Will traveled with a friend to cowboy in Argentina and eventually ended up on a horse ranch in South Africa in 1902.

Late that same year in South Africa, he joined Texas Jack's Great Wild West Show and Circus and later, in 1903, he became the Cherokee Kid.

In late 1903, he left Texas Jack's and joined Wirth Brothers Circus for a tour of Australia before returning to the United States in 1904.

In 1904, he joined Zack Mulhall's "Cowboy Carnival" where he worked with Tom Mix and Jim Minnick.

In 1905, still with the Mulhall crew, he was part of incident in which a steer jumped into the crowded stands at Madison Square Gardens. According to various accounts, Will either roped it or ran it back onto the arena floor.