We’ve all heard the old adage, “the two happiest days in a boat owner’s life are the day he buys it and the day he sells it.” Sounds straightforward enough, but there’s another side to “selling day” that you may not have thought about.

The old saw implies that by selling your boat you escape the expenses that go with ownership. No more slip fees, winter storage fees, maintenance and upgrading costs, insurance costs, not to mention the time you invest in prepping your boat for another season. If financial concerns are your sole motivation for selling, then the day you sell your boat would indeed be a happy one. But I’m guessing they’re not. I’m guessing that guilt, and the avoidance of it, is a bigger reason.

When we buy our sailboats, many of us justify the sizeable purchase by convincing ourselves that we’ll be spending every free moment aboard. Many of us spend hours comparing the cost of boat ownership with weekends at the beach or a cabin in the mountains or country club memberships for the next decade and decide that by spending every in-season weekend, holiday and vacation day on the boat, we’ll be getting a bargain.

When we make those computations we fully intend for the boat to occupy our every leisure moment, but intentions don’t always become realities. Little League baseball games, Sunday visits with the in-laws, charity golf tournaments with the boss, that early season Ravens-Steelers game, etc., have a tendency to weave their way into the fabric of our everyday lives. It’s not that we love sailing any less. It’s just that life presents so many demands on our “free” time.

So the end result is that many of us start to feel guilty. “We’re not using the boat as much as we should,” we think. “It’s just sitting there in the slip on this beautiful weekend. We should be out there sailing!” Sadly, for many of us, our boat becomes a source of anxiety rather than the source of joy it once was.

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Even though the annual costs may be easily manageable, we start thinking that our reduced usage doesn’t justify the cost, so we do one of two things. We either consider selling the boat that we love, or we make up our minds to use it more often, regardless of whatever else might be happening in our lives. Either way, we’re trying to rid ourselves of that gnawing feeling in our gut everytime we spend a sunny, breezy weekend ashore.

That said, though, who determines how often we should be using our boats? Our sailing friends? Our banker? Our neighbors? Nowhere is it written that to justify boat ownership, we have to be aboard every weekend. These are self-imposed standards, and as our lives change, so should our expectations.

The question comes down to quality versus quantity. Is sailing your boat still fun? Do you still love the feel of the tiller or wheel in your hand as she moves to windward? Would you miss that feeling? If so, then it doesn’t matter whether you’re sailing every single or every fourth weekend. In fact, many of those who force themselves to go down to their boats every weekend out of guilt and obligation, might enjoy them more if they skipped a weekend once in a while.

It’s naive to assume that our boats should be our sole source of recreation. We all have other interests, and boat ownership shouldn’t keep us from enjoying those too. Allowing that to happen can only end in resentment and resentment often leads to “the saddest day in a boat owner’s life.” Stop feeling guilty. Enjoy your sailboat as frequently—or infrequently—as you choose.