TrivWorks CEO: What’s it Like Having the “Best Job Ever?”
Recently, my two kids (ages 11 & 13) found me preparing one of our newly-announced TrivWorks Escape events (corporate team trivia with an escape room twist). They looked at me on the floor, materials splayed out before me while I stuffed clues into lock boxes and wrote secret messages with invisible ink.
After a moment, they both blurted out almost in unison: “Daddy, you’ve got the BEST job EVER!”
Sometimes, I do have to stop and remind myself of this fact. It may not seem like in the moment, when I’m up to my eyeballs in the daily grind of running a business. But you know what? I DO have the best job ever!
I’ve written before about what a day in the life of a professional trivia host and producer is like. Today, I’d like to explore further, from a more top-level view. What’s it REALLY like running a professional corporate entertainment and team building company, specializing in trivia events?
It’s Really Fun
First of all, my kids are right – this is the best job I could have ever asked for. It is perfectly suited for my peculiar set of strengths and skills: sharp wit with a pension for puns, a passion for creating unique and memorable experiences, an uncanny ability to remember really random things, a zest for writing. Seriously, in what other job could I spend the half the day crafting pop culture trivia and dreaming up new offerings/collaborations, then at night be onstage making strangers laugh and cheer for hours on end? I even get to work with celebrities occasionally, as well as travel to awesome places throughout the country, bringing enjoyment to those not in the New York City or Southern California areas.
As such, I consider myself extremely fortunate to have found this unique line of work, to carve this employment out for myself and achieved such a level of success with it.
I Set My Own Hours
This is easily the best “perk” of my job. I took TrivWorks full time in 2011, a whopping two weeks before the birth of my first child. While in hindsight I probably should have rethought diving headfirst into two challenging new endeavors at once, I did recognize right away that being my own boss has its advantages. I’d never have been able to get my business off the ground or be available to raise my kids without the flexibility my gig affords. When the pandemic hit five years ago and everyone was suddenly working from home, the only thing that changed as far as my workday was that my kids were there with me. Being able to do what I want, when I want, without having to seek permission, absolutely makes this a great job.
It Can Be Stressful
The flip side of having my own business and setting my own hours is, I still only have so much time and energy available throughout the day. Most days I pick my kids up from school at 3pm, and from that point on I’m basically out of commission for work. What this realistically means is, I must cram in ALL of the work I must do earlier in the day. This varies depending upon what’s happening at that moment, however generally it includes responding to inquiries, sending proposals, drafting service agreements, servicing clients with scheduled events, prepping event materials, communicating with staff and, of course, writing lots of trivia questions. On days when I’m personally emceeing something, this also means I have to plot out my own schedule/travel getting to the gig, and actually performing at the event.
Combined with my childcare/household duties, it can be a lot – but I’ve learned to handle it (spoiler: exercise, eating right and plenty of sleep helps).
There’s Plenty That’s Not So Great
Of course, I still have to deal with all the headaches every self-employed business owner faces. Mountains of administrative dreck, putting out fires, scheduling challenges, staffing issues, unexpected technology disasters, and unwelcome distractions ranging from spam calls to construction vehicles outside to name a few. That’s to say nothing of the fact that money doesn’t magically appear in my bank account every month – I have to go out there and sell, and the market can be extremely unpredictable. Yet even with the aforementioned stresses and tribulations, I still at the end of the day get to be my own boss, with flexible hours, doing a job I love and that I’m good at.
Bottom Line: I Feel Really Lucky
Before I made this my full-time job thirteen years ago, before it was a side gig sixteen years ago, before I even hosted my first bar trivia night twenty years ago, I never dreamt this is where I’d wind up. I spent almost all of my 20s feeling adrift without direction, aimlessly bouncing between entry-level jobs I wasn’t at all suited for. Once I found trivia, however, I knew I finally had my shot at doing something fun, something geared towards my strengths, something I actually had a chance of being successful with – I’m even considered an expert in! Now, twenty years later, I truly am in a place where I get to be myself and set my own agenda, to shine as brightly as I can, on my own terms.
I gotta say, this is the best job ever.
To learn more about my unique profession, visit “TrivWorks CEO Notes: The 5 Work Modes I’m In at Any Given Time”