While working as a carpenter with his father, Ross lost his left index finger. It did not affect the way he held his palette while painting.
Ross enlisted in the United States Air Force at age 17. The Air Force transferred him to Elmendorf Air Force Base (in Alaska), where he first saw the snow and mountains that later became recurring themes in his artwork. He developed his quick-painting technique to create art for sale in brief daily work breaks. Having held military positions that required him to be, in his own words, "mean" and "tough," "the guy who makes you scrub the latrine, the guy who makes you make your bed, the guy who screams at you for being late to work," Ross decided that if he ever moved on from the military, "it wasn't going to be that way any more," vowing "never to scream again." During this time Bob met Jane, who would become his second wife, when they worked in the medical field.
During Ross' stay in Alaska, he worked as a bartender part-time, when he discovered a TV show that was called The Magic World of Oil Painting, hosted by a German painter, named Bill Alexander.
After studying with Bill Alexander, Ross discovered that he was soon able to earn more from selling his work than from his Air Force position. Ross then retired from the Air Force after 20 years of service with the rank of Master Sergeant  and became famous worldwide hosting the television program, The Joy of Painting, with the help of Annette & Walter Kowalski.
Before the show was launched, Bob would try to promote the painting technique but with little interest. He also had to find a way to cut back on spending, so he decided to have his hair permed, just so he could save money on haircuts. The perm hairstyle was not comfortable for Bob, but ultimately became an iconic feature of the painter.