Which one of the following sentences of the same meaning are more natural to a native speaker's ear?
My poverty is a result of my failing to assert myself.
My poverty is a result of me failing to assert myself.
Which one of the following sentences of the same meaning are more natural to a native speaker's ear?
My poverty is a result of my failing to assert myself.
My poverty is a result of me failing to assert myself.
In my mind it depends on how I interpret it.
My poverty / is a result of / my failing to assert myself.
In this case, my is a possessive adjective, modifying "failing".
or
My poverty / is a result of me / failing to assert myself.
where me is an objective pronoun, part of the prepositional phrase "to me".
It makes no difference in meaning whether you use the possessive pronoun (my) or the object pronoun (me) in the sentence presented. The use of the possessive pronoun is considered more appropriate in formal English.
Frankly speaking, as a non-native speaker, I would like to use "my failure", as commented by Catija, to avoid any confusion.
My poverty is the result of my failure to assert myself.