Decluttering my WorkSelf at Home

I am currently reading a (library) book called, "Throw Out Fifty Things" by Gail Blanke. It is an amazing little book. She spends a lot of time in the book talking about the emotional side of our physical belongings. For me, books and papers are an overwhelming source of clutter in my little 1 bedroom, 1 den apartment. Gail tell us that a lot of our "work paper clutter" is really about hanging on to outdated versions of our professional selves. Do I really need that award I got 20 years ago for volunteering with victims of crime? Does my serving it right certificate from 15 years ago actually still have any value?If I answer no to both of these questions, why is it that I have paid professional movers to bring these items along with me each time I move. At some point, this professional certification becomes meaningless clutter.
As I reflect on how my previous professional jobs, I realize that I am knowledge worker who has always invested in learning. I have books/papers/certificates that are not useful to me anymore but I can't seem to throw them out because somehow they have become part of my work identity. Gail's book describes that gnawing feeling I get when I consider throwing out this stuff, but she goes one step further to insist that the best of me (professionally) is yet to come and that much of this old work self actually drags me down. What do you think? Is it easier to throw out an old dress or pair of shoes than a professional certificate,even though none of these items has seen the light of day in years?