The one thing that might make you more comfortable carrying the weight would be to change from a messenger-type bag to a backpack. In my case, I made that change for my (heavy!) laptop and IT-service bag, and it helped me substantially.
I asked my mom which was more inconspicuous, a backpack or a messenger bag. Despite living in a college town, we don't reside in that particular area. According to my mom, a messenger bag is the more subtle option for our area. I plan to continue reducing the weight of my shoulder bag wherever possible.
Jeanette Isabelle