Chapter 4 - HELP WANTED: Tales of a Free Spirit Professional

The partnership was growing fast and some of us were forced to take on additional people to support. I was assigned to George Walker, a new partner who was brought in to build our SmartCard business – whatever that meant. While Scott was like a dreary winter day in England, George was a bright, fun day at the beach. He wasn't Ivy League like the rest of the partners which made him less pretentious and more productive.


George was there to work and after years of listening to Scott whine about all the work he had to do – but never did – I was happy to put more energy into the new addition to my desk. Scott of course, didn’t like that and things between us became rather tense.

Something was shifting in me and the desire to keep the peace with people was overshadowed by the respect and interesting work George was providing. While I still managed to keep Gina laughing long enough not to stab me in the back, I needed a new shtick.

With the firm rapidly expanding, Gina’s boss, Tim, was traveling a lot to visit our newly opened offices in Europe with Scott in tow – of course. I loved when they were gone. We all did. The mornings were filled with phone calls and video conferences, but because of the time difference, we basically had the afternoons to ourselves.

Our corner, normally strained, jumped to life with activity and laughter as we’d sit around and bullshit with the other assistants. Gina was always nicest when Tim was away and it felt good to relax around her and be myself.

Three days before he was supposed to come home, Tim called Gina at home and told her wanted to leave London that day. I’d seen him do it so many times before – create havoc for the sheer purpose of satisfying a whim. I thought it was more ego than whim, but my opinion didn’t really matter.

If Tim was coming home early, so was Scott. However, I didn’t get a 6am phone call at home. While traveling, Tim and Scott were a package deal and Gina bore the brunt of scrambling to find them flights home in First Class, seated together – no small feat when you’re working with a time difference that put you behind five hours.

But Gina was good and stupid enough to answer her phone at six in the morning. I knew better. Plus, I had call waiting.

Unfortunately, I had to deal with her resentment when I got to the office. That was one of the many tricky things about Gina. She wanted to be a part of everything, but she resented the hell out of those of us who weren’t and didn’t want to be.

Tim and Scott were successfully en route back to the states and I had endured a morning full of her martyrdom and snappy “I’m handling it,” retorts.

I couldn’t take it anymore and I knew a Scott imitation wasn’t going to cut it.

“Do you think it would be bad if I did a cartwheel in front of Tim’s office?” I asked, the mischief dripping from my voice.

“I dare you,” Gina said, spinning around in her chair and cracking a smile for the first time all day.

And there it was – a new shtick had been born. When things got really bad, all I had to do was a couple of cartwheels down the hall and all would be right in the world at The Madsen Group.

Chapter 3 - HELP WANTED: Tales of a Free Spirit Professional

The only way to get on Gina’s good side was if you could make her laugh. I learned this one day, when out of frustration, I imitated Scott - hunching shoulders and pinching my nose to replicate his nasal and whiny voice. Gina loved this, clapping her hands like a five year old with delight.


“Do it again! Do it again!
And so it went. I became the sideshow in our tense little corner, imitating the partners and making private, inappropriate comments at their expense just to keep the peace with Gina. Her reaction was a little odd and it made me wonder if there was much laughter in her own home. She’d become almost giddy to the point I thought she might shed tears of joy if I took my antics too far. Still, she was a good audience, laughing right on cue which only encouraged me to go further.

I didn’t mind. Life at The Madsen Group was losing its luster. Two years in and I was bored out of my mind. Scott didn’t really want to get organized.  He liked to keep his desk piled high with papers to make it look like he was busy. The respect I’d had for him in the beginning had dwindled down to almost nothing.

The irony was that the crappier I treated him, the nicer he was to me. Go figure. I sure didn’t. I just went with it, rolling my eyes when he asked me to make copies and pleading, “Do I have to?” It wasn’t right but Scott ate it up and shuffled off to the copy machine.

I’d always had an innate respect for my superiors, but I wasn’t a kiss-ass. I never cowered either. Gina’s boss sent many-a-partners into an uncomfortable squirm with a soft pat on the shoulder and a “Have ya got those numbers for me, Kevin?”

I never understood that. He was just a person too. He was also a bit of an asshole, but I never minded him. Several times, he’d call out from his office for Gina and in her absence, I’d appear at his door because if I didn’t, he’d go on screaming until somebody went to him.

I had dreadlocks at the time which was often the topic of conversation around the office slating me as the “cool assistant.” Tim, though, didn’t quite know how to take me. Whenever he had to address me, he’d scrunch up his face and look over the reading glasses that sat on the tip of his nose with confusion as if to say, “How the hell did you get into my corner?”

