Eye in the sky, feet on the ground | Women in Business

Jackie Hamilton dons her air ambulance flight suit for a tour of the hangar and the fleet of aircraft of Island Air.

It’s mid-morning in mid-autumn and the skies over Friday Harbor are crystal clear.

But out in the distance a thick bank of clouds stretches low across the horizon and the phones lines are abuzz in the headquarters of Island Air. The low ceiling has grounded flights elsewhere in the islands and people who had hoped for a quick hop from here to there are calling Island Air to see if Jackie Hamilton might be able to step in and get them to where they want to go.

It’s not how Hamilton, owner, president and director of operations of Island Air, expected to start off the day, but that’s pretty much par for the course.

“The schedule you have when you show up in the morning is almost always completely different from what it turns out to be when you leave for the day,” says Hamilton, who started the San Juan Island-based chartered air carrier from scratch 21 years ago. “You have to be adaptable.”

An ability to adapt has helped Hamilton to turn a fledgling business into a solid and successful aviation company over the past two decades. She’s learned a few other helpful hints along the way. Like it helps if your endeavor involves something you truly love. But don’t expect that that will make it any easier, so be prepared to give it all you got.

“If you’re looking to give it a minimum amount of effort or a minimum amount of work, it won’t fly,” she said.

You might say that Jackie Hamilton was born to fly.

The daughter of a commercial airline pilot, she got bit early by the flight bug, learned to fly in the San Juans after college, followed in her father’s footsteps for a time, looking to land a job as a pilot with the airlines, and then decided to strike out on her own, hoping that creating a company offering chartered flights  would enable her to live and work in the place that she knew she wanted to call home, the San Juan Islands.

She started small, with just a single aircraft, a Cessna 172, and threw everything she had into it.

“It was just me for the first four years,” she said.

By her fifth year at the helm, Island Air appeared stable enough that Hamilton began hiring other pilots, and the business took off.

Today, Island Air operates a fleet of five planes, employs eight pilots, boasts an award-winning safety record, provides fixed-wing air ambulance service in partnership with San Juan EMS, and though it remains a family run business (Hamilton’s husband, Will, is a significant part of the operation, “He’s instrumental in every way. He’s kind of my right arm.”), it is the largest air carrier in the U.S. founded and built by a woman.

While there may be a bit more time nowadays to indulge in a hobby or two, like gardening and horseback riding, Hamilton clearly recalls what it takes to weather the ups and downs, and lessons learned from the day-to-day battle of getting a small business off the ground.

“I think it really boils down to being a personality that’s tenacious, you just keep doing it,” she said. “It sounds like a cliche, but it helps to love what you do.”

For more about Island Air, http://sji-islandair.com/