In 1941, he enrolled in Florida Agriculture and Mechanical College (Florida A&M) in Tallahassee.  A year later, his studies were interrupted by World War II when he answered the call of his country and served in both the European and Asiatic Theatres of the armed forces. When the war ended in 1945, Holland returned to Florida A&M and earned a Bachelor of Arts degree in History. He sought admission to the University of Florida College of Law, but was denied because of his race. Holland then applied and was accepted at Boston University College of Law. There, he met the Rev. Martin Luther King, Jr., and as a young law student, Holland worked under the direction of Thurgood Marshall. In 1951, he earned a Juris Doctorate degree.

Upon graduating from law school, Holland returned to Florida and with a great deal of immediacy, he, along with his law partner I.C. Smith and other colleagues began attacking racial injustices in Palm Beach County. He persuaded the Palm Beach County Commission to change its policy prohibiting holders of taxicab franchises from transporting blacks into the city from the Palm Beach International Airport voluntarily. Travelers of color would often spend more hours at the local airport waiting to take a taxi into the city than on the entire journey from cities afar. Holland was also successful in prompting department stores and other retail establishments to change their policies which forbade blacks from trying on clothing, dining in restaurants or using elevators on the premises.  He challenged the City of West Palm Beach’s policy at Woodlawn Cemetery that denied blacks the right to be buried there. Using the law, Holland, his colleagues and others, brought integration to the West Palm Beach Municipal Golf Course, swimming pools, parks, playgrounds, libraries, rest stops on Florida's Turnpike and other public places.

Holland’s most significant accomplishment was the desegregation of the Palm Beach County School System. On May 17, 1954, the United States Supreme Court in Brown v. Board of Education ended government-sanctioned segregation in public schools and held that the doctrine of “separate but equal” had no place in public education. The Court declared unanimously that separate school facilities are inherently unequal. Two years after the Supreme Court’s decision, public schools in Palm Beach County remained segregated.  Holland worked diligently to convince members of the black community to challenge the school board’s policies. Fearing they would lose their jobs, property, homes or even their lives if they took a public stand against segregated schools, no one came forward. As a lone warrior, Holland persevered, making his fight a personal one for the benefit of the community. When his son was old enough to attend first grade in the fall of 1956, Holland, who weighed approximately 130 pounds, courageously took his child by the hand and submitted an application to Northboro Elementary School in West Palm Beach. The principal denied admission. However Holland, his law partner, attorney I.C. Smith, and colleague, attorney F. Malcolm Cunningham, Sr. had anticipated the principal’s response. Armed with the Supreme Court’s decision in Brown, a lawsuit was filed immediately in federal court in Miami. For 17 years, Holland and his colleagues fought for equal educational opportunities for students of all races in Palm Beach County. During that period of nearly two decades, Holland endured death threats and violence.  He was ostracized by many in his community who feared losing the few gains accomplished. Holland was committed and sacrificed tremendously, often paying court costs and other fees from his pocket. With truth and justice by his side, he stood steadfast against the powerful and championed the rights of the powerless. In 1973, an integrated public school system became a reality. Today, the Fulton-Holland Building, which is the headquarters for the Palm Beach County School District, is named in part, in his honor.

In 2001, the Florida Bar and the F. Malcolm Cunningham, Sr. Bar Association honored Holland for 50 years of outstanding service. On July 23, 2002 , the quiet giant who devoted his life to tearing down legal barriers and walls of discrimination departed this life, leaving his labor to inherit his reward.