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This past weekend, I was in beautiful, bustling Chicago for a wedding – and to learn an important lesson. But before we dive in, let’s back up a bit.

Growing up in Connecticut, I was convinced my adulthood was destined to play out in Manhattan – specifically NYU and on stage as a Broadway star. I was going to become a big city girl with a big city life, jazz hands paving my way.

I grew up a little, and my family moved down South. My blood thinned and my dreams changed (as I realized the shower was more forgiving than the stage). It was quite a contrast to my North Eastern roots, and I loved it.

I have been in Nashville for five years now and love our area, but I have always wondered what would have happened if those big city dreams came true. Is the grass (or pavement as the case may be) greener in a big city? Are opportunities grander? Did I whimp out, settling for creature comforts in a smaller, Southern city?

Maybe you can relate. Are you a mom with four kids, day dreaming about being a newlywed again? Do you sit in your cubicle, wishing you could be leading a hiking group up the Appalachian? Have you let your mind wander away from the present, drifting to another place, wondering if you’ve missed out or if a different choice would have made you happier? I think we all have, at some point in our lives.

Okay, now that you’re caught up – back to my weekend in The Windy City –

I’m a big fan of the energy of Chicago – vibrating with a similar intensity to that of Manhattan but warmed by a Mid-west charm that softens its edges. And like a lot of the big city destinations, it is a place I used to see myself living and really enjoying.

But as the weekend unfolded and I bundled up to explore, I became very aware my soul was out of step with the pithy movement of my feet. I felt more nervous than I was used to – a fish out of water unsure what the social protocols were to be safe and smart surrounded by a lot of harsh scenes, sounds and smells sprinkled throughout the blocks. As I tried to picture what my life would look like there, or in any big city, it simply wasn’t a fit. Surely I would adjust if I ever made the leap, and there is so much to love about Chicago, or any big city, but it became quite clear it is a leap I have no desire to make. The contrast of that kind of lifestyle made me appreciate my suburban life with an incredible but charming city just 20 minutes down the road. Don’t get me wrong – it wasn’t bad – it just wasn’t home.

All the energy I spent wondering if I was meant to be somewhere else was a waste of time, and in fact, stole from the beauty of my here and now.

Are you in that rut? Then I encourage you to go out in the world and sample the different, the unknown, the unexplored, and the undone. Shadow someone who has your dream job. Take a trip to a city you’ve always daydreamed about. Have a girls weekend away from the kids (we all know you’ll be missing them like crazy by the last day of your trip).

Take a small step, even if just for a weekend, and put yourself in the contrast of your current life to determine what is truly well with your soul.

You may find it is time for a change, or you may realize you are exactly where you are meant to be. Either way, contrast for the win.


Jenny Cupero lives in Nashville, TN and is currently the Director of Business Development for 5by5 – A Change Agency. Jenny specializes in building relationships with changemakers like you to connect them with the marketing and digital solutions they need to optimize their clarity and reach. Jenny loves to stay active and is known for her shameless love affair with cheese, Disney World and Celine Dion. She is very excited to contribute to this incredible group of visionaries and changemakers making the world a better place.

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