There's a first time for everything.
Louis Freeman remembers his first time flying a plane with his instructor.
"There's something magical about being in that cockpit," he said.
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Though things didn't quite go as planned.
"I was relaxed because I really thought he was going to take over and land at any minute, and when we got right there above the ground, I'm like, 'Are you going to land it?' And he's like, 'You can do it,' and by then it was too late to be scared," Freeman said.
We've all been there. Firsts can be intimidating.
"Is it something I planned on doing? No. It's something this company allowed me to do," Freeman said. "I don't see myself as special, but by happenstance, I happen to be."
Looking back, Freeman wouldn't have it any other way.
"I was the first African-American pilot with Southwest. I was the first African-American chief pilot with any major airlines," he said.
Soaring to the top wasn't easy. He was raised in Dallas in a society that was mostly segregated.
"I wasn't really, really smart. My parents weren't really, really rich, but I was really, really determined," he said.
It's no surprise he's often the center of attention, and on this day it's for good reason.
"I want to fly until they make me retire," he joked. "In my mind, I'm leaving on top."
After 37 years, it's time to say goodbye to the cockpit. The Federal Aviation Administration mandates that pilots retire at age 65.
"There's sadness and there's happiness, too," he said. "It brings tears to my eyes to think about."
Retirement is a new first, but if history is any indication, Freeman will be just fine.
But as he took off this week from Dallas Love Field for his final flight, you couldn't help but wonder, what's next?
"Figure out what your dream is and make it happen, " he said.
Freeman now lives in Chicago, which was the destination for his final Southwest flight before retirement.