Those of you who quit their jobs and went bike touring indefinitely, any regrets?

I am contemplating doing this in the not-too-distant future, and it's been in my head for a while. Up until now, the longest tour I have done has been around 3 weeks. While that was great, I have always semi-fantasized doing an extended, multi-country bike tour (whether in Europe, South America, or Africa - or all of the above). Unfortunately, this would mean giving up a permanent position, and the part of my brain that craves security (perhaps in all of us) does make me somewhat hesitant (even though I have been considering a change in environment for a while, and could potentially find a better job and another permanent position in the future).

For some more context, I'm in my early 40s and single with no kids - I felt vaguely sad writing that : ) - and while I'm not rich I have a decent amount of savings.

Would love to hear from others' experiences.

Edit: Thanks everyone for all of the messages! They've been quite motivating.