
When I wrote about the willingness to try new things being a cruising skill — and one you could practice in the years or months leading up to untying the dock lines, my friend Pamela Douglas Webster added a wonderful comment about an associated skill. I loved it and we talked back and forth some. Finally, I asked if she’d be willing to elaborate in a post because her thoughts were just so perfect for all of us who are a little fearful of trying something new in case, you know, we aren’t wonderful at it.
You can follow her blog about life with her golden retriever Honey (and husband Mike) at Something Wagging This Way Comes.
Not enough people who write advice for wannabe cruisers highlight the need to be willing to try new things. Because when you move onto a boat, nearly everything will be new to you.
Even Carolyn’s post on the topic didn’t quite get to the heart of the issue. Not only do you have to be willing to try new things, you have to be willing to stink at them while you improve your skills. And until you get better, stinking will result in near misses, boat damage, and bruises.
But the pain of scratching your hull or breaking a toe is nothing compared to the emotional pain that accompanies the discomfort some people feel when doing stuff badly.
Being a Bad Sailor
I got a lot of practice being a bad sailor when I started lessons at the community sailing program in my mid-40s.

Although I could describe the Bernoulli effect and how it caused a sailboat to move forward, to this day, I still don’t understand it in a concrete way. After the hundredth time pushing the tiller the wrong way from where I wanted to go, my only source of hope that I would ever improve came from something my first instructor told me: “Don’t get discouraged. I find that people who take the longest to figure things out are usually really good sailors once the information clicks.”
That encouragement kept me going with sailing until it did click. And when each new skill found its place in my muscle memory, sailing felt more natural.
From the start, my husband was a much better sailor than me.
His superior grasp of physics and geometry made him a stronger boater than me from the very beginning. But my husband lacked one emotional skill that made cruising a special challenge for him while to me, it felt natural.
What Makes An Unhappy Cruiser
My husband has the blessing (or perhaps, curse) of doing many things very well—much better than the average person. But with few serious struggles, he’s never learned to deal with doing things badly.
On land, if Mike found something hard, he’d avoid it. Why make yourself miserable stinking at something you don’t have to do? And besides, it’s easy to pay other people to do things for you that you do poorly or don’t enjoy.
But cruising, you don’t have that luxury.

Even in our far-from-remote cruising grounds of the Atlantic Intracoastal Waterway and the Chesapeake Bay, we have to rely on ourselves to fix a finicky outboard or deal with a furling jib that gets hung up at just the wrong time. And when solutions didn’t come easily, my husband experienced a lot of frustration.
Our boat served as the setting for a creative range of curses, the likes of which have probably never been heard over such relatively minor issues.

What Makes A Happy Cruiser
In contrast, I came to cruising expecting it to be hard and knowing I would stink at it. I assumed that most things would start out hard and that over time, I would get better at them.
After all, I started out stinking at just getting the boat to move under sail. But every time I docked without an engine or trimmed the sails so the telltales fluttered perfectly, I felt a sense of accomplishment.
I expected the same growth curve for cruising too.
And because I didn’t dissolve into a puddle of self-hatred every time I bumped a dock or failed to bring a mud-covered anchor up solo the first time I tried, I felt free to notice things I actually was doing well.
I feel a great sense of accomplishment at hand-steering a straight compass course in a rough Georgia sound or suggesting the solution that quickly helped us unwrap the anchor rode from our keel in a confused anchorage.

Expecting to be bad at cruising skills and not letting it defeat you gives you emotional room to notice and feel a sense of pride when your skills improve.
And when the next new skill comes along (because cruising is a never-ending skills test), I tell myself, “You’re going to stink at this. Do it anyway.”
The Most Important Cruising Skill
If you ask my husband, you’ll find that I’m not always a Zen master of calm when things go badly. Luckily, he loves me enough to follow my cruising dream, despite his discomfort with the learning curve and my less-than-perfectness.
And I’ve been privileged to watch his growth in the essential skill of feeling comfortable with doing stuff badly.
In fact, I don’t think any skill is more important for cruisers than the ability to feel relatively comfortable doing things badly—at least until your skills and knowledge base improves.

