When We Can't Let Go, And When We Feel Guilty

This is Josh's box.

It it packed as full as possible with 2 things: his scouting memories and his mission memories.  Plus his graduation cap on top.  Sunday I made him go through cardboard box's and put stuff into this bin so we can put it outside instead of letting it sit in our closet.  This tub is only holding 1 1/2 small cardboard boxes, and the lid won't even snap on.  This box has everything he can't let go of.  When i saw this a part of me wanted to get angry and tell him that I fit all of my stuff into a 1/4 of a bin (maybe I was jealous?).  In my anger I thought I haven't seen most of this stuff before in my life, so I wanted to go through it myself - I'm glad I restrained myself.  The other part of me was happy that his teenage years and early 20's were filled with good memories that he can't let go of.  But our lives are transforming, and if we don't get rid of it, someday our kids will be throwing it out.  So while most things will stay in this box, here is what will be reused, recycled, and lastly thrown away.

Reused:
- he has probably 200-300 letters he received on his mission sitting in their envelopes.  The envelopes and the unimportant letters will be reused and eventually I will use them to make paper :)
- some stuff in here can easily be donated, ie. random church training books, some scouting handbooks
- if he wants to ever get rid of his graduation cap i can pull it apart and use it in so many ways

Recycled:
- some of the letters and paper have writing all over them and I can't use the back for anything

Thrown away:
- the stamps from the letters
- the plastic covers and plastic rings from his schedules
- everything else must be sentimental so it won't be thrown away

What to do with the rest?:
- the letters he keeps from those 200-300 will go into a binder
- hopefully the important, memorable days in his schedules can be put in a binder as well

 Basically with the letters, schedules, random papers, and donated items that tub can be cut in half!  I was excited by the feeling at first, but now I'm left with this nagging feeling that I'm trying to take away something that he shouldn't have to let go of.  Should I feel that by simplifying our lives I am doing something wrong?  The answer is no.  That being said, they are his memories, I can make suggestions of things to keep but they aren't mine.  If he gets rid of just enough to close the bin I'll be happy.  Luckily he's agreed on the aforementioned changes.  Plus he still has the 3/4 of my bin to use up.