Milwaukee woman pursues pilot dream to honor father’s aviation career

Milwaukee woman soaring after a dream

A Milwaukee County STEM teacher inspired by her late father is pursuing a career as a pilot, training in Wisconsin and preparing for acceptance into a competitive aviation academy.

WATERTOWN, Wis. - A Milwaukee County woman is chasing a dream rooted in family, faith and a lifelong love of aviation, as she works to become a pilot in a field where Black women remain underrepresented.

Inspired by her father

What we know:

From the moment the engine roars to life, Valencia Caldwell says she feels at home. Her appreciation for airplanes was sparked by her late father, Terrance Caldwell, whose career in aviation inspired her at a young age.

"I wanted to be a pilot since I was little," said Caldwell. "He was airforce – that is where a lot of that love for aviation came from [...] and when he became an air traffic controller, I would find myself at the towers with him prior to 9/11."

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After her father died in 2019, Caldwell said the passion they shared for aviation resurfaced in a powerful way.

"I would find myself back at airports watching the planes because that was kind of our thing," said Caldwell.

By day, the 36-year-old teaches STEM in Wauwatosa. Outside the classroom, she spends nearly all of her time working toward her private pilot license.

"I’m either training or I’m studying right now, that is my life," said Caldwell.

From classroom to cockpit, Caldwell is earning her wings one license at a time, training at Watertown Municipal Airport through Wisconsin Aviation.

Training toward a license

What they're saying:

Charles Allen is Caldwell’s flight instructor with Wisconsin Aviation and works through New Beginnings Aerospace Ministry, a program that helps young people of color pursue aviation careers through grants and support.

"Valencia came in, and she was very ambitious and very determined that she wanted to be a pilot and I said we can make that happen," Allen said.

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"The only thing that’s getting in their way, or her way, is money financing," said Caldwell.

Caldwell has been accepted into United Aviate Academy in Arizona, a major step toward her goal of becoming a professional pilot and honoring her father’s legacy.

"There is less than 1% of Black women as professional pilots, so just knowing that now, in 2026, that I could be a trailblazer," said Caldwell. "That legacy is impactful in itself, and I’m grateful for the opportunity."

Breaking barriers in aviation

What you can do:

Caldwell said the 14-month program would require her to stop working, prompting friends to encourage her to start a GoFundMe to help raise $125,000 for training and living expenses.