I stepped back from the microphone and rested my “script” on the music stand beside me. I glanced down at my feet, then up at my stand-up comedy teacher, bracing myself. She pursed her lips, tilted her head thoughtfully, and said:

 

 

A familiar pressure built behind my eyes, and my left eye started its nervous twitch — a sensation I’d come to know well. I glanced at the faces of my classmates, then down at my notebook, where I had scrawled a reminder to myself across the page: “Don’t fall apart.” (You can see that line written right there in the middle of the page below.)

Why had I registered for this class and put myself through this torture? 

 

Simple — I thought it would be fun. 

 

Sometimes I have a stressful idea of fun.

 

I decided to sign up for an eight-week stand-up comedy class right before signing my book deal for Tidy Up Your Life, thinking that learning how to write and perform jokes could bring a lighthearted touch to my writing. In hindsight, the idea was almost funny itself — there are easier ways to learn how to write with humor. 

 

But stand-up comedy had always been on my “I wonder” list: I wonder if I could do that? I’d convinced myself that I’d be good at it. I mean, I’m used to running my classroom like a daytime talk show, and people have said I have a dry sense of humor — so I decided to go for it! But here I was, after mustering all my courage to perform for a class full of strangers, and the first piece of public feedback I got from my teacher was: “I wouldn’t characterize what you just did as stand-up comedy.”

 

 

My teacher continued on, giving me line-by-line feedback on what I had performed. I tried to stay composed, but inside, I was crumbling. I wrestled with thoughts like, Doesn’t she get how hard this is? I thought this would come naturally!

 

In that moment, I had to try to silence those thoughts and just listen. My teacher was there to help me, and although feedback isn’t easy to hear — especially in front of strangers, right after you’ve put yourself out there — I knew I had to absorb it.

 

After class, I approached her and admitted how hard it had been to pull together that five-minute story. She cut me off: “Stand-up isn’t just about recalling a story. It’s about getting your audience to feel what you felt. That’s where the funny is.”

 

Her words stuck. I realized that moving beyond simply telling a story to inviting the audience into the experience was a craft worth working on. 

 

In the weeks that followed, I became a student of stand-up comedy, filling my notebook with anecdotes and focusing on her tips for “finding the funny”.

 

And six weeks later, I finally did. I performed my first real set at Gotham Comedy Club. It's the club in NYC where fellow dad comedian Jim Gaffigan sometimes drops by to test out new jokes — and in a twist that still feels surreal, he stepped onto the stage immediately after me and performed a set — so I guess I can say that I opened for Jim Gaffigan.

 

 (And for the first time you can watch my FULL set below. I've only shown it to close family and friends, so welcome to the very exclusive club.)

Stand-up comedy classes reminded me that trying something new for the first time is no small feat. I also learned that feedback — however tough it sounds — usually comes from a place of care. The key is to listen, learn, and, above all, not fall apart.

 

Write about a moment from your day, but let your feelings take the lead. Instead of simply recounting the events, describe the emotions that surfaced. 

Practice bringing these moments to life on the page by focusing on what you could see, hear, smell, taste, or touch. This approach of including. your senses adds depth and authenticity, allowing others to feel the moment with you — humor and all.

If you want to read previous editions of “Behind the Stories”, check out the archives!