“If Hunter Thompson was still alive he’d be a Rideshare driver,” said a friend after a year of stories.

A few years ago a couple of my friends started Rideshare driving, they didn’t know each other but around the same time both decided to acquire purpose driven vehicles and started shuttling people around. My first reaction(s) was, “Why are you doing that?!” They both had established construction related careers and this didn’t make sense to me; I even looked down my nose a bit. Basically Steve wanted something flexible to fill unwanted downtime and Rick needed a change. They both found this self-scheduling – pay as you go opportunity to work for them. Over the next months (turned years) I found my curiosity growing and often asked them and the occasional Rideshare drivers that I rode with about their travels..they all liked it.

Gig work driving is a blend of different experiences. The driver doesn’t know when the next request will appear on their app, where the rider is nor where they want to go, never-mind who they are; it is like fishing. Learning and tracking demand is a constant navigation of social trends, using past observations to predict future needs. Moving the driver’s position icon on the app map to chase down surge bonus pay icons and trending demand arrows is much like an 80’s video game. When the ride ends the driver is automatically paid.

While finding the work schedule flexibility and paid upon completion appealing I wondered about other potential gig work – something other than driving strangers around.

Things change. With a slow winter approaching I found myself at an intersection of want and need, so I chose to try, to drive through it. A few months down this detour the pandemic came around, shifting everything.

After two years and over four thousand trips down the road of this experience – it seems time to capture some of it. Every trip yields an adventure and each personality contributes to these short experiences..some are worth sharing.