Start With the End in Mind

Terrified of public speaking? There’s an easy hack to make sure you say something others appreciate

It’s almost my turn, oh my god, what am I going to say?

I was sitting in a circle of 30 people at a group retreat, listening as each participant introduced themselves. I was at the end of the line and had plenty of time to prepare for my 15 seconds of fame, but I didn’t need it.

As I listened, a part of me was judging the others mercilessly for going on too long, or for rambling without a point or an end to their story. Yeah, I can be a dick, I’m working on it. Many of them of course gave excellent, concise introductions.

When my turn came I gave a quick intro, got some cheap laughs with a joke about knowing the specific episode number of a podcast because I recommend it so often, and closed by saying how much I looked forward to getting to know everyone.

As the microphone went back to the host, my daughter leaned over and asked, “That was great, I never know what to say. How do you come up with an intro?”

I told her, “I figure out the last line of what I’m going to say, first. That way I can build everything else up to that line and the structure creates itself.”

What I didn’t tell her is that I learned to think about the end before I start the hard way. That story involves Drake.

I own a speakeasy in downtown Toronto, Coffee Oysters Champagne, hidden behind a coffee shop. When I opened it, my father said, “Son, don’t tell anyone you own a bar, people get shot in bars.” So ok, it’s a cocktail lounge.

One afternoon our coffee shop manager found me in the back. “You’re a Leafs fan, right? You might want to come out to the coffee shop, but come quickly.” I peeked through the door and there, having a hot brew, was Auston Matthews, with a teammate who might have been Mitch Marner. I’m not sure, because I immediately ducked back into the lounge.

My manager asked, “Aren’t you going to say hi? You’re the owner.” No way. He was there to have a coffee, not to be pandered to by some idiot who thinks he’s a big shot because he owns a bar/lounge/bistro. I texted my friends instead.

The next day my friend Kevin said, “Why didn’t you talk to him? He’d appreciate it, you’re the owner after all.” I respect the hell out of Kevin, and I took his advice to heart. Auston Matthews never came into the shop again, but.

Drake did.

A few weeks later he brought an entourage in through our even more secret back door, and our staff ensconced him in a curtained-off private booth with a couple of bodyguards outside. With Kevin’s advice echoing in my head, I decided that this time I was going to say hello. I imagined him smiling and shaking my hand, telling me what a great place we had, maybe inviting me to sit down for a few minutes. I imagined.

I told one of the guards I was the owner and wanted to say hello. They opened the curtain, and Drake looked up at me with a quizzical expression. I said, “Um, hello, my name is Sanjay, I’m one of the owners here and I just wanted to say thank you for coming in, we appreciate your business.”

He smiled uncomfortably, accepted my outstretched hand, mumbled something like “Sure sure, thanks,” and turned back to his companions. I was left standing there while everyone ignored me, so I backed out of the booth and went to hide in another room.

I felt like a complete idiot. What did I think his reaction was going to be? I’m not a Drake fan, I wasn’t going to tell him how much I liked pineapple fruit or whatever that song was. He was probably thinking, “Geez, I hope this dork doesn’t ask for a picture. Can’t a guy just have a drink?”

Drake wasn’t the problem. I was. I walked up to him with no plan and no idea how I wanted it to end, only a vague sense that I should, and that my status as an owner somehow offset his status as a celebrity. The difference was, he was the customer.

Drake hasn’t been back since. I tell myself it’s because we don’t play hip hop at my bar-lounge-grotto, but I know the truth. He doesn’t want to run into that dork owner again.

Starting with the end in mind is great advice in any field, but it matters most when you’re about to open your mouth. Before you speak, before you write, before you walk up to someone, know what you want them to be left with. Think about what the other person is thinking. Taste your words before they come out of your mouth. Then build everything else up to that.

Yes, spend time on your title and on your opening line, but to make something memorable, focus most of all on the last sentence. You know.

This one.