Do you find it hard to get reconnected after you haven't played in a while?

One of my favourite things is to come across backups of my old games. I love to incorporate old sims in my new stories. I don't often continue on with an old game though. But I'd consider a game old if I hadn't played it since 2009 or 2010 or maybe 2011. Anything started after that would probably be continued. Such as my Big Game - that is something I went looking for and finally found on an old DVD I'd burned as a backup. It is central to most of my videos I currently do.