In the Event of Your Dream Being Compared to a Brewery

Updated: Aug 18, 2020

In 2010 My boss - we’ll call him boss number five - decided he was going to leave Westin. He was my fifth boss, so that is where the name comes from. Every year we did what they called the Big 5. We would meet once a quarter to review our goals, evaluate how well we were doing, and discuss in-depth the elements of our performance that needed improvement.

We had our review just like we had many times before. Being, from what I remember, his last day at Starwood he ended our review meeting strangely. I thought he would say “it’s been real” smile and offer me a handshake, clean off his desk and go off on his merry way. I would then proceed to dance in the hallway and the day would be over. In true boss number five fashion that is not at all what happened. These meetings were already what nightmares are made of. I’ve never met a soul on earth who doesn’t get anxious over these reviews. I don’t really remember the context of my review that quarter. I think things were going fine - although I don’t know how I could have even remembered after he delivered his next statement. He said something along the line of “I know about East of Ellie.” My boss wasn’t exactly known for his management style. I would have to compare my day-to-day at Westin during that time like what it would be like if I was the star of a non-stop episode of Punked.

My heart stopped. My biggest fear for what I remember being 2 or so years was this exact scenario. He went on to basically tell me everything he knew, how long he had known, that my secret was in fact not a secret. Later I did find out that everyone knew. Not from me personally telling them and although my drive to try to keep it quiet kept me from telling very few people at Starwood - others who had just kind of found out made it a topic for the water cooler.

He proceeded to tell a story about a boy and a brewery. He mentioned that he had a lifetime friend who had a dream to brew craft beer and sell it from his own self-run brewery and he wanted boss number five to do it with him. He outlined all the reasons why that would have been a dream, but then delivered what I think he thought would be a game-changer statement to me. He said that all dreams can’t be realized. And that the solid and unwavering path to be on was the one I was already on at Corporate America. He told me that my dreams would always be challenging, that if I even managed to make any money, how would I really manage to achieve my full potential as an event planner? He gave me some advice to not be foolish, buckle down at Westin and all of my feelings for wanting to do events would eventually migrate to something new. It would be then that I achieved some level of happiness.

One thing I don’t think he realized, is his little pep-talk-reality-check did exactly the opposite of what he came to do. Knowing that he thought I couldn’t do it gave me that much more fire to show him that I actually could. Within a year or two I left Westin. I still did the harder things I did in my professional life and continued living that double life after our “pep-talk”. I have many examples where this came back to really bite me in the ass. It was hard for me - I hated lying to people about things, but the fear of being found out and losing my source of income was terrifying to me.

When I first started East of Ellie I did a lot of anything kind of event planning. I wanted so badly for EOE to work that I can think of countless times I did things that seem crazy to me now just to have that feeling like this whole event planning business thing was working. There may have even been a handful of times that I thought boss number five may have been right. Just that thought being in my head pushed me back up and reminded me of that day, and my personal pledge to never, ever, prove him right.

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