When A Bad Boss Helps You Realize Your Dream

Taking the leap from Wall Street to entrepreneurship

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I spent nearly thirteen years in finance working on Wall Street. In all this time, I only had one or two what I’d consider to be “good” bosses. Most were benign, but one was particularly terrible. It was his bad behavior that ultimately helped me leave the safety of the corporate world to take a chance on being an author and entrepreneur.

I got lucky early in my career when it came to good bosses. I had just enough to show me the ropes and help me succeed. They guided me and on occasion pushed me into the deep end before I was ready. As a Southern girl working on a trading desk, I already felt out of place and this was terrifying, but that push made me realize I knew more than I thought. It built up my confidence in myself and my skillset, two things that were crucial when it came to dealing with bad bosses later in my career. They also made me tough and taught me how to stand up for myself on the trading desk, an environment where anyone (not just women) will be bullied if they don’t learn how. This was the most valuable lesson of all.

As years passed, my bosses seemed to get worse and went from benign to downright vicious at my last Wall Street job. He tried to steal my accounts because he didn’t make enough of his own P&L. He bullied me, or tried to anyway. My earlier bosses made sure I knew how to stand up to bullies on a trading floor, something this boss didn’t appreciate. At the end of the year, despite outperforming in every way and doing everything I was hired to do, I still received a poor performance review. This was when I knew I had enough and needed to be in control of my own destiny as an author and entrepreneur. I wasn’t going to work tirelessly and still fail.

It’s hard to leave the safety of the corporate world, especially one that pays as well as Wall Street to try to make it as an author and entrepreneur. I had wanted to strike out on my own for years, but that safety net of a good salary and bonus kept holding me back. While that job and boss was one of the worst experiences in my life, it did give me fodder for my novel The Debutante’s Guide to Wall Street. It ultimately helped me lose my fear of the unknown that comes with life as an entrepreneur.

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