I, personally, have no plans to sell my bitcoin and get back into fiat. I will, however, at some point, feel "financially independent" and may scale back on my work. At that point, I might need to convert some of my stack to fiat only to pay for things that won't accept bitcoin.
I'm not using bitcoin as a way to have big buckets of fiat. But, I am using it as a nest egg that I would tap into at some point. I'll work as long as I can, but I also am working more than I'd like currently so at some point I would scale back but would like to have a similar lifestyle.
I'm hoping that by the time I do have to tap into my bitcoin that more places will accept it and then I won't have to "sell" the bitcoin at all. Maybe at that point I'll move down to El Salvador, or something.