Alumni Stories: Ian Kilgore

Image featuring an alumni story from Portsmouth Christian Academy with a photo of a woman named Kathryn Bailey, class of 2002, appearing next to the academy's logo and background of the school building.

Alumni Spotlight: Ian Kilgore, Class of 2003

Meet Ian Kilgore. Ian Kilgore is a PCA alum from the class of 2003. Read about his journey—physical and mental—from global traveler to grounded husband and dad, and why he believes that “when the Lord closes one door, He opens another.”


Let’s begin with your time at PCA and talk about the highlights for you.

I started at PCA in seventh grade and that was a time when all grades were in the Lower School building.

A highlight would be the camaraderie. There was always a sense of family here. Everyone got along (except for one instance that ultimately ended well).

Prior to PCA I was a Montessori student, and I was homeschooled. So it was a weird transition to PCA from homeschooling. I used to get up at 4:30 in the morning with my dad who was a general contractor and would hop in the truck to go to his jobs. I would do my math homework and read books, and then noon time rolled around, and I was off in the woods playing. All of my schoolwork was done. I was sweeping up the job sites and getting paid by my dad. So to come to school, it was a weird transition. However, it was overwhelmingly welcoming, and the people were awesome. The teachers made it an easier transition.

Do you have memories of any specific teacher?

Yes: Pete Beal, Steve Foley and Dr. Gamble.

Mr. Beal didn’t take any guff from his class, and it was the thing that pushed me to be a better writer. I was writing a 15-page paper a week. There were three or four drafts before the final draft and it was very demanding, but Mr. Beal was fair and fun, and a really great educator.

I felt the same way about Mr. Foley. At the time, I was a diehard Yankees fan and Mr. Foley was a diehard Red Sox fan.  Mr. Foley and I used to go at it [in a friendly way], because that was back when the Yankees were stronger than the Red Sox most of the time. So, every morning I walked into class, and it would just be a back and forth between us. It was a great dynamic.  

Writing was painful for me, but Mr. Beal and Mr. Foley pulled it out of me. I even entered some poetry and writing competitions because of them. They were fun teachers of a subject that I could have otherwise not really cared about, so I needed that.

Then there’s Dr. Gamble. That guy… that guy is a legend. I am fascinated with history, and he had such a passion for teaching history. The notes were college-level note-taking in that class my sophomore year here, which was very demanding (and in hindsight, I appreciate it).

I can’t think of where you would find an education competitive to PCA anywhere around. Which is why this is our first and only hope for our son, Devin. The education and the family atmosphere is amazing at PCA. And then there’s the overarching presence of God. It was a magical time here for me; it really was. I had so much fun. I met so many great people. I always thought when I left school, I would not be one of those people who would want to come back and see my teachers but I am. It’s kind of one of those times you don’t realize what you had until it’s gone.

Where did life take you after graduating in 2003?

I went to the University of Maine at Orono for Chemical Engineering. I spent a little bit of time there and decided that chemical engineering was not the major for me. I had a gross misunderstanding of what I was going to be doing. I had taken a lot of AP classes and stuff like that in my senior year, so I was taking some of these college classes and they really boring. It made me really realize how much lower of an education I was receiving than when I was at PCA my senior year.

I started at the University taking two interesting classes: Physics and Chemistry. The school advised me that it was too much to take both at the same time, but I knew I would be fine. I aced them and investigated the following year only to learn that it was more of the same. “Why am I taking psychology and microeconomics for chemical engineer? Where is Chemistry II? Where’s Organic Chemistry?” And it wasn’t cheap for a guy going to college full time. I ate Ramen Noodles heated up in a bowl of water; that’s what I can afford. So, I decided I was not going to keep paying money to pursue something that I’m already fairly certain I have no interest in.

I came home and got a quick job at Kittery Trading Post. I worked in the outdoors and camping area.  At the time, I was doing tons of hiking and skiing and stuff like that and was getting all this cheap camping gear. The backpacking went nuclear pretty quick. This “quick job” was just supposed to hold me over, but it ended up leading to amazing experiences like the 48 4,000-footers.

Next came sailing. I worked on tugboats as electrician. I’d been sailing since I was about seven years old. My folks put me in a learn-to-sail program and I loved being on the water. I loved sailing. I wanted to move back towards the water if I could.

I got a job at Wentworth Marina where I met a lot of interesting, important people on the seacoast. I was hired as a dock hand and quickly made a dock master. I was managing the younger, summertime help. I ran maintenance and took care of anything that the boaters needed: catching their lines and tying them up; fueling boats; taking reservations for short-term stays; etc.

I did that for a little while and I met one gentleman who was a captain of one of the bigger permanent resident boats of the Marina. I did side work for him when I wasn’t working for the Marina. One day, he said, “If you want to do this stuff and you want to make some real money, come down to Fort Lauderdale for the Fort Lauderdale Boat Show and you can get a real job working on a real boat.” I thought, “That sounds pretty awesome.

