One of the lessons that my dad taught me is to not be afraid to try anything. “How hard can it be?” he would ask. He would also encourage me to “Do something a little crazy. You’ll stand out.”

This was almost always great advice. Almost, because it derailed my career as an advertising copywriter. Originally, I wanted to be like Peggy Olsen from “Mad Men” (except the show wasn’t on yet to inspire me.) My dad was an executive at Chrysler, and he knew a guy who knew a guy who was CEO of a large Detroit ad agency. The one that did the commercials for Chrysler. Through diligence and hard work nepotism, I got to meet the CEO, who graciously invited me to his office where he shared insights about the ad biz. He even indulged me and listened to my TV spot idea, which included two props I brought with me: a Barbie-sized cooler and star-shaped sunglasses. “No one’s ever made a pitch like this before,” he said. (Probably not a compliment.) Then he told me that they weren’t hiring at the moment and gave me a polite “We’ll keep you in mind” send off.

A couple months later, the CEO was in Mexico during an earthquake. It was a big one, hitting 8.1 on the Richter scale. My dad had a “do something a little crazy” idea: attach bells to the rim of a sombrero and deliver it to the CEO with a note that said, “Wear this on your next trip. If the bells make a jingling sound, it’s time to get out of town.” So, I did. And I never heard from the man again.

You think I’d have learned my lesson, but no. Many years later, I was a writer for The Tennessean, Nashville’s daily newspaper. I covered fashion, then home design, then family events. My beat pretty much followed my life trajectory. What I really wanted to be, though, was a humor columnist. Like Dave Barry or Erma Bombeck. I would read their columns as soon as the paper hit my driveway each morning. (Anyone remember those days?)

I read that Dave Barry was taking time away because he had shingles. My dad’s advice, “How hard can it be?” and “Do something a little crazy” bubbled up, so I tracked down the email address for Dave’s editor and sent a message, offering my column-writing services while Dave was “off fixing his roof.” Get it? He had shingles.

I received a swift answer: “No.” Actually, it said “Our legal team won’t allow it.” I guess it would break Columnist Law #143, which states, “Write your own damn column.” I decided to go away silently since I was now on Dave’s legal team’s radar.

Several years later, I was hired to help a teenage philanthropist with her book. One of the tasks was to infuse humor. Who did I turn to for inspiration?

Conan O’Brien. Unlike Dave, Conan hadn’t shunned me. At least he hasn’t yet. But after realizing that Conan’s brand of humor might not be right for our audience, I went back and read Dave Barry’s columns. Lots of them. He became my imaginary Sensei, and I channeled his humor and timing as we wrote.

Why am I telling you this? [Insert the song, “The Long and Winding Road.”]

Because I got to meet Dave when he came to Nashville to promote his new book, Class Clown!! After waiting patiently in the signing line, I stepped up to him and said, “I’m a writer.” He immediately got that look on his face (see photo) that said, “Here we go … she’s going to ask me to read her novel/script/short story/grocery list. She looks more like a pharmacist. Or maybe a professional mermaid if I squint my eyes. Oh, wait. She has feet.”

And he was right. I do have feet! And I did ask him to read my book. One that was already published, and by Simon & Schuster, no less, just like his book! I told Dave that he had been my humor inspiration, and that I thanked him in the acknowledgements of the book. (For the record, I did not thank Conan, although, somewhere towards the end of the book, it’s noted that he and Roget, the thesaurus guy, are my imaginary boyfriends. But that’s another story for another day.)

Dave’s face seemed to relax a bit, and he sounded slightly amused to hear this. I considered telling him about my offer to write his column decades ago, but the line behind me was long, and I wasn’t sure if his legal team was lurking in the shadows. Dave posed for a photo with me, and I was on my merry way.

The WOW! of the story is this: Take my dad’s advice. Do something a little crazy. How hard can it be? If you fail, so what? You tried. And you have an amusing story to tell someday. You might even get a chance to revisit that story in the future, turning it into a double WOW! moment. (However, think twice about making earthquake jokes. Especially to a potential employer.)