Episode 2 Why you still don’t feel confident sailing NEW SERIES: From Passenger to Confident Skipper!  episode artwork

EPISODE · Apr 27, 2026 · 24 MIN

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

from Your Pocket Sailing Instructor Podcast · host Penny Caldwell

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 second-guessing decisions at the helm to feeling uneasy in changing conditions. If you’ve ever wondered why confidence seems to come easily to others but not to you, this episode will help reframe that thinking.Most importantly, we talk about how to move forward. You’ll learn practical ways to take ownership on the boat, build trust in your decisions, and turn passive experience into active learning. Confidence isn’t something you wait for—it’s something you build, intentionally, one skill and one decision at a time. key topicsBuilding sailing confidencePracticing skills in controlled environmentsHandling crew overboard and emergency situationsHead over to sailnelson.com to download your free Episode 1 download!⁠ A cheat sheet of all the different things you can practice, and when, after your first course. Connect with Penny:- ⁠⁠⁠⁠Support Penny on Patreon! ⁠⁠⁠⁠- ⁠⁠⁠⁠Learn more about Penny's sailing school!⁠⁠⁠⁠- ⁠⁠⁠⁠Get in touch!⁠⁠⁠⁠- ⁠⁠⁠⁠Take a course! ⁠⁠⁠⁠- ⁠⁠⁠⁠Penny's sailor resume⁠⁠⁠⁠-⁠⁠⁠⁠ Instagram⁠

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 second-guessing decisions at the helm to feeling uneasy in changing conditions. If you’ve ever wondered why confidence seems to come easily to others but not to you, this episode will help reframe that thinking.Most importantly, we talk about how to move forward. You’ll learn practical ways to take ownership on the boat, build trust in your decisions, and turn passive experience into active learning. Confidence isn’t something you wait for—it’s something you build, intentionally, one skill and one decision at a time. key topicsBuilding sailing confidencePracticing skills in controlled environmentsHandling crew overboard and emergency situationsHead over to sailnelson.com to download your free Episode 1 download!⁠ A cheat sheet of all the different things you can practice, and when, after your first course. Connect with Penny:- ⁠⁠⁠⁠Support Penny on Patreon! ⁠⁠⁠⁠- ⁠⁠⁠⁠Learn more about Penny's sailing school!⁠⁠⁠⁠- ⁠⁠⁠⁠Get in touch!⁠⁠⁠⁠- ⁠⁠⁠⁠Take a course! ⁠⁠⁠⁠- ⁠⁠⁠⁠Penny's sailor resume⁠⁠⁠⁠-⁠⁠⁠⁠ Instagram⁠

NOW PLAYING

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

0:00 24:43

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

Eat to Live Jenna Fuhrman, Dr. Fuhrman Our health is our most precious gift and smart nutrition can change your life. Each month, join Dr. Fuhrman and his daughter, Jenna Fuhrman as they discuss important topics in the world of nutrition. Eat to Live will change the way you eat and think about food. French Your Way Jessica: Native French teacher founder of French Your Way Boost your French listening skills and test your comprehension with this one of a kind series of podcasts. Get the chance to listen to a real conversation between native speakers talking at normal speed AND customise your learning experience through carefully designed sets of questions (2 levels of difficulty) available for download at www.frenchvoicespodcast.com. All interviews also come with the transcript. French teacher Jessica interviews native speakers of French from around the world who share a bit of their life and passion. Where else would you meet in one same place a French yoga teacher based in Melbourne, a soap manufacturer from Provence, or a couple cycling around the world? That Hoarder: Overcome Compulsive Hoarding That Hoarder Hoarding disorder is stigmatised and people who hoard feel vast amounts of shame. This podcast began life as an audio diary, an anonymous outlet for somebody with this weird condition. That Hoarder speaks about her experiences living with compulsive hoarding, she interviews therapists, academics, researchers, children of hoarders, professional organisers and influencers, and she shares insight and tips for others with the problem. Listened to by people who hoard as well as those who love them and those who work with them, Overcome Compulsive Hoarding with That Hoarder aims to shatter the stigma, share the truth and speak openly and honestly to improve lives. The Small Business Startup School – Business Notes | Financial Literacy | Retail Psychology – For Professionals & Entrepreneurs The Small Business Startup School Inc. Starting or buying a small business? While personal circumstances may vary, business patterns remain timeless. On The Small Business Startup School, we explore strategies, insights, and practical solutions to help entrepreneurs confidently navigate their journey.Hosted by Ola Williams—a retail entrepreneur, fintech founder, and financial coach with over two decades of experience—this podcast marries financial awareness and retail psychology with optimism to deliver actionable takeaways.Join us to learn, grow, and connect as we uncover the keys to business success.Let’s continue to learn together and be encouraged to keep on connecting!

Frequently Asked Questions

How long is this episode of Your Pocket Sailing Instructor Podcast?

This episode is 24 minutes long.

When was this Your Pocket Sailing Instructor Podcast episode published?

This episode was published on April 27, 2026.

What is this episode about?

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...

Can I download this Your Pocket Sailing Instructor Podcast episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!