a city with a body of water

Adios, Chicago – It’s Time to Hit The Road! First Up? Madison, WI.

It’s been just over three years ago that I arrived in Chicago after spending seven months living on the road. On Friday I bid adieu to the Windy City, and closed the chapter on my time here as I head back on the road.

My First Day in Chicago…I Knew I Belonged Here

I’d traveled to Milan, Puerto Vallarta, Bali, Las Vegas and Tulsa, OK (to name just a few) prior to “crash landing” in Chicago. Fresh off a red eye from SFO, I headed to a vacant 25k sq ft. warehouse that early May morning back in 2016. Little did I know that I’d actually move in and live the “loft life” for over a year.

My first day in Chicago…I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.

Oprah Winfrey

There’s so much about Chicago that drew me in. Being an east coast kid, I felt drawn to midwestern manners and sensibility like a moth to a flame. This is a city that I’d wanted to live in from my very first visit back in 2009. Now, I saw an opportunity to put into practice some of the things I’d learned visiting 500+ coworking spaces and countless developments all over the world.

a room with a brick wall and a table

I look back on my time living in Chicago with mixed feelings. If anything the three years I’ve “lived” in Chicago I’ve flown more than I did while “on the road”. I feel gratitude and pride for working with the famed Second City and Deskpass to launch an exciting coworking initiative and helping turn that 25k sq ft. warehouse into Bridge410, one of Chicago’s Best New Event Spaces. If there was one thing I regret, it’s having to travel as much as I did while living here.

I Didn’t Choose the Nomad Life…It Chose Me

Many might think that being a digital nomad is glamorous, or envy road warriors who travel for a living. As with anything in life, there are pros and cons. It’s not that I was necessarily tired of living on the road. It’s more that it felt like for the time being, Chicago was where I belonged. For the opportunities mentioned above but also to easily travel the world via O’Hare International Airport. You see, I didn’t necessarily choose this nomad life. It chose me.

a man sitting at a desk with papers in his hand

I look back at my time working in a cubicle, having a “real” job and how badly I wanted to travel. Never in my life could I have imagined that I’d be traveling like I have and continue to do. The fact of the matter is that coworking is a “global phenomenon” and if I want to pay the bills, my consulting firm needs to take jobs wherever they are. Be it in Bali, Dubai or…Madison, WI.

That’s why after spending only five nights in my own bed this past April, I knew that it was time to let go of idea that I still lived in Chicago. I count myself blessed every day for the opportunity to work with such amazing people from all over the world. This fall already is stacked full. Imagine trying to figure out this flight itinerary: Belgrade, Serbia -> Cancun, Mexico -> Orlando , FL -> Puerto Vallarta, MX -> Warsaw , Poland -> Bermuda. All in about six weeks.

What’s Next?

Back in January I honestly thought I’d be moving to Mexico. We had a project that seemed fairly long term, until the government changed its mind. Also, turns out I’m more of a Puerto Vallarta guy than a Cancun guy. I’ll still be there frequently but realized it wasn’t the kind of place I’d want to “settle” down. Also, spending the winter in Mexico is WAY different than enduring the hot, hot summer. So, what’s next?

aerial view of a city with a body of water

Next up is spending the summer in Madison, WI. Working with my AgoraRDM Co-Founder on upgrading the building that’s home to Matrix Coworking. Summer time is a wonderful season in Madison and there’s a reason why I tend to avoid flying as much as I can this time of year. It’s vacation time for everyone, airports are stretched to the max and weather is far more volatile than in winter.

So, now Madison, WI is officially the new “HQ”… and just like with anything in life, that’s the plan until it’s not the plan anymore. There have been countless times where I had 6-8 months planned out “perfectly” only to change 3-4 times. Living out of a suitcase, spending every night in a different hotel or on a couch at this point almost feels more normal than having an apartment.

I’m excited to get through all this travel in the fall with the hope that I’ll be back in Mexico (Puerto Vallarta) for the winter. That said? I’m sure these plans will change more than a few times. All I know is that when the time comes, I’ll be ready to pack up and head out for the next adventure no matter where…even if that’s back in Chicago.

The post Adios, Chicago – It’s Time to Hit The Road! First Up? Madison, WI was first published on Coworkaholic.

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