Let’s say your dimwitted former room-mate, who owes you $500, calls and says, “Dude, I’m at the airport, how do I get to your house?” You give him simple instructions, like “go west on I-90” and “turn left on Main”. He parks himself on your couch, inhales 6 slices of your pizza, naps, and then asks to borrow $100. You hem and haw but oblige and he leaves.

Simple is what simple gets.

Sailing isn’t simple. Done well, it might be among the most complex pastimes we might select. True, almost anyone can learn to tail a winch, raise a mainsail, or tie a figure-8. But in concert with others over long periods of time, sailing takes more than basic instruction. It takes an environment.

I sail with teachers. My wife (who manages the pit), our headsail trimmer, and one of our bow crew are all teachers.

Teachers make great sailing mates, partly because they have summers off. More importantly, they understand how people learn. We often apply best classroom practices to sailing as a team, so that every member can learn and achieve. We have pre-sail goal-setting chats. We swap roles routinely. We challenge newcomers to learn one new skill and then another. We ask natural leaders to step up, share, and then let go. And we debrief afterwards to answer questions and share new ideas. Then we build on the experience the next time. We do these things whether racing, gunkholing or just bombing around. I’m sure you do many of the same things, and you may do much more.

The point is that it is possible to offer an ideal environment for developing confidence, building skills and then mastering sailing’s complexities, but it requires more than rote steps. Most important is the creation of real free space in which all can learn and solve problems both collaboratively and independently, with optional guidance and support when needed.

I like to describe it as mentor-led immersion; like learning a language by moving to the country of origin, but having someone who speaks your tongue available in a pinch. It takes work to make and keep something like this going, but it’s worth it for everyone.

I’ve written extensively about why we shouldn’t try to “sell” sailing as simple or easy, because it’s not. Research shows that sailing schools or clubs that promise “easy” often run into trouble keeping their students for more than a few sessions. So-called “keep-it-simple-stupid” super-structured curricula fall short on four dimensions:

1. It’s the same thing, over and over.
2. It doesn’t provide a compelling vision to engage for the long haul.
3. After a while, it isn’t interesting to the instructors.
4. It doesn’t provide the free space where trial and error and creativity matter most.

As a rule, sailing is dynamic; every moment potentially different from the previous or the next. It’s an exercise in free-form adaptability, best guesses and finesse informed by past experience and better judgement. But alas, sailing has been organized in an attempt to try to make it easy. We’ve positioned it against other easy things like video games and bingo, and in doing so, we’ve made it disposable, and even boring.

Many sailing programs have gone wildly overboard in terms of structure. Youth sailing is often about repetition and routine, since the only long range vision is an olympic berth where lottery probabilities apply. For adults, a sailing class is often a shrouded pitch to “get you into your own boat”, so it’s more about simple gear and just-enough instruction. Talented sailing instructors are often stuck teaching the same thing year after year after year on the same boats, with the same sails and at the same time every day. And very few people are sailing for the sake of sailing. How often, for example, have you seen sailing school boats on the water in the middle of the night?

It’s time to break every one of these paradigms. Step one is to just go sailing and take your friends. Step two: consider volunteering to create new, innovative offers at your club or center that celebrate the complexity of sailing. Here are some great new ideas brewing around the country.

• Toddler sailing: Put parents and kids from 2-5 in boats together.
• Night passages: Share the magic of sailing all night long.
• Destination racing: Instead of racing around plastic buoys – race to places, and include shoreside skills as a race element.
• Rebuild to own or share: Donated boats refitted by teen/parent teams become the boats of the refitters or part of a shared fleet.
• Different boat every day: dinghies to keelboats to multihulls to sportboats all in one program.

Think these ideas might be impossible? Can’t insure them? Can’t convince the board? Can’t find the volunteers? Not the way you’ve always done it? Not sanctioned? Sure, change is hard, and that’s the point. Sailing is hard too, but it’s within reach and it’s always worth it.

Let’s say your room-mate calls again. This time, you’re ready. You give him a choice: he can work off his debt by mowing, weeding and painting for a month, or you will see him in court.

The right thing to do is often the hard thing to do.