The Great Line


I straight-up loved doing the Sickboy Podcast.  My buddy Jeff (who hooked me up with the guys initially) told me that it was going to be “more fun than any other podcast you’ve ever done”.  He hit it on the head, and to be honest, I really kind of needed this experience when it happened.

We recorded the episode on a dreary Sunday morning in Toronto a few weeks back.  At the time I was battling with a pretty significant depressive phase of my bipolar.  Knowing this, a friend of mine was checking in with me every few days to make sure I was staying connected to the world outside my apartment, and when he called that afternoon I was singing the praises of Sickboy and its hosts.

“Nice,” my friend said. “Was it the best podcast you’ve ever done?”

It’s that notion of the “best of something” I wanted to touch on for this post.  As part of my strategy for dealing with the depressive phases of my disease, I’m always on the lookout for “perspective hacks” that can shift my mindset in positive ways.  One of my favourites come from two extraordinary men I met on a train trip across Canada several years ago.

Jimmy and Earl were 91 and 89 years old.  Veterans of WWII, they had actually met on the beach on D-Day and had been best friends for over 60 years when I met them over lunch one day in the dining car.  When I told them I ran the leadership development program at the University of Toronto, Jimmy said:

“Ah, so you work with students?” 

“Yes sir,” I told him.

“Well then, if there was one thing that you want your students to walk away having learned, what would it be?” He asked.

I thought about it for a few moments.  “I want them to recognize that they are leaders already, but that they can be better ones if they create a plan to do so every day.  The problem is, a lot of my students are focused on the wrong things.”

“Oh really?” Said Earl, raising his eyebrow.  “What do you mean?”

“Well,” I said.  “Let me give you an example.  The first time I get a group of students together, I ask ‘how many of you know what your GPA was last semester?’  Every hand in the room goes up.  Then I ask them, ‘how many of you know how much money you made per hour at your last job?’  Every hand in the room goes up.  I ask them, ‘How many of you know who sings ‘Party in the USA’?  Every hand goes up.”

“Miley Cyrus,” Earl offered helpfully.

“He’s a fan.” Jimmy said in response to my shocked look.

I laughed.  “Well, yes.  But marks, money, Miley Cyrus…they know them all.  Then I ask them, ‘how many of you can tell me the single happiest moment of your life?’  And hardly any hands go up.”

I sat back. I have told that story a lot, and had gotten used to people shaking their heads in disappointment at my students – a tacit confirmation that I was in the right for showing them the problem with their priorities. 

Earl looked at me for a moment before offering his take on it.

“That’s because that’s a dumb-ass question you asked.”

This was not the reaction I was used to.

“What? ‘What’s the happiest moment in your life?’ is a dumb ass question?” I asked incredulously. “You don’t think it’s important for someone to be self-aware enough to identify the happiest moment in their life?  To prioritize knowing that ahead of how much money they make or what their grades are?”

Earl shook his head.  “If you’re someone who’s teaching people, I think it’s more important that you’re aware of how dangerous that question is.”

“Dangerous? What do you mean?” I asked.

“Look,” said Earl. “The problem with asking people to think about the happiest moment of their life, or the most beautiful sunset, or the most delicious meal, or the best kiss, or the greatest sex, is that there’s only ONE of those things in anyone’s life.  There can be only ONE happiest, greatest, most beautiful of anything.  That’s what those words mean – the single best one. “

He leaned forward.

“But Drew, there are so many moments in our lives.  So many sunsets, so many meals, and,” he gave a mischievous grin, “if you’re lucky an awful lot of kisses and sex.  The problem with your question is it reinforces the idea that only the things at the very top deserve celebration.  I think that means that moments and meals and sunsets that are actually amazing get diminished in our minds just because they’re not the greatest we’ve ever had. I think it’s dangerous to teach people something that might make them diminish good things in their lives.”

I was stunned at how much sense his logic made.  “I honestly never even considered it like that,” I told him.  “But what do you suggest I do instead?”

“Tell them to draw a line,” Earl replied, dragging his finger horizontally across the table in front of us. “A line in their mind that represents ‘great’.  For everything they experience in life their question should only be, ‘did that fall above the great line?’?  If it did, file it there.  There’s unlimited room above the great line.  Your goal in life should be to create as big a collection of things above the great line as you can in as many different categories as you can: a big pile of great conversations, meals, successes, views, and yeah, some more of the sex too.” 

“Think of it like poker,” jumped in Jimmy. “Your goal is to have the biggest stack of chips.  That’s the same thing with life.  If you only focus on the greatest of everything in your life, you’ll get one chip for each category: sunsets, laughs, whatever.  But if you just focus on collecting things above the ‘great’ line, you can create this monstrous stack in every category.  That’s a lot more chips than someone who just looks at the greatest of everything.”

“Basically Drew,” Earl jumped back in. “’Greatest’ is the enemy of ‘great’”

The idea of “The Great Line” is one that I’ve embedded in my consciousness and it’s been a tremendous tool in creating opportunities for me to celebrate the things around me every day.  The “best” of anything in my life used to come around rarely, but something lands above “The Great Line” almost every day.

Is Sickboy the best Podcast I’ve ever been on?  I don’t bother asking myself that.  I just give love to Brian, Jeremie and Taylor for giving me the opportunity to stick another experience above The Great Line.

- Drew Dudley 


Drew has spoken to over 250,000 people on 5 continents, been featured on The Huffington Post, Radio America, Forbes.com, andTED.com, where his “TED talk” has been voted “one of the 15 most inspirational TED talks of all time” and viewed over 2.5 million times. 

Be sure to check out our conversation with Drew on our website or over on iTunes!