An aging ad executive reflects through the years in snapshot scenes about his ex-wives, a troubled friend, an awards ceremony, and an unlikely love story.

In New York, a young woman befriends her quirky roommate, who is trying to make it as an actor. While she watches her roommate attempt to accomplish her dreams, the woman reflects on her own life’s direction and what possibilities (or lack of) lie ahead.

Ruthie, an experienced writer, reflects on the scholarship opportunity that set her career in motion.

A writer wakes up every day hoping each day would be the day he finally manages to write, though each day he finds new reasons to delay his writing.

An accomplished but ineffectual columnist searches for fulfillment, until a death in the family causes him to question the family he took for granted.

As a man tosses out his old things during the pandemic, he thinks back to the lives he lived with them.

A man looks back on his father-in-law's life after he passes away, thinking of the many jobs he held and his military service.

A man who is trying to find his place in the world tries his hand at multiple professions but ultimately settles with painting. Though he has talent as a painter, he leaves his patrons unsatisfied, taking wild artistic liberties he takes with commissions—a lesson which his two closest friends will come to learