In a PR career that has spanned almost 20 years, I’ve been asked to do some crazy things on behalf of clients and employers, all in the name of ‘PR.’ In an effort to keep whatever job I had at the time and to go that extra mile, I developed a problem saying, ‘no’ to strange challenges and assignments. The definition of crazy is subjective, so bear with me if my version of crazy seems tame to you. For the millennials that have read this far, never fear an ‘off the books’ assignment for it is not only a great client retention exercise, but also could represent a career growth moment. At worst, you’ll own a treasure trove of funny stories to share when you too, become a gray hair.

Here are 3 examples of some of the crazy things I’ve been tasked with in PR:

1. Red Robin CEO and the singing telegram:

As an intern working for a firm in Denver called PRA, my very first mentor, the late Fred Hobbs, challenged me to sneak a birthday cake past the CEO of Red Robin’s secretary, somehow get into his office and sing him Happy Birthday. The only problem that Fred didn’t factor into the maneuver was that I can’t sing. I’m beyond horrible. So getting by the secretary and bursting into the CEO’s office was a snap. Him asking me to stop singing because I sucked so bad? That hurt, momentarily, until I got back to the PRA offices and got a hug from Fred for a job well done. They got the account. . .

2. KRFX, the G’man and the losing season:

Shortly after the Red Robin caper, Fred put me on an even more difficult challenge. It was the perfect storm. The Denver Broncos were on a rare losing streak and as a result radio sports personality the G’man was living on the top of a Denver hotel in the middle of a harsh winter, replicating an infamous stunt from 1990. To boot, Fred’s son was opening an ice cream store in downtown Denver that day I showed up for work, and wanted me to get to the G’man to share a sundae with him so he’d be persuaded to share the grand opening news on a live report. I think our conversation went something like this:

Me: Okay Fred. I can do this, but you know he has security?

Fred: That’s not a problem. You can get by security right?

Me: Sure. That’s easy, but then who wants a sundae for breakfast in the middle of winter?

Fred: This is a no lose proposal. Do what you can.

So I walked out of PRA with a frozen banana split in my hand, hopped in my crappy old Acura and drove straight to a coffee/bagel place, where I spent my last $10 on a warm breakfast for the G’man. And then I went to the hotel. With a sundae in one hand and a bag full of breakfast in the other I snuck by security and within minutes was on the roof standing in front a Tuff Shed. I knocked on the door. I heard a muffled, ‘what the f?’ Then a scruffy, cold-looking G’man opened the door.

G’man: Yes?

Me: I brought you breakfast.

G’man: Thanks, man. Who are you? And what’s behind your back?

I explained myself and my frozen banana split. The G’man was impressed, mostly by the coffee, but also by my ability to get past his security team. And as a reward he put me on the air and made me deliver the promo for the grand opening. I then returned to PRA a hero, at least for a day.

3. Archie Manning and the worst round of golf ever:

My first job out of school was a plum, working for the American Junior Golf Association. Not only was this a PR gig, but a sponsorship relations job, an operations and rules officiating position and a million other odd things. It was also an eye-opener to the ways of the Fortune 1000. Each Monday we hosted a Pro-Am at our tournament sites, which typically involved hosting local celebrities to pair with the top junior players in the world. In New Orleans at English Turn Country Club (my very first event), we were down a local celebrity and so I was asked to play, as I had mad skills back then.

My tournament director told me I was paired in the golf cart with Archie Manning, and instructed me to put his bag on the cart, which I did. It was hard to miss his bag – it was huge and his name was on it. I had other loose ends to take care of before teeing off and made it to the first tee box about a minute before our time. Introductions were made all around – I noticed how huge Archie’s hands were as we shook hands, and that he wouldn’t look me in the eye. After we hit our tee shots we got in our golf carts. I sat next to Archie and the conversation went just like this:

Archie: Son, we are going to make a deal today.

Me: Excuse me sir?

Archie: The deal is, you don’t talk to me and I don’t talk to you. I don’t want to hear a word you have to say and would prefer you just shut your mouth in my presence.

That was that. It was the quietest, most insulting round of golf I’ve ever played on one of the most exclusive (and racist) golf courses in the South. I thought a bit about quitting my job during that round, but then I grounded myself in the game and rather than feel bad about the man’s attitude next to me I decided to take him to task without words. And rendered a beating through my strokes that I’m hoping Archie remembers. I’ll never forget.

And then, shortly after I walked off of the 18th green sans handshake from Archie, my tournament director asked me to ferry an angry Mike Ditka to the airport. . .