Liftoff: How One Pilot Is Helping the Next Generation Take Flight

Pilot Diane Dollar almost quit flying. Now, she’s using her experience to empower future fliers.

It’s a bright summer day in August when a group of young students in sky blue shirts walk out of Hangar 21 and onto the tarmac at the Fullerton Municipal Airport. The words, “I’mForever on the Fly…” stretch across the backs of Dare to Dream participants in a nod to the non-profit organization behind the event–the first in a planned series of free-to-the-public aviation career days. 

Forever on the Fly, dedicated to educating and empowering the next generation of pilots, is early in its inception, but making good on its commitment to providing education, mentorship, and hands-on experience in aviation. After five months of careful planning, Diane Dollar, the organization’s Founder,  Executive Director, and a pilot herself, takes a deep breath as the day’s event begins to unfold.

The helicopter ahead is a Robinson R44, a high-performance aircraft used primarily for law enforcement, private charter, and training. Today, it’s flying a group of young dreamers, many not yet teenagers, who are in the passenger seats now, but one day, may be at the helm. After the pilot, three kids pile into the vehicle filling each available seat. The interior is snug but no one seems to mind. Wide eyes scan the array of buttons, knobs, and switches spanning across the cockpit. 

Thumbs-ups are given all around as headsets are secured and seatbelts fastened. Nervous smiles give way to laughter as the engine roars to life and with a gentle bump, the helicopter lifts off the ground. 

156 kids are embarking on discovery flights today, an experience that may inspire some of them to join the aviation industry. “I’m so excited that I get to share my passion with all of you!” Diane says to the group. It’s 2021 and despite the mask over her face, you can see the edges of her cheeks turn up in a smile. The diverse crowd before her is not representative of the current industry demographics, but rather a hopeful visualization of what–with advocacy, education, and mentorship–it could be.

Diane is part of the 6%of pilots in the United States who are female. Entering such a historically male-dominated industry can sometimes feel like a “good ol’ boys club,” but now, nearly 12 years after her own first day in a helicopter, Diane is repositioning the challenges she endured as opportunities to improve the industry for future pilots. 

Women, though still a minority, have been flying since the early days of aviation. In 1911, Harriet Quimby made history as the first female in the US to earn her pilot’s license, just eight years after the first powered flight by pioneer Orville Wright. By the 1960s, as commercial air travel started to popularize, the US had 12,400 licensed female pilots, making up 3.6% of the nation’s aviators. 

While female presence in the workforce has grown considerably in recent decades, the ratio at which women are represented in aviation versus other professions is imbalanced, with growth lagging considerably behind that of other industries. In the 1960s, 6.7% of practicing physicians in the US were women. By 2020, that number had grown by more than five times to 36%. Comparing those same years, the percentage of female lawyers in the US grew more than ten times from 3.4% to 37.6%. Female pilots, by contrast, have less than doubled.

With Forever on the Fly, Diane is working to combat some of the barriers to entry and give everyone a sense of belonging in aviation–whether that’s providing young women with someone to look up to, or encouraging young men to be a part of the conversation. She readily admits that aviation is a challenging industry, but for her, it’s been a fulfilling one. 

It’s been three years since the first Dare to Dream event. The foundation is growing and has hosted events in California, Texas, and Colorado. In addition to her work with Forever on the Fly, Diane is serving as a pilot and check airman in Denver today. Flying makes her happy, and even in the more routine aspects of her job, she exudes a positivity that can chase clouds away.

It’s an early workday morning when Diane arrives at the hangar. She’s wearing a navy jumpsuit and brewing a pot of coffee (which she calls, “go-juice”) in the small adjacent office before beginning her preflight checklist. She approaches the EC130 helicopter in the center of the hangar, opens a hatch, and buries her right arm in a section of the engine control. “Well that manicure was a waste of money,” she laughs seeing the state of her hands during the meticulous mechanical inspection. At 34, Diane is younger than most of the pilots she’s worked with yet she knows her aircraft with expert precision.

She’s been flying for more than a decade now, but before ever stepping foot in the cockpit, Diane was a jetsetter in her own right. She shares photos of her escapades from sailing in Thailand to surfing in South Africa to posing with a camel in Israel. “Adventure is calling me y’all,” she writes in one Instagram caption. 

Growing up, Diane would occasionally accompany her father on international medical mission trips. Her father is a cardiologist and is involved with a number of organizations doing doctors abroad work. He has a way of bringing people together, tending not only to the physical heart but the emotional one too. Diane is the third youngest in her Atlanta-based family of 13, with eight adopted siblings and two biological. Her mother is the perfectly matched matriarch, caring for the ever-growing family. 

At 17 and fresh out of high school, flight hadn’t crossed her mind yet. Diane wasn’t sure what she wanted to do with her life, but she knew that, like her father, she wanted to find something meaningful. 

Medium height with a slender build, Diane carried herself like a “little punk rocker.” Dyed pink hair swept over the gauges in her ears and a Marilyn Monroe piercing adorned the top of her lip. These ornaments of self-expression were traded for the regimented environment of basic training upon her decision to enlist in the US Coast Guard. 

What did I sign up for? she asked herself, almost panicked upon receiving her orders for deployment at the close of boot camp. Where am I going? She stared down at the words Ilwaco, Washington, a “one stoplight town” home to the US Coast Guard station at Cape Disappointment. 

Cape Disappointment feels like a misnomer for anyone visiting the beautiful Pacific Northwest park’s jagged cliffs and picturesque rocky beaches. Moody shoreline, speckled with driftwood, is framed by towering, moss-covered basalt cliffs with 2,000 acres of camping and walking trails. To the service members stationed there, however, the name feels more like an understatement. Cape Disappointment is a nightmare.

The site got its name from British trader John Meares in 1788 when, in search of the mouth of the Columbia River, he mistook the large estuary for a mere bay. The sandbar beneath it, where Pacific Ocean waves meet the freshwater of the river, contributes to the formation of one of the most treacherous bar crossings in the world.

Along this calamitous shore is Fort Canby, teenage Diane’s new home. Established in 1877, the Coast Guard conducts a staggering average of 450-500 search and rescue operations here each year. She remembers her time at Canby as being relentless, but it was here she realized her desire for flight.

An alarm rang out in the middle of the night; a familiar routine. Diane, one of the outpost’s 48 assigned crewmembers, rushed to respond. Canby houses four search and rescue boats, including a large motor lifeboat, two smaller motor lifeboats, and a utility boat. She boarded one of the shorter vessels and attached the metal clasp of her cable harness to the boat. The watercraft was built with the ability to roll and self-right in the turbulent surf, and the safety harness kept anyone onboard from getting carried away in the sea. Her gloved hands grasped an iron railing as they disembarked.

A few miles out, a sailboat was taking on water. This wasn’t a unique mission. The cape was nicknamed  “The Graveyard of the Pacific” for its regular ability to shipwreck sailors.

Standing two stories high on the open bridge, Diane grimaced as cold water smacked her face. The lifeboat rocked side to side in the surf, slapping its hull against the waves. Thick fog obscured the bow of the boat as it swung upright, then rocked steeply to its side again.

At the end of these missions, the lifeboat would be met over the choppy waters by an aircrew ready to transport the rescued for medical evacuation. With eyes stinging from the salt water, Diane would watch as the helicopters took off, feeling as though that was the side of the mission she belonged on. She wanted to be in the air.

After four years with the Coast Guard when her service term was complete, Diane enrolled in flight school to become a helicopter pilot.

As part of the female minority, Diane was met with skepticism upon entering the aviation field. Harsh gazes regarded her as “just the DEI [diversity, equity, and inclusion] hire,” with her credentials questioned before having a chance to prove herself. One company requested an extra round of checks before clearing her, “just to be sure.” Situations like these tested her internal strength. Even for tenured female pilots, the onslaught of unfair assumptions can feel relentless.

In early 2024, during a televised hearing, Laura Haynor had just addressed the room introducing herself as a pilot testifying on behalf of the Airline Pilots Association International. Sen. Gene Dornink of Minnesota fidgeted in his seat. “I don't know why I said that,” he stammered after asking Haynor to describe her typical workweek “as a stewardess.” 

“I’m a first officer,” she politely and confidently reiterated. “For Delta.”

Dornik apologized, but the fumble (as well as his use of the antiquated term “stewardess”) sparked intense discussion online with comments suggesting that had Haynor been a man, such a mistake would not have been uttered.

During a period flying passenger tours out of Las Vegas, Nevada to sightsee over the Grand Canyon, Diane endured a barrage of remarks herself ranging from poor-spirited jokes to inappropriate heckling to downright rude jeers. 

“I don't know how I feel about flying with a lady pilot,” one man snickered. 

“Who’s in the kitchen making the sandwiches?” cackled another. 

She doesn’t let tone-deaf comments get to her, but it’s difficult to ease the irritation. For Diane, it isn’t about being right but doing what’s right–and that means maintaining composure and taking the higher ground. She’s a professional, and while the industry can feel predisposed to men, there’s no reason a woman like herself is any less capable.

Despite what may seem obvious on the surface, the gender imbalance in aviation doesn’t feel like a men versus women battle to Diane, but rather an issue of old norms in a modern world. Her position in the industry and work with Forever on the Fly is helping inspire change by promoting diversity (and the normalization of diversity), by welcoming, educating, and supporting pilots and pilots-to-be of all backgrounds, ages, and genders. She’s providing young women with mentors to look up to and encouraging young men to be a part of the progress. 

During events and career talks, Forever on the Fly introduces students to a diverse group of pilots, challenging the historically ingrained expectation of the “old white men” demographic. “When kids see someone that looks like them,” she says, “They can feel a little bit more inspired.”

Geoff Murray, a pilot and writer, in Forbes, calls the absence of female mentors an “obstacle to attracting more women pilots” and “an organizational blind spot” in aviation. He continues, explaining how nearly all female senior managers surveyed in a 2020 report cited this lack of mentorship as a “key recruitment and retention challenge.” Less than half of the male executives reported the same. 

Beyond merely shifting systemic norms, vocational mentorship, as shown in a 2007 study in the Journal of Vocational Behavior, can have a positive correlation to one’s cognitive health and behavior. This is particularly important in an industry where the topic of mental well-being is as sensitive as it is critical. Reporting a mental health challenge can mean a loss of license and reputation for aviators. As a result, many pilots will instead try to mask their symptoms or self-medicate–which can result in dangerous repercussions. 

One instance occurred in late 2023 when Joseph Emerson, a 44-year-old pilot with Alaska Airlines, experienced a dangerous episode mid-flight during a battle with an unreported, untreated mental health challenge.  He was seized and arrested and charged with 83 counts of attempted murder. 

While other professions often encourage employees to seek proactive counsel for mental health challenges, pilots go to extreme lengths to avoid confronting a potential diagnosis, putting themselves and their passengers at risk. 

“It's such a taboo thing in our industry to talk about mental health because nobody wants to admit they're struggling,” explains Diane. 

The industry puts pilots–and passengers–in a dangerous place by making necessary care a thing to be feared. But tending to mental health and emotional well-being is something all pilots (all humans) must face at some point. For Diane, one instance in particular tested her own resilience.

