I was just thinking of how comfy and broken in my hiking boots were. I turned them upside down to discover that the tread was worn down in several places nearly to the substructure. I guess I broke them in too well. This is terrible! The last thing you want to do is set out on a long trek with brand new boots. Your boots will take a lot of abuse and are the very foundation that you will be walking on.
This brings up the lesson that you should do a complete equipment check a month or 2 before departure. If some items are worn out, broken or missing you still have time to make wise decisions about what to purchase, and order it if necessary. Check to see if the mouthpiece and the water bladder are in good shape in your hydration system. Can you imagine starting a trek with a leaky hydration system that gets everything in your pack damp, wets your pants for you, and does not quench your thirst to boot? Think about any pack straps or buckles that rubbed you wrong and do something to correct the situation. Make sure your camera and phone batteries will take a charge, and if they will not buy new ones. Re waterproof your pack, boots and jacket. Well, you get the idea: I am talking about a very thorough equipment check.
When I realized the poor condition of my boots I immediately walked the 2 miles to REI and selected new ones. Of course the model I loved was no longer available, so I had to choose a different style and brand. I walked in those for a week and realized they were not quite right, so it was back to REI. I finally got a pair that I hope will be great. I have adequate time to field test them and break them in before I leave for Spain. Of course this means wearing them 24-7, and my husband does not like that very much in bed at night. It is my turn to disturb his sleeping for once!