The best of times. The worst of times. (I’m back.)

by | Oct 25, 2023 | Blog Posts, Transitions, Uncategorized | 0 comments

In August 2022, after almost a year on the road, investigating possible places to relocate from Chicago, I wrote about “when things fall apart.”

Welp, they kept falling apart…

Short-ish story:

When I last wrote, I was in Richmond and it was the height of a housing shortage. Even as an organized, financially stable, stubborn 44-year old, I couldn’t find a long-term place to stay.

Worthy of a 2022 country song: apartments would get double-digit applications within an hour of being listed, while houses were being swept up by the highest cash offer on their first day on the market.

After three months of living in a basement Airbnb, it got harder to get out of bed.

Ding, ding, ding. πŸ””

As a coach, I know it’s tough to get perspective when you’re stressed.

So I decided to leave Richmond.

I’d go back to Chicago for some long-scheduled doc appointments and then get an Airbnb for a month in Charlottesville, VA.

I’d rest and figure out my next step, without straying too far from Richmond, in case I wanted to go back.

Despite all its five stars, when I arrived at my C’ville Airbnb a few weeks later, it was filthy. Complete with cat puke on the carpet and hair on every pillow.

Airbnb gave a full refund. But with folks flocking for fall foliage and college football, it was impossible to find another nearby, long-term place to stay.

I backtracked 8 hours to Louisville, KY, where an Airbnb I’d just stayed in (on my way back to VA from Chicago) was available for the next three weeks.

While I was still rolling with the punches, it was getting harder not to double over.

That’s when I decided to come back to Chicago.

But as a long-time Midwesterner (and Covid long-hauler), I knew better than to make my grand re-entrance just in time for hibernation.

I stuck to warmer weather until I rolled back into town this past May. To Evanston actually, just north of Chicago. Only to have another month-long Airbnb not work out. (Yes, seriously.)

In June, *not my plan* but because I really needed to stop, I leapt at an opportunity to rent a great apartment in Chicago proper.

A few months later, here I am! Mostly un-burnt-out.

Things I’ve heard a lot lately:

~ “I’m sorry it didn’t work out.” –> I’m not sorry and who says that it didn’t work out?
~ “You ended up back in Chicago?” –> Ended up here? (I’m taking a year to rest, find perspective, and figure out what’s next… just like I hoped to do in Charlottesville twelve months ago.)
~ “You couldn’t find someplace you liked?” –> I couldn’t find someplace I liked enough to trade what I’d built during 15 wonderful years in Chicago for it. (My exploration in 2021, 2, and 3 was of a very different country than it would’ve been in 2019.)

So, I’m back in Chicago for now.

As you can imagine, I experienced A LOT during 22 solo months on the road.

A lot of awesome. A lot of not.

I’m excited to be in a place, mentally and physically, where I can start sharing what I learned with you.

I’m going to be sharing *leadership lessons from outside the office.*

From personal experiences (so many atrocious Airbnb hosts!) to what’s notable in the news, we’ll look at lessons you can easily swipe…so you don’t make the same mistakes.

Join my mailing list to get emails sent directly to your inbox!

I’m so happy to be back.

Love you, mean it,


Sheila Devi is an Executive Life Coach.

–> One-on-one, she helps clients to navigate professional and personal challenges so they have more time to focus on what’s most important (and can be more successful in all of it).

–> Sheila also works with high-pressure organizations, such as law and accounting firms, to increase employee morale, engagement, and retention.

Currently in Chicago, Sheila works primarily virtually so she can help no matter where you’re based.

To talk with Sheila about how she can help you and/or your company, please email

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