It often pays to be a contrarian. It can be as simple as going around the amusement park clockwise so you spend half the morning entirely free of the crowds. Buying winter gear as late in the season as possible means you get less of a selection but you also get a huge discount.

Having a basic supply of what you need means you can avoid the rush and risk of being caught in an oncoming blizzard. There is a certain smug satisfaction sipping hot cocoa and watching people rush off through the storm to get vital supplies.

On the other hand you want to be reasonable. Wearing nothing but Speedos during a blizzard, or arctic parka in summer, is foolish. Being arbitrarily contrary doesn't mean you are right or wise. Conventional wisdom and timing works pretty well for most people most of the time.