Headwinds, Tailwinds, No Winds: In sailing and cycling, as in life

When we were on Guemes Island a few weeks ago, we watched a large sailboat come up from the south. Even without binoculars, I could see the sail straining as the wind filled it. The boat tilted slightly and then glided across the water. As it came around the tip of Samish Island, it stopped. The wind spilled from the sails. The boat sat upright. It simply stopped.

I have to confess my complete ignorance of sailing here as I predict many of you are going to be thinking, if not saying, “Duh” in a moment. The sum total of my experience sailing consists of a summer babysitting for a couple who competed in catamaran regattas. One time they took me out on Lake Lanier. It was beautiful. I was terrified. I never went out again.

Back to present times: I asked my husband, “So, what do they do now?”

He said, “They fire up the diesel or they sit there and wait.”

I should have known they would have an engine.

“If they sit and wait, won’t the tide push them into the shore?” I was now invested in their plight.

“That’s what anchors are for.” My husband was raised in a coastal town in Alaska and has much experience with watercraft. That being said, an anchor was an obvious response, and I should have guessed that after a millennia of water travel, sailors would have a way to avoid crashing into land.

Still my curiosity was not appeased, and I started making connections to cycling, also a thrilling sport but with the advantage of being done on land. And yes, I do hear the irony in my words in light of my recent broken wrist.

tail·wind   /ˈtālˌwind/ n.:  

a wind blowing in the direction of travel of a vehicle or aircraft; a wind blowing from behind.


I love a good tailwind. The feel of the wind propelling me forward, making me faster than I would ever be alone. It gives me a break without causing me to lose ground. I can feel even the slightest tailwind. It is exhilarating and hopeful. I don’t have to earn a tailwind, it just comes out of nowhere and pushes me forward.

That’s true in life as well. I have my tailwinds—the things and people that propel me forward. I don’t have to earn them or ask for them. They just appear. And some, I don’t even deserve or notice. My husband is a tailwind. No matter how hard or painful something I am facing is, he is right there telling me I can do it and helping me over the obstacles in my path. My daughter, sisters, and friends who cheer me on are all tailwinds. When I run out of steam, I can count on them.

There are other things that make my life easier even when challenges appear. Some of these tailwinds, I take for granted—education, financial resources, health insurance, access to technology, a car. Some are inherent qualities (bad and good)—persistence, stubbornness, pride. Others are a luck of the draw that I don’t notice most of the time—the color of my skin, speaking the prevalent language, living in safe conditions.

head·wind   /ˈhedˌwind/ n:

a wind blowing from directly in front, opposing forward motion.


I don’t love a good headwind. The feel of the wind in your face blowing you backward. Struggling to move forward. Losing ground and momentum. I want to stop but I know that it will be even harder to start again and I will be farther from my goal. If I do stop, I might end up back at the beginning. I may not love a headwind but I have discovered that they make me stronger. Peddling into the wind forces me to work harder and, though I may not go faster or farther right then, in the long run I will be faster and stronger for having done it.

As I sit here and reflect on my headwinds, I am struck by how small they now feel to me, though I know they were gale force winds at the time. That speaks to how our headwinds make us stronger and can become our tailwinds. We don’t become persistent without having to practice it. I had a back injury when I was in my early twenties. It happened the weekend before my first head coaching job was to begin. I was devastated. Because of the nature of the injury, the surgeon told me that I would not coach that particular sport again. He also challenged me to find another sport. Knowing my age and what lay ahead, he turned the fan on high. He pushed me to rehab my injury and find a way to live my dreams. I was angry that everything I had been working toward was wiped away by a defective gene. I had to fight hard to come back from that. I had a choice, one I am still living today, push through the headwind or give up. I am stronger for my choice. When I am hit with a new headwind, my first reaction is not to look for shelter but to confront it head on.

To say I have met every headwind alone would be wrong though. Tailwinds in my life have given me a boost. One time I accepted an offer to ride on Whidbey Island with a couple who were very accomplished cyclists. Though I had been on the island hundreds of times in my life, the sheer number of hills never registered because I was always in a car. Lacking the long legs, lithe body, and uncompromised spine of a typical cyclist, I was dying toward the end of the ride. I remember we were headed up one of the last hills and I was lagging behind. The husband was at the top and he turned around to head back down—a maneuver I would not have done even if it was the only way to avoid being eaten by a bear. I kept going. He past me on his way down. I thought, I am going to die of embarrassment if this guy goes up and down this hill until I get to the top. I peddled harder. And then I felt it. He came up next to me, put is hand on my lower back, took five strokes with me,  and then propelled me forward. Not far but enough that I could pick up my cadence and make it to the top. He was my tailwind. When I got to the top, he was cheering me on.

I believe we can be tailwinds or headwinds for others. We can make things easier, or we can make them harder. We can put our hand on their back and push them forward or we can wait for them impatiently. We can be an obstacle, or we can help them overcome one. We can recognize when someone is facing a unjust headwind and stand up for them.

dol·drums   /ˈdōldrəmz,ˈdäldrəmz/ n.:

a state or period of inactivity, stagnation, or depression.


I had to look up the nautical term for no wind. According to the online Oxford Languages Dictionary, the word is doldrum. I don’t like that word. It sounds like something Eeyore would say. Doldrums. There is a time for ‘no wind’ and it doesn’t have to be a time of sadness or depression, which is the feeling I get from that word. Anchored isn’t quite the right word either. I will use floating. There is a time for floating. Tailwinds are exhilarating, and headwinds are challenging. I don’t think I have to always be moving forward or fighting to get stronger. Sometimes, I need to float and just enjoy the ride—no speed and no struggle. Society and the media often send the message that we have to be productive and on the go all the time. We have to strive and reach. There is a time for those and there is a time to float. We can give that to each other too. Do we allow ourselves and the people we live and work with to find balance in their lives, to recharge and rejuvenate? Do we make room for recreation and relationships or do we demand accomplishment and action?

Take the opportunity to float when you can. Use your tailwinds to move you forward. Thank your headwinds for making you stronger. Remember you can be a tailwind or headwind for someone else.

Copyright Catherine Matthews 2022

7 thoughts on “Headwinds, Tailwinds, No Winds: In sailing and cycling, as in life

  1. What a great piece of writing! Love the metaphor of the helper tailwinds and the headwinds making you stronger. Look up “tacking”. That is where you maneuver the boat into the wind in such a way that you eventually make forward progress.

    Liked by 1 person

  2. I really enjoyed reading this. Your strength is beautiful. I’m taking some time to float along next week and leave productivity behind for a few days. So important!

    Liked by 2 people

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