Confessions of a Trivia Company Founder: Finding Your Passion Takes Time

Corporate.trivia.event.entertainer.jpgCorporate trivia event entertainer

I’ve been up today since 4am. On most weekdays I set my alarm for 5:30am – which is insane, I know, but it allows me to get a couple of hours of work in before the wife and kids wake up – however, this morning I had a bad dream, and couldn’t fall back asleep.

The dream? That I was back in college (or just out of college, I couldn’t really tell).

I assume that for most people, a dream such as this would be a joy – who wouldn’t want to go back to their late teens/early 20s, even for a brief moment, to relive their glory days and forget about the stresses and complications of adulthood? For me, however, this period of life wasn’t that much fun at all.

I was an extremely insecure kid growing up, lacking confidence, social skills and direction. While exceeding academically – I was always in honors programs, and eventually enrolled at an elite university – I completely lacked focus, never really knowing what I wanted to do with my life. This absence of direction would come back to haunt me as I entered the “real world.”

When I arrived to college, I was lost. My insecurity had always affected my social skills, and I couldn’t seem to make any friends, or find people I connected with. I was taking a random hodgepodge of introductory classes, but nothing that excited me. To make matters worse, I was assigned to the top floor of a 5th-story walk-up dorm room on the extreme outermost edge of the campus, atop a remote hill which nobody ever ventured towards. I found myself feeling extremely isolated and alone.

As many insecure, isolated college freshmen do, I tried joining a fraternity. This turned out to be a big mistake; I’m not a “frat guy,” and really didn’t belong in that sort of environment. The brutal hazing I went through also exacerbated my feelings of insecurity, and my grades suffered (I wrote another post last year year on the cruel hazing I endured). Though I eventually received my fraternity “letters” and a place to live in the frat house the following year, I was still no closer to finding a direction, and in many ways was worse off emotionally than I had been before.

I remember in college I was always extremely jealous of the pre-med kids. They knew EXACTLY what they wanted, and seemed to have a clear path laid out before them from the moment they arrived: take these prerequisite classes, take this MCAT prep course, maintain this GPA, apply to these med schools, then do this residency, apply to this fellowship, etc. I was the complete opposite – I never had ANY focus on what I wanted to do – yet somehow I had this naïve notion in my mind that everything would just work itself out. There was something romantic about not really knowing “what I want to be when I grow up,” yet still trusting that in the end everything would be fine.

And so, instead of focusing intently on a specific career path and trying to gain relevant work experience, I just went to my classes, did my assignments, joined clubs, spent long hours in the practice room with my saxophone, and read books for fun.

No internships.

No recruiting.

No career fairs.

No plan for after graduation.

I had absolutely no idea what I wanted to do after receiving my diploma. By the time senior year came along, I had already mentally checked out of college. I was spending less and less time on campus, using my weekends to visit friends at other schools in the region and basically biding my time until graduation. I would fire off my resume here and there to random jobs posted on the university job board, but nothing serious.

It was only after moving back home after graduating when the gravity of the situation hit me: I had no idea what I was supposed to do now. For the first time in my life, I had absolutely no structure: no classes to attend, no tests to pass, no assignments or applications due. For me, the path had ended – with the vast abyss of “real life” staring back at me.

I was lost.

While other kids were preparing for their first semesters of graduate school or starting the jobs they had prudently lined up or been recruited for senior year, I found myself literally searching through the “Help Wanted” ads in the back of the local newspaper in my parent’s house in Connecticut. My resume was pathetic; aside from a bachelor’s degree, it had nothing on it which would make any employer want to take me on (my only work experience to date was as a camp counselor, and one summer selling shoes at the mall). I was unemployed for three months, temping where I could and eventually finding a full-time data entry job at a big company nearby – but this turned out to be a complete disaster, as you can probably imagine (you can read more about that by clicking this link).

Though I had no way of knowing it at the time, it would be about ten years before I would find the right fit. This would include two more stints of unemployment – six and nine months, respectively – as well as six entry-level jobs, seven apartments, countless temp/side gigs, and a lot of sleepless nights. There was very little career progression or focus during this time; I was just trying to pay the rent and survive, by doing something I didn’t absolutely hate.

For an entire decade out of college, I was floundering around, trying to find myself. With TrivWorks, I truly did find something special which allowed me to combine all of my skills, strengths and interests: creativity, writing, humor, public speaking, producing fun and memorable experiences for others. Finally, I now have the focus I so desperately needed all those years, and apply every ounce of my daily energy towards building the greatest corporate trivia company I possibly can. It’s exactly what I should be doing, and I count my lucky stars that I get to wake up every morning (albeit at that ungodly time of 5:30am) and do something that I genuinely enjoy, which I am actually quite good and successful at.

But as my dream illustrates, a part of me is still wrestling with just how ill-prepared I was to enter the “real world.” I have deep regrets about not having more direction and career focus from an earlier age, and wonder – both awake and asleep, I guess – what could have been had I actually been more focused early on? Had I not been afraid to explore my interests, to truly follow my passions? Would I have founded TrivWorks 20 years ago instead of nine? Or would I have embarked on a completely different path – and if so, where would it have led me?

Alas, I can’t live in the past – only the present, with an eye towards the future. I’m what you might call a “late bloomer,” and I did indeed have a delayed start out of the gate – but I DID eventually find a career that I’m passionate about, and for that I am so very grateful.

For another article on my unique path to producing and emceeing trivia events for corporate groups, visit

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