Anaconda does not parse conda command

Question

It turns out that my Anaconda-Navigator isn't working right so as my Anaconda installation is slightly out of date (4.2.0) I figured I'd start troubleshooting by updating. However, any conda Terminal command (I'm on Mac (Monterey)) gives a massive error, such as:

$ conda list conda
Traceback (most recent call last):
  File "~/anaconda/bin/conda", line 4, in <module>
    import conda.cli
  File "~/anaconda/lib/python2.7/site-packages/conda/cli/__init__.py", line 8, in <module>
    from .main import main  # NOQA
  File "~/anaconda/lib/python2.7/site-packages/conda/cli/main.py", line 46, in <module>
    from ..base.context import context
  File "~/anaconda/lib/python2.7/site-packages/conda/base/context.py", line 13, in <module>
    from .constants import DEFAULT_CHANNELS, DEFAULT_CHANNEL_ALIAS, ROOT_ENV_NAME, SEARCH_PATH, conda
  File "~/anaconda/lib/python2.7/site-packages/conda/base/constants.py", line 15, in <module>
    from conda._vendor.auxlib.collection import frozendict
  File "~/anaconda/lib/python2.7/site-packages/conda/_vendor/auxlib/collection.py", line 6, in <module>
    from .compat import text_type
  File "~/anaconda/lib/python2.7/site-packages/conda/_vendor/auxlib/compat.py", line 11, in <module>
    from ._vendor.five import with_metaclass, WhateverIO as StringIO  # NOQA
  File "~/anaconda/lib/python2.7/site-packages/conda/_vendor/auxlib/_vendor/five.py", line 80, in <module>
    absolute_to_nanoseconds = CoreServices.AbsoluteToNanoseconds
  File "~/anaconda/lib/python2.7/ctypes/__init__.py", line 375, in __getattr__
    func = self.__getitem__(name)
  File "~/anaconda/lib/python2.7/ctypes/__init__.py", line 380, in __getitem__
    func = self._FuncPtr((name_or_ordinal, self))
AttributeError: dlsym(RTLD_DEFAULT, AbsoluteToNanoseconds): symbol not found

The only way I could even assess my Anaconda version (as $ conda -V throws something similar) was via

$ python -V
Python 2.7.12 :: Anaconda 4.2.0 (x86_64)

Weirdly, I also get

$ python3 -V
Python 3.7.3

[no Anaconda reference] despite the fact that Anaconda is definitely doing something for Python 2, and Anaconda 4.2.0 comes with Python 3.

Any help with sorting through this would be wonderful.