Your Pocket Sailing Instructor Podcast

Penny Caldwell

Hey sailor! My name is Penny and I have been a sailing coach with Sail Canada for over 25 years! I have helped thousands of sailors find their passion and love of all things sailing. I'm here to help you live your best sailing life. I provide gear reviews, sailing tips, habits to perfect and much more! So, sit back and enjoy some informative, entertaining, unique sailing content! See you on the water ;-) Don't miss an episode! https://wavve.link/_QdonK50x/episodes

About PodLP

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Your Pocket Sailing Instructor Podcast

Episodes (100)

Yesterday SERIES: From Passenger to Confident Skipper - Episode 2 Why you still don’t feel confident sailing
Mon Apr 20th SERIES: From Passenger to Confident Skipper - Episode 1 You've taken a course... now what?
Mon Apr 6th #86 SailTies: Turning Every Voyage Into a Story

Your Pocket Sailing Instructor Podcast

Apr 27, 2026
25 minutes
23 MB

In Episode 2 of our series From Passenger to Confident Skipper, we dig into a frustrating but incredibly common feeling: you’ve spent time on the water, maybe even taken courses, yet that sense of true confidence still hasn’t clicked. Why? This episode breaks down the hidden gaps between knowledge and real-world decision-making, and why simply “getting more experience” isn’t always enough. We explore the subtle factors that hold sailors back—like over-reliance on others, lack of deliberate practice, and not fully understanding the “why” behind key skills. You’ll hear relatable scenarios that many developing sailors face, from...

Your Pocket Sailing Instructor Podcast

SERIES: From Passenger to Confident Skipper - Episode 2 Why you still don’t feel confident sailing

Penny Caldwell

00:00 -24:43