Navigating Vermont Winters: A Sailboat Captain's Guide to Finding Joy in Hobbies. 

“So, what do you do in the winter???”

This is the most frequently asked question that I get as a sailboat charter captain in Vermont. Vermont is not the first state that you’d picture for a boat captain, but it makes me a pretty in-tune expert on living seasonally. Come October, temperatures drop, boats come out of the water, and we are forced to live for 6 months as landlubbers.

When we get this question on the boat each crew member has their own answer. Sailors wear many hats, so on our crew we have folks who are also teachers, yoga instructors, bartenders, accountants and artists. We’re used to adapting and fulfilling different roles.

But really, I think the core of this question is a different curiosity. It’s more about how we survive the long cold dark winters of northern Vermont — and to this we all have a very similar answer.

We say that the winters in Vermont are bearable as long as you have a good hobby.

This season in particular I’ve been thinking a lot about hobbies because mine are beginning to shift. As time goes by, we begin to have fun in different ways. I’m pretty comfortable in my opinion of fun at every age. I don’t subscribe to the idea that “I used to be so fun and now I’m old and boring”. As we grow and shift, we get to experience joy from new things, and that’s a pretty beautiful thing.

But sometimes, we get comfortable and set in our ways about the things we spend time with. It can be easy to continue doing certain things out of habit, instead of focusing on things that bring us true joy.

In this spirit I’m reminded of a quote that one of my college professors introduced me to - it’s attributed to Socrates: “The unexamined life is not worth living.”

Dramatic I know, but still - I urge you to take some time to examine your hobbies. Each season, as my boats come out of the water, I’m forced to re-evaluate how I spend my new abundance of time. Here are some basic things I consider when taking inventory of what to do for fun:

What are your current hobbies??

This one seems like it would be SUCH an obvious question, but when is the last time you really thought about it? What are your hobbies? Think about how much joy they bring you and if you spend enough time with them. Think about how long you’ve been doing them, and how your experience has shifted over time.

And it’s ok if you come to a sudden realization that you don’t really have any hobbies! That just makes these questions even more important. When I thought about this one this year, I realized that I spend a lot of my spare time working on my growing small business, which I’ve found is a great way to burn out.

What might you let go of?

This one can surprise you. Sometimes we do things out of habit, and it can be hard for us to realize that we don’t enjoy them as much as we used to. We don’t have to stop doing this hobby all together, but maybe we prioritize it less.

If you have a hobby that you really love but don’t feel you get to spend enough time with, think about if there are other things that just matter less now. Or maybe there’s something you do every weekend that you used to love, but now find yourself silently dreading. It’s ok to realize that your idea of fun is shifting!

What might you bring back?

When you say “I used to be so fun” - what exactly do you mean by that? There can be some real clues here. Perhaps there are activities you used to really love, but the busyness of life caught up to you, so you stopped prioritizing them. Maybe it was a sport or an outdoor activity you were super into. Or maybe you feel that you used to laugh with your friends more.

This intuition is important to listen to! Think about the activities that used to bring you so much joy and try to dip your foot back in.

What (or who) is catching your eye?

This part can be really fun. For this one I’d recommend making a list. List out all of the activities that have interested you. Things you’ve seen on social media, in the newspaper, or in your friend circles. The things that have intrigued you but you’ve “never had the time” to try. Make the list as long as possible; the idea is to really think about all the possibilities as if there were no limits on your time. Even if they’re unrealistic - they’ll be a hint into what kind of life you want to live.

Once you have your list, prioritize just the one or two that are really calling to you most. Find ways to fit them into your schedule. It can also be helpful to get folks in your life involved. Want to start hiking more? Invite a friend on your first hike! Want to try baking bread? See if your kids want to help!

Hobbies are such an important part of the world we live in. They bring us joy, help us with finding connections and give us a sense of fulfillment. Yet it can be so easy to deprioritize them. (But it can be so easy to put them on the back burner). Giving yourself time to examine what you do for fun and give yourself permission to change.

Hannah O’Brien

Hannah is a boat captain, artist and writer. She runs a block printing business which is currently based in Vermont. When she isn’t printing, you can find her sailing, swimming, reading or writing - depending on the season. Her perspective is shaped by her experience of living and working on the water, and she loves to spend time thinking deeply about human connection with each other and the planet.

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