I always wanted to ride across the country. As I was preparing to be "downsized" in the wake a corporate acquisition that was a couple of years away (federal approval required, and then implementation), I began looking at options. Supported trips were relatively expensive, and I thought the daily mileage would not leave much time to fully enjoy the experience. As such, I started considering the unsupported option. I was a road snob and always thought I would never want to ride with all that junk strapped to my bike. Moreover, that was just an excuse to wear t-shirts and tube socks from Sears, eat granola and ride slowly.

But I ended up settling on a group, unsupported tour with Adventure Cycling Association. Nothern Tier from Seattle to Bar Harbor, ME in 93 days. Conveniently, their Atlantic Coast route passed very close to my hometown, so I planned to ride home from ME solo at the end of the trip.
So that is what I did. Accumulated the necessary bike and gear. Took Amtrak from the east coast out to Seattle in late May. Started riding two days after I arrived. The first day of the tour marked only the second time I had ridden a fully-loaded bike. The first night of the tour marked the first time I had ever camped. (When I was a camp counselor, we took the kids and our mattresses down to the model campsite for sleep outs a couple of times, but that doesn't count.)
The fourth day of the trip it poured a cold rain until, as I would discover often happens, the day's ride was pretty much over. The sixth day of the trip we crossed the North Cascades Highway in rain that turned into snow before the first pass. Got snowed on crossing Sherman Pass a few days later. Despite that beginning, the awful heat and humidity from southern MN through IA, IL and IN, and having to ride a few miles in the early bands of a hurricane to hole up in a motel, I fell in love with the activity and did, in fact, ride home to my front door and then to New Jersey shore and back a few days later as part of a charity ride I did every year. Even though the ride was supported, and I had a room for the night, I carried all my gear.
Before I left for the trip, someone I know asked me why I would pay someone (ACA) to ride across the country. I told him my goal was to gain experience from others who might have experience in areas that I did not. I did, and I gained enough experience and confidence that I took two seven-week trips the following year.