How Working at 92NY Prepared Me to Run TrivWorks
2026 marks seventeen years since I started TrivWorks – fifteen since taking it full-time – and twenty years since I hosted my first trivia night. As I wrote about recently, there is no traditional career path to becoming a professional corporate team building trivia host. Like stand-up comedy, improv or other performance profession, you simply have to dive right in.
Lewis Black sums it up best:
I had already hosted/produced something like 1,000 public & private quiz nights by the time I took this business from a side gig to full time back in 2011. However, for six years prior I was working full-time at New York’s 92nd Street Y (since renamed 92NY), a prestigious cultural and community center on the Upper East Side of Manhattan. My job was in event programming, specifically in adult education – first as an associate, then as director of the entire division. In this capacity, I was responsible for programing and executing over 500 individual classes, events and lectures a year. This was enrichment stuff, open to the public, who could purchase tickets to all sorts of things: foreign language classes, cooking demonstrations, mahjong lessons, singles mixers, guided tours throughout the city, expert lectures on all manner of subjects.
I was definitely a fun job, one which I excelled at. The work lent itself to my strengths and interests, namely being creative and putting fun experiences together for others to enjoy, while getting to explore the people, places and food that the greatest city on the planet has to offer. I actually became something of an expert on adult education classes, and was even interviewed by Reuters on the subject! The schedule was also pretty flexible, meaning I could essentially make my own hours, so long as the work got done. This allowed me to build TrivWorks as a side hustle, working gigs basically any time I wasn’t at the office.
And let me tell you, there was a LOT of work to be done.
Here’s how my unique job at 92NY prepared me for my even more unique job as a professional trivia host for corporate events.
Mastering the Art of Plate-Spinning
I’ve always been able to compartmentalize aspects of my life well – I used to think of it as having a mental file cabinet. Whenever I have to turn my attention to something, I can put whatever I’m currently doing on hold and just pick up wherever I left off on the next task – or close one drawer in the cabinet, if you will, and open another. This served me well at 92NY when I suddenly found myself managing upwards of a dozen simultaneous programs a night, and scores per week. I had to make sure that the wine tasting event on the second floor was set up, before bringing the chess sets up to the sixth floor, then running back to the lecture hall to greet a speaker and make sure I had his intro printed out.
I soon learned that this wasn’t really opening & closing drawers, so much as it was keeping plates spinning. Such it is with what I do now at TrivWorks. At any given moment, I’ve got dozens of events booked – some of which are coming up, some which may be right now. As I write this, I’ve got two events happening today, on opposite sides of the country; this coming off of four events last week, each held in a different city! But learning how to manage simultaneous events is a skill I really owe to my time at 92NY, and I’m really glad I was able to hone my ability to do it – to keep the TrivWorks plates spinning.
Honing Client Service Skills
Even prior to working at 92NY I was working in client service, spending two years at global PR firms in Manhattan. It was truly grueling work, a grind like I’ve never experienced before or since. But I learned the rudiments of providing excellent client service: being highly responsive, anticipating needs, going above and beyond. Once I got to 92NY, this commitment to service only grew, because now instead of dealing with just a handful of clients, I was dealing with literally thousands: patrons, instructors, lecturers, etc. I was also working with colleagues in other areas of the organization, whom I had to provide a level of professionalism and service as well: marketing folks to sell my programs, facilities and IT staff to help get my rooms set up, fellow event programmers whom I had to coordinate with.
I carried this commitment to excellence directly to TrivWorks, and strive every day to deliver not only a high-quality trivia team building product, but high-quality service as well. Providing an exceptional level of service to TrivWorks clients and emcees alike is something I pride myself on, and I really do owe it to my time at 92nd Street and Lexington Avenue.
Thinking in Terms of Past, Present & Future
What do I mean by this? When working as a programmer at 92NY, I was constantly dealing with all three timeframes at once – although it would probably be more accurately described as “present, future, past.” My first priority every day was making sure that that night’s programs went smoothly. That meant I was dealing with the immediate issues: does everyone know where to be, and at what time? Have I done everything that needs to be done? Has the cheese platter been ordered for the literary discussion group? Is the PowerPoint equipment set up in the French class? So many details.
Only once I was sure everything was under control could I then focus on my next priority, which was planning future programs. Back then the Y had a print catalogue, which came out three times a year with a six-month lead time. That meant I had to have all of my programs for the following season line up by the six-month print deadline: dates, times, instructors, descriptive “blurbs,” prices, everything. It was stressful, working with deadlines so far out – but it had to be done.
Finally, I had to go through my Emails and the dozens of voicemails I received daily, and deal with things that have already transpired: someone who missed a class and wants to reschedule, someone was upset about the quality of the wine tasting and wanting a refund, someone who left a shawl at an offsite cooking demo.
With TrivWorks, my day-to-day activities are surprisingly similar. I start each morning making sure that my upcoming booked events are handled: contracts drafted, gigs staffed, trivia written, client and emcee communication up to date. Only once I know my immediate events are taken care of can I look ahead: responding to inquiries, making sales calls, working on my Website, crafting blog posts like this one. The only difference is that I don’t have a ton of “past” to deal with; once a gig is done it’s done, there’s not a whole lot that needs to happen beyond my comprehensive recap call, which I kind of consider to be part of “present.” But I do like that familiar flow which I learned through my time at 92NY, which transferred pretty easily to my day-to-day here at TrivWorks.
Putting Out Fires and Adapting
You can’t plan and execute over 500 annual classes, events and outings without something not going right. Any number of things could not go as planned, and often did: weather forced me to cancel outings, too few people signed up for program X to run it, too few guys showed up to singles events. A lot of times we wound up having to cancel stuff, and believe me that sucks for everyone: the people that bought tickets and were looking forward to it, the instructor who had scheduled their time, my fellow staff who had promoted and set up the event space.
But just as often, we didn’t have to cancel, but had to make changes on the fly. This might involve a last-minute room switch, meaning I had to scramble to find a new space, get tables and chairs in there, put up signage, let the box office know, etc. Or it could mean a postponement, meaning I had to contact every single person who signed up and make sure they got the new date.
Fortunately with TrivWorks, there really are no cancellations unless something truly extreme happens. However, we ARE forced to make changes on the fly, and adapt to situations as they unfold. How many times over the years have my emcees and I arrived to an event space, only to find that the room is set up in a weird configuration, or that the sound system doesn’t work, or that the group is running late – or early? We need to be able to manage these changes in real-time, because hey – that’s showbiz! I credit my years working at 92NY and dealing with last-minute stressful issues on a regular basis with giving me the ability to take a step back, catch my breath, and deal with the unexpected in a calm, logical way. (For a related article, check out “What Goes into Producing a Corporate Trivia Event?”)
Conclusion
TrivWorks has now been my full-time job for almost three times as long as I worked at 92NY. But the lessons and skills I learned from my time there have no doubt formed the foundation for what I’ve been able to do working for myself. The ability to stay focused and organized when things can otherwise seem overwhelming, to be able to manage multiple important events at once, to deal with clients and colleagues professionally and to handle crises and the unexpected as they occur, all of this I owe to 92NY. It’s been a while since I stepped foot inside the 152-year old institution’s lobby on 92nd and Lex, but I appreciate the valuable lessons I learned there, as well as the opportunity to have planned and produced events for a prestigious world-renown institution.
For more on my unique journey from PR grunt to event programmer to corporate trivia host, check out “What Kind of Person Starts a Trivia Company, Anyway?”