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Life’s Headwinds and Tailwinds

This past weekend I went for a run. The wind was gusting, and during the first half of my run I headed straight into it. It was blowing so hard that each step was difficult. The headwind was all I could think about!

And then I finally reached my turnaround point. As I planted my foot and turned, the strong wind that had been so difficult to run into suddenly gave me a boost. I remember how great it felt for the first block or so to be propelled, instead of impeded, by its force. Again, the wind was all I could think about as I began the second half of my run.

And then after the first block I forgot about it. For most of the run back I was oblivious to the tailwind pushing me along. While at first the tailwind provided great relief, after a minute or two it just felt normal.

I wasn’t conscious of this headwind/tailwind experience at the time. It was only later in the day, when I popped in my earbuds while taking the dog for a walk, that a coincidence occurred that inspired me to explore this issue further. I downloaded and listened to a recent episode of Freakonomics Radio (one of my favorite podcasts), in which the discussion focused on a “Headwinds/Tailwinds Asymmetry” research paper written by Professors Tom Gilovich and Shari Davidai.

The paper, and the episode, both began by explaining the headwinds/tailwinds asymmetrical phenomenon that runners and bicyclists experience, and that I had noted in my subconscious earlier that day while out for a jog. They used this phenomenon as a gateway to try to answer a broader, more interesting question: Why does life feel so hard sometimes?

The professors explained that their research found that most of us feel that we face more obstacles in life than everyone else. This leads to feelings of resentment. We also tend to undervalue the advantages and circumstances that help us. This leads to unhappiness and ungratefulness.

An example of the former is that many people believe that their parents were tougher on them than they were on their siblings. An example of the latter is that we discount the role of luck or happenstance when good things come our way, and instead attribute our success solely to our own hard work.

We also have a tendency to overlook the impact of factors in our lives that the paper’s authors call the “invisibles,” such as our opportunities for education and advancements in health and technology. They cite a great bit by comedian Louis CK called “Everything is amazing and no one cares” to further illustrate this point:

“I was on an airplane and there was internet, high-speed internet on the airplane. That’s the newest thing that I know exists. And I’m sitting on the plane and they go, ‘Open up your laptop, you can go on the internet.’ And it’s fast and I’m watching YouTube clips. I’m on an airplane. Then it breaks down and they apologize. The internet’s not working. The guy next to me goes, ‘This is bullshi*t.’ Like, how quickly the world owes him something he knew existed only ten seconds ago.

The big problem with this type of asymmetrical thinking is that it leads us to take things for granted, and not be nearly as grateful as we ought to be. This matters because an attitude of gratitude leads to all sorts of benefits beyond a present positive state of mind. Numerous studies have shown that feeling more grateful about one’s circumstances leads to a multitude of benefits, including more happiness, more friends, better health, and career success, to name a few.

This leads to another question: If gratitude is so good for us, why aren’t we chasing it more often?

The authors suspect that it has to do with what psychologists call the “availability bias,” which suggests that people tend to overweight experiences that are readily available in our memories. And because life’s obstacles, or headwinds, require attention in order to overcome them, they stay top of mind. The things that boost us along – like the wind at our back on a run – don’t require as much attention. Hence, we don’t feel as grateful as we should because problems crowd out the positives.

Gratitude Must be Cultivated

I think the big takeaway from all of this is that, like most good things in life, gratitude doesn’t come easy. Feelings of gratitude are not instinctual or automatic, they must be cultivated. {tweet that}

So how does one cultivate feelings of gratitude? Well, I’m certainly no expert in the matter, but I’ve played around with a few techniques that seem to work – if you stick with them, that is, which I haven’t! But, nonetheless, they work for others who have made them part of a daily habit.

Here are three ideas to get more gratitude in your life:

Gratitude Journaling: There’s nothing like sitting down with pen and paper to focus the mind. And if the point of your writing is to record all of the good things happening in your life, it’s hard not to walk away from the exercise feeling more grateful. Multiple studies have shown that a five-minute-a-day gratitude journaling habit can increase long-term well-being by more than 10 percent. That’s the same amount of impact that is gained by doubling your income. Sounds like a good investment!

Building a Stoic Mindset: Stoicism is a 2,000 year old philosophy pioneered by the Greeks and popularized by the Romans. At the root of Stoic philosophy is a mindset that recognizes that while you can’t control the circumstances around you, you can control how you react to them. In this way, Stoicism helps keep you from fixating on life’s headwinds, and frees up mental bandwidth to be grateful for the tailwinds that give you a boost. Want to learn more about Stoicism? Check out Tim Ferriss’ Four Hour Workweek podcast (he’s a big Stoicism advocate), as well as Ryan Holiday’s excellent book, The Obstacle is the Way.

Meditation: When you’re caught in a cycle of despair about a negative life circumstance, one of the best ways to step out of it is by consciously calling to mind all that is positive in the situation that is causing you frustration. Cultivating gratitude about the good things in life requires similar mindfulness. A daily meditation practice is a great way to focus the mind and give thanks for who you are, for where you are, for what you have, for your success, and for the success of your friends and loved ones.

I’m grateful for the opportunity to share these thoughts with you. It has definitely taken longer than five minutes, but writing this post was a great exercise in cultivating gratitude about the positive things in my life. It also made me remember an old Irish blessing that my parents had hanging on the wall in my childhood home, which starts: “May the road rise up to meet you, May the wind be always at your back….” Here’s to fewer headwinds, and more tailwinds, in all of our lives.

What are some ways that you cultivate gratitude in your life? We’d love to hear your ideas.


  • Tom Nixon

    I was once given advice, about starting a business. A business coach advised me to notice “when the headwinds become tailwinds, you’ll be on your way to a successful outcome.” I think that’s true, whether starting a business, a new hobby, or a new relationship. Eventually, those headwinds will become tailwinds. Be sure to look for it, then pat yourself on the back for having gotten that far. That’s the turning point.

    • Heather Harrington

      So true! I love this – thanks so much for sharing Tom!