I’m 68 and starting a new career as a stand-up comedian. I’m spending my retirement years in dingy bars telling jokes.

• I spent 42 years working in IT in an office.
• Instead of playing pickleball or traveling to Portugal like people my age, I’m launching a new career.
• I know it’s hard to be good at comedy, but this is my passion.

The Metro North train to New York City got stuck due to torrential rains, which meant that I missed one of the few “Ladies Night” open mics of the week. I usually travel three hours round-trip, then pay $5 to get five minutes of stage time. That night, I had traveled five hours to miss five minutes on stage. I got a delicious cup of coffee at Grand Central Terminal for those five bucks, though.

At 68, I am launching a career as a comedian.

I’ve spent the last 42 years working in Information Technology; no one outside my industry knows exactly what I do. My parents went to their graves wondering. I paid the bills, got married, bought a house, and had kids. In my free time, I wrote humorous essays and performed comedy in obscurity, with little to no compensation.

While friends my age are playing pickleball, visiting Portugal, or hitting the golf course, I’m hanging around a rag-tag collection of high school students, ex-lawyers, college dropouts, Wall Street bros, housewives, and older folks, in the back rooms of dingy bars, telling jokes and embarking on a long slog to fine-tune my craft.

I feel like my life is just beginning.

I was the family jester

I chased laughs even as a kid. As the middle of five children, I was the family jester and the only chubby one, and humor was one way I could get attention in a crowded field of brilliant, talented, average-sized siblings. My family laughed at my jokes and loved to see me onstage, even if that stage was the local Y’s all-purpose room.

I wrote parody songs as a side hustle while pursuing somber endeavors, embarking on a career as a technical writer/promotional writer/quality assurance analyst/business systems analyst/project manager.

People often ask me, “Why didn’t you pursue a comedy career sooner?” The answer is simple: It’s because I love spending money — I like to shop at Whole Foods and Williams Sonoma, and I favor a steady diet of restaurant food (in order to keep the Williams Sonoma sauté pan pristine). Luckily, I discovered that I also love the predictable grind of office work.

I used humor at work

But even in the office, my humor seeps out. At my first professional job, I worked in a glass cubicle in a psychologically toxic environment, and my sarcastic asides so entertained my cubicle mate that he recorded them in a notebook we called the “quote log.” I wound up marrying that coworker, we are still married, and we still have the notebook.

I have jokes in journals and papers all over my house. For my entire life, I’ve lived in fear that I will forget a great line, so I always write things down. I don’t remember where the notes are stashed, but they surface serendipitously while I am looking for my phone charger or missing tax receipts.

I know it’s hard to be good

So why now? With menopause in the rearview mirror, the relief of having survived the pandemic, and analysis from my financial planner indicating that I will be able to live until 96 years old at my current level of spending (which I had previously lied about), I am finally ready to ditch the office.

I’m not one of those annoying senior citizens who stumble into a new vocation and claim, “I’m here! This is easy! What’s TikTok? How do I download the app?” I am humbly aware that becoming a comedian is a long haul — it’s exceedingly difficult to be good, nearly impossible to be great, and all too common to be awful.

You put in hours, years, and decades of hard work, building a set word-for-word, discarding scores of failed jokes until a precious few comedic gems remain. Even then, there’s additional tinkering and paring back. Every word is intentionally uttered, even if it looks like the comedian is just riffing. But you also have to be so in-the-moment onstage that you can seize on a spontaneous comedic line when something funny happens. Comedy is more poetry than prose.

There are more like me

Most people give up or just settle for a chuckle. But I want to get better and better, and that’s why I drag my plantar-fasciitis feet and arthritic hips to open mics. Actually, my aches are fodder for my performance, as is my age, my girth, and my grumpy husband.

The most surprising thing about my new passion is that sometimes I am not the oldest comic on a show. There is a community of retirees and second- or third-acters chasing this crazy dream. Striking comedic gold means hitting on something that is at once unique and universal — a nugget of truth about our shared existence with a twist that whacks the audience upside its head and brings forth a huge laugh.

I’m thrilled to have joined the gold rush.

Ivy Eisenberg is a writer living in White Plains, New York. She is working on a memoir about growing up in the groovy and turbulent 60s in Queens, a New York City borough.

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