There’s One Little Problem With That Famous Wayne Gretzky Quote About Pucks.

Chicago Blackhawks Vs Detroit Red Wings

There’s a Wayne Gretzky quote that’s been repeated in a thousand PowerPoint presentations, and I’ll repeat it here: “Skate to where the puck is going, not where it has been.” It’s a wonderful thought: Instead of chasing what’s already happened, try to get a step ahead! And hey: Wayne Gretzky once scored 92 goals in an 80-game season, so he must know something about success.

But there’s a flip side to Gretzky’s mantra, and I think it’s just as interesting: Everyone’s trying to skate to where the puck is going, and when they make their move, they usually move in packs.

If you’ve ever seen “Trading Places,” you know what I’m talking about. There’s the famous scene at the end where the Dukes try to corner the market, and everyone else starts following their lead. The other brokers don’t know why the Dukes are doing what they’re doing — they’re just chasing them blindly in hopes that there’s money to be made.

I haven’t been around for very long, but I’ve seen enough to know this: That kind of scene happens all the time. When one big player in an industry makes a move, a bunch of smaller ones often go chasing after them — even if they don’t quite understand why. Most aren’t trying to find the puck; they’re just watching bigger players for clues, and hoping they can beat the giants to the right spot.

And when you have this sort of movement in packs, with everyone trying to be first to the next big thing, it’s incredibly hard to stand out. There are too many competitors.

I’ve always taken a different approach: Watch where everyone’s moving, and then go where they aren’t. Some of the best stuff I’ve worked on (longform journalism, email marketing, responsive design) were spaces that didn’t have any buzz when I got into them. In time, they were all tapped as “the next big thing.”

Not everything I’ve done has turned out quite that well. (I started Stry.us as a replacement to the Associated Press. That, uh, didn’t quite work out.) But it’s been a pretty good policy: When you’re a little fish, don’t go swimming into big ponds. Ignore the hottest trends. Ignore what the experts are saying.

To bring it back to Gretzky: Find pockets of space where you can work, and if you do things right, the puck might even come your way.

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That hockey photo comes via Flickr’s Nicole Yeary.

The Window Is Open.

When I was about 3 years old, I used to walk around my house pretending to play guitar on this red plastic pan. By middle school, I’d walk around school breaking into occasional air guitar. By high school, family friends would grab my mom and ask, “Why doesn’t Dan actually take guitar lessons?” And she never had a good answer for them.

When I got to college, though, I had this realization: If there was ever a time to learn to play guitar, it was right then. My freshman year, I made friends with a guy on my floor who played. He needed roommates for the next semester. I agreed to move into his place under one condition: He teach me how to play.

College happened to be an amazing time to learn a new skill.  I had a LOT of free time, and I spent much of it the next 3 years learning how to play. It was just a matter of recognizing that the moment was right to learn a brand new skill — and then putting in a ton of work to learn that skill.

The same thing happened when I realized that I was ready to start Stry.us. The same thing happened when I realized that I was ready to move to New York. I recognized that the window of opportunity was opening, and I had to have the guts to go ahead and take my chance before the window closed.

There are ways to know when the window is opening for you. Sometimes it’ll be obvious: a friend will extend an invitation to do something, and you’ll recognize that you’ve got a chance to do something special right now. Sometimes, it opens when you’re frustrated with what you’re working on, or when an idea nags at you for weeks. Sometimes, there’s no sign — you just know.

But if the window opens, take your shot. It doesn’t always stay open very long.

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That photo has nothing to do with the window of opportunity — I just like it :-) It comes from Mikael Kristenson on Unsplash.

A Note To My High School Self, 10 Years Later.

me at 18

10 years ago this month, I graduated from high school. (It’s only been 10? It feels like more.) But as I look back on 2005 — an age of flip phones, buddy lists, printing out Google Maps before road trips, limited text messaging plans, no Facebook, and a whole host of stuff that had absolutely nothing to do with the internet — I’m thinking about what it would be like to be 18 all over again. If I could go back, I’d have a few words of advice for myself, among them:

-Learn how to work hard and how to build good habits. It’ll make all the difference.

-You’re going to mess up a lot. That’s OK! You’re young! One screw-up doesn’t define you. You’ll have lots of chances to do something great. Don’t let one mistake stop you.

-You have some pretty exceptional friends. Stay in touch — they’re going to do some amazing stuff, and you’re going to want to be a part of it.

-And keep in touch with your classmates, too. They’ll be the ones running cool businesses and projects in the future. (They might even be able to get you a job.)

-It’s OK to ask for the stuff you want. If you don’t ask, you’ll never know.

Don’t fake it ’till you make it. Just be confident in who you are and what you want, and keep working to become the person you want to be.

-Take advantage of your windows of opportunity. Once you get a real job, there are no more summer vacations. You’re never going to get a month or two off again. Enjoy it.

-You could always spend more time reading.

-You could always travel more, too.

-Surround yourself with great people. You’ll never regret making time for people you love.

-Don’t waste too much time wondering, “What should I do with my life?” You might never know, and that’s OK.

-Don’t overthink things. Just try to be happy. Life doesn’t need to be much more complicated than that.

And don’t try to skip ahead. Enjoy the moment, 18-year-old Dan. You’ve got some great stuff ahead of you.

So What Do You Want To Ask?

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I’ve been lucky to meet some exceptional people in my life, and there’s something interesting that I’ve noticed about almost all of them. They have a lot of the common traits you’d expect — they work hard; they surround themselves with good people; they’re highly skilled; you get the idea. But there’s something else:

Almost every one I’ve met has asked excellent questions.

I think anyone can come up with an answer to life’s weirdest questions. But it takes a different kind of person to ask a good question. To ask a good question, you have to be curious, and you have to be genuinely invested in asking that question. (Anyone can tell when they’re being asked a question by someone who doesn’t really care about the answer.) I find that people who ask good questions tend to be detail-oriented.

To put it simply: A person who asks great questions is someone who actually wants to understand how and why the world works, instead of just taking it all at face value.

And I don’t just see it in the journalism world! Open up a biography about Warren Buffett or Sam Walton and you’ll find countless stories of men who were constantly asking questions, always probing beyond the surface for answers. (Walton’s biography, in particular, is full of stories about him going to Wal-Marts with his tape recorder in hand, spending hours asking his employees questions about the way they really worked.) Doctors, artists, bankers, coaches — I’ve met all sorts who know how to dig for answers.

I think it’s everyone could get better at — myself included! I think we’d find that there’s a lot more to learn about the people in our lives, if only we’d learn to ask.

Want to get better at asking questions? I’d recommend this quick guide to asking questions by a former investigative reporter.

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That photo of someone searching for something — higher meaning, or probably just a bird in the woods — comes via Unsplash and photographer Caleb George.