I actually removed almost every blog post I had written until last May and saved them as word docs on a USB stick. All my other blog posts that are still on there I have other versions of, so it’s not painful. It was more the techy side I was attached to because I had opt in pages, lightboxes and sales pages that were useful templates to easily create new ones. And I am not someone who is happy to spend days building the techy parts of a business — I would rather be creating and networking.
However, I have lost the manuscript of a short book I wrote a couple of years ago when my hard drive failed, which was a big lesson. Again, fortunately, I wasn’t that attached to it, since I think it was probably pretty shit, but just had the desire to prove to myself that I could write a book, and had it in my mind that I would turn it into a kindle book when I had time to take the next steps. So yes, I can completely understand why you would have so many backups.