So, I finished out the season at the marina in 2006 and my dad gave me a push, “You’re going. You need to get out of the house.” He bought me a one-way plane ticket to Florida. I went and that started a pretty epic journey.

Th abbreviated version is that I got down there and the captain who’d encouraged me picked me up, brought me to his crew house during the boat show, and gave me a mattress to crash on. I did a two-week course, SOLAS (Safety of Life at Sea) and then he put me in touch with a captain of a yacht who was looking for someone who could perform day work. I was paired up with the first mate and worked on the deck and got familiar with the job. I was basically washing the boat, polishing stainless steel, varnishing handrails and stuff like that for showing the yachts. I’m thinking to myself, “This is pretty cool, but not awesome. I don’t want to be a professional wiper.” The captain ended up asking me if I wanted to be permanent crew and I said yes to becoming crew on my first boat. I did tons of traveling for about three years, visited 40 countries, saw the Atlantic four or five times.

It was a pretty amazing lifestyle: you made a lot of money, paid for very little, and visited the most-beautiful places in the world. But it was unhealthy: drugs, drinking, and expendable income. That wasn’t me.

I had my surfboard and I’m like, “Where can I go surf?” Thankfully, the first mate was more like me. When we were in Europe, we would drive into France and go to wine country and go to some vineyards because it was quiet and it was more respectable. You know, you kind of find people who have the same mindset, right?  If I’m going to spend my money, I want to go experience something and not waste my time.

It also helped that the owners of that boat, when we weren’t chartering it for guests, would bring us along to sight-see. One of the coolest stories for me is my time in Rome. I got the billionaires’ tour in Rome because they rented a van and took us with them. We got the backstage tour of the Coliseum, went into the Vatican and skipped all the lines. It blew my mind to get to experience how the wealthy live and then seeing so much history. I was over the moon at that opportunity. I learned so much about the world during this time of my life.

How long did this adventure continue, and what inevitably brought you home?

In 2009 I decided: “This is too much of a rock star highway for me to be on. It was a fantastical life. It was fun. I loved it. I could do it for a while, but there’s this girl back home and I like her.” We were dating and I flew her to see me a handful of times and she’d been patient. She’d been persistent, but I knew she wasn’t going to wait forever. I didn’t want to miss out on that opportunity.

Meanwhile, Jennifer, Ian’s wife, shared with me:

Ian’s parents had texted me and asked me to go to dinner. I’d kept in contact with them, so this wasn’t a weird invitation. I kept in contact with Ian, but I became pretty close with his parents. I did wonder why they just wanted to go out to dinner just the three of us. I get to dinner and who is sitting at the table, but Ian. I remember looking at him and saying, “What are you doing here?! You’re supposed to be in the Mediterranean.

Back to Ian…You came home and began to settle down?

I came home, worked in a landscaping business, applied to the Naval Shipyard and I have been there ever since. Jennifer and I got engaged in December of 2013, and we were married in September of 2014. I wasted no time.

Now we have our son who will be 5 this year, and we enrolled him at PCA for the fall. We run a homestead in Maine that allows us to feed our family and others. We have chickens and eggs for everyday needs, and we process Thanksgiving turkeys, too.

Three people, two adults and a child, sit outdoors on a sunny day with trees and blue sky in the background. They are smiling and dressed in casual clothing.

Do you feel like PCA had any influence on this path you took?

The two biggest influences PCA had on me were academics and spirituality. The classes and the teachers prepare you. The idea of “never stop learning” has stuck with me.  There’s a lot of that came from the educators at PCA; they put in their efforts to instill a desire to learn and to help me grow. They showed passion and made education fun, interesting, and challenging.

Furthermore, I came out of PCA confident in my beliefs. I’ve carried that through my entire life. Particularly, Dr. Pleticha was always receptive to challenging discourse. Those sorts of discussions were commonplace for me back then. That really helped to strengthen my faith and defend my faith. That was huge. For those who want to call themselves a Christian, they need to be able to tell people why they are one. PCA helped me make good moral decisions, which were important in my story.

If you had one piece of advice to give to the PCA upper School graduates or just Upper School students in general, what would it be?

I would give a piece of advice that my mom gave me when I was having a hard time. She used to say, “Where the Lord shuts one door, He always opens another.”

So don’t be afraid to go out and try new things. Life will become mundane quickly, if you force yourself to do something that you don’t enjoy doing and it will trickle down into everything. You’ll become bitter. You’ll have a hard time maintaining relationships. You’ll have a hard time coping with yourself. Be sure that what you’re doing in your life brings you joy. If God shuts one door for a reason, He’ll open another. Just walk through that next door. It’ll work out. I’m living proof.