Everything was going great until you showed up. You see me across the crowded room, make your way over, and start talking at me. And you don’t stop.
You are a Democrat, an outspoken atheist, and a foodie. You like to say “Science!” in a weird, self-congratulatory way. You wear jeans during the day, and fancy jeans at night. You listen to music featuring wispy lady vocals and electronic bloop-bloops.
You really like coffee, except for Starbucks, which is the worst. No wait—Coke is the worst! Unless it’s Mexican Coke, in which case it’s the best.
Pixar. Kitty cats. Uniqlo. Bourbon. Steel-cut oats. Comic books. Obama. Fancy burgers.
You listen to the same five podcasts and read the same seven blogs as all your pals. You stay up late on Twitter making hashtagged jokes about the event that everyone has decided will be the event about which everyone jokes today. You love to send withering @ messages to people like Rush Limbaugh—of course, those notes are not meant for their ostensible recipients, but for your friends, who will chuckle and retweet your savage wit.
You are boring. So, so boring.
Don’t take it too hard. We’re all boring. At best, we’re recovering bores. Each day offers a hundred ways for us to bore the crap out of the folks with whom we live, work, and drink. And on the Internet, you’re able to bore thousands of people at once.1
A few years ago, I had a job that involved listening to a ton of podcasts. It’s possible that I’ve heard more podcasts than anyone else—I listened to at least a little bit of tens of thousands of shows. Of course, the vast majority were so bad I’d often wish microphones could be sold only to licensed users. But I did learn how to tell very quickly whether someone was interesting or not.
The people who were interesting told good stories. They were also inquisitive: willing to work to expand their social and intellectual range. Most important, interesting people were also the best listeners. They knew when to ask questions. This was the set of people whose shows I would subscribe to, whose writing I would seek out, and whose friendship I would crave. In other words, those people were the opposite of boring.
Here are the three things they taught me.
Listen, then ask a question
I call it Amtrak Smoking Car Syndrome (because I am old, used to smoke, thought that trains were the best way to get around the country, and don’t really understand what a syndrome is). I’d be down in the smoking car, listening to two people have a conversation that went like this:
Stranger #1: Thing about my life.
Stranger #2: Thing about my life that is somewhat related to what you just said.
Stranger #1: Thing about my life that is somewhat related to what you just said.
Stranger #2: Thing about my life…
Next stop: Boringsville, Population: 2. There’s no better way to be seen as a blowhard than to constantly blow, hard. Instead, give a conversation some air. Really listen. Ask questions; the person you’re speaking with will respect your inquisitiveness and become more interested in the exchange. “Asking questions makes people feel valued,” said former Virgin America VP Porter Gale, “and they transfer that value over to liking you more.”
Watch an old episode of The Dick Cavett Show. Cavett is an engaged listener, very much part of the conversation, but he also allows his partner to talk as well. He’s not afraid to ask questions that reveal his ignorance, but it’s also clear he’s no dummy.2
Online, put this technique to use by pausing before you post. Why are you adding that link to Facebook? Will it be valuable to the many people who will see it? Or are you just flashing a Prius-shaped gang sign to your pals? If it’s the latter, keep it to yourself.
Tell a story
Shitty pictures of your food are all over the Internet. Sites like Instagram are loaded with photo after photo of lumpy goo. What you’re trying to share is the joy you feel when the waiter delivers that beautifully plated pork chop. But your photo doesn’t tell the story of that experience. Your photo rips away the delicious smell, the beautiful room, the anticipation of eating, and the presence of people you love.
Instead, think of your photo as a story. When people tell stories, they think about how to communicate the entirety of their experience to someone else. They set the stage, introduce characters, and give us a reason to care. Of course, that’s hard to do in a single photo, but if you think in terms of story, could you find a better way to communicate your experience? How about a picture of the menu, or of your smiling dinner companions? Anything’s better than the greasy puddles you have decided any human with access to the Internet should be able to see.
Expand your circles
Several years ago, my wife and I went on a long trip. We had saved a little money, and the places we were staying were cheap, so we could afford private rooms in every city but one. Guess where we made the most friends? In Budapest, where we were jammed into a big room with a bunch of folks, we were forced into situations we never would have sought out. I wouldn’t have met Goran, the Marilyn Manson superfan who was fleeing the NATO bombing of Belgrade on a fake Portuguese visa. Or Kurt, the Dutch hippie who let us crash on his floor in Amsterdam. Stepping out of your social comfort zone can be painful, but it’s one of the most rewarding things you can do.3
As you widen your social circle, work on your intellectual one as well. Expose yourself to new writers. Hit the Random Article button on Wikipedia. Investigate the bromides your friends chuck around Twitter like frisbees.
When you expand your social and intellectual range, you become more interesting. You’re able to make connections that others don’t see. You’re like a hunter, bringing a fresh supply of ideas and stories back to share with your friends.
The Big Bore lurks inside us all. It’s dying to be set loose to lecture on Quentin Tarantino or what makes good ice cream. Fight it! Fight the urge to speak without listening, to tell a bad story, to stay inside your comfortable nest of back-patting pals. As you move away from boring, you will never be bored.
Lots of books exist because of how boring you have made the Internet. Books like The Information Diet focus on the consumption side of things: how are we, your readers and friends, supposed to deal with the junk you keep sending us? Instead, I’d like to look at the supply side: if you were more interesting, then there would be less junk out there that we would have to deal with. ↩
You don’t have to go back to the ’70s to find good listeners. My friend Jesse Thorn is a great interviewer who also listens in an engaged way. Check out his show, Bullseye. Or if you’d like to shoot for something a bit more academic, BBC’s In Our Time features great conversation led by another master, Melvyn Bragg. ↩
Scott Simpson is a writer and performer from California. He spent over a decade in the digital media business at Amazon.com and Apple, and is co-host of the comedy podcast You Look Nice Today.