Creating an if statement using var1 is None | var1 < var 2

I am trying to make what I thought would be a simple if statement. It goes as follows:

if (Main.longest_word is None) | (len(Main.longest_word) < len(word)):
            Main.longest_word = word

My issue is that I keep getting TypeError: object of type 'NoneType' has no len()

This makes sense to me, and I have solved the issue by simply turning my original if statement into two separate if statements.

My question is: Is there a way to make this if statement works as one, or am I forced to make two separate if statements in this situation.

Thanks for any advice.