SNOHOMISH, Wash. — On a sunny Sunday in May, Jason Feld prepared to face his greatest fear – heights. 

 "I just cant believe I'm going through with it," he said as he and his wife Rebecca looked up at little parachutes twirling down to Earth. 

"I think I'm going to be sick," Rebecca said. 

The couple was at Skydive Snohomish, not by choice, but because Jason was fulfilling a promise he made to his senior class. 

"Good education is about getting out of your comfort zone, trying some new things and experiencing life to the fullest, and I guess I am practicing what I'm preaching," he said. 

Jason is the new head of school at Northwest Yeshiva High School, a Jewish prep school on Mercer Island. 

Before coming to Washington, Jason worked at a school in Los Angeles where they sent students on a trip to Poland and Israel to experience Jewish history firsthand and to be able to celebrate their heritage. 

Jason knew that his students at NYHS would get a lot out of that experience, and he wanted to make sure every member of the senior class would be able to go. 

"The idea for our seniors to finish off their education by going on this transformative trip to Poland and then to Israel together as one of their last experiences as students at NYHS was just so important to me," said Jason. 

Hence the challenge posed: if the seniors were able to raise $10,000 to go on the trip, Jason would jump out of an airplane. 

They exceeded that goal, and that landed Jason in a blue and red jumpsuit. 

His biggest fear is heights; Jason won't even go on roller coasters. 

"They're too high up and fall down too quickly," he said with a laugh. 

Taking the literal plunge from a small airplane is a big deal to him. However, he says this is way more than him facing a fear; this is about showing his students the importance of going out and experiencing life, no matter how scary it may seem. 

"The biggest challenge is in our own minds," he said. "If we set our minds to do something, whether it's raise money to make sure everyone goes on a trip or makes good on a pledge to jump out of an airplane at 13,500 feet, then there's no barrier to making that happen."

With Rebecca watching, Jason jumped out of the small airplane and landed with a big smile on his face. 

"The lesson here is you really have to live life facing your fears, you gotta go out of your comfort zone," said Jason. 

"Oh great, you're going to do something else reckless like this?" said Rebecca.