Life has a recurring habit of lending us its lessons, "there's nothing new under the Sun"(Ecclesiastes 1:9). If you pack your raincoat at the bottom of your pack, when it rains, you and your kit will get wet! Your sleeping bag is not an urgent item during the day; pack it first, inside and at the bottom of your pack!
Mountain and trekking skills are important for safe and enjoyable wilderness passage. The greatest skill, for me, is preparation. Being prepared helps so much as we journey along any path in life. Be it a contortious trail or contentious trial. Extensive preparation becomes an intrinsic process of being ready. Good equipment helps, but mostly our mind needs to be ready, for set and go.
The Swiss army penknife is a classic analogy of preparation. If you research them, each part of them has several uses, it's not just a blade or a can opener! I'm not one for taking anything unnecessary on any journey. My rule of thumb is, if you don't need it every day, why take it? All you need is less; less is more.
Prepare for the worst, hope for the best, trust God for the victory.