I'd feel fantastic and I'd probably start taking some out, or at least moving it to a stable coin to secure the gains,

That would be the time, right? :D The worry is, how much to sell, how much to keep - what if it goes to 20...

I am with you on the lottery. Unless it was an obscene amount, I would likely just keep doing what I do - investing it away.

In other words, the security of knowing I don't need to worry about money anymore would be beyond wonderful, but that wouldn't stop me from enjoying what I do now.

This.