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How a horrible boss gave me my most valuable career advice

Michela Montgomery graduated with her B.A. in Creative Writing from California State University, Long Beach. Although born and raised in California, Ms. Montgomery considers Boston her second home. She enjoys singing, dancing, yoga, co...

A bad boss taught me three career lessons I'll never forget

There are periods in everyone's life when they are forced to examine whether the emotional cost of something is really worth the stress, the anxiety and the fear that thing brings. Most working-class people don’t have the luxury of simply deciding to ditch their jobs, even if their boss straddles the sanity fence.

What happens if your boss goes beyond that level? What if you’re dealing with one who not only embodies malevolence, but embraces it?

I’d been with the same company for nearly seven years when she came on board. She worked her way up through middle management, moving when the company required it, devouring each position like a locust and moving on to the next meaty target. She staged a coup of the current director, a man who was beloved by all who met him, and she won the position with a greedy smile that told everyone that our happy days were over.

We all felt like that moment in a Disney movie when the sky goes black and ice settles over the entire land in a blanket of pain.

Over the next two years, meetings became her opportunity to make people swim in condescending criticism. Each blow was lovingly called a learning opportunity, so dissolving into tears in the conference room would have seemed extreme. Most of us waited until the meeting had ended to cry.

We watched as, one by one, hard-working people succumbed to her tactics and either quit, went on stress leave or were fired. By the end of the second year, our staff was a skeleton crew, the weakened, remaining few in a herd that had once been strong and healthy.

Most of us fantasized about the building being hit by a meteor, one that conveniently destroyed only her office, or being the subject of a hostile takeover where the only one laid off was her, or finally that one of us — and there were multiple bets on who would reach the breaking point first — would finally snap and take her out. Like I said, most of our money was on the latter.

With each passing day, life at work became more and more difficult.

One week, she peeked under the stall doors in the women's bathroom and took note of who was wearing shoes she deemed unprofessional. She would then send scathing emails to the boss of the unsuspecting employee. The next week, she waited outside the building to see who was running late and then posted the names on an inter-office email as a warning to all on punctuality.

Like most of the staff, I was applying for other jobs faster than a Kardashian at a sale in Neiman Marcus. Mercifully, a position opened with one of our subsidiaries two months before my ten-year company anniversary. It was a sign, one that required a pay cut and five weeks of training away from home.

At that point, the training could have been in a prison in Guatemala and I’d have jumped for joy. In fact, had they told me I’d be working for food and water only, I’d have actually paused to consider the option — and asked my family if they would mind terribly — before turning it down.

Years passed, and the scars of working for her have mostly faded. I still flinch when going into a big meeting, even though the most daunting thing in the room is the box of donuts on the conference table. Through the grapevine, I heard how the remainder of the staff fared until she moved on to another position, glad I didn’t have to endure one more grueling day under her regime.

The three lessons I learned from making it through those years will stay with me forever.

  1. No amount of money is worth a job that makes you hate your existence.
  2. The only way to get out of a horrible situation is to work your heart out every single day to try for something better — and hope the universe is kind.
  3. Bosses like her only succeed in destroying you if you stay and allow it to happen.

Every once in a while, when I consider where I am now as opposed to where I came from, I will close my eyes and be thankful I love my job and the people for whom I work. Then I will look down at my shoes and smile.

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