Most Embarrassing Career Moments

Back in my finance days, I strove to be a serious and professional business lady.  Capable.  Competent.  Composed.  Unfortunately, I never quite pulled it off.  Perhaps it was my forty-dollar power suit.  Or my unconvincing business voice – I typically end every statement like a question?  Or maybe it was the fact that I embarrassed myself on a regular basis.

As an aspiring humor writer, I’ve learned to embrace my embarrassing moments.  They’re my gift to share with the world.  So here are my top 3 embarrassing career moments, painfully relived for your enjoyment...
 

#3  Inappropriate Contact with the Intern

I was working at an investment bank on Wall Street.  It was the last day of the summer intern program, and a female intern, who I barely knew, approached my team to say thank you and good-bye.  With all of my co-workers watching, I made an unusual decision to forgo the traditional business handshake and instead ambushed her with a hug.  Now normally, in social situations, I go to great lengths to avoid the awkward hug, so I have no idea what possessed me to initiate one in a workplace setting.  It was the most awkward hug in the history of awkward hugs, and I have since vowed to never hug anyone again.

#2  Wrecking the CEO’s Office

When I was 24, I went on one of my first business trips.  The client that I was visiting had me work out of the CEO’s office, since he was away.  I was having a really great time swiveling around in his fancy chair and pretending to be a very important businesswoman… until I got up for coffee and accidentally knocked over a stack of framed artwork that had been leaning precariously against the wall.  All of the frames shattered.  The secretaries came running and found me standing in their boss’s office in a pile of broken glass.  I dealt with the situation by pretending it never happened.

#1  Worst Conference Speaker Ever

My boss was scheduled to speak at a conference in Holland but was unable to go, so he sent me in his place.  I was one of several speakers, all of whom were middle-aged men with intimidating qualifications.  I was a 25-year-old girl with limited experience as a cocktail waitress, shoe saleswoman, and gas station attendant.  Needless to say, I was nervous.  Very, very nervous.  Throughout the presentation, I kept hitting END instead of PAGE DOWN, so I would have to flip all the way back to the current slide.  I did this ten, maybe fifteen times.  The people in the audience found it hard to watch and stared down at their hands, thinking “Please God, let her find the PAGE DOWN button.”  After the presentation, I was supposed to go to a dinner honoring the conference speakers, but I was too mortified to show up.  Being the mature business lady that I was, I snuck out the back door and hopped a train to Amsterdam, where a Dutch friend took me out and got me wasted.  A few months later, I received my conference speaker evaluation forms in the mail.  Let’s just say that I will never be invited back.


Believe it or not, I’ve witnessed a few embarrassing career moments that topped even these stories.  At one work party, my co-worker’s wife announced that she had been with another woman, much to the surprise of her husband.  At another work function, a client of ours, whose wife had left him earlier that day, decided it would be a good idea to get hammered and grope the female consultants.

Just another reason to switch careers every few years.