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The single most important way of ensuring a safe and enjoyable trip is by taking the time to properly plan that trip. The most important part of any trip is the time we spend planning before we leave. If we choose to skimp on the planning process we're almost certain guaranteed that our group will receive a healthy dose of adversity and discomfort, and we will possibly be putting our lives and the lives of others in danger.
Stories of groups who arrived at the put-in point at the beginning of their trip only to discover missing food, tents, paddles (yes, even canoes!) are not uncommon. Even sadder are the tales of the groups who put in a hard day of paddling before realizing their omissions.
These stories may sound amusing, but they involve experiences which are at best inconvenient and at worst dangerous. Having to drive back two or three hours from your put-in is a major pain. It means that we're going to have a grumpy group of paddlers waiting for us when we get back five or six ours later. We are going to be running half a day behind schedule. We probably won't get to our planned campsite that night, or if we do it will be by paddling long and hard in the afternoon. Setting up tents in the dark is not the best way to spend the first evening of our canoe trip.
Worse than that scenario is that there is sometimes a temptation to look at the long backtrack for forgotten gear, and say "forget it." The temptation to get the canoes into the water and get going may mean that we abandon good sense and decide to leave without the third tent and say "we'll squeeze in together", or to ignore the fact that that last food pack is missing by saying "we'll stretch the menu by catching fish." These scenarios have the makings of a nightmare trip.
These errors are not the exclusive domain of the novice paddler, either. The old cliché that "familiarity breeds contempt" has been the undoing of many an experienced tripper. Experience can make us lazy. We know that all of the gear is in a pile in the basement from our last trip, so we don't have to check it against a list. We just throw it in the truck and get going. We think that we don't need a detailed menu or grocery list - we have a "pretty good idea" of what to bring.
Careful planning and written check lists are important whether you are leaving on your first trip or your fiftieth. If you are not the organized type, or you aren't confident about your ability to plan the trip down to the very last detail, ask for help or delegate.