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Jonathan Stone

By: Jonathan Stone on June 26, 2020

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How is IT and Cybersecurity Like Flying a Helicopter?

Cybersecurity | In the Media | News

Last fall, I had the amazing experience of being interviewed by Chion Wolf—a familiar voice and personality to anyone who listens to WNPR—for the Connecticut Voice Podcast. The podcast highlights LGBT individuals from different areas of expertise across Connecticut and I was honored to be included.

Our conversation touched on everything from coming out to helicopters, to cybersecurity—including my favorite interview question I’ve ever been asked comparing working in IT to being a pilot. Pride Month seemed like a good time to share some highlights from this interview, so below are two moments that stood out to me as well as the full audio recording.



Listen on Apple Podcasts here.


Being gay in the workplace


CHION: Why is it important for you to be out at Kelser Corporation?

JON: Because it’s very much a family environment so all the employees here interact a lot at work and then we interact a lot socially, outside of and after work. So, it would be like really, really awkward and hard to have that social interaction if I was kind of walling off a part of my life and nobody knew about it, I guess.

CHION: When did you know – it’s funny – because you know this question is coming.

JON: Yeah, yeah. It’s a standard one.

CHION: It totally is and it’s funny because maybe someday the question will be when did you know that you were straight, but when did you know you were different? How old were you? What was the circumstance?

JON: I started to know maybe something was a little different when I was really, really little, maybe even like six or seven or eight. It was very, very early and certainly there was no name for it or a thing to call it but I guess I probably knew something at that point.

Then over the years it kind of became more rather than less apparent for me. You know, I think through high school and college, although I pretty much clearly knew what it was and what the situation was at that point, it just wasn’t something I wanted to talk about, deal with, have to figure out what to do about. So, I just didn’t and I kept it off to the side.

CHION: So when did you do something about it?

JON: It was, I think, 29 or 30 so maybe late in life, compared to some other people, but everybody on their own schedule, I guess. It was after I had worked at Travelers for maybe six or seven years and it was just like I wasn’t able to be so engrossed and busy in my work that I could ignore it.

I think I had used my work as a thing to keep me busy and occupied so there wasn’t free time or free energy to have to deal with that. And it just got to a point where it was like, you know, this is kind of crazy. Let’s figure out what to do and start talking to other people about it.

CHION: Since coming out is something that you do over and over for the rest of your life.

JON: Yes.

CHION: That means that you sometimes have conversations, especially when you’re first coming out, that you’re not really good at having or you don’t know how to say the words or depending on the audience, exactly how to keep safe and also come out. And so, what are some ways that you would have really liked people to receive your coming out?

JON: I think the most important thing that without exception I was looking to hear, was that me coming out didn’t change someone’s perception of who I was. Like there’s still the part of me that you knew before this and I’m still there afterwards.

CHION: Still the same Jon.

JON: Yeah, exactly.


How being a helicopter pilot is like being an IT professional



CHION: How did you get into helicopters?

JON: So, I’m an engineer. I love knowing how things work and like understanding how the pieces all go together. I had a chance a couple times at Travelers to hitch a ride on the company helicopter from Bradley to New York City when I was doing some work down in New York. And it was the coolest thing. One night I came back on the last flight of the day and I think my car was somewhere other than where the helicopter left me. I was waiting for somebody to pick me up and I asked the pilot could I look around up front in the helicopter and he said, “Oh, yeah, come on in. Sit down. Here’s all the stuff.” I’m like, “Okay, now I got to figure out how to do this.” So, I found a school and an instructor and learned to fly.

CHION: What was it like the first time that you were totally in control from beginning to end of a helicopter ride?

JON: Oh, so that took a while.

CHION: How long?

JON: A couple months of lessons before I was totally accountable for all phases of flight. The first time I flew without someone else was just an amazing experience because it’s like I was completely in charge of what was happening and being safe and watching everything and getting to where I needed to get.

CHION: Have you ever been scared?

JON: So, yes. When I’ve learned and practiced some of the emergency things that I have to know how to do as a pilot, some of that is a little bit scary. Power off landings in a helicopter are always a little bit nerve wracking and in the beginning they’re downright scary because it feels very unnatural, but after a while you kind of get to know what it feels like and it’s less scary, I guess.

CHION: It is unnatural, right? I mean when I’m in an airplane, I don’t have any fear of flying, but I can’t shake the feeling that we are not intended to be up here. This is not our natural state.

JON: Yes, it’s not our natural state, you’re correct.

CHION: And so, when I think about you in the unnatural state of being a helicopter pilot, also the work you do is this unnatural state, this world that we’ve created of cyber everything. I’m wondering if there are overlaps in being a helicopter pilot and working for Kelser.

JON: Being ready for a whole bunch of different things that could happen and being ready to the point that even if it’s something pretty catastrophic that comes to pass, you have a plan already figured out, or at least the beginning of the plan.

Like when I’m flying, all along the way even though everything’s working fine and the flight is going perfectly, I’m always looking field to field. If something happened where would I go? Where would I put the helicopter? The whole time, always thinking, “What would I do? Where would I go if there was a problem?”

There’s a lot of that same thinking that goes on here at work when we’re designing a new network for a company. What are the things that could go wrong? How is this going to keep going? How would we react as a support organization if it breaks? What’s the first thing we would do? How would we get it going again?

About Jonathan Stone

Jon is a longtime executive within the technology industry with nearly 30 years of experience.

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