Coming of age in the golden era of digital hospitality had an enormous effect on my expectations for flexibility on the road. I rarely book ahead, I never worry about finding a place to stay, I overpack luxuries and I am always uncomfortably on the hunt for my personal totemic signifiers of safety. You need things on the road to keep your rituals intact so you don’t drift.
I know how to search for a place to rest and I restlessly pursue it on the road. Singles browse dating apps like I browse Airbnb. I spot red flags on apartment listings like a woman who has been on one too many bad dates.
I spent much of my childhood traveling. My most potent recurring nightmare is packing for a trip that never arrives. I have lived in a perpetual state of readiness to get up and leave. I bring endless tiny compacts and one singular pair of high heeled shoes for a night out I never go on. I am ready for glamour on the road but all I find is the anxiety of instability.
It’s this perpetual readiness to flee that has made me an exceptionally good picker of hotels, rental units, vacation homes and other short term stays. I couldn’t afford a deposit for an apartment in New York for so long that I could find an under-market illegal sublet on Craigslist on a moment’s notice. It’s a handy skill set.
Naturally I’ve come to take this talent for granted as I’ve cultivated it. I’m confident that I’ll pick a decent rental because I can spot issues from miles away. I admit I’ve looked down on complaints about how bad Airbnb has become. I thought I’d avoid the quality control issues. It’s no longer a better value than hotels generally speaking but the real crime is that it’s troubles are not worth the hassle for many. It’s not seamless like a branded hotel.
I felt the hassle was worth it for the comforts of home on the road. But I think I’ve crossed my personal Rubicon on Airbnb in Prague. I won’t default to it any longer. The costs are now basically identical. You’ve got to weigh the costs of friction against having your life a bit disturbed. Hotels specialize in hospitality. It’s probably worth remembering.