Packing is an essential part of any trip, and also probably the most daunting. “What do I need to have for this trip?” A simpler question to answer for short trips than long. People tend to procrastinate, put it off to the last minute. The race to get that last load of laundry done before the flight/hitting the road always adds a little more stress to the process.

Something always gets forgotten. Whether it’s something overlooked, like appropriate clothes when visiting a different climate, or something essential, like your clothes bag, something always gets left behind. It seems that with me, the longer the trip, the more trivial the missing piece. A four-day trip to Kansas City and a five-day trip to Vegas each saw me leave my cell phone charger behind (I was on-call); fortunately, I had my car charger for when I really needed juice. A two-day trip to Chicago found me without socks or underwear… the department stores around downtown offered sufficient replacements. This first leg of the road trip leaves me without a razor – I use an electric so Mountain Man Nick is likely coming your way until I get home.

The other fun part is re-packing: making sure you leave with everything you brought. You’re at such a sensory overload from everything you’re experiencing in this new and different land that you easily space off and leave things behind. This is another area where I’ve historically failed: I left a cell charger in Seattle (I have terrible luck with chargers). My sunglasses disappeared the last time I was in Denver. I left my cell phone in Chicago. We’ll see what sprawl gets left behind throughout this trip. Hopefully, being aware of it will make me more likely not to forget things this time.

You know how, sometimes, late at night, you get these crazy ideas? You know, the really wild, poorly thought-out ideas that sound awesome on the surface? Ideas like opening a restaurant named “Pie in the Sky,” where an overhead train that drives slices of pie through the dining area. Or buying a commercial waffle iron just like they have at the Waffle House because you really want to go to Waffle House, but the nearest one is almost 200 miles away. Or taking a cross-country road trip to meet all those people you’ve met online. The kind of ideas that come up when it’s two in the morning, and you’ve been at work since nine the previous day.

Generally, these ideas are merely forgotten. You weren’t really awake to begin with, so if you did happen to scratch out half a business plan on the back of a likely brazenly-stolen Village Inn menu, you quickly wonder what you were thinking and throw it in the trash. Others survive the late night, but the more you think about them, the worse the idea sounds. Some, unfortunately, end up being too approachable, and you find yourself with a receipt for one Wells WB-1 Waffle Baker (picture courtesy Marcus Ross, the person with the waffle idea and the waffle iron).

The more I thought about the road trip, though, the more it sounded like a good idea. Round up as many people as would take me, plan a route that reasonably efficiently hits as many cities as needed, take a camera and several changes of clothes, and go have fun. The trip starts Friday with a trip to Denver, then Salt Lake City, Las Vegas, Seattle, and a brief stop home before heading East. The East leg is not nearly as well planned yet, with the only known destinations so far being New York and Washington, DC. Stay tuned here, on Flickr, and on Twitter to hear about all the destinations and events.

Oh, and one more thing before I wrap this up. A big thanks to Danny over at Silicon Prairie News for selecting my blog for his new 5 in 5 series. It was great fun to shoot that video (a single take; hard to believe, I know), and I’m looking forward to future entries.