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It was early 2023 and he was thumbing through photo albums at his grandmother’s house. Suddenly, there it was: a snapshot from 1994, taken in an airplane flight deck, depicting him as a toddler, sitting next to his pilot dad.

In this picture, Flowers is looking at his dad in admiration. His father smiles at the camera, ready to fly the plane.

Flowers had forgotten the photo existed, but seeing it again, he was flooded with memories of growing up, inspired by his father. He’d loved their trips to the airport, tagging along to the training center, taking a go on the simulators. He’d beamed with pride when his dad talked about his job at the school careers day.

And the timing of the rediscovered photo was perfect: Flowers, now 30, was just about to follow in his father’s footsteps and begin flying as a First Officer for Southwest Airlines.

Meanwhile Flowers’ father – also called Ruben Flowers – was nearing retirement and readying for his final Southwest flight as Captain.

The two men were excited to briefly overlap at Southwest and hoped they’d get an opportunity to fly together.

“It was a dream of mine to make it to this point to fly with my dad, it was probably my number one aviation goal,” the younger Flowers tells CNN Travel.

After rediscovering the old photo, the two Flowers men added a coda to the goal: not only did they want to fly together, they wanted to re-create the 1990s flight deck photo, over two decades later. Not just as father and son, but as colleagues and co-pilots.

Cut to March 2023 and the older Flowers was flying his final Southwest flight, piloting an aircraft from Omaha, Nebraska to his home city of Chicago, Illinois. His son was by his side, as his first officer.

“That was an awesome feeling,” says the older Flowers. “To look over there and see my son, next to me, for my last landing.”

And, naturally, they re-created the 1994 photo, both grinning happily in the 2023 version.

“It was just great to be able to re-create that moment,” says the younger Flowers. “It was a dream come true moment.”

Also on board the older Flowers’ retirement flight was his brother and his cousin, who both work for Southwest too. In case you hadn’t realized by now, flying truly is a family affair for the Flowers.

“There are seven of us,” explains the older Flowers. “Me. My brother’s a pilot. I have three kids, all pilots. And my brother’s son is a pilot and my cousin is a pilot. And it’s just amazing to me that they all wanted to be pilots.”

At family events and on holidays, the Flowers family try to keep work talk to a minimum “but there’s always a story that sparks it off, and then it gets into aviation,” as the younger Flowers puts it.

The Flowers family aviation legacy began when the older Flowers was a kid growing up in Michigan in the 1960s and 70s.

“A pilot one day asked me if I wanted to come up to the cockpit. And I did it,” he recalls. “And oh, my God, it was like the bug bit me – I wanted to be a pilot. And from that point on, I just focused on being an airline pilot.”

Once he qualified, the older Flowers made it his mission to inspire others to follow in his footsteps. The fact that ended up including many of his loved ones was accidental. He says he always encouraged his kids to explore whatever they loved, whatever that might be.

The younger Flowers says that while he grew up in awe of his dad and proud of his work, he didn’t officially decide to become an aviator until midway through college.

Looking back now though, he thinks the signs were always pointing in that direction.

“It was always something that was probably in the back of my head that I probably wanted to do all my life,” he says.

The older Flowers’ retirement flight was always going to be emotional, and having his son by his side only made it more so. He says it’s not surprising that when they pulled into the gate “some tears came down.”

The younger Flowers says the in-air, father-son working dynamic wasn’t dissimilar from “doing the lawn together, or something of that nature.”

“It just worked out smooth and naturally, and it went great,” he says, although he adds he was definitely trying to “impress” his dad with his skills and competency.

The older Flowers says he was aware the flight was a one-off opportunity for him to pass on flying intel to his son in situ.

“It went really well, it was nice and smooth,” he says of the experience. “And it was an awesome feeling – making a PA to the passengers, and they find out there’s a father and son up there in the cockpit. Everybody clapping…”

While the older Flowers has now left Southwest, his legacy lives on at the airline – not only via his son, but via other aviators he worked with and mentored over the years.

Flowers speaks fondly of his own mentor, Louis Freeman, who became Southwest Airlines first Black pilot when he was hired in 1980.

“He was a mentor to me,” says the older Flowers of Freeman. “And now I’m trying to be a mentor to others. And I hope my son can be a mentor to others, not just family members.”

While at Southwest, Flowers was part of the airline’s Adopt-A-Pilot program, working with elementary school kids to inspire them to explore careers in aviation.

He’s also a longtime member of the Organization of Black Aerospace Professionals (OBAP), where he works to uplift Black aviators.

He encourages prospective pilots to do their research online, look out for programmes, and speak to anyone and everyone they can to get inspiration, information and advice.

The younger Flowers echoes this – he’s actively involved in mentoring young pilots via social media, but he’s also had the occasional in-person conversation with a prospective pilot while transiting through the airport. He says if he can, he’ll always stop and pass on a few words of wisdom between flights.

As for his own personal goals, now that he’s achieved his dream of flying with his father, the younger Flowers next dream is to fly side-by-side with his younger brother, who has just recently completed pilot training.

He’s already had the pleasure of flying with his pilot sister several years ago and says it would be incredible if he could complete the family trifecta.

“That’s what I’m looking forward to, is to be able to fly in the plane with my brother,” he says.

The older Flowers is excited for that day too, and says he’s unendingly proud of his three children.

“It’s unbelievable,” he says. “It’s an awesome feeling to know that my son is flying, and my daughter and my youngest son, all three of them are flyers.”