He was equally miffed when he’d ask me for something and I’d get it to him quickly and efficiently, looking at me with uncertainty and mumbling, “Uh, thanks” under his breath.

I wasn’t a bad assistant. I was a bored assistant.

Chapter 2 - HELP WANTED: Tales of a Free Spirit Professional

Faye was right. The something great turned out to be just that – at least for awhile. I was going to work at The Madsen Group, a hot new onsulting firm with a concentration in Financial Services.


“What kind of company is that?” my friend in California asked when I told her.

“Dunno. But they have beer night on Thursdays.”

The pay was good and I could tell people about it without reference to war. I was the Executive Assistant to Scott Rivkin, a short, rail-thin man whose waist was smaller than mine.

“They tell me I should have someone organize me,” he sighed, his head barely clearing the pile of papers on his desk. “I guess you’ll do.”

Scott was in his forties, single and in desperate need of a good haircut. He had unruly, dark hair that, with the proper hair product, might have had some hope, but Scott wasn’t into the kind of stuff. His frameless, square glasses were something out of a bad 80’s geek movie and his suits were always navy.

The office was being renovated when I started and my desk was down the hall from Scott’s office. There was a reception area just beyond my desk separated by large, wooden doors. We had two receptionists out front and they had to buzz you through to get to the actual offices.

I was in the “hello cube” – though, I didn’t have a cube; just a desk. Sitting just inside those doors, every time someone entered, I felt compelled to say, “Hello!” At first, I didn’t mind it because it was a nice way of getting to know people. But, after awhile, getting any work done became difficult.

My desk became the stomping ground for anyone who was bored or passing by and felt like making some completely uninteresting conversation. I quickly tired of being the hello cube girl and when the renovation was finally complete, I insisted on being moved elsewhere.

Elsewhere turned out to be hell. Tim Sherman, the CEO needed to have “Scotty” as he liked to call him, close by at all times. The new layout had Scott’s office sitting about twenty feet from Tim’s. Their assistants sat in an open are in-between.

It was in this bullpen like setting where I met Gina – Tim’s assistant. Gina was there since the beginning and loved to remind people of that every chance she got. She was from Iowa and lived in New Jersey with her landscaper husband.

Gina was good at what she did and I’d hoped to learn a lot from her. She was the quintessential secretary. She knew everything about Tim. His wife. His kids. EVERYthing. She took her job very seriously and I was impressed by the level of respect she had.

At first, I wanted to be just like her. I wanted to know everything about Scott, so that he couldn’t do a thing without my help. I wanted to be the smart, efficient gatekeeper she was, coolly maneuvering people away from my boss’ office until he was ready to see them.

Unfortunately, there some major problems with my plan. Gina was a bitch and Scott was a control freak.

“Don’t pick up Tim’s phone,” she snapped at me one afternoon when she was tied up with another call and the other line was ringing off the hook.

I thought I was doing her a favor as I envisioned the two of us working as a team. But Gina liked to keep things under close watch. I later realized it was severe insecurity on her part, but at the time, I was afraid of her and spent a lot of time tiptoeing around her.

Aesthetically, I had no desire to be like her. She was nice looking woman with dark blonde hair that was always styled perfectly in a neat bob. She wore perfectly matched suits in various colors which always made me wonder if she shopped at Dress Barn. And the white sneakers for commuting and ornate pins made her seem much older than her early thirties.

She and Scott got along well mostly because he was her boss’ whipping boy and their commiseration on being treated like crap made for a strong bond.

Scott was a miserable person. Period. He had no life. This I learned very quickly when, about month into my new job, I greeted him with a cheery, “How was your weekend?”

He stopped, slumping his shoulders even more than usual and let out a long, dramatic sigh. “It was,” he said, staring into space.

It took me about six months to stop asking as I finally realized that he’d never have a good weekend.

Life in the corporate world was a mix of monotony and challenge. Scott wasn’t the most respectful boss in the world as his waves of dismissal when I walked into a meeting to pass him a note sometimes sent me to the bathroom to have a little cry. Gina was mean and if she was in a bad mood it was best to keep my head down and stay out of the way.

I’d made some friends with the other assistants which made my time there bearable and sometimes fun. The perks were the best part of all. There were many partners in the firm and Scott was one of them. He was a founding partner and as his assistant, I was in charge of things like the company Holiday Party and annual Partner Off-sites in places like Paris and Jamaica.

