Things I wish I knew before I stepped on Board
- Lowell Sheppard
- Sep 3, 2025
- 2 min read

Buying a boat is a bit like starting a business or launching a career—you never feel entirely ready. You prepare, you dream, you leap. And then the real learning begins.
After six years living aboard my sailboat Wahine, I’ve been thinking about what I wish I had practiced or studied before I bought her. Not the big, flashy stuff—these are the practical, day-one skills that would have reduced my anxiety and accelerated my learning curve.
So, here are my top six, in reverse order.
#6 – Electrical Systems
I knew just enough to swap a fuse, but boats run on complex systems. If you don’t understand them, little problems become big ones fast.
Life and Career Analogy: Don’t wait until the lights go out to learn your infrastructure.
#5 – Diesel Engines
Engines are reliable, but needy. They require care, attention, and confidence. I wasn’t naturally mechanical, and that cost me peace of mind early on.
Life and Career Analogy: Operations aren’t glamorous, but they keep everything moving. Respect them.
#4 – Collision Regulations
I studied the rules just enough to pass an exam, but not sufficient to feel fluent. Lights, buoys, right-of-way, they’re not optional knowledge when other vessels are nearby.
Life and Career Analogy: Know the rules of your industry, both written and unwritten.
#3 – The Language of Sailing
Sailing is its own dialect—terms for gear, weather, directions, repairs. I learned slowly, on the job, but I wish I’d built that vocabulary earlier.
Life and Career Analogy: Every field has its jargon. Learn to speak it fluently if you want to be taken seriously.
#2 – Weather Patterns
PredictWind and Windy are great, but apps can’t replace the ability to read the sky. Understanding clouds, tides, and currents from the start would have saved me a lot of worry.
Life and Career Analogy: Don’t just look at the data, learn to recognize the elemental signals before the storm hits.
#1 – Knots
If I could shout one piece of advice to my beginner sailor self: learn your knots. They’re simple, tactile, satisfying—and you need them the moment you step aboard. A bowline, a cleat hitch, and a few others. I had to ask a friend to remind me mid-job how to tie a bowline. It was humbling.
Life and Career Analogy: Fundamentals matter. The small, repeatable skills—done well—make everything else possible.
Final Thought
These six things aren’t glamorous, but they’re the foundations that make sailing safer, smoother, and more enjoyable. And here’s the good news: you don’t need to own a boat to practice them. You can start now.
Whether it’s sailing, business, or life, the principle is the same—master the basics, and the rest follows.



