A One-Way Flight from Chicago to the Life of an Entrepreneur

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Over six years ago I boarded a one-way flight from Chicago to Charleston, taking my own proverbial leap from the life of a corporate career girl, into the wild unknown of entrepreneurship.

 

Wild. Unknown.

 

Two words that perfectly describe those first few years, and yet I couldn’t have anticipated just how much this new life would rock me to the core.

 

Working in corporate was predictable. I knew that the quality of my work and work ethic, combined with connecting to the right people at the right time, would lead to future growth. And it did. I climbed the ladder at MillerCoors (formerly Miller Brewing Company) from my very first job as the Sales Manager in Tampa, Florida, all the way to the Sports Marketing & Entertainment Manager in Chicago, Illinois.

 

My job definitely had some perks and this was one of them! 

My job definitely had some perks and this was one of them! 

 

Five cities. Four relocations. Nearly eight years.

 

It was a whirlwind looking back, but I’m grateful for the experience. On one hand it taught me everything I know. Best in class marketing, promotion, events, sales, and negotiation skills. The ability to manage complexity, and manage relationships upstream and downstream. And how to throw down a few Miller Lite’s and party with the best of them.

 

On the other hand, it revealed to me the gap between the life I was living and the life I wanted. I wanted freedom, independence, and the ability to get up every day and do what I wanted to do. I was sick of flying across the country every other weekend for work, having to constantly board my dog, and bundling up in ankle length down-filled coats just to step outside. Chicago is not for the faint of heart.

Winter in Chicago...my least favorite part.

Winter in Chicago...my least favorite part.

 

So after two years of diligently planning my escape, I resigned and embarked upon my new life as an entrepreneur.

 

Wild. Unknown.

 

I landed in Charleston with a heart full of excitement because I was finally doing it. I was launching a business, witnessing all my hard work and planning come to life before my eyes.

 

It was amazing.

 

Spring Jam Music Fest during the one year it actually didn't rain!

Spring Jam Music Fest during the one year it actually didn't rain!

 

And it was painful...beyond measure. There were so many things I didn’t know. Everyday it felt like I was getting up and cutting my teeth on another new facet of running a business.

 

How to use Quickbooks. How to get a beer license from the SC Department of Revenue. How to get the City to approve our events. How to get the Police Chief on our good side. How to set up a keg toss. How to get Ed Sheeran on stage to perform after one of the worst rain, thunder, and lightning storms in history. How to get a stuck van out of the mud. How to get a replacement key for the U-Haul truck.

 

How to….INSERT . NEXT . PROBLEM . HERE.

 

It’s like a game of Whack-a-Mole. Beat one problem into submission and up pops another. And that my friends, is the life of an entrepreneur. In a world of trial by fire, entrepreneurs are undoubtedly the best problem solvers around and we have the battle wounds to prove it.

Foul Weather Gear in full force at the 1st Annual Spring Jam Music Fest

Foul Weather Gear in full force at the 1st Annual Spring Jam Music Fest

 

I traded a life of predictability for one that is anything but. And yet I’ve never been happier. I understand now that owning a business, just like everything else in life, will come with it’s own highs and lows, but my experience of it is different now. Rather than riding a blood-curdling roller coaster, it feels more like riding the waves.

 

So to all you amazing women and men out there who dare to dream, who dare to launch businesses of your own, who dare to take the leap...bravo! Entrepreneurship might not be for the faint of heart, but it is a damn good ride...wild and unknown.

 

XO

Hilary

Hatch Tribe Founder & Entrepreneur Enthusiast

 

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