Juggling family, work and community


Bobby Highsmith knew his sophomore year at Duke University (he attended on a football scholarship) that he would return home to Key West. Celebrating his 30th high school reunion this weekend, the valedictorian will attend as a prominent lawyer with Highsmith & Van Loon, P.A., and important member of the Monroe County School Board. In order to find a niche in Key West, Highsmith attained board certification as a specialist in wills, trusts and estate law, the highest standard of excellence established by the Florida Bar. As a father of two and son of two Monroe County educators, joining the school board also was a natural fit. “I am enjoying it more than I thought,” said Highsmith, who will run for a second term in 2018. “The board is very dynamic and determined in the best possible way.”

Do you have a life credo or motto? Work hard, play hard. That was kind of our unofficial motto when I was at Duke, and it has served me well throughout the years.

What is something you never thought would happen in your life, and surprisingly changed everything? I never thought I would nearly go bankrupt, but I got caught pretty bad in the real estate market crash of the late 2000s. I discovered mindfulness meditation, which has been a Godsend. Through mindfulness, I have attained a whole new perspective on life, and try hard to truly appreciate everything I experience, both good and bad, because it’s all part of this life we’ve been blessed with.

What’s one thing you have yet to achieve on your “bucket “ list? And one thing you did achieve? Playing for and starting on a Division 1 college football team. Other than watching my kids grow up hopefully as happy, healthy and responsible adults, my life feels pretty complete. I am happily married, have two great kids, two great jobs and live in paradise. I am an avid reader and would love to write a book one day.

Who’s your favorite TV lawyer? Jimmy McGill / Saul Goodman

What’s an accomplishment of the school board since you joined? The board has taken significant steps in returning stability and has created an environment conducive to a successful school system. Our state ranking has improved from 23rd to 12th since I joined the board. In addition, the voters have repeatedly given us renewals of our ½ cent sales tax and the half mil property tax which has enabled us to complete rebuilding all of our schools into state of the art facilities.

What are your goals before your term ends on the school board? Will you run again? To push back the Key West High School start time from 7:30 to perhaps 8:15 or 8:30. The superintendent rejected this request this past year citing an inability to find sufficient bus drivers. I am going to continue pushing the district to find a solution to this issue. My second goal is to bring mindfulness meditation practices to our students and teachers. Pritham Singh has offered to help facilitate this effort. The research on mindfulness training in schools, and the positive effects it can have on student achievement, behavior and overall well-being is quite impressive.

Why so cautious about drug testing in schools? The one thing we have protecting us is the U.S. Constitution and the Bill of Rights. I personally believe that suspicion-less, random drug testing of students is a violation of their Fourth Amendment rights of freedom from unreasonable searches and seizures. I don’t want our students, the citizens of our tomorrow, getting used to this as I am fearful that this will eventually undermine our society’s recognition of the paramount importance of upholding the Constitution and its protections.

Which TV, movie or superhero character is your alter ego? Bond. James Bond. I wish.

If you were invisible, what would you do in Key West? Follow people who allow their dogs to poop in other people’s yards and leave it on their own front porches.

If you could grant Key West one wish? Eco-friendly, high speed monorail from the mainland.

If not a lawyer, what would your secret dream job be? Landscape architect.

Lunch with one famous person: whom would you choose? David Sedaris

Finish these sentences..

My friends and family would describe me as … weird.

My autobiography would be titled … Lucky Conch

One secret I shall never tell … Which of my kids is my favorite.

When I go, I will go …. Enthusiastically on to the next adventure!

We want to do everything to keep kids in school.” – Bobby Highsmith, Monroe County School Board.

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