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Picking the Destination Of the two of us, Will is definitely the aggressive planner. At any given moment, he can tell you the locations and dates of the next ten to fifteen hiking trips we have planned, as well as the major international trips we’ll take for the next four years. In a way, he feels the same about planning trips as George R. R. Martin feels about writing—the good ones end up being epics, but he enjoys the state of having completed the task much more than the act of doing it. (As for Heather? She prefers surviving the day.) But Will continues on with his type-A planning personality because it is the sole act that has taken us on hundreds of hiking trips. And even though we’re nearly halfway through our lifetimes and our bodies are nearly half dead, we intend to head out on hundreds more. If you are a first-timer, planning a trip into the wilderness can be intimidating. For clarity, you will make mistakes and you will do something like pack the wrong gear. (We can talk later about that time Will brought three extra-large sweatshirts and four gallons of water on his first backpacking trip, or that one adventure when Heather thought canned soup was the best way to cut her backpack size.) Bottom line: The biggest mistake you can make is not to go. We are not advocating for lack of preparedness, but we are strongly endorsing the 40/70 Rule: You need at least 40 percent of the available information to make a decision, and once you get beyond 70 percent you should lean on intuition to fill in the gaps rather than postpone actually doing something (mad thanks to Colin Powell for that life advice). Start by simply focusing on your destination selection. Decide on one of the types of trips outlined below, do a reasonable amount of research on your destination, find a friend and/or unsuspecting significant other to join you, and then set the date to sleep on some dirt. If you really want to emotionally overcommit, make it Facebook official and tell everyone else who is scrolling their phone in some corporate meeting that you are GOING CAMPING. Nothing says commitment like declaring intent on social media. We like to break hiking trips out into three categories: day hikes, overnights, and dispersed camping. The distinction among the three drive the destinations we are interested in as well as our gear loadout. Ergo, depending on how much time you have and how many times you want to cry because of your heavy pack weight, you may lean toward one particular style more than another. Of course, many blur the lines among the three. For example, most civilized humans treat Colorado’s iconic Four Pass Loop as a four-day backpacking trip, but there are absurdly ambitious individuals who hike/run the twenty-eight miles in a single day under the auspices of “fun.” You do you.DAY HIKES This could be a low-key hike to a backcountry hot spring, or it could be a twenty-mile Jake-and-Elwood Mission from God. The punch line is that it is a hike you complete in a day, which means that finding a destination with a particular highlight will likely make the day more interesting. For our family, this usually means peak-bagging a Colorado fourteener (a summit with an elevation of at least 14,000 feet), although we’ve also made a day of tracking down champion trees in the Eastern Sierra, secret waterfalls in Montana, and the perfect whale-watching outcropping on the Channel Islands. The real perk here is the lightweight backpack. Unfettered by the trappings of overnight accommodations, your pack weight may be only around ten pounds, making it much easier to cover unholy distances or scramble up a talus field. Or you can be a real mensch and secretly stash a six-pack of summit beers. Even if you don’t imbibe, you will be an instant legend when you deliver a life-changing libation after a grueling high-altitude climb. Whatever you carry, don’t be a rube and skimp on the Ten Essentials (which we reveal) because you want to save a few ounces. Even if you don’t end up needing the gear, you could save someone else’s tail on the trail. A further word on safety: Anecdotally, day hikers are the most likely to get stuck in an unintentionally undesirable situation. When you’re backpacking, you have your entire world on your shoulders, and in most circumstances, you can safely pitch a tent if the weather takes a nasty turn. With a lightweight daypack, you are either going to have to construct a shelter out of the flimsy shell jacket and granola bar from the bottom of your pack, or optimistically hope Les Stroud is sharing your trail today.