Rediscovering Herself: Kaylavon Middleton emerges as a top insurance broker

By Christina Fuoco-Karasinski

Kaylavon Middleton is a proud, card-carrying Medicare member and, as a licensed Certified Medicare Insurance Planner, she enjoys helping others navigate the system. 

“I’m there as a bridge when people get ready to retire,” Middleton says.

She’s a retiree herself, well, sort of. She left BlueCross BlueShield after 16 years and knew how to tread the Medicare waters herself. Five years ago, she founded MediSolutions.

“I was excited when I retired, but I wasn’t done working,” Middleton says. “I wasn’t one of those seniors who were ready to rock in the chair for the rest of her life.”

The MediSolutions role came to her organically. She joined a fledgling Medicare agency that eventually shriveled to merely her.

“We went through all the training, the government testing, insurance carrier credentialing,” she says. “Things were slow. As with any new business venture, you have to really hunt for your business.

“The other people needed income to sustain their lives and families. I didn’t have that problem. I had my core basic responsibility net. I had health insurance because I was retired. I could fish for a long time and not get any fish and be OK.”

Middleton was the sole employee who was producing, so she asked to be released from the agency so she could work for herself.

Successful career

Middleton started her career in the health care industry in 1977. She served as a manager in the medical claims division for a major hospital in California and as an account manager for a major insurance company in Arizona.

When she decided to retire at age 56, she had the support of her husband. She served as a consultant occasionally, which she calls a blessing.

“It was a nice little salary to smile at people,” she says with a laugh. “I can smile.”

Now she specializes in all things Medicare. Her core area is working with employer groups as an extension to human resources professionals to help them manage their employees who are turning 65. They may have family members who are dependent on their group plan. She helps her clients understand what happens if they remain working, if they have a health savings account, and if it makes sense to turn to Medicare and still work.

“I’m there as a bridge when they get ready to retire,” Middleton says. “I inform them about drug plans by analyzing the medications they’re on to make sure they have the right plan.

“There are 30 drug plans in Arizona. Not all of them are the same. It’s really a skill to be able to navigate through that and find the best plan. I save people thousands of dollars. Last year, my father had a broker, but I asked him if anyone looked into his medications.”

Licensed in California, she scrutinized his benefits and realized he was on the wrong plan. She saved him $1,200 annually on medications. Middleton looks out for everyone’s best interest.

“I tell people the one thing that’s not talked about when you’re getting ready to retire is what you do with the rest of your life,” she says.

“They say, ‘Make sure you have enough money to retire,’ but they don’t share the spiritual and emotional side of being retired. When I retired, it was really a reintroduction to myself, meaning that no one was telling me what time to get up in the morning. No one was telling me when have lunch, when to take a vacation, what projects to get done and the deadlines. You’re left to yourself. You do get reintroduced to yourself. You have to find out who you are now and in this new space.”

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