When things go wrong! My 5-step organized approach

Why do we need an approach?

Life is full of ups and downs. Curve balls coming our way constantly. However, you can’t let them shut you down! You need to keep moving forward and pushing along. So I have a 5-step approach that helps me keep things moving in the right direction. I find that on the boat I need to come up with an organized approach to tackling boat projects. Otherwise I get overwhelmed and wonder I how I got myself into this mess!

Step 1: List


The first thing I do when I’m overwhelmed or have hit a wall with a project, is write a list! Get everything out of your brain so you can organize it. At this point I am not censoring anything. I am just writing it all down so I can get it on paper.

Step 2: Organize

Once I have my list, I start to create an organized approach to how I want to tackle things. Hopefully there are several categories that I can put projects into an tackle a couple of things off my list at once. I call it chunking… there’s probably an actual term for it, but you get the idea. The idea here is to see if there are like things that I can work on at the same time.

Step 3: Prioritize

Once I’ve established my list and organized my items into categories, I prioritize what needs to be done. For boat projects this will often be dictated by what I need for a project. In other words, does the boat need to come out of the water? Do I need power tools or specialized equipment? This may change when, where and how I get this items off my list!

Step 4: Scenarios

Once I’ve figured out what I want to work on, I start thinking about all the different scenarios of how to fix the thing, or even all the different ways that the project might not go according to plan! This may seem like a doomsday kind of thing to do, but I find that it helps me create an organized approach to tackling my boat projects if I’ve tried to think ahead.

Step 5: Adapt

Finally, I execute the project and adapt as I go! Part of the adaptation is thinking about alternative scenarios and outcomes and knowing how I would tackle them. I find that if I can prep myself enough, then I am in a better position to successfully finish a project!

Happy planning!

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About Penny Caldwell

Penny Caldwell is a Canadian sailing educator, Sail Canada Instructor Evaluator, marine consultant, and host of the Your Pocket Sailing Instructor podcast. With nearly three decades of teaching experience, she is passionate about helping sailors of all skill levels build confidence, develop practical seamanship skills, and enjoy a lifetime on the water. Through her articles, podcast, instructor development programs, consulting, and sailing adventures, Penny shares real-world knowledge that makes sailing safer, more enjoyable, and more accessible for everyone.


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Sailing is a lifelong learning journey, and some of the best ideas come from fellow sailors. Have a question about this topic, or a tip you’d like to share? Leave a comment below—I read every one and enjoy hearing about your experiences on the water!

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