I struggle with this to the extreme, not just with technology but with anything — I’ve held onto paper work years after the projects have ended, clothing that I MAY fit into again one day, etc.
One thing this article really made me think of is — my phone and laptop carry a lot of my work as most peoples’ do today, but they also hold a bunch of useless things — games or photos that no longer matter to me, incomplete work I thought was great but the moment has passed and I’ll never finish it.
But yet, I don’t delete. I don’t know why but recently my computer had to be wiped because of a virus and it was one of the most freeing things to happen to me. (I hope that doesn’t sound silly!) I also try to reset my phone to factory settings when I feel it gets far too cluttered, it’s a GREAT way to weed through all of your apps for example and see what was / is really important to you.