Pickens grew up in Auckland and rose through the ranks of New Zealand's open-wheel speedway scene, competing in Quarter Midgets, 3/4 Midgets, Midgets, Sprint Cars, and Karts. His dominance on dirt ovals in New Zealand established him as the benchmark talent in the country, and his reputation soon attracted international opportunities in Australia and North America.
In 2005, Pickens made his debut at the Chili Bowl Midget Nationals in Tulsa, Oklahoma, one of the most prestigious indoor midget races in the world. Racing from the 19th starting position, he drove to a sixth-place finish and earned Rookie of the Year honors. His performance attracted attention from NASCAR's Roush Racing, who invited him into their Driver Development Competition Program that year. Pickens advanced to the final round of the program but was ultimately not retained, partly because his background was entirely on dirt ovals — there are no pavement oval circuits in New Zealand.
Also in 2005, Pickens won the 55th Australian Speedcar Grand Prix at Avalon Raceway in Victoria, and finished second in the Australian Speedcar Championship at Perth Motorplex.
In mid-2007, Pickens raced for Ken Hendricks' American Speed Association Late Model team, Urban Force Racing, competing primarily at Madison International Speedway. He left the team in July of that year and transitioned back to a mix of midget and pavement car events for various owners. During the 2008 season he raced midgets weekly at Angell Park Speedway and ran the No. 30 car in ASA Late Model Series events.
Pickens's connection to Australian competition deepened over the following decade. He regularly drove for Brett Morris in the Australian Speedcar Championship and the World Midget Series. In 2011 he finished third in the Australian Championship in Lismore, New South Wales. In 2016 he captured the Australian Speedcar title at Parramatta Raceway, becoming the first New Zealander ever to win that championship. He also won the 2015/2016 International Midget Series Overall title, taking victories in both the World 30 Lap Derby and the 50 Lap Classic.
At home, Pickens's record is unmatched. He has won the New Zealand Midget Car championship ten times and the New Zealand Sprintcar championship once. His domestic achievements include 200 A-main victories in New Zealand — including nine consecutive A-main wins — six New Zealand Midget Grand Prix titles, five wins in the Barry Butterworth 40 Lap event, multiple Herman Tros Shield victories, and multiple North Island championship titles. His regular New Zealand car is his own #54A CRC King Chassis Midget; he also campaigns a #54A CRC Sprintcar.
Pickens has qualified for the Chili Bowl Nationals A-main six times, with a career-best third-place finish in the 2011 event. He has recorded multiple feature and pole wins in USAC, POWRi, and Badger competition in the United States. He has also won the UMRA TQ feature on debut, and taken an ASA Pavement Late Model Series feature victory. He is a two-time winner of the Australian Super Series Speedcar Championship in midgets and a winner of the Australian Midget Grand Prix.
Michael Pickens's career spans three continents and multiple disciplines within open-wheel speedway racing. His longevity, his ten New Zealand Midget titles, and his status as the first New Zealander to win the Australian Speedcar Championship place him at the apex of his country's motorsport history. He continues to represent New Zealand at the highest levels of international midget and sprint car competition.