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.

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SharonKurheg
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Welcome to the neighborhood! Once all this coronacrapola is over, let’s get together!

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[…] I Left the City and Moved Into a Resort Bubble: See this post on Coworkaholic. Florida with a pool? Sounds good to […]

Howard
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Howard

American traveling abroad right now, having an amazing time. Doing a 7 week stint, quick trip to US, then 8 months in a row of world travel. The fact that people continue to be scared of travel, is, at this point, borderline insanity. I mean, as a simple fact, people should never get in a car, never swim in a pool, and be scared of lions, tigers and bears (oh my). Been flying almost every week since January. As long as you’re a bit flexible, it’s… wonderful. I am not sure what people are scared of, but, I think at… Read more »

John
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John

what community is it in florida? and how did you find them?

Gio
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Gio

Very cool that you’re able to do that (and escape winter in Chicago!) I just left Chicago myself to rejoin the family on the West Coast. I do grapple with the fact that I’ve left my social life behind me, and of course there’s occasional FOMO knowing that I’ve given up my social life once I’ve moved away. Is this an issue for you moving to Orlando? How do you cope with it?

Mike Saint
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Mike Saint

Great move. I’d hate to get stuck in. Chicago during winter if another shut down hits. Not sure what it will be like with a horrible flu season mixed in with COVID. I live in a gated community in San Diego and amazing to be able to walk around and have tons of room. It was fabulous during the pandemic to have our own space to roam around.

House prices in my neighborhood have skyrocketed as everyone is looking for this type of house/community now.

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[…] not super interested in flying right now, but who knows what could happen in a few months time. If you have reason to travel during the […]

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[…] it on living in my resort bubble. Or perhaps it’s the time spent in a social media bubble full of my fellow liberal, […]

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