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Challenges fuel motivation

Master Sgt. Kaipo Cowan, 25th Air Support Operations Squadron first sergeant, and his father, Nelson Cowan, spend time together before Kaipo left for Basic Military Training at Austin, Texas, May 27, 2021. Kaipo joined the Air Force shortly after returning to high school to earn his diploma. (Courtesy Photo)

Master Sgt. Kaipo Cowan, 25th Air Support Operations Squadron first sergeant, and his father, Nelson Cowan, spend time together before Kaipo left for Basic Military Training at Austin, Texas, May 27, 2021. Kaipo joined the Air Force shortly after returning to high school to earn his diploma. (Courtesy Photo)

JOINT BASE PEARL HARBOR-HICKAM, Hawaii --

Leaving work from Wheeler Army Airfield, it dawned on one Airman that this was the same road he walked on as a 20-year-old high school dropout. 

Eighteen years later, Master Sgt. Kaipo Cowan, 25th Air Support Operations Squadron first sergeant, agrees his challenges motivate him each day.

“I have this toolbox of experiences and lessons from my life, and it would be selfish not to share with other people,” said Cowan, who grew up a military child moving around the country, but calls Hawaii home. 

Most of his lessons stem from his childhood experiences with his cognitive issues and speech impediments 

“I didn’t learn how everyone else did,” said Cowan. “It was difficult for me as a child and in school.”

As a child, Cowan lashed out for attention, and was expelled from two high schools and dropped out before moving back to Oahu to work for his uncle’s pool company. 

“I looked around and realized I was 20 years old and had no money or education,” said Cowan. “I wanted to be a fireman but they wouldn’t take me because I didn’t even finish high school.

‘I realized I was responsible for my own future and it wasn’t anyone else’s issue but my own.”

Cowan finished high school. Then, he joined the Air Force with the projected job as a fireman, but after a wrist injury in Basic Military Training, he was switched to maintenance. 

In technical school, Cowan’s learning disability proved challenging again and he was almost administratively discharged from the Air Force for failing too many tests. 

An instructor enrolled him in a note-taking class and Cowan found a method that worked well for him and led to him passing his classes. He later returned as an instructor. 

Dealing with learning challenges didn’t end in technical school. Later in life, Cowan’s son and daughter were diagnosed with Autism Spectrum Disorder.

“When my son was diagnosed with Autism, I was an instructor and a staff sergeant and I had to go to work and I had no idea what to do at the time,” said Cowan. “I didn't have a first sergeant and the resources were okay for the time, but I didn't feel I had the help I needed.” 

Cowan and his family became part of the Air Force Exceptional Family Member Program, a Department of Defense program that offers assistance to families with special needs. 

With his history of learning disabilities, Cowan wanted to be a first sergeant and teach Airmen. 

“People don't realize that shirts [first sergeants] are waiting to help, and if they reach out or make that call, we are waiting to jump on and help out,” he said. 

Coming full circle and returning to Hawaii for Cowan means being able to raise his children where he is from and taking them surfing or on hikes around the island. 

“My family is my rocket fuel, they are why I want to be successful,” said Cowan. “My son struggles. He was non-verbal at 3 years old, but he has made so much progress. 

‘He is still making progress, so what’s my excuse?”