My parents have always supported my dreams. We've figured out a pretty good system for my longer trips. Before heading off to explore the trails, I'll leave my resupply boxes in my parents living room. The boxes are left open, with lists and dates sitting in each box. This allows me to adjust gear and food supplies during the hike, and allows my parents to add family and news updates in my boxes. For instance, during the PCT hike I called my parents ahead of time and told them to pull my ice axe from my Sierra resupply box. Its not perfect- I've got to call from a few towns ahead- but it works pretty well. In addition, my parents have been known to drive me to and from trailheads, as well as leaving some random trail magic for other hikers. In exchange, I check in as often as possible. Since I don't carry a cell phone this can be rough. One time, while at a pay phone but without any change (too heavy to carry) or phone card, I actually called a coworker via the company's 800 number and got him to call home for me. Family is good. Friends are too!
My good friend, Straw, has had a part in most of my adventures. He helped me to plan, train, and resupply for my AT trip. He also hiked with me for a few weeks on the AT. In 2009 Straw drove from his home in Montana to Colorado where he picked me up and drove me to Mexico. Then he kicked me out of the car and I walked to Canada! I don't know many people that would drive across the country specifically to drop a friend off in the middle of a desert. Friends like Straw are hard to come by! Hopefully he will be able to hike some of the CDT with me as well!