Best Laid Plans

It was my escape hatch from one horrible job to the next: I was already in the financial industry, why not follow friends out of high-stress personal insurance and into high-stress investment banking? If I was going to live with high blood pressure and chronic migraines, why not make $80k a year doing it?

After a third coworker departed for Lehman Brothers, another friend reached out from a huge brokerage house. Come try it out, she urged. She claimed to love her job and she, knowing I’d been burnt out by the second day of a three-year “career,” made the offer sound like an interesting new challenge.

“Brace yourself,” someone warned me in the elevator on my first day. “This place is no Utopia.” I smiled, “I survived three years at XXX; I can survive anything.” His eyebrows raised. “Noooo thank you. No one survives there for any period of time. You’ll be just fine.”

Three months in, my eye was already on the door. From one grist mill to the next, I moved rapidly through three different positions and three very different bosses in the year I was there. This was not better; it was far worse. The infighting, the lying, gossiping, underhanded behavior was mind blowing. Weren’t these people supposed to be professionals?

Dress code was casual. Jeans were considered acceptable in the summer months, which was unheard of in the Financial District. (No longer having to maintain a wardrobe of proper suits and stockings meant considerably more expendable income.) During the rest of the year, business separates were encouraged but enforcement was lax. Department heads were almost always male and wore chinos and button-downs, the downright rebels going without ties. (The *one* female department head wore a sharp suit and pearls to work. Every. Single. Day.)

With the dress code, or lack thereof, I noticed a mindset I hadn’t seen in any of the other brokerage houses in the city: We were back in high school. Girls who could afford Seven jeans and cashmere sweaters were clearly superiors, looking down upon those who dared shop in the jobber stores found throughout the city. (Let me put it this way: when you’re a young family of three in NYC, even shopping full-price at The Gap feels financially reckless.) Dressing for success was clearly not a thing at XXX, which was unusual for NYC, and I discovered quickly that the best way to drive my department supervisor out of her mind was to dress each day as if I were interviewing on my lunch break. (Because on some days I was doing just that.)

HR at Lehman scheduled interview after interview, with one department head after another. Many mornings I left my house before six to catch a very early ferry. Scheduling morning interviews were tricky, especially when the interview took place on Park, in Midtown, and my job happened to be along the waterfront in Lower Manhattan.

Shaking hands with two junior staffers, I noted the woman’s eyes traveling from my face, to my suit, to my borrowed Furla. Her lips tightened and I realized we were not off to a good start, whatever the reason. Somehow I was making a bad impression.

I was interviewing this time for an assistant position to Mr. Top-Super-High-Level-VP. He needed a Girl Friday and HR had assured him I was up to the task. He shooed his junior staff out of the room and sprawled in the chair, leaning an elbow casually upon the conference table. He grinned, trying to be charming and disarming–I knew how this worked.

“I’m not very up on what’s PC,” he started, and I knew it was the beginning of the end. He could ask my religion, sexual preference or number of children and by refusing to answer I would automatically invalidate myself. (Let’s not pretend that level of discrimination doesn’t go into hiring practices every single day.) We had discussed my language skills, willingness to travel internationally, typing speed and salary requirements. This was going very well until… “I would love to send you to conferences in my place. With your background, I can count on detailed notes and you’ve got good presence. I hope you’re willing to travel a lot, and you know we’ll have to work long days. But tell me…do you have any kids?”

There it was. Just like that, I was going to be crossed off the list because I had a toddler at home. And indeed, that was exactly how it transpired. After months of stonewalling from the hiring team, I found out they’d filled the position with someone who had “fewer personal obligations.” Apparently having a son and a husband meant I was unfit.

The day LB sent staffers home with filing boxes filled with the contents of their desks, it felt like a normal workday–to me. I’d taken another job, and finally I was working with people who were largely competent, friendly professionals.

I watched the drama unfold on the TV screen in the reception area, a hand over my mouth. I’d laid such careful plans and tried so hard to land a job there, sure that the opportunity would open doors to a lucrative career. Instead, I’d have been another resume’ flooding the market, worried about how we were going to pay both the mortgage and the daycare bill.

Being a ducks in a row kind of person, I don’t enjoy uncertainty, or do well with it. Despite my best efforts, I hadn’t landed what I’d thought would be a great job. The disappointment had been surprisingly dispiriting. It felt like failure.

Sometimes what feels like a failure is a blessing in disguise; we’re being saved from ourselves. Accepting that we have very little control is an extraordinarily difficult thing, especially when we don’t know the “why.”

If something isn’t working out despite your best efforts, give yourself the time and head space to examine what it means to you. Why do you want it so badly? What will attaining that goal, landing that job or dating that person give you? Will life go on without it?

So often we’re directed to prepare ourselves for success: work hard, get a good education, find a way to set yourself apart. What we’re rarely taught is how to deal with disappointment. Remembering that life is a collection of passing emotions, prepare yourself for better days. This too shall pass.


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