As Turtle said, you really need to be comfortable being alone to begin with, the need to be comfortable in your own skin. Then for me it was a matter of setting my Cargo Van up so I could stay out 3 weeks at a time and be able to be comfortable. My van has a twin size bed, frig, micro wave heat and ac so i don't have to idle. From there I read new outlets on the internet on a ongoing basis i visit over 50-75 news sites from all over the world. I have a Flat panel TV with a builtin DVD player and also have a digital antenna to watch local news and shows. The internet keeps me in touch with friends and family as well as 2 cell phones.
I run another business from my van. I take calls, set appointments, collect the money via credit cards, schedule the people need to perform their jobs, (Chef and massage therapists) and work with my Ad agency about advertising.
Music is a big part of my day so there is the I-pod and CD's...I also listen to talk radio, both national and from my local hometown stations. Books, i keep a few that i can read in a few days each then i have a hardback copy of "Atlas Shrugged" that i read for a while then put down for a while and go back to it.
When I am empty on a weekend, I come from time to time, usually a steak on a grill pan and a baked potato and watch college football or Nascar...if I don't cook ten I'll find a place that serves good food from the local fare....
Then there are times that when the weather is nice, I'll get the folding chair sit outside and BS with other drivers.
All and all, i enjoy my life out here up to a certain amount of time away from my wife and kids. Usually after 3 weeks I need to get home to spend time with them even though we stay in touch regularly (wife multiple times a day, kids several times a week)....LOL, but then after 2-4 days at home, I am ready to get back out on the road...so its cook a bunch of food, load up the frig and get back to the road to relax....
Oh and one more thing, when it comes to meeting people (other drivers) I have 2 EO stickers on my van, 1 in front on the windshield and one on the back doors.....works great for meeting other members from here...last week i spent a day with 2 othr members at the Flyin J in KC MO.....And the stickers are FREE...just ask EO for them....