Olaf began his career in 1986 as a billboard painter, creating large-scale works across North America, often working in difficult outdoor conditions. As technology advanced, he shifted away from mural painting and found inspiration in motorsports, honoring his late birth father, race car driver Wayne Kelley. Transitioning to oil painting, Olaf captured the energy of racing and gained recognition selling a piece to Michael Andretti in 1996 and having another signed by Michael Schumacher. His work is featured in the Canadian Motorsport Hall of Fame and a Montreal gallery. Building on this success, Olaf later explored horse racing art, with one piece now hanging at Woodbine Racetrack. During his 2003 honeymoon, he branched into landscapes and still life, using subjects like flowers, marbles, and glass. This marked a more intimate artistic phase, and one of these works now hangs in the Louvre in Paris.