diff --git a/README.md b/README.md
index e1e9dab..c56065f 100644
--- a/README.md
+++ b/README.md
@@ -10,7 +10,7 @@ pairing with smart people at Hashrocket.
 
 For a steady stream of TILs, [sign up for my newsletter](https://crafty-builder-6996.ck.page/e169c61186).
 
-_1509 TILs and counting..._
+_1510 TILs and counting..._
 
 ---
 
@@ -888,6 +888,7 @@ _1509 TILs and counting..._
 - [Access Instance Variables](python/access-instance-variables.md)
 - [Create A Dummy DataFrame In Pandas](python/create-a-dummy-dataframe-in-pandas.md)
 - [Dunder Methods](python/dunder-methods.md)
+- [Override The Boolean Context Of A Class](python/override-the-boolean-context-of-a-class.md)
 - [Store And Access Immutable Data In A Tuple](python/store-and-access-immutable-data-in-a-tuple.md)
 - [Test A Function With Pytest](python/test-a-function-with-pytest.md)
 - [Use pipx To Install End User Apps](python/use-pipx-to-install-end-user-apps.md)
diff --git a/python/override-the-boolean-context-of-a-class.md b/python/override-the-boolean-context-of-a-class.md
new file mode 100644
index 0000000..28b46ba
--- /dev/null
+++ b/python/override-the-boolean-context-of-a-class.md
@@ -0,0 +1,86 @@
+# Override The Boolean Context Of A Class
+
+Everything in Python has a truthiness that can be checked with `bool()`. An
+empty list (`[]`) is falsy. A non-empty list (`[1,2,3]`) is truthy. Similar
+with numbers:
+
+```python
+>>> bool(0)
+False
+>>> bool(1)
+True
+```
+
+Any instance of an object is going to be truthy by default. If you want to
+control in what context an instance is considered truthy or falsy, you can
+override
+[`__bool__()`](https://docs.python.org/3/reference/datamodel.html#object.__bool__).
+If that's not implemented, but
+[`__len__()`](https://docs.python.org/3/reference/datamodel.html#object.__len__)
+is, then it will fallback to that.
+
+Let's look at a few example classes:
+
+```python
+class CartZero:
+    def __init__(self, items=[]):
+        self.items = items or []
+
+class CartBool:
+    def __init__(self, items=[]):
+        self.items = items or []
+
+    def __bool__(self):
+        print("__bool__() override")
+        return bool(self.items)
+
+class CartLen:
+    def __init__(self, items=[]):
+        self.items = items or []
+
+    def __len__(self):
+        print("__len__() override")
+        return len(self.items)
+
+class CartBoolAndLen:
+    def __init__(self, items=[]):
+        self.items = items or []
+
+    def __len__(self):
+        print("__len__() override")
+        return len(self.items)
+
+    def __bool__(self):
+        print("__bool__() override")
+        return bool(self.items)
+
+cart1 = CartZero()
+cart2 = CartBool()
+cart3 = CartLen()
+cart4 = CartBoolAndLen()
+
+print("CartZero() -> %s" %(bool(cart1)))
+print('')
+print("CartBool() -> %s" %(bool(cart2)))
+print('')
+print("CartLen() -> %s" %(bool(cart3)))
+print('')
+print("CartBoolAndLen() -> %s" %(bool(cart4)))
+```
+
+An 'empty' `Cart` be default is truthy. However, we can override some
+combination of `__bool__()` or `__len__()` to give it a boolean context that
+goes `false` when "empty".
+
+```
+CartZero() -> True
+
+__bool__() override
+CartBool() -> False
+
+__len__() override
+CartLen() -> False
+
+__bool__() override
+CartBoolAndLen() -> False
+```