It is about getting out there AND being safe. In a lot of backpacking environments, so-so gear is just fine. However in some environments, like winter backpacking, you better be sure that old stuff works! Just as important, are your skills. Often, you are better off updating your skills, instead of your gear. For example, there is nothing more humbling and informative than camping out in your backyard in a raging storm! You may find that the beloved old tent leaks after several in the downpour. And all of us could get a lot out of an orinteeriing class or how to use our trekking poles most efficiently (REI offers lots of free classes). You are never too experienced to learn more or practice a skill.