Some Careers Take the Road Less Traveled

Recently, I had lunch with a friend from the film industry who shared a bit of his career story with me. Instead of starting out after high school in the arts, he began his career in the military. From the military, he leapt into the world of theatre to try his hand at acting, and later screenwriting. It wasn’t until his mid-thirties that he enrolled in the American Film Institute and off he went to Hollywood from there.


Another friend of mine, a successful lawyer, recently confided that it took her over a decade of working in different organizations to finally find the right fit for herself. I’ll admit it was a relief for me to hear these stories, because for years I thought I was some kind of oddball who lacked the magical “ten-year plan” that you’re supposed to have if you’re a serious professional.


It got me thinking about the different paths that we take in our careers: some of us are straight shooters from college to career to retirement, while others struggle on the road less travelled to find our happy place in this world. My career path has taken me from criminology to English literature to security intelligence to communications (and more recently, I’ve been dipping my toes in the film industry). But now, instead of feeling like a freak, I can continue trekking forward a little more lightly knowing that I have other comrades out there on the roads less travelled, à la poet Robert Frost:


Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.


- Robert Frost, “The Road Not Taken”


Now that I’m in my late-thirties and feeling more secure about my career choices, I’m able to look back and distill three specific influences that have shaped my job interests over the years: the stories I heard, the people I met, and the events of the times:


Let’s start with a little theatre called the IMAX: When I was a kid, I wanted to be a tornado chaser, thanks to the tornado IMAX film at the Air and Space Smithsonian in Washington, D.C. I wanted to be where the action was (like inside a tornado!) and to do heroic things (like warn people that the tornado was coming, i.e. save lives). A wise elementary school teacher advised that I consider a career with the police instead. Sure enough, come senior year in high school, I waltzed into a local police station in Montgomery County, Maryland and somehow convinced the station chief to let me do an internship.


My first career choice: Tornado Alley (Source: IMAX)


At the end of high school, I immigrated to Israel and enrolled in the criminology department at Bar Ilan University. It was during my undergrad studies in the Tel Aviv area that I met a special person, a fellow immigrant from Russia, living in the same apartment building near the university. His name was Roman and he was serving in an elite commando unit in the Israeli military at the time. He was only a few years my senior, but he was way more savvy about life and definitely more fluent in Hebrew than I was. He quickly became like a big brother to me, helping me navigate the tumultuous waters of new immigrant-hood in the Middle East.


Studying criminology in Hebrew quickly proved to be too hard; I dropped out after the first semester and enrolled in the English literature program instead. I quickly became obsessed with my new realm of studies, with the world of storytelling. Over watermelon and cheese on the beaches of Tel Aviv, I would talk incessantly to Roman about the Irish literary renaissance, about the history of gothic horror in the 20th century and the brilliance of Shakespearean symbolism and the everlasting impact of Aristotelian metaphysics.


One day, possibly to shut me up, Roman handed me Sun Tzu’s The Art of War. It was a slim volume that packed a lot of punch. My enthusiasm for learning soon started to lean more toward Roman’s world: now I wanted to hear more stories about war strategy and counterterrorism and the military. I grilled Roman about the hostage rescue missions he had participated in and why some objectives were necessary when others were scratched last minute. I interrogated him so intensely at times that I’m sure he would have preferred to be confronted by a gang of rabid squirrels instead.

This sweet little book made me so happy. Thanks, Roman!


Eventually, I started to meet some of Roman’s friends from the army. They were a rough and fascinating bunch, the kind you might meet in a daredevil action movie. Overlooking the twinkling skyline of Tel Aviv, we soaked in a friend’s rooftop jacuzzi sipping vodka and talking warfare into the wee hours. Sometimes the men spoke about the Palestinian riots in the West Bank, in Gaza, in East Jerusalem, the utter dread of those riots that nearly burst like a tidal wave into Israeli towns. They talked about the disguises they wore, the weapons that almost blew up in their faces, the terrorists that nearly killed them, the infiltrations that almost went awry, and the rescue missions that were thankfully successful.


I listened to their stories with exquisite attention. It was exciting to imagine myself in their world, uninhibited and unafraid, constantly evolving to survive. Naturally, I began to bombard the men with questions. At first, they were amused by my interest and happy to indulge in my interrogations. But eventually their expressions started to change to something more serious, until one of them turned on me and asked: “Hey Jessica, why aren’t you working in our field?”


I burst out laughing. As far as I was concerned, my career was already on a straight path. “I’m an English lit major,” I told the men. “When I’m done with my studies, I’m going to be an English lit professor. I even have a scholarship lined up—”


They cut me off. “That’s not a good fit for you. You should come work with us.”


“Leave your English lit program, Jess, and join SPARTA!”

(Source: “Developing Warrior Like Mental Toughness”)


It seemed outlandish at the time that an awkward little nerd like myself would even consider stepping foot in warrior land, but life sometimes has a funny way of sending you on detours. If you had told me that night that a few years down the road I would indeed switch gears and do a master’s degree in security intelligence, followed by a stint in the Israeli military and a security career that would span three countries, I wouldn’t have believed you. I couldn’t see that far down the path yet.


The last factor that influenced my career trajectory were the events of the times. I immigrated to Israel in 2003, during the Second Intifada, a violent Palestinian uprising that rocked the country with suicide bombings, gunfire, and rocket attacks. In 2005, there was the Israeli disengagement from Gaza, a territorial pullout that brought complex national security challenges that would affect the country for years to come. The year after the disengagement, the Second Lebanon War broke out, sending civilians across Israel running to bomb shelters.


I’ll never forget huddling in a bomb shelter with one of my textbooks. But I wasn’t reading literature—instead, my mind was racing with questions that I wish I could ask Roman and his friends: What kind of counter-airstrikes are the commanders initiating right now? What are the strategic implications if we lift the naval blockade too early? What will be the reaction of the international community if there’s a ground invasion? What will happen to the structure of governance in Lebanon if Hezbollah is uprooted?


Following the Second Lebanon War, during more peaceful times: That's me, hiking Nimrod’s Fortress on the Israeli-Lebanese border


Just like the tornado IMAX film that excited me as a kid, I knew I wanted to be part of the action, and I wanted to help save lives. Shortly after the war, I dropped out of the direct-PhD program in the English literature department and started thinking about a new career path in the security arena instead. As much as I’d love to say that I turned into an ass-kicking commando like Roman and his friends, it didn’t exactly work out that way. My adventure through the security field was a circuitous route, trying on many different hats until I found the role that truly fit.


Today I’m a communications strategist, video producer, and writer in the U.S. defense industry, and in a way it’s all come full circle. Every odd job along the way, every skill I gained, now makes sense and has its place in my career. It wasn’t an easy ride and there were times I felt completely out of place in the security community, but I’m glad I kept trying until I found my calling.


So, if you’ve been making some career switches lately (or are thinking of doing one), don’t be intimidated. Consider the things that excite you and the contributions you want to make. We all deserve to find our place.


To learn more about my experience as an American in the Israeli security community or to sign up for my newsletter, click here.

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