It’s a skill that you need no matter how many years you cruise. Because every cruiser will continually face challenges to their skills. This is something we recently learned when an 18-year, single-handing cruiser with experience on two oceans let the current catch him by surprise and ended up wrapping our anchor rode around his propeller trying to regain control.
Since we moved on board in September 2015, we’ve learned more about weather, currents, anchoring, navigation, diesel engines, electrical systems etc. than we could have ever imagined.
But I don’t think any skill has been more important in cruising than being willing to stink at new things without it making you want to give up.


RickG says
Thanks for the great post. Good attitude check.
Cheers, RickG
Anonymous says
Merran Sierakowski
Anonymous says
Such a timely and profound article! I’m a newbie and it takes me a lot longer to learn (most) things than my husband. However, I feel I get such a greater sense of accomplishment when I finally “get it” than he does. I’m learning to be more patient with myself, and get over the fact that I’m going to make stupid mistakes and will inevitably look stupid in front of others.
Anonymous says
I think that is everyone’s biggest fear. It is mine. I keep trying to remember as I’m failing that everyone else has had equally embarrassing moments.
The Boat Galley says
Hang with it. You really will get it. Most of my articles stem from things I did badly at first. There is always learning, and being comfortable with it is hard.
Anonymous says
The Boat Galley, your articles are such a huge help! Thank you so much! 🙏🏻
Jodi Stone says
I’m glad you stuck with it, and are following your bliss.
For me, I learn by doing. I can watch and read all I want, but until I ‘get my hands dirty’ it’s lost on me. Sometimes it takes me a while, but when I get it, I get it.
Thanks for sharing and reminding me of this valuable lesson.
Pamela says
Many of us will learn better once we dig into it. But if we’re afraid to start because we don’t want to look silly (or dirty), we’re going to miss out on a lot.
Glad to know I’m not the only slow learner who “gets it” only after something clicks.
GROOVY GOLDENDOODLES says
What a story!!! Well written as always. Pam has such a captivating way with words.
Carolyn Shearlock says
Yes, I love her honesty.
Anonymous says
When I was learning to play hockey at age 39, I was awful. As I got better, and newbies joined us, I realized one of their jobs was to be so bad that I could realize and appreciate how much better I was getting. It’s a tough job, but someone’s gotta do it. As we move aboard our 46’ cruiser, I’m going to help a lot of you realize just how far you’ve come!
Pamela says
He he–maybe the other job we have as newbies is to encourage new people. THey’ll say, “Heck, if they can do it, so can I!”
BTW, really impressed at taking hockey up as an adult. That ice is a hard practice area.
The Boat Galley says
Oh, I love that!
Irma says
Thank you for the excellent article. We are newbies and sure have raised a few eyebrows docking our boat in the marina. But oh well , we live and learn and before long we hopefully “get it”. This article serves as a good reminder not to get discouraged; we all had to start somewhere. Thank you!
Pamela Robertson says
Thank you for lots of interesting and encouraging articles. So enjoy reading the newsletters.
Cheers
Cathy Berry says
Thank you for this. My husband has sailed since he was around 11, lived aboard for a time, raced, etc. I got on my first sailboat at 60! I was prepared for not knowing, but the sheer scope of not knowing was amazing. Fortunately, I do not get sea sick and felt completely safe and at home on the water, despite the fact that I had no idea of how to handle the boat! I’m slowly learning and understanding that it is a process. We are not live aboards but have been out in the ocean for a few days and done intercoastal travel.
Alicia says
Thank you for an amazing, insightful, encouraging article! I have now moved onto my 36’ Mariner Ketch, with my partner, and we are in the planning stages (and learning to sail for me!) for our departure of September heading south from Havre de Grace, MD, in the Chesapeake Bay down to Florida, then around Bimini and the Bahamas, and the rest we’re still looking at and reading about thanks to your adventures and advice.
Love all you do and write about at tbg…!!! Thanks!!
Peter Grimes says
Wow 😮 If only I had read this article before our sail yesterday, this may have gone a little sweeter. I am guilty of getting frustrated when the windlass I had recently “fixed” decided to go down but not up! Thanks for a much needed reminder that it is ok to suck at stuff until you no longer do 😎⛵️