Your Pocket Sailing Instructor Podcast27 Apr

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

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 topics

Building sailing confidence
Practicing skills in controlled environments
Handling crew overboard and emergency situations

Head 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

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Episoder(106)

Episode 8 Your First Trip as Skipper NEW SERIES: From Passenger to Confident Skipper!

You've learned to handle the boat, make decisions, communicate with your crew and deal with things when they go sideways. Now comes the exciting part. It's time to stop preparing to be the skipper and...

2 Nov 34min

Episode 7 The Skipper Mindset Shift NEW SERIES: From Passenger to Confident Skipper!

There comes a point in almost every sailor's journey when you realize something interesting: you probably already know more than you think you do!You can steer the boat. You understand the sails. You ...

12 Okt 26min

Episode 6 When Things Go Sideways: Staying Calm Under Pressure NEW SERIES: From Passenger to Confident Skipper!

Every sailor eventually has one of those moments.The docking approach isn't working. The wind suddenly picks up. The engine won't start when you need it. A crew member becomes sick. Something breaks. ...

29 Sep 29min

Episode 5 Anchoring: Stop dragging for good NEW SERIES: From Passenger to Confident Skipper!

This episode we talk about anchoring! What, how, when, where... all the ins and outs of making sure the boat stays put, so you can have a great sleep. Chapters00:00 Understanding Different Types of An...

8 Jun 38min

Episode 4 Docking Without the Drama (Even in Tight Marinas) NEW SERIES: From Passenger to Confident Skipper!

Episode 4 of my new series From Passenger to Confident Skipper is all about docking! What equipment you need, how to practice and prepare for all scenarios, what to do with your crew, and more. Learn ...

19 Mai 25min

Episode 3 The key decisions every skipper must get right NEW SERIES: From Passenger to Confident Skipper!

One of the biggest shifts in sailing happens when you move from simply operating the boat to making the decisions that keep everyone safe and confident on the water. In this episode of Your Pocket Sai...

11 Mai 22min

Episode 1 You've taken a course... now what? NEW SERIES: From Passenger to Confident Skipper!

I am staring an 8-episode series called "From Passenger to Confident Skipper". Each episode will focus on a different aspect of your voyage to becoming the most competent skipper you can be!This episo...

20 Apr 24min