My expense account was ridiculous. I took cars everywhere, ordered breakfast, lunch and dinner on the company and even got to buy a few things for myself when shopping for Scott. It wasn’t right, but everybody did it, so why shouldn’t I?

One night, I was having too much fun at my friend’s apartment to go home and walk my dog. Instead, I sent a car for him.

Yep. Perks.

Introduction - HELP WANTED: Tales of a Free Spirit Professional

photo courtesy of www.photobucket.com

When I was a kid, my father used to have “Private Talk” with each of the three children in my family. Our household was a busy one and my Dad worked a lot, so having him all to myself for an hour every so often was better than ice cream or any shiny new toy.

As the youngest, I didn’t have much going on in my five year old life, so I chose to ponder the unusual predicament of getting butter stuck under my fingernails. While I wasn’t losing any sleep over this greasy situation, I’d milk that hour for all I could even if it meant discussing the finer points of butter.

Often times, my father would ask me what I wanted to be when I grew up. I’d rattle off a plethora of things from famous gymnast to waitress to “robber.” I loved this question and I could go on forever dreaming up all the things I’d be as an adult. My guess is that this enormous list of potential career paths was more of an attempt to keep the conversation going and less of an indication of my wide ranging vision of the future.

Or so I thought.

Fast forward thirty years and I’m still proud to say, when people ask, “What do you do?” that I’ve narrowed it down to four things. It’s no small feat to pay your bills and follow your dreams.

Welcome to “Help Wanted – Tales of a Free Spirit Professional ” – the story of creative desire and fiscal responsibility.



To be continued……..

Chapter 1 - HELP WANTED: Tales of a Free Spirit Professional

Part 1 - The Corporate Challenge



I was 26 years old and sick of being broke. After a short stint in Atlanta as a waitress, a Fitness Manager and an office assistant, I was ready to make some money. I’d answered an ad for Executive Assistant and met Faye, my upbeat and very persuasive recruiter.

She was in her forties with brown curly hair, a great tan and a sparkly diamond wedding band that screamed, “I don’t really need this job, ‘cuz I’ve got a rich husband.” Faye was awesome and made me feel like I could do anything. She sent me on tons of interviews urging me to, “Go get ‘em tiger!” each time I’d check in beforehand.

She also taught me that positions in fashion, sports and entertainment all paid less because they were the “fun jobs” and Financial Services was where it was at. When she mentioned I could make as much as $80K in some jobs, I got over my fear of working in a stuffy environment and started dreaming about all the clothes I could buy with that money.

My sister, who was already in the corporate world told me that $80K for an assistant job was “combat pay” and that I should be prepared to work long hours and be treated like crap. I, of course, thought I knew everything and decided my sister didn’t know what she was talking about. I was going to be rich, dammit!

The combat pay job was for the CEO at Ernst and Young, a major accounting firm in midtown. I wore my best navy blue suit for the interview feeling a little like the classier version of Melanie Griffith in Working Girl as I showed up ten minutes early to make a good impression.

The elderly assistant interviewed me first and I assumed she was getting ready to retire simply because she looked to be around 70 with her light gray hair pulled back into a neat bun.

“Have they told you about Mr. Casey’s,” she paused. “….particular ways?”

I nodded enthusiastically and delivered the lines I’d practiced with Faye about loving a challenge and not being afraid of difficult people.

The assistant nodded, sizing me up as she went over the job duties and hours. After some time, she leaned in and asked, “Will it bother you if Mr. Casey comes out of the office and hangs up on whomever you’re speaking with because he wants your attention? Are you okay with yelling? He likes to yell. He also likes his food to be hot. If it’s not hot, he’ll throw it away and insist on something else.”

She was so calm and matter-of-fact in her delivery, it sounded like the easiest job in the world. But, thankfully, my sister’s words kept ringing in my head, “Combat pay. Combat pay.”

As I sat there listening, the honey-stained walls and plush leather couches no longer seemed as inviting as when I first arrived. The warm, study-like energy transformed quickly and I felt like I was in a stodgy men’s club where enthusiasm and individuality was met with sharp looks and icy stares.

I was too young and afraid to stop the interview right then and say, “No thanks.” Instead, I nodded and smiled going through the motions wishing the minutes away.

Afterward and on the street, I called Faye.

“How’d it go?” she breathed with excitement.

I wanted to please her, but I didn’t think $80K was worth getting beat up on everyday.

“I don’t think so,” was all I could say.

And, Faye - because she had that sparkly ring, I’m sure – was unfazed. “No problem!” she sang. “I’ve got something really great for you on Friday.”