Honestly, I'm a real proponent of keeping a clean digital life. I practice 0 inbox, aggressively delete old documents, photos on a regular basis. If I haven't touched anything in a few years, the chances that I'm going to need it later on down the line are slim and so off they go.

Important documents like tax info etc, are obviously kept for the minimum legal period but then again they don't take up all that much space.

I've been doing this for around 10 years now and so far I have not had any problems with missing old stuff, _touchwood_.

Long story short, just delete stuff you don't need altogether, makes backups a breeze and frees you from worrying about hackers exposing your musings from when you were a teenager :)