Even as a child, I was pretty indifferent to stuff (A 9th grade essay wanted us to write about our most prized possession and I couldn't come up with anything except my computer). But I think the final break for me happened when inadequate backup procedures caused me to lose several years worth of digital photos.

I was initially heartbroken but then I started thinking how many times I had actually looked at any of those photos since I took them and, for the majority of then, the answer was zero. After that, my relationship with stuff shifted radically.

A few years later, I lost a wooden spoon which was pretty much the only thing I held an emotional attachment to anymore. That thing was older than I was and had been the one constant in cooking which is a huge part of my life. I moped for a year, shrugged and got a new one.

I'm starting to seriously consider that, once a year, I will find the thing currently most precious to me and get rid of it.