I rented out my place to support my freelance lifestyle. While the money flowed in, I slept at the office

It was a little after 2am one Friday morning two Novembers ago when I found myself on the Red Line train, on the north side of Chicago, though I had been all the way north and south a few times already that night. I was tired, a little cold, and things were getting sketchy. I’d never been on the L that late before, and my plan to ride all night was seeming less and less safe the more stops we made. My car was empty, finally – the only other passengers had been two drunk men who kept asking where I was going and if they could come – and at each stop I tensed up, hoping no one else would get on.

It was a far cry from the private bungalow in Bora Bora where I had been just 24 hours earlier, but extreme contrasts were becoming the story of my life. I’m a freelance travel writer, which means I get to visit amazing places and stay in some of the world’s most beautiful hotels. It also means I don’t make very much money, thanks to rapidly decreasing magazine rates; so to afford my apartment in Chicago, I used to rent it on Airbnb while I was gone, which was often. This worked well. Too well, actually. So well that I found it hard to turn down guests even when I was in town.

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