a inflatable unicorn in a pool

Why I Left the City, Moved into a Resort “Bubble” & Won’t Fly Until 2021

After four years of calling Chicago home, it’s time to say goodbye. This 35 year old single guy is leaving the city life and jet setting behind to dive head first into a self-imposed bubble in a gated resort community outside of Orlando , FL. Welcome to 2020. What a weird time to be alive.

Farewell, Chicago

Last week I packed up my cute city apartment, rescue pup in tow, and took one last trip down Lake Shore Drive. It was sad. Like the ending of a book, a few chapters too short.

I was a newly minted digital nomad prior to landing in the Windy City. In fact, when I first arrived, I hadn’t expected to stay more than a few weeks, let alone four years. As business opportunities evolved, it made sense to have a proper US “home base”.

Already on my way to earning United’s top Premier 1k status, it made even more sense as Chicago is after all, their hometown. Why not “enjoy” the routes/amenities offered at the ORD hub? (The joke was – and still is – on me.) Flying direct to almost anywhere was too easy. I was on a plane two to three times a week, coming “home” just to do laundry.

But it only takes one pandemic to turn the world upside down. What went from being the “perfect” city apartment became isolating and depressing. Especially with no access to private outdoor space and windows with only northern and southern exposure. If your plants aren’t getting enough daylight, chances are the same goes for you too.

A Complete 180

Early on into a 90+ day shelter in place, I realized I couldn’t do it again should there be a second wave of COVID-19 cases this fall. Even though I had “lived” in Chicago, in the winter months I did my best to work on projects in warm weather. Tough to complain about commuting weekly to Cancun in January and February. They don’t call it the Windy City for nothing.

The last time I’d felt like this was in 2012 when I struggled with overwhelming anxiety and depression when working from home. That’s why I love coworking so much. It literally saved my life. But – alas – even coworking spaces were closed. Many of which are now slowly re-opening. And, while they might be safe and extra clean, not all the “accelerated serendipity” magic is back.

There’s also the fact that when we can work “from anywhere” or just work from home, we can live in places that are way cheaper than the city.

I’m sure I’ll get flack for heading to Florida, but I’m literally locking myself down at home. I’ve found a resort community renting out houses by the year now, rather than on Airbnb. Working from home (bleh), limiting myself to 1-2 errands a week and having a party for one (and a dog) nightly in the pool and on the lanai. 🙂

Desperate Times Call for Desperate Measures.

Even if there isn’t a second wave, I just don’t see people wanting to travel by air. Or even wanting to do anything involving more than a drive down the road. And, after my experience flying during a pandemic, why would you? Traveling on commercial flights was already a borderline miserable experience. Hence why we all hack the world of points and miles – trying to scrape together the best experience for the least expense. Lounges are closed, service on board is meager and everyone seems to be more on edge than ever.

Sure, Americans can find ways to travel internationally, but should we be doing so already? Even if the tickets are “so cheap”. Also, as the chaos around the 2020 election goes on, is this really a time when you want to be traveling abroad? Dependent on a government to protect you should something happen?

I know that I’m blessed and privileged to be able to pull off such a move. I also know that I’m not alone and that this isn’t permanent. We’ll all travel once again. Are you moving somewhere new because you can work from home? How has 2020 changed your travel/living plans?

The post Why I Left the City, Moved into a Resort “Bubble” & Wont’t Fly Until 2021 was first published on Coworkaholic.

0 0 votes
Article Rating