A friend of mine who’s worked for Amtrak for decades started a side hustle in Chicago in the 90’s that gave some people the creeps. There was no such thing as Airbnb until 2008. “You’re letting people stay in your house?!” they’d ask incredulously. But I couldn’t be picky. As a hotel concierge, I never knew when the property would fold or the hospitality company would undergo a major downsizing. I needed the money, so I signed on.
The experience of welcoming a stranger into your home who doesn’t know the city can be mutually rewarding. As a concierge, it was already in my nature to get truly invested in creating happy memories for people from other places. Back home in New Orleans, I had learned about different kinds of travelers during my senior year in college when I stayed in a funky old guest house in exchange for working the front desk. Travelers from other countries were completely fine with staying five or ten minutes from the French Quarter in a charming guest house for an affordable nightly rate – while sharing a bath in the hall with others. Travelers from the U.S., not so much. We had some tirades.
But that taught me to be like the folks who focused on fun. I had witnessed how they loved the breakfast that was served buffet style in a cluttered parlour with dusty paintings and a storied piano. But I knew they were in town to get out there, not pick on the quality of the bath soap. So I felt certain my vintage walk-up in Boystown Chicago with creaky floorboards and a thousand coats of paint could please a sojourner with an eye for the authentic.
And I was right. For sure the booking process was complicated before the age of internet. But being able to pay the bills made it worth every hassle.
It comes down to the fundamental human-to-human interaction.