I signed up with a drive-away service. Car owners would pay to have their cars delivered from one place to another. Rather than shipping it on a train or putting it on a car carrier, they would hire a drive away service, and the service would provide a driver to personally drive that car and deliver it to the destination.
I was 22 and living in Chicago. It was 1995. Still in the age of pagers and AOL. No full blown internet yet. I didn't know what I wanted to do, so I signed up to be a driver for this drive away service. I'd check in with them every other day, to see if they had cars that needed to be delivered and where. It took a few weeks, but finally they let me know of a car that needed to go to Seattle, which is where I wanted to go.
Apparently, the owner thought it would be a good idea to take his wife and 3 kids and DRIVE to Disney World in Orlando, FL..... from Seattle. Well, they made it all the way to Chicago before the guy couldn't take it anymore. They flew the rest of the way and left their brand new 1995 Eddie Bauer Edition Ford Explorer at the drive away to get delivered back to them.
Since the family was still in FL on Vacation, I had about 10 days to get it to Seattle to deliver it back to them. The deal was simple. I had to leave a $350 deposit for the car, pay for my gas, and then when I delivered the car, I would give them their keys and they would hand me a check for my $350 deposit back. Awesome.
I loaded that SUV with all the belongings I could fit in there. Basically clothes, music, TV... that's about it. I started driving west and I took my time. I had plenty of it, so I stopped and hung out with some friends I had In Denver. It was the best road trip I ever went on.
I got to seattle with about 4 days to spare. I was going to stay with some friends I had there temporarily, until I rented an apartment and got a job. I had enough time to unpack my things, look for a place and put in a bunch of applications. A few days later, I washed and gassed up the car and delivered it to the family, who were glad to be back home and get their car back. I used the deposit I got back as first months rent on a studio.
I lived in Seattle for a few years. Chicago, though, is home, and it always calls me back. I fell in love with Seattle, though, and would love to do that road trip again.