Yes, you need one.
Why? Um, well, because you love your shoes, obviously.
Okay, maybe that's not the obvious answer so allow me to explain. A good shoe guy (aka cobbler), is not as easy to find as you might think. Most of them, I've found, don't really even know how exactly a shoe is made and therefore are hard pressed to know how to fix them. And, at worse, will simply tell you to buy a new pair - as if replacing a beloved pair of shoes is simply about having another pair of shoes!
However, if you look hard enough, you can still find a genuine cobbler. One who not only takes your love of that favourite pair of shoes seriously, but who understands the art of a beautiful and well designed shoe. This my friend is a hard find, and when you find one, know that it is one of the last original, genuine few.
They will tell you honestly when it is time to replace your shoe, but only after looking at the shoe, touching it, inspecting it. But before that, they will be able to skillfully replace the sole, fix broken heels (not just replace the heel tip - please! I can do that myself!). Furthermore, they will also tell you ways you can make them last longer and give you advice on any modifications based on the way you walk and the list goes on. In short, a real cobbler will help you extend the life and love of your shoes.
This is not a task to be trusted to the first place you come across with the words "shoe repair" thrown into some part of their service description.
In my personal experience, the older the person the better... and if you find someone who has an "apprentice", even better. You know he's taking this seriously.
If you're in the GTA and would like a reference to such a rare creature, just let me know :)