Wise Thinking #5: Headwinds vs Tailwinds and a Bear

Thanks, Pixabay!


Imagine you’re on a bicycle in Colorado. The day is perfect. You bought a new bottle with the filter inside so you can refill it in a cold mountain stream. Your backpack is a party with a zipper, carrying a bite of lunch, your awesome new camera, rain gear and sunscreen. You pass someone with no backpack and give yourself a thumbs-up. You Super Scout, you! Your legs feel strong, and you pedal harder just because you can.

You’re grateful for the time off work. Your boss was impressed with your vacation plans, but you discounted it by saying, “Well, I haven’t trained as hard as I could have.”

That’s called self-handicapping. Before we try something, we come up with reasons we might fail. It’s an attempt to save face just in case. If we succeed, we feel doubly good.  It’s a comfort move you should lose. To your boss—an Achiever—self-handicapping is like going on stage with a pacifier.


Created with Pixabay and Enlight



“What’s Hamlet saying?”

For a better impression, say, “Thank you! I’m excited.” Confidence is attractive.

As you pedal, thoughts of work buzz at the rhythm of your strokes.  It’s strange to have a boss who’s brand new to the company. You’ve been there for years, and this lady just strolls in with her resume and lands the job you wanted. Some people can charm their way into anything.

Whoo, this uphill thing is tough. You hear water around the bend and push work out of your mind. Immediately, you notice the cool breeze on your sweaty skin. Birds call from one tree to another and the calls telegraph up and down the mountain. You stretch a little, and the packless cyclist pedals by. He waves cheerfully, and suddenly your pack weighs 50 pounds. You set it down and fill your bottle in the stream. As you drink, you think of the cheery, packless cyclist. “That guy probably works out every day. Some of us don’t have that kind of time.” You think about lightening your pack. The sun is out—if you leave your rain gear behind that bush, it’s not exactly littering. You’re just leaving something behind for someone who might need it.

You only think about it. You’re not actually a litterbug.

You hoist your pack and get back on the bike. Three miles to the top. You told people you might not make it. You could quit. Self-handicapping makes quitting easier. You’re not a quitter, though. Even if you don’t win, you go all the way. That’s the kind of person you are.

What kind of person are you? Adventurous. Prepared. A Finisher.

James Clear says, “Each action you take is a vote for the type of person that you believe that you are.” Vote with your feet!

The last half mile is a doozy, but you rock it. When you reach the peak, you celebrate with a little lunch. Squirrels like Fritos®, so you share a little. King of the World, that’s you.  The real king comes out of the woods and you freeze. You’ve seen minivans smaller than that bear. You hoist your pack and jump on your bike. It’s a downhill ride—your legs needed a break. Sunset is coming—you needed to get back. These things don’t cheer a mind filled with black fur and claws.

We naturally give more attention to our challenges, or “headwinds,” than the ways in which we’re being helped. When you’re escaping the bear who wants to share, you’re unlikely to give thanks for the downhill slope and boost in speed. They just don’t feel important.

This is called The Headwinds/ Tailwinds Asymmetry. We focus on the task at hand, so we can overcome it. Unchecked, it can become a joy-blocker.  It’s rare to be chased by a bear, but daily life brings us plenty of challenges, right? When headwinds fill our heads, we don’t appreciate the tailwinds. We’re happier when we take note of events and people that make life easier. Our future gets brighter as well. How is that possible?

You work hard, so when someone else sits in the boss’s chair, you assume she was lucky. What if, instead of being resentful, you make her job easier and she teaches you things she’s learned from previous positions? You’ll become more marketable and enjoy work more.

You came to the mountain prepared, so when someone whizzes by you, you identify all the ways you have it tough. Shai Davidai and Tom Gilovich, who researched the Headwinds/Tailwinds Asymmetry found that nearly everyone assumes they have it harder than other people. In nearly every sibling pair they interviewed, each claimed to have had the tougher childhood. Do you know the other cyclist’s story? Would you have been happier unprepared? Think of resentment as an off-switch to gratitude. When the light is off, it’s easier to trip. People who feel things are unjust are more likely to justify making moral compromises. That explains the rationalization around lightening your pack. Thank goodness you didn’t do that.

Ask questions. Learn the stories of those who seem to have things easy. Try the Gratitude 365 app and instead of reading rants, give yourself a lift. Challenge yourself to give thanks each day for:

  1. Someone who helped you,
  2. Something that inspired you or made you smile, and
  3. Something you accomplished.

What not to do? Don’t tell someone, “You have so much to be grateful for!” It’s totally true. God sprinkles every day with delights, but people bristle when we accuse them of ingratitude. Just model it, and they’ll be asking you why you’re so happy.


If you’re enjoying this series, please share it with your friends. If you’ve missed any of the posts in the series, check them out here:

Wise Thinking #1 – Peanuts to Shortcuts

Wise Thinking #2 – Your Thermostat

Wise Thinking #3 – The Availability Goldmine

Wise Thinking #4 – Overcome Hindsight Bias with Gratitude

You might also enjoy Freakonomics, where host Steven Dubner asks some fascinating experts why people do what we do.

Michael Bridges
Michael Bridges

11 Responses

  1. Hey there!
    I love this. Your mom sent it along. I am her Etsy friend.
    Thank you for the insight.
    Joey (johanna)

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