My full commute to work is 28 miles and takes me through 6 towns, on country backroad (hills!), skeevy neighborhoods, strip-mall highway, suburb, bad-part-of-city, and city streets. I start in the dark and, on the way home, end in the dark. It takes me two hours one way. But that two hours flies by. It is one of the most interesting ways to see where I live, and I enjoy it very much. But I don't do it every time. Sometimes, I ride to the halfway point where there is a park-and-ride, and do the more reasonable (and flatter) 14 miles in. Other times, I ride to the bus (5 to 12 miles from the house, depending on which bus I take) and put my bike on the rack and ride. When I first did it, I chose a Saturday and did the full thing, and got really lost, and had some fun with it, and mapped it when I got home on mapmyride.com When I finally commuted with traffic, it was hairy at first but after awhile you really do get the hang of the flow, and how to be visible, and communication with drivers (mostly good), and packing a backpack, and all that good stuff. I guess I just wanted to say it is DOABLE and the best way to do it is to do everything above and just go for it. Give yourself extra time, and be willing to get off the bike if you have to or change your plans. Have a backup plan. Keep trying.