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The original was posted on /r/sailing by /u/lintonqwuesi on 2025-08-13 22:39:49+00:00.

Hi all, I’m just curious about when you all who are more seasoned than I started to feel more confident as a sailor. Namely, I’m thinking about when helming and heeling started to feel less overwhelming and more natural.

For context, I came to sailing rather recently, but I’ve spent a fair bit of time on boats in the past few years, learning during two weeks in the Med a bit after COVID and then getting a baptism about a year later during a week in the intense sea state of the Caribbean. This summer has been my first full season as part of a sailing club, going out and sharing skipper duties 2-3 times per week on 25’ boats, racing (as crew) usually an additional 1 or 2 days on 25’ or 40’ boats. Though I’m qualified as a skipper on paper, I never quite feel equipped to be so, preferring instead to double-check things with someone more experienced aboard. Things like excessive heeling and weather helm situations usually find me seeking to reduce genoa size and let out the main a bit to avoid finding myself more ‘out of control,’ despite how complex that concept of control sometimes seems on a sailboat. Perhaps that’s a safe mentality, but it often feels more of an abundance of caution than explicitly safety.

Though I’ve experienced enough to understand proper danger while on boats—accidental jibes on downwind stretches in significant swell, heeling well beyond what is reasonable, overpowering, battling through intense seasickness, thunderous squalls—I have a hard time generating the game-time confidence in my abilities and my knowledge when it comes to being the skipper myself. My instinct is telling me to get some experience on a dinghy so that I can understand the limit a little better on a full keelboat (experiencing capsizing, for example), but in this post I’m also looking for what helped it all come together for you.

I love sailing and shall continue in my journey to conquer the various waterways I can, but I don’t exactly feel entirely mentally equipped to be the one to do it. Or at least, despite my knowledge of what is going on while on a boat and how to be good crew, I have a hard time being the main guy in charge of it. Thanks everyone for any responses!