June 2, 2020
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Ahead of the Game

William Harold Calloway is enjoying the fruit of his labor after a successful career

William Harold Calloway is not your typical insurance man.

His successful 34-year career with State Farm might appear to prove otherwise at first glance, but Calloway is as quick to bring up childhood memories from his family’s farm as he is his success in insurance.

After retiring from State Farm on Oct. 31 last year, it is the first time since Calloway was 5 years old that he hasn’t held a job. It has been an adjustment, he says. His first job was plowing on his family’s farm in Philadelphia, Mississippi, where they raised everything from cows, hogs, chickens, and turkeys to apple, peach, fig, and pecan orchards.

Though the Calloways were an African-American family living in rural Mississippi at the height of the civil rights movement, he says because his family owned their land people left them mostly alone. Others, however, were not as lucky. In June 1964, Ku Klux Klan members murdered three activists in Philadelphia. The county, Neshoba County, became known as “Bloody Neshoba” because of how many black people were murdered in the area.
“Philadelphia, Mississippi, has been trying to live that stain down ever since then,” says Calloway. “It’s a different place now when you go back, but it was a tough place.”

While attending Mary Holmes College, West Point, Mississippi, on a basketball scholarship, Calloway remembers one game vividly. His team traveled to Selma, Alabama, to play. On their way back, they stopped at a fast food joint where a man started causing a scene and hitting the bus.
“Before you knew it, the bus was surrounded by people who didn’t want us to be there,” says Calloway.

He went on to Lane College in Jackson, Tennessee, where he graduated with a degree in history in 1968 and met his future wife, Frankye. He had $10 after graduation, enough to take him back home to Philadelphia or go to Evansville, where his brother-in-law Dr. Rev. W. R. Brown, Sr. pastored New Hope Missionary Baptist Church.

Today, more than 50 years later, Calloway still is a member of the congregation, a church deacon, and chairman of the church’s board of trustees. The current senior pastor, Rabon Turner, says Calloway was the first person he met when he came to Evansville from Oklahoma to interview for the position.

“It can really be boiled down to the Lord placing him in places to have access,” says Turner. “I think every time the Lord has elevated him, he brought someone along with him. Every door God has opened, he has brought someone through. He has been a champion to give someone else a seat at the table as well.”

When Calloway first came to Evansville, he didn’t stay for long before he was drafted into the military to fight in Vietnam. Before he left in 1969, he and Frankye were married.

“He went to Vietnam two weeks after we got married,” she says.

“We got married on June 21, and I went to Vietnam on July 7,” he says.

His attitude was to get in and get out as quickly as possible. With a bachelor’s degree under his belt, unlike many men drafted, he was hoping to escape assignment in Vietnam. However, he had no such luck. Calloway says his time in the military taught him discipline, and he quickly rose the ranks to platoon leader and was sent to Pleiku, Vietnam. In the central highlands and jungles of Vietnam, he learned a new lesson — how to survive.

“When you’re in a situation where everybody is along the same constraints, you don’t find no racists,” says Calloway. “Ain’t nobody mad at you because you’re white. Ain’t nobody mad at you because you’re black. Because we’re trying to cover one another, we’re trying to live.”

On Feb. 3, 1971, Calloway was discharged from the U.S. Army and returned home to Evansville. Along with newfound grit, his time in the military also afforded him the opportunity to go back to school at the University of Evansville where he earned a master’s degree in education.

After his military life, he worked for the city’s Department of Public Welfare before becoming the director of the Head Start Community Action Program. In July 1973, Calloway went to work at Indiana State University-Evansville (now the University of Southern Indiana) as the director of financial aid and was the first African-American administrator at the university. His time at USI began a path that continues today, with Calloway serving as a university trustee. In 1982, State Farm came to recruit him to open an agency in Evansville, but he wasn’t interested and declined.

“I had a great career at USI,” says Calloway. “I liked them; they liked me. I was around a lot of young people. I thought I had a job that really helped people be able to reach their dreams and aspirations, being the financial aid director. It was satisfying.”

State Farm was persistent, though, and returned two years later. This time, Calloway heard them out. He had to pass an insurance test to qualify, so he decided to take the test. Whether or not he passed would be his sign.

Calloway passed the test, turned in his resignation, and started his State Farm agency at 1125 W. Mill Road in 1985 without a single policy in his portfolio. For the first six months, he struggled and worried he might have made a mistake.

“There was some concern an African American couldn’t sell to white people, because the predominant ethnic groups here at the time were basically white people and black people,” says Calloway. “The general consensus of the black community was that white folks aren’t going to buy from the black man.”
His perseverance paid off, however, and business started rolling in. He says about 70 percent of his business came from white people, and watching his fears being proven wrong was one of the most gratifying parts of his career with State Farm.

“Part of my mission has been to let people know that if you got your stuff together, if you hold yourself like you’re supposed to, and if you back up the product with the company you recommend, people don’t care what color you are when it comes down to that,” he says. “The good thing I found out in this business is we have a good town. I am really sold on our town.”

While Calloway was no longer working to counsel and help students, it didn’t stop him from being a mentor. One of the students he worked with as ISU-E’s financial aid director was Vicki Brasel, an agent with State Farm since April 1, 1987. She ran into Calloway after he had left the university to start his agency, and he mentioned they were looking for another agent.

“Long story short, I became a State Farm agent,” says Brasel. “I owe everything to Harold, because he gave me an opportunity and saw something in me.”

While Calloway is humble about his career and impact in the community, he carefully admits his agency was among the top agencies in Evansville. Frankye’s pride in her husband is not as easily hidden. His record speaks for itself, she says.

“He was one of the top agents in the state,” she says. “And the top African-American agent in the state for years.”

One aspect of his career Calloway doesn’t shy away from, though, is the amount of work it took to be in the top — Sunday evenings in the office, long days, and late nights writing policies around clients’ kitchen tables.

“During that time, you wrote a lot of insurance around kitchen tables,” he says. “A lot of people who I have insured now, I had them insured since I started. Because we wrote it around the kitchen table. You can’t hardly do that anymore. Now, everybody is on our do not call list, so you have to figure out other ways to market your product.”

When Calloway began at State Farm, the office had no computers — only telephones. You were lucky if you had a push button phone, he adds. State Farm as a company isn’t the same company Calloway joined 34 years ago. If it were, he says, the company would no longer exist. Change is part of life. 

Retirement may be Calloway’s biggest change yet. He is looking forward to traveling, mostly to see his two grandchildren. His son William Calloway Jr. and daughter-in-law Karina live in Los Angeles with their two children Kennedy, 12, and Lincoln, 4 months, and his daughter Anika Calloway lives in Atlanta.

Calloway’s other goals in retirement are to give more time to church service and counsel young men in the community. By sharing his life story, he wants to inspire others, especially people of color, to go into business or work toward their dreams.

“There are a lot of people who think the cards are dealt against them,” he says. “And not to say they are wrong, but you ever play poker? So even though you have a bunch of sixes, fives, sevens, which aren’t good for nothing unless you have a straight, you’re going to have to be careful and hang in there until you get a full house. A full house is in the deck. It’s whether or not you can last long enough to get it. What I want them to know is you can get a full house, because what I’ve done in life, where I live, what I drive, the people I talk to, there ain’t no tricks to it. God put enough out here for everybody.”

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