I think there's a few different elements to ceasing to work with having something to replace the time with and finances as part of it. I think also, for singles, it can be a social thing as well. We're all different and have different needs and situations.
For me, I'll have so much to do (so much I'm unable to get to at the moment) and I think I'll be fine. That's not to say I'll never go back to work, I may, but it'll be different I think due to not having to be there. For now I work though and it certainly feels a little different now I'm set on an end date, life seems to have opened up a lot. It's a difficult thing to describe.
With regret, I think it's good to see it, feel it, as long as it's put into perspective which is what I try to do. Holding onto it though, well that only causes the event/situation to have a hold still. Just my opinion.