Document "the Any trick"

CONTRIBUTING.md

@@ -570,6 +570,61 @@ It's a "to do" item and should be replaced if possible. `Any` is used when
 it's not possible to accurately type an item using the current type system.
 It should be used sparingly.
 
+### "The `Any` trick"
+
+Consider the following (simplified) signature of `re.Match[str].group`:
+
+```python
+class Match:
+    def group(self, __group: str | int) -> str | Any: ...
+```
+
+The `str | Any` seems unnecessary and weird at first.
+Because `Any` includes all strings, you would expect `str | Any` to be
+equivalent to `Any`, but it is not. To understand the difference,
+let's look at what happens when type-checking this simplified example:
+
+Suppose you have a legacy system that for historical reasons has two kinds
+of user IDs. Old IDs look like `"legacy_userid_123"` and new IDs look like
+`"456_username"`. The function below is supposed to extract the name
+`"USERNAME"` from a new ID, and return `None` if you give it a legacy ID.
+
+```python
+import re
+
+def parse_name_from_new_id(user_id: str) -> str | None:
+    match = re.fullmatch(r"\d+_(.*)", user_id)
+    if match is None:
+        return None
+    name_group = match.group(1)
+    return name_group.uper()  # This line is a typo (`uper` --> `upper`)
+```
+
+The `.group()` method returns `None` when the given group was not a part of the match.
+For example, with a regex like `r"\d+_(.*)|legacy_userid_\d+"`, we would get a match whose `.group(1)` is `None` for the user ID `"legacy_userid_7"`.
+But here the regex is written so that the group always exists, and `match.group(1)` cannot return `None`.
+Match groups are almost always used in this way.
+
+Let's now consider typeshed's `-> str | Any` annotation of the `.group()` method:
+
+* `-> Any` would mean "please do not complain" to type checkers.
+  If `name_group` has type `Any`, you will get no error for this.
+* `-> str` would mean "will always be a `str`", which is wrong, and would
+  cause type checkers to emit errors for code like `if name_group is None`.
+* `-> str | None` means "you must check for None", which is correct but can get
+  annoying for some common patterns. Checks like `assert name_group is not None`
+  would need to be added into various places only to satisfy type checkers,
+  even when it is impossible to actually get a `None` value
+  (type checkers aren't smart enough to know this).
+* `-> str | Any` means "must be prepared to handle a `str`". You will get an
+  error for `name_group.uper`, because it is not valid when `name_group` is a
+  `str`. But type checkers are happy with `if name_group is None` checks,
+  because we're saying it can also be something else than an `str`.
+
+In typeshed we unofficially call returning `Foo | Any` "the Any trick".
+We tend to use it whenever something can be `None`,
+but requiring users to check for `None` would be more painful than helpful.
+
 ## Submitting Changes
 
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