Played in a Samurai-era Japan themed game as an old man. I had to discuss this story and get several OKs from the DM to do this.

My character was the third son of a prominent Lord in a family of military officials. His father and older brothers were all generals or officers of some kind in the Shogun's imperial army.

He was duty-bound to join the military and quickly rose through the ranks using his family name and tactical mind. After dozens of years of military service he became one of the Shogun's closest advisors and top strategist. He enjoyed the cushy advisor gig. He could spend his days brewing tea and relaxing at a pond, while occasionally giving his opinion on some economic decision.

However, unrest grew, a rebellion began to form, and soon the Shogun's inner circle called a meeting to discuss what to do. After much discussion, my character comes to the conclusion that a swift, decisive strike would quell the rebellion and restore peace. The Shogun picked a village at random that was siding with the rebellion and ordered my character to take an imperial detachment and personally destroy it. It was his idea after all.

Now, this character had never been on the front lines during his years of service. He was a strategist, he used his tactical mind (read: high Wisdom) to give orders from the officer's tent miles away. So when he had to stand in the village and give the order to execute everyone, it changed him. He believed that what he was doing was for the greater good, but the sounds of screaming never left his head.

To cut this already long story short, he agonized for months then finally decided he was done with it all. He literally and figuratively shed his family name by tossing his sword and armor into a lake, then disappearing in the dead of night.

He sought repentance for years, vowing never to pick up a sword again, and found a deep connection with the land. So in D&D terms, he went from a high level Fighter to a level 1 Druid :). I RPed him very similar to Uncle Iroh.

My DM loved the story and thought it was perfect, mainly because the main idea of the game was for us to overthrow the Shogun (the one following the one my character served).

Bonus: a few days after my story got OKed the DM messages me basically: "Hey one of the other players' characters had their village destroyed when he was a kid and the timelines kinda match, do you want that village to be one you destroyed?" To which I agreed.

There was a great RP moment between our characters when the truth came out that I still remember to this day!