How Did You Become the World's Worst and Highest Paid Waiter?

A story that answers the most frequent question I am asked about my career.

It Happened by Accident

For the last 20 years I’ve regularly been getting calls from Fortune 500 companies asking me what I would charge to disrupt their corporate event. Seldom do they pause at the price tag. They’re too excited to sign a contract—ensuring I will subject their guests to my incompetent service. 

I am, in fact, the world’s worst and highest paid waiter.

As you might imagine, this occupation wasn’t something I planned. It happened literally by accident.

I was standing in the food plating galley of the hotel kitchen that was hosting this event, waiting to exit the staff doors and walk on stage. I had been working as a corporate comedian for years, entertaining guests at the events of some of the most successful corporations in the world. I had worked my way through the ranks as a child actor, theater major, and street performer who got “discovered” by a General Electric executive. Once my big break into the corporate world was offered I enjoyed gigging for many years, strictly as a stage comedian, until the accident occurred.

On this day, 400 hungry bankers (whose neckties looked uncomfortably tight) were waiting for two things.

• Lunch

• And the same physical comedy show I had perfected as a street performer.

But before either of those could happen, an unplanned agenda item showed up on the conference schedule.

A fire.

A last juicy steak on one of the grills in the kitchen went ablaze. It produced just enough smoke to set off the industrial fire sprinkler system, and completely ruined the 400 plated lunches that had been laid out for delivery to the bankers. Had that last steak made it safely off the grill it would have been plated along with the rest and the lunches would have been served.

Instead, I watched those lunches drown in a kitchen car wash. As the mayhem ensued I knew this was going to put the entire event into a tailspin. Feeling sorry for the event-planner, I asked myself what I could do.

My background is in theater, street-performing, and comedy. There’s only one thing you can do in theater when things go wrong.

Improvise.

Searching for a solution, I noticed there was a server apron hanging next to the kitchen door. My brilliant spontaneous plan was to put on the apron and become a “bad” waiter. I imagined entering the room, tripping over chair legs, over-filling water glasses, and reaching over the heads of guests to fill the table with unnecessary sets of silverware.

Since the event planner would be scrambling for a while — making calls to local hotels to import food for the guests — I thought I could fill the gap with some entertainment.

I threw on the serving apron and dove into the crowd.

It was so much fun to be absurdly bad as a server. But as I kept making passes through the room from table-to-table, I wasn’t getting the reaction I had imagined. Despite the ridiculousness of filling every water glass to the brim and asking the guests if they had enough water, no one seemed to catch on that it was a joke.

The fourth time I returned to the kitchen to find props for my ruse, I realized I had just discovered comedy GOLD.

I Became a Living Rorshach Test

Once a slapdash version of lunch had been served it was time to start my comedy show. But I didn’t just launch into my usual juggling routines. Instead, I slunk to the stage as though I had been asked to apologize for my poor service.

The crowd, still thinking I was a server, threw a combination of damning, judgmental, and pitying expressions my way as I stammered out these words. 

“I’m, umm, really sorry for my service. My banquet captain asked me to apologize, and uh, well, it’s my first day.”

Inside was a feeling of sheer power that was both exhilarating and a little scary. I was waaay out on the comedy-improv ledge. 

I had led a roomful of 400 professionals into a dark corner of their mind where, what was supposed to be a comical routine, turned into a miniature sociology study. Each person in that crowd was having their own experience and reaction to what was happening. Each making up their own story about what was really going on and what should be done about it. I was a living Rorshach test. And now, I was about to tell them the truth.

“Um . . . so, thanks for letting me apologize. Again, I’m really sorry . . .and um, oh yeah, there is one other thing I need to say. I’m actually your entertainment for the afternoon.”

The ballroom went completely silent as the slow dawn of comprehension turned every face in the crowd from irritation, judgment, and concern to wide-eyed shock, surprise, and then collective delight. Waves of guffaws and relieved laughter swept the room. As I launched into the full proper comedy show, I knew this would be a routine I’d be keeping forever.

And that’s how I came to include this now infamous stunt at the outset of my corporate presentations. Because of it, my career as an event comedian — and subsequently a speaker — took off.

Today I am regularly presented with a five-figure check for spending an hour being the worst waiter in the world.

A Story of Transformation

Fundamentally I’m a storyteller and I always have been.

But what the discovery of this waiter routine drove home is that we’re all storytellers — all the time. By default, we’re constantly making up stories that are designed for one purpose; to protect us from the worst thing that could happen in any given moment.

• An event participant once pulled out his notepad and drew a diagram to show me how full the water glass should actually be. 

• A psychiatrist once tried to whisk me out of the room for a walk. 

• Another attendee phoned her spouse to ask what she should do. 

They were all worried when I wasn’t conforming to their idea of how a waiter should be. The actions they took were an attempt to restore the safe territory of their story.

When I finally reveal to audiences that I’m not their waiter, we all get to have a good-natured laugh at the stories we make up in our minds when things aren’t going as planned. 

And when we become self-aware about an unconscious or limiting way we’ve been thinking — something truly exciting occurs.

The opportunity to think differently.

Stories about transformation light up our human spirit. Tales that depict the potential to change our thinking, perspective, attitude or sense of identity are particularly inspiring. We all want change, growth and transformation, and yet we’re also preoccupied with avoiding death — not just physically, but the death of our attachment to who we’ve been until now.

Every time I go to work I get to tell this theatrical story about a bad waiter who becomes a keynote speaker. The attendees then have the opportunity to transform their relationship to their projections, assumptions, and the conclusions they jump to in their daily lives.

The transformation of our character is the most compelling story there is.

• Scrooge becomes a generous Ebenezer. 

• Down-on-himself Rocky Balboa realizes he’s a champion because he can go the distance. 

• A wooden toy becomes a flesh and blood boy.

What about you?

What transformation of character is waiting for you?

We all attempt to fix, dismiss, ignore, or get rid of the parts of our lives that don’t fit our story about the way things should be.

What if you got curious about:

• The colleague who rubs you the wrong way

• What your kid was thinking when they drew on the walls

• Why your spouse ignored your request to finish up the dishes

• Why your leadership team keeps wasting your time with meetings

• Or why a part of you keeps putting off the real passion you want to pursue?

Maybe that “bad waiter” isn’t who you think he is.

You may not be able to change what others are doing, but your open-mindedness and curiosity about things that don’t fit in with your plans could transform the stories you tell everyday.

And what if transforming your stories was the key to transforming yourself?