I have a love/hate relationship with upgrading. I love the new things it enables me to do/experience but I hate the actual process of doing it. Upgrading computers is expensive and largely a hassle. When I get a new phone it makes me download all of my apps again, sign in again, etc. All of the things are out of date so quickly it sometimes seems worth it at all. It is a question of sustainability on multiple levels. Ecological and financial sustainability are the two major areas of concern, but I think psychological/neurological concerns are also valid. The unceasing newness is enough to drive people mad.
Our technology does not grow, yet. It is introduced to us in installments. In theory our computers were conceived of as evolutionary devices which were able to be upgraded piece by piece as new and better things came along. You can upgrade the RAM or hard drive in your laptop or other components in a desktop computer but that requires intervention that is not always possible.
There are many emerging technologies that are beginning to address this question of synthetic growth. Self healing materials and self assembly are going to start showing up in a phone (very) near you. The programs that run on your device may start to grow too through the use of self-modifying code which will be unique to the user. It could also extend the lifetime of our devices if we have self repairing batteries and screens (or just do away with screens as we know them altogether as Google Glass would like to see happen)
Of course there will always be new generations of technology. Just as all the the other plants and animals of our planet are born, they also die. In the meantime though, they grow and learn and change along with their user to enhance and augment their life in a hyper-individualized way.