On a cold January evening in 2018, a plume of smoke rose from the bottom of the Grand Canyon. Scott, a pilot and close friend of Diane's, had been in a helicopter crash. Later investigation revealed that nothing could have been done by the pilot to counter-maneuver the weather event that caused the vehicle–bound for an evening dinner in the famed canyon–to crash-land. After six months in a coma, Scott awoke to face a new reality–80% of his body was badly burned and he’d lost both of his legs. Five of the six other passengers aboard did not survive the catastrophic accident and had been buried before he woke.

Less than a month later, Diane, still reeling from the tragedy, was notified that the company she flew for was mourning a fatal crash of their own. The prospect of loss is always a possibility in this industry, but two incidents so close together were a heavy burden to bear.

She needed time to think, to clear her racing mind. Thoughts swirled of the accidents, the crashes, the burns, the people–people who died. This once unlikely possibility felt uncomfortably close to home. I don’t know if this is worth it anymore, she thought to herself.  I don't know if this is what I want to do anymore.

Diane had overcome so many obstacles to get to where she was; it didn’t seem likely that anything would rattle her confidence in being a pilot, but she found herself wondering if she wanted to continue to fly. The challenges of aviation felt stronger than ever. There weren’t many women who’d been through what she had. Diane thought she was done flying helicopters.

One month before she was set to make a career shift, Diane got a call offering her a position as an Emergency Medical Service (EMS) helicopter pilot for a hospital. It would be a tough job, but she’d been wrestling with feeling like she hadn’t yet done what she set out to do as a helicopter pilot–like there was something still left undone. In those difficult moments, having a strong community of colleagues was more important than ever. She wanted to work in service of others and feeling like she could make a difference here, accepted the position. 

Today, after years of flying air ambulances, she’s found her niche as a check airman (or check airwoman, as she likes to say) certifying EMS pilots and using her experience to prepare others. 

“I won't know when my instruction has saved someone's life,” Diane explains, but after she’s completed a successful training with a pilot, they report feeling safer and more confident in their ability to handle emergency procedures. She knows the work she’s doing now is saving lives. 

In the difficult years following Scott’s 2018 crash, Diane has reconnected with the importance of her work–the passion of her work. Flying is about being a part of something bigger.

In 2021, Diane officially launched her non-profit organization, Forever on the Fly, with a team of close friends and colleagues. The past three years have been a labor of love as the culmination of her own experience is defined in the foundation’s mission of inspiring the next generation of pilots. Her goal is to turn aspirations into impactful careers for industry hopefuls of all ages and backgrounds. 

One mentee with the program is Justin Matejcek, whose involvement with the organization has provided him with career opportunities he would not have known otherwise. Agreeing with the creed of Forever on the Fly, Justin acknowledges the challenges aviation poses for women but is encouraged by the growing numbers of female pilots he’s worked with. He advocates for the work being done to make the industry more accessible and helps foster community in his own network, saying, “That mentorship is [...] invaluable.”

“We are at a critical time in our industry,” Diane adds, thinking about the challenges of pilothood. “We have to take the reins on inspiring the next generation.” While large-scale change in an industry like this one will take time, she trusts the process; and more so–the dedicated team of peers alongside her.

Since their first Dare to Dream event, Forever on the Fly has encouraged a diverse group of more than 1,000 participants to “dream big.” Diane is sharing her story and building a community around mentorship, networking, education, and scholarships. Her work is helping future pilots overcome barriers and prepare for industry challenges.

As the sun sets over Hangar 21, the blue-shirted students, head home. The memories imprinted on them will serve as a critical source of inspiration for what their futures can hold. Connecting with new friends and mentors means they won’t go it alone. Diane’s work has given them a gift they don’t even know the value of yet.

For many, the Dare to Dream events are the first time they’ve ever flown in a helicopter, but certainly won’t be the last. Diane has dared them to dream–dared them to imagine the next time they’ll step into the aircraft, adjust the headset, and one day, clasp their own hands around the pitch controls. The engines roar to life. The ground lowers beneath them. 

Liftoff.

Graduate journalism coursework, Harvard University / 2024