John Gilliland ’89, a problem-solver scoring big career wins

John Gilliland ’89 packed ambition and a detailed life plan in his suitcase when he arrived at Cornell College as a first-year student. It didn’t matter to him what major he graduated with, just that he prepared himself to be ready for law school. Little did he know what would come his way and how his Cornell education would support all the twists and turns of his career. 

Not having a predestined major allowed him to take courses that would cover subjects he wanted to explore. His curiosity led him to double major in history and philosophy with a fine amount of English literature courses sprinkled throughout. 

Gilliland’s father, a financial advisor, discovered Cornell during his work travels visiting clients and was intrigued by this unique system of education, the block plan, where you take One Course At A Time. At the same time, Gilliland had a successful high school senior year on the football field and began to correspond with the football coaches, including Head Coach Jerry Clark, (Cornell’s head coach from 1959 to 1986) who was inducted into Cornell’s Hall of Fame as its all-time winningest coach with a record of 159-85-1. 

“Being a very good academic school, being unique with One Course At A Time, and the opportunity to continue to play football, all that brought me to Cornell,” Gilliland says. “One Course At A Time isn’t for everyone. I was a fairly disciplined student so I was able to keep up on the reading. I quickly learned that you could not procrastinate on the block plan, which made me a better law student. I didn’t let myself get behind in the reading I had to do in law school even when going back to a semester plan.”

Although confident in his life plan and goals, Gilliland was less secure when it came to building new friendships. After all, he went to school with the same group of kids his entire life back in his small hometown of Knoxville, Iowa. He didn’t know anyone at Cornell when he first arrived with the rest of the football players and he was homesick. But after the first few weeks rooming in Tarr Hall, the loneliness began to recede, and he learned how to make new friends. By the halfway point in his first year, he was well acclimated having developed lifelong friendships with two Tarr Hall guys—David Hughes ՚89 and David McGill ՚89, who also played football with him and were in his wedding later in life. They still are great friends to this day. 

Professor of History Phil Lucas was Gilliland’s advisor and he feels he became a history major in part because of Lucas. Cornell’s Chaplain, the Rev. Richard Thomas, who was also a history professor, became another mentor of Gilliland’s. Gilliland fondly remembers turning to Thomas, who was the Gammas’ advisor, (Gamma Tau Pi) when there were situations the Gammas had to work through. When Gilliland was 29, Thomas married Gilliland to his wife. 

“My generation had the mindset that you had to follow a plan. I’m going to sound like the old guy here—I had a plan. I was going to go to college. Then, I was going to go to law school. Then, I was going to run for president. I had a plan, right? But many young people today don’t have it mapped out like that and that is fine. Things don’t always follow your plan. That’s ok, you can change gears and change places.”

Law school was always part of Gilliland’s plan and he earned his law degree from Creighton University, in Omaha, Nebraska. He never wanted to be the kind of lawyer that was in court every day. He had interests in history, politics, business, and government. He wanted the law degree to allow him to do a lot of different things and the professional degree did set him up well for a successful first career that spanned 20 years—first as a judicial law clerk for the district court judges of Black Hawk County in Iowa, where he helped research and write opinions on cases that spanned the breadth of the law—from murder to child support. 

He advises young lawyers to pursue judicial law clerkships because it provides experience across all the different specializations in law which can provide you with first-hand experience that can inform what area of law you might want to shape a career in for the long term. 

When asked what his advice for Cornell students would be, he says, “Remember there are other people in your same circumstances. The kids walking to class are feeling the same way you are. Don’t be afraid to say hello to somebody. Don’t be afraid to try a different kind of class. Try a lot of different stuff. You may think you may want to be a chemical engineer, but then you find out you’re really good at psychology. Try different courses. You’ll get your credits. You’ll graduate on time.”

After the clerkship, Gilliland was invited by Iowa Secretary of State Paul Pate, to be the Deputy Secretary of State which aligned with his ongoing interest in politics. After four years, he ran for Secretary of State while Paul Pate ran for the Office of Governor. Although he didn’t win the general election (Tom Vilsack won as Governor and democratic tickets down the ballot followed suit), his experience in politics earned him a position in the law firm Bradshaw, Fowler, Proctor, and Fairgrave in Des Moines, Iowa, where he worked to start a lobbying practice from scratch. 

Then, another opportunity that centered on one of his other interests, business, emerged—working for the Iowa Association of Business and Industry (ABI). They were looking for a business lobbyist and Gilliland fit the bill. He worked at ABI for 12 years. 

Ten years ago, looking for better work-life balance and to spend more time with his growing family (his wife Holly and their four kids), Gilliland took an exit off that career track and started a new career in finance. Twenty years after taking the Bar Exam, he found himself studying for the Series 7 Securities Exam and followed in his dad’s footsteps by becoming a financial advisor. Today, he is the vice president at the Gilliland Group at Morgan Stanley in West Des Moines, Iowa, which he commutes from his small bedroom community of Van Meter, Iowa, which is west of the Des Moines metro area. 

“You cannot underestimate the value of a Cornell liberal arts education because you can have a broad experience on the block plan,” Gilliland says. “You really learn how to problem solve. How to not procrastinate. All skills you can take to any profession. Being a lawyer is about problem solving and so is being a financial advisor.”

He enjoyed serving a couple of terms on the Cornell Alumni Board and also served on the Board of Trustees business affairs committee. He feels he learned some great lessons from the Trustees about business and finance and found that to be just another way Cornell has given him an education. He has been the class agent for the Class of 1989 for the past five years and loves to reconnect with classmates and plans on being back for his next reunion. 

When asked what his proudest moments have been in his career and life, Gilliland’s face brightens and his voice sounds more emotional, as he says, family. 

“I’m proud of my kids and the people they are becoming. Holly and I have been married 25 years, raising four great kids,” he says. “When we get all four of the kids around the dinner table at the same time, and we get them talking, just listening to them and their different interests and thoughts—I just sit there and keep my mouth shut happy to just to listen to them interact.”