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Exclusive: “Just Do It!” Hard Work and Great Mentors Powered Herb To an Airline Cockpit

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Every dream is within your reach.

When Herb Jackson, Jr., was 33, he had been working for United Airlines for about a decade. A latent desire to change his career path led him to cash out his stock plan to finance what he wanted to do with his life.

“The lady on the other end of the line wasn’t sure I knew what I was doing,” Jackson recalled. “She said, ‘This is money is for your future.’ I told her, ‘Yes, I know … and I’m investing in my future.’”

In Jackson’s mind, his future was becoming an airline pilot. His father worked in management for United so as a youngster, Jackson was on a lot of flights. He thought the pilots were god-like and when he was able to view a cockpit he was amazed at all the instruments.

Like many young males, Jackson dreamed of becoming a pro athlete (basketball) but he also thought of being a pilot. It just him longer than usual to reach that goal.

His initial job with United was as a customer service representative based in Albuquerque, N.M.

“I just wanted to be around airplanes and it kinda kept the dream alive,” he said. “My dad had told me when I was younger that if I wanted to work for an airline, the best job is being a pilot. He said just take care of your business and don’t bend any metal and you’ll have a great career.”

After moving up to on-board manager, he was on a flight to Sydney. He knew the pilot, who had worked his way up from being an engineer working on 727s. The pilot recalled conversations with Jackson about his desire to fly commercial aircraft. The pilot’s advice? Just do it.

With the money from his stock plan, he was able to finance his training. He remembers the day he started his journey – April 1, 1997. No fooling.

“When I made that decision to pursue that dream, it felt like a weight lifted from my shoulders,” he said. “I didn’t have background flying in the military, I’m just a civilian, a regular guy with a dream. Other than being a pilot, I didn’t have a Plan B.”

Plan A has worked out. He worked his way up with several smaller companies. Unfortunately, his dream of flying with United changed with that carrier’s tragic involvement with the 9-11 terrorist attacks. But he feels fortunate that he was hired by Southwest in 2006.

“You’ll end up where you’re supposed to end up,” Jackson said. “I also had a dream of flying wide bodies but there aren’t that many opportunities to do that. I’ve ended up flying 737s.

“It’s a really good place to be. Our schedule flexibility is envied in the commercial industry. If you’re a morning person, you can schedule your flights and be done by early in the afternoon. If you’re an afternoon person like me, you can schedule so you don’t have to get up for the dawn patrol. It really allows you to have a career and have a life.”

About eight years ago, he became involved with a school and its “adopt a pilot” that called for him to visit the school in downtown Phoenix for at-risk students. He has been making regular visits to talk to the students about aviation.

“The fact that a pilot would come in and talk to them made an impact,” he said. “The closest they’d ever been to an airplane is one flying overhead.”

As an African American who is an airline pilot, he believes he can be a positive influence in overt and subtle ways.

“I owe a debt of gratitude to the Tuskegee Airmen and all of the first black pilots,” he said. “They paved the way. They had to meet higher standards and I take the responsibility to uphold those standards. When I walk through the terminal, there are a lot of eyes on me and it’s not because I’m good looking. I’m a tall black guy in a pilot’s uniform.

“I’m just a regular guy who had a dream.”

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A photo posted by Herb Jackson 💯 (@herbjacksonjr) on

Written by Wendell Barnhouse

Wendell Barnhouse is a veteran journalist with over 40 years of experience as a writer and an editor. For the last 30 years, he wrote about college sports but he has had an interest and curiosity about aviation since he was in grade school.