For myself, as a mainframe programmer I'm always on the CLI.
In micros (I was part of the POS project that bought the first PC sold
out the IBM product center in my city) I stuck with DOS until Win3.0, at
that point I saw functionality that had previously only been available
on SPARC stations start to become a reality on the PC and became a
(reluctant) believer.
At this point I really don't care too much, the fact that Windows (tm)
is a bloated mess, likely impossible for any single human to understand,
_it works_, it gives me what I want at the moment and I'm more than
willing to throw hardware at it as long as the hardware is cheap since
the alternative is to wait (possibly for a long time) to get the same
capabilities in properly optimized code.