A quiet Itachi Shinden flashback follows a younger Itachi through village politics, a stray-cat mission, and the friends he could not save, closing on his Sharingan awakening while infant Sasuke looks on.
Cradling his baby brother, Itachi drifts into memory. After the Nine-Tails devastated the village, the Konoha Council debates resettlement with the assembled clan heads, and both the Aburame and the Uchiha are moved to a new quarter. Villagers still greet Fugaku warmly along the streets, and Itachi tells his father he is proud to walk beside him. The two set out for dumplings only to find the shop cleaned out, then run into Izumi, who frets that she let his promotion pass without a gift. Beside a lake she presses her own dumplings on him until Tenma appears with orders.
Team 2 reports to Nekobaa, who sends them after one specific ninja cat. Tenma cares more than his squadmates, since the animal's whiskers are an ingredient for medicine to treat his ailing father. The cat claws Yūki and drops the rest of the group, but Itachi corners the creature and yanks Tenma clear when he lunges for the whiskers. Heading home, Shinko scolds Tenma for skipping his thanks and needles Itachi for hiding behind mission talk when the four of them are truly friends.

Naruto vs Luffy with the twist nobody asked for: Luffy tickled Hinata on date night, and she kind of liked it. We break down the whole fight and commit to a winner....

Naruto built the transformation jutsu himself, and the Hidden Leaf has been quietly not talking about it ever since. The story behind our 90s R&B record about the Naruko question everybody dodges....
The recollection darkens as Itachi remembers a masked assailant, revealed later as Obito, cutting Tenma down on a separate assignment. That grief stirs his Sharingan to life, and the infant Sasuke catches the red glint in his brother's eyes. Itachi quietly wonders whether the same power will one day surface in Sasuke.
The Pain of Living is an Itachi Shinden flashback episode following a young Itachi through village politics, a mission to catch a ninja cat, and the deaths of friends, ending with his Sharingan awakening as infant Sasuke watches.
Nekobaa sends Itachi's Team 2 to catch a specific ninja cat because its whiskers are needed as an ingredient for medicine to treat Tenma's ailing father.
Itachi's Sharingan awakens after he remembers a masked assailant, later revealed as Obito, killing his teammate Tenma on a mission, and the grief from that memory triggers the transformation while infant Sasuke looks on.
Izumi is a young Uchiha who regrets missing Itachi's promotion, so she shares her own dumplings with him beside a lake before Tenma interrupts with new orders.
The Pain of Living is episode 453 of Naruto: Shippuden, part of the Itachi Shinden Book: Light and Darkness arc. It aired in Japan on March 17, 2016, and in English on August 28, 2018.
Looking for more on The Pain of Living? The Naruto Wiki on Fandom has a dedicated page with community notes.
View on FandomThis content is original writing by Daddy Jim Headquarters based on the Naruto anime series, manga, and official materials. Episode and chapter references are cited where applicable.
Rights holders
All rights belong to their respective owners.
Character and scene imagery on this site is original artwork by Daddy Jim Headquarters, not screenshots or licensed imagery. Official cover art is used on three types of pages for editorial commentary:
Official resources:
Daddy Jim Headquarters maintains this encyclopedia. If you spot an error, a translation issue, or something that doesn't look right, let us know.