwell Conner on a hot summer day in Chicago. I was temping at a stuffy marketing firm in the Loop. And he was an executive creative director re-branding the company’s website. I very clearly remember my boss leading Max up to the front desk, where I very casually manned the phones and sat on Facebook all day. Max wore a white linen shirt, that was soaked with sweat, wavy dark Prince Eric hair, and what I would later learn was his perpetual smirk.

“Could you find Max here some parking?” My boss asked.

I looked at Max. He felt like a gift.

Every day for four months when Max came in, he lingered at the front desk. We laughed at this place I was temping and clearly didn’t give a shit about, and one night at an after hours party he said, “I have no idea why you are working as an admin assistant. You’re so smart and funny…”

“Well, I was improvising and writing sketch. Now I feel like that’s over.” I replied. He listened while downing a drink. I sat for a moment with what I was about to ask… “Hey, would you read my stuff?”

“Absolutely. E-mail it to me.”

A week later, I sat in Midway Airport about to board a plane to be in ANOTHER wedding, nervously, neurotically going over what to e-mail Max. I settled on a fictional day-in-a-life of Sarah Palin piece and two sketches I wrote in Second City’s Writing Program. For two weeks, I heard nothing. Until I got an e-mail back:

“Solid stuff here… we should discuss.”

We had a company Happy Hour a week later, Max leaned on a railing waving at architectural cruise passengers on the Chicago River.

He sighed, “No one here talks to me except you.”

“Well, it works both ways, you could go talk to people….”

He ignored it and pointed at my notebook, “What are you writing about.”

“Oh.” I felt my impulse to lie tighten, but then relax. “Cheaters. People with failings.”

“You know a lot of people when they get married and there are kids and they aren’t getting as much attention, cheat.” He said to the river.

I didn’t reply. And he turned and looked at me.

“I don’t cheat,” he said. And for the first time, I realized he was married.

About two months later, he came in on a Friday and announced to my boss that he was hiring me. I went to work for him in the West Loop, about a 10-minute walk and a world away from the boundaries and formality of the Loop.

Max had a small staff. I annoyed many with my mere presence. I had no experience. Max didn’t seem to care. He called me into his glass office twice a day to chat. We had a similar way of seeing the world and and he often could get far into my mind by mirroring my feelings. This transcended to work and I started to see how my emotional threads between products and people helped with his big ideas.

A couple of months into the job, Max, my immediate boss, and I went to a private club within the House of Blues for a client concert, Max wrapped his arms around me.

“I’m so happy you came to work for me,” he said into my ear.

I looked around the room. Where the drinks were free, two women in fringe jackets and hot pants danced on pillars, and listened to him complain about getting older.

“Looks go. Confidence and intelligence doesn’t,” he said, rubbing his hands together.

“Where’s your wedding ring?” I asked.

He shrugged.

The next morning he apologized for being to touchy feely with me. His wife came in for lunch and invited me to their house to look through clothes she was giving away.

She was kind and motherly, overly eager to find common ground with me. After I looked through her clothes, Max bounded up to her closet with his laptop asking her if me and him could go to a bar and think about ideas for a project he was working on. With two children on her hip, she sighed and said go. I was never invited back over.

As I turned a year old with Max, my reputation became solid outside him. Our clients took notice. Our biggest artist wanted me to the lead on all her social and digital creative. When my peers’ ideas didn’t feel right, they came to me for help.

Max and I grew closer as I started to go on more trips. I’d take breaks from live social campaigns and watch Max entertain clients from a distance, we’d meet eyes and he’d come over, lubricated and laughing, he’d tell my story. I’d beam, proud that this successful, handsome dude white knighted me out of career purgatory.

Max’s attention meant a lot. My peers chased it. And like lots of things you chase, it recoils when it sees desperation. I craved it more than anyone, but on another level. Nothing was good enough, funny enough, smart enough if Max wasn’t finishing my joke, sentence, or thought. But I knew better than to be all over him, so I played the opposite. I casually ignored him. Which dug at him. He’d beg to tell me what was wrong and carve out time to “get to the bottom of it.”

Usually this came via my walks. I was known for my solitary walks

It’s how I got a lot of ideas. And the last night at one of our events, when I was mad at a slight, he asked to join mine. We walked the empty littered fairgrounds, sitting on a bench in the moonlight. Talking about office gossip and the vulnerable parts of ourselves until we sat in silence, watching each other’s feet make circles in the grass. The next week at the office he told me it was his favorite moment of the event.

“I even told my wife that.” He said.

I didn’t know how to take it. I smiled and felt elevated.

More trips came, and after two drinks, he always asked me on a walk. And I always demurred.

Until a company retreat, that I loathed being on, found us in the middle of the Rocky Mountains. Unhappy and lonely, I said yes to his walking request.

“I never get to disappear,” he said as we shared a beer against a fallen log in the woods.

It was pitch black and cold. We both shivered and laughed, backs against the log. He put his arm around me.

We took a beat. He removed his arm.

“You probably think I’m a creep.” He said.

“No. I don’t.” I replied.

We fell against the tree, curled into each other until one of our names was called from a megaphone.

The next day was going to be an apology but instead it escalated. He asked for another walk. It started to rain and we took shelter in a cabin. He didn’t ask for permission to kiss me and neither of us stopped what came next.

“I love my wife.” He said after combing his hands through his hair. “I know you look for it but -- there’s no subtext in that statement.”

It was the first time him knowing me so well didn’t feel uplifting, but cutting.

There were no crying wives or HR departments arriving at our office unannounced on a Thursday morning. No declarations of love.

All of that seems like it’d be easier. No, clearer.

Instead it was a strange descent. He wanted to write songs with me after hours. I kept track of how long he was gone to lunch with a gorgeous new female hire. He threatened to punch my boyfriend at a party. I ignored his wife at events. He told our web developer he couldn’t date me.

I never exalted Max as a perfect person. I had seen his cracks but now that I was one of the cracks, it was different. I knew if he’d had cared more I’d never been on this side of the fence. That I was joining a cadre of women I’d only heard a snide whisper about.

We weren’t Don and Peggy. I was a secretary Don had made a mistake with.

I was hurt he didn’t want me more. And that hurt made me uncover more. I felt his ability to turn emotional intimacy into a weapon and saw it in our revolving staff. I started having lunch with people who called him a "casual sociopath," manipulative and flippant. I read his wife posting Facebook statuses about the "best man I know" and knew if he deceived the mother of his children that he loved, how could he ever be honest with his employees. My work suffered, but I had so much good will surrounding my performance that no one noticed until new turnover unveiled my lack of interest.

Hearing and seeing my fatigue with my current position, Max promised me a new role. No timelines when or how but I think it would have worked out. However, it wasn’t enough.

When I told him I was leaving, he said, “I feel like you’ve felt like this for a long time” but then coupled it with “You’ll be moving up into something you want though! Doesn’t that mean something?” And it does mean something. I do want that title. That role. But I don’t want here. I don’t want it tied up in him.