Moving ever skyward

Terry Callaghan, captain with IBM Flight Operations.

If the words “corporate life” summon thoughts of sitting in a tiny cubicle, a schedule filled with endless meetings in bland conference rooms and always looking for the chance to sneak away for gossip over the watercooler, then Terry Callaghan’s story will shatter those preconceptions.

The Brookfield woman is indeed a corporate employee – with IBM for some 18 years, to be precise – but when she reports for work, she focuses her attention skyward.

Callaghan is a captain with IBM Flight Operations, a job with the computer multinational that finds her flying corporate aircraft out of the Westchester County Airport.

Sure, she has her share of paperwork, dealing with supervisors and yes, chatting with colleagues, but Callaghan is far from the proverbial nine-to-fiver.

On call 24-7 for IBM flights that might see her piloting a helicopter for a quick jaunt within the Northeast or a jet to locales including Canada and South America, Callaghan is ever ready to take to the skies.

And it’s always been that way for the woman who got her first taste of flying at age 14.


Callaghan clearly remembers a 1970s trip from her Rockland County hometown of Stony Point to John F. Kennedy International Airport where she would visit her older cousin, then a chief pilot for Eastern Air Lines.

“It was exciting for me,” she says. All she could think was, “Oh, I want to be like him.”

As part of a “hard-working, Irish family,” Callaghan says her parents were also impressed.

“They saw an opportunity,” she says. “They worked hard, with overtime, and got me my first flight lesson.”

Callaghan was soon taking to the air with lessons out of the now-defunct Spring Valley Airport.

It was a time, she says, when young girls were challenging traditional expectations. She clearly remembers her father encouraging her: “Don’t marry a pilot. Be a pilot.”

And she did, going on to earn her private pilot license by 17. She would graduate from North Rockland High School in three and a half years, get ahead with a semester at Rockland Community College and then attend Nathaniel Hawthorne College in Antrim, N.H., to study aviation.

At 18, she earned a flight-instructor certificate, and, as Callaghan says, “With that, I was able to teach my fellow classmates.”

Both teaching and working on her own studies, Callaghan was, she admits, “pretty driven.”

Her students, many of them older than she, didn’t always appreciate it.

“They didn’t like me very much because I was getting them up at 4 a.m.,” she says with a wry laugh. But many have kept in touch, she says, and now thank her for helping them toward aviation careers.

Callaghan would herself earn bachelor’s degrees in both aeronautical science and business administration – in three years and with flight honors also coming into play.

“They asked me to stay on, since I was Instructor of the Year, to start a helicopter program,” she says of the next step that would earn her the title of chief pilot.

“Once I started flying helicopters then I found my passion,” she says. “With the helicopter, you’re near the ground all the time.”

She likes not only the ever-changing scenery but also the numerous takeoffs and landings.

“That’s where your skill comes in,” she says. “I love that challenge.”


Callaghan was ready to enter the corporate world – where helicopters join jets in the flying fleet – and took her first job with New York Airways, a helicopter company.

In the early 1980s, Callaghan was one of the pioneering women who were flying the Sikorsky 76 helicopter. She would go on to fly for two large insurance companies in Hartford for more than a decade before landing at IBM.

Throughout, she says, challenges are what one might expect, primarily weather conditions and keeping up with new technologies.

“We do flight safety recurrent training twice a year,” she says.

Earlier in her career, her challenges also included proving herself to the mostly male colleagues.

“In the early days I was put to the test, very much. First of all I was a girl, and I was short.”

She says she had respect for the male pilots, many of them Vietnam veterans, but was, in fact, once told “I do not want a woman in that other seat.”

She wasn’t about to say, “I’m 23. I got the job” and deal with it.

“I figure I’m going to have to handle it. You can’t yell and scream.”

Instead, she let her training and skills speak for themselves.

“I’m still doing it today,” she says. “Then you make your mark.”

Callaghan says her biggest reward is having the skills to do her job – and do it well.

“A reward would be if you’re faced with an emergency that you handle it well,” she says.


Callaghan has the rare distinction of having dual certification as an Airline Transport Pilot, which authorizes her to fly both helicopters and airplanes.

“Less than 1 percent of women are dual rated,” she says.

With 29 years in the profession, she says there is also an ease that comes with her tenure.

“It becomes second nature,” she says. “You train so much.”

But, she says, there is no complacency. Safety is always at the forefront of both captain and his or her co-pilot, one of the things she loves at IBM.

“We have great professionalism here,” she says. “They’re sharp pilots, and we try to have each others’ backs. That’s what we’re proud about here, what we can do for each other.”

While her schedule is unpredictable, Callaghan says the job has taken her far – even if she can’t always enjoy the destinations.

After all, she is not a tourist but rather a pilot taking care of post-flight protocol and pre-flight prep.

“It can be lunch in L.A., but to see the sights, no,” she says.

Coming home, she adds, is always welcome.

“There’s nothing better (than) to see the skyline of New York City at night.”

And when not at work, don’t expect to see Callaghan piloting a little two-seater for pleasure. No, the woman who has been called fearless more than once instead prefers to take to the road with her custom-carpenter husband, Jeff deJong.

“My husband and I ride the Harleys.”

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