He figured there would be times when the available food would be less than healthy.
And he got ready to be away from his wife of 35 years for the longest period since their marriage.
But with all his preparations for the 59-day journey from Florida to California, Friedman said he was not at all prepared to experience the land and people of America while traveling at 10 miles per hour.
"People took us into their homes and fed us and just wanted to talk with us about their lives," Friedman said while looking over photographs of his trip. "What blew my mind the most was how friendly the people in this country are."
Friedman, who is 66, biked with four friends who all spent time in the Peace Corps in the Philippines from 1965 to 1967.
The five men -- who are spread out between Vermont, Maine, Virginia and Maryland -- stayed in contact through the years.
When the trip was first being planned, Friedman did not think he would be able to make it because he was working as an editor for a magazine.
When the struggling economy forced layoffs in his office in December, Friedman got a pink slip.
His first thought? "How am I going to find another job and what am I going to do next?"
Then, within a few days, he was on the phone to his buddies to tell them he wanted to join the cross country trek.
"Being laid off turned out to be the greatest thing in the world," he said.
Friedman was not a serious cyclist before his trip.
When asked about exotic treks, he mentioned climbing Mt. Monadnock.
Midway through his seventh decade, and out of work, he decided that if he was ever going to try something like this then now was the time to do it.
"I was really out of shape," he said. "There was really nothing philosophical about it. I just wanted to see if I could do it."
He trained over the winter and left Maryland, where two of his friends lived, on Feb. 28.
Three days later the five friends dipped their front tires in the Atlantic Ocean in St. Augustine, Fla., and pointed their bikes West.
Friedman said there were days that tested his stamina.
He talked about cold rain in New Mexico, head winds that never gave in, dust storms in California and a long narrow tunnel he went through with an 18-wheeler blowing an air horn where he actually feared for his life.
Then there were the cramped nights in cheap hotels and restaurants where they were forced to eat what could hardly be considered training food.
"I lost 20 pounds but I haven't checked my cholesterol yet," he said.
The group traveled with a van that carried most of their gear, and each of the five took turns driving.
They arrived in at the Pacific Ocean on April 28 outside of San Diego, Calif.
And while they were moving by old fashioned human power, the trip was recorded with high-tech gadgets.
One of the men, Art McMurdie, is a professional photographer and he kept an ongoing blog.
They talked with their families back home with cell phones and even traveled with a GPS tracker that was synched to GoogleEarth.
Friends back home could click on their computers and see a real-time photo of the very roads they were biking on.
Sitting in his home this week, and going through photographs on his computer, Friedman said it is the people and sites that mostly remain in his memory.
He looked at a shot of a restaurant that served barbecue and sushi.
There were depressing trailer parks in Mississippi, blooming cacti in Texas, a narrow and winding road that hugged the sides of mountain in New Mexico, and an interested rattlesnake in the California desert.
He talked about a "skinny rancher" who raised rodeo bulls, an author in New Mexico who writes books on straw bale houses and visited one in Dummerston and a Texan who peppered his language with the "N word."
"These people are out there. They exist," he said. "There's some scary stuff, but overall it's a beautiful country with beautiful people."
A record of their trip is online at www.jambl.net/biketrip.
Howard Weiss-Tisman can be reached at email@example.com or 802-254-2311, ext. 279.