Lessons From A Little Blue Sailboat

When I was 17 years old, I accepted an invitation to go out on a little blue sailboat with a boy I liked. And his grandpa.

I had never been on a sailboat before. I had no idea what it would be like. Even though I knew the grandpa, I was still intimidated to spend time with this male sailing duo. It seemed like a rather intimate “date.”

Our sailing day started at 6:00am when the boy came and picked me up and we drove the 5 miles to his grandpa’s house. His grandmother was making sandwiches and packing up drinks and snacks for us in the kitchen.

I learned that she never went sailing but she was happy to see her husband and grandson enjoy it so much. That moment was huge for me, having very limited grandparent time in my own life.

I was drinking in the whole scene as if I were watching an old movie. One in which I was lucky enough to get to play a part. You know, like those lifetime movies where the grandmother always has fresh cookies in the cookie jar. Except that was really happening.

Meanwhile, the boy and his grandpa were readying the sailboat on a trailer and attaching it to the van that would carry us and haul the boat to the lake. I watched all of this, amazed at how much went into the preparations. It seemed like so much work and super complicated.

When the boy invited me to go sailing, he told me that he and his grandfather did this regularly and that they raced other sailboats. Listening to the conversation on the way to the lake, I realized that they took this racing thing rather seriously. I had no idea how to prepare myself for that. What the heck did racing sailboats look like?

Thirty minutes after we left the grandparents’ house, we pulled up to the lake and I saw a pack of other small sailboats in various states of readiness. They were all so impressive, bright, shiny, and new-looking. I peered over at the little blue sailboat, paint cracked, wood varnish flaking off, and the letters that spelled the name “Vandal” peeling off of the back. I wondered why they would even consider coming to this expensive yacht club and racing all of these much newer and more impressive looking rigs.

It took longer than I thought to get everything rigged up and eventually slip the boat off the trailer into the cold lake water. As soon as the boy and his grandpa maneuvered us away from the dock and glided the boat out into the lake, they both seemed to change. It was like each of them took a deep breath of the same crisp, clear air and were transported to a different reality.

It was infectious.

A few pleasant breaths and suddenly they were on their game. They had only so much time to get everything set up so that they could get in the best position before the starting alarm rang out. They were angling this sail, tugging that line, shoring up that other line, and waiting, waiting, waiting.

Then words came at me like a firing squad, TACK, BOOM, COMING ABOUT, TIGHTEN THE JIB, GRAB THAT LINE, and other words and phrases that didn’t make sense — had no meaning to me, but were instantly critical!

All the peace and delicious quiet of 30 seconds ago was gone in an instant. Now we were racing!

Racing a sailboat was not like any other race experience I was familiar with. We spent hours out on that lake and we had time to look out at the gorgeous scenery around us, time to pause and eat the lunch that the grandmother had packed for us, and even time for the boy and his grandpa to regale me with tales from previous races.

But it was all so unpredictable. I could be getting a lesson on the difference between a main sail, a jib, and a spinnaker when mid sentence that foreign language would come blustering out of the grandpa again, COMING ABOUT, WATCH YOUR HEAD, PULL THE THING! In a split second, the little blue sailboat would be tipping over so far that I had to scramble to the opposite side just to counterbalance and hope that I didn’t slide into the chilly lake water. Cookies and sandwiches were forgotten in that flash of excitement and everything was focused on the immediate.

As quickly as everything went crazy, everything would go calm. It was the most incredible dichotomy I’d ever experienced.

I learned so much sailing that day. I had no idea that life would mirror such a similar path. What a huge lesson I was given. I’m still learning from it.

The wind can change on you in a second. You can’t predict it, though you can try. One thing I learned from watching the boy and his grandpa, was that if you waited to react to the wind, you were already behind. They had weird little tools and gadgets set up all over the boat with the chief purpose to help them see where the wind was coming from and what it was doing.

They weren’t even fancy tools. Nothing digital. There were strings and an old weather vane. It was not shiny or showy. Remember the peeling paint and flaking varnish?

Even so, the better prepared they were and the more they paid attention, the better these two could control the boat and the faster the boat moved through the water.

The boy and his grandpa didn’t know how to do any of that the first time they tried. After many funny stories were told of their first efforts, I was awed at their determination to figure it out. But they had to start somewhere and they weren’t put off by their imperfect vessel.

You can start with a little, unassuming, slightly run down boat and still win the race.

Yep, we WON THE RACE! All those shiny boats would glide by and congratulate us. It was obvious that they couldn’t figure out how that humble little vessel kept beating them.

As we loaded her back up on the trailer, that small, modest boat suddenly looked like a winner!

It’s really true that life is just like that. You can’t predict every little thing that will happen, but you can put things in place to help you deal with the wind, adjust yourself, and use it to your advantage.

If you don’t feel shiny and fancy, that’s ok. You can still win the race! You need to see the winner under the peeling paint and know that you are totally worth it. It starts with the tiny tweaks. And eventually you keep building on those until you are sailing right along instead of being battered about by the wind.

But you have to start somewhere. I’ve listened to many stories that people have shared with me and combined them with my own personal experiences to come up with a simple starting point. I would love to share this insight with you in my 5 Day Reset Challenge.

I once got an invitation to take a chance on a day spent sailing. That changed my perspective. I invite you to take a chance on 5 days making a few tiny tweaks with some simple tools.

If you’re interested, sign up here.  It’s free.  As in no cost.  Zero dollars.  All you have to do is decide you’re worth it.  Don’t hold yourself back.  This could be the beginning of a really cool adventure.

That was an unforgettable day out on the water. My first sailing experience was the start of something wonderful for me. A love affair with the water in a new way. I was so happy to be invited back out many more times.

I’ve learned much more than sailing terms on that boat, which I clearly needed to know. I learned that dragging my feet in the water is one of life’s greatest pleasures. I learned that racing a sailboat and trying to read a novel is quite tricky. And probably the biggest one is  that no matter what happens (the little engine runs out of gas, the wind stops blowing, the winds blow at gale force out of nowhere, we get stuck on a sandbar… yes, literally all of these things have happened to me!), that I really can adjust myself, my attitude, my behaviors, and totally win.

I eventually married that boy and we still sail on that little blue sailboat as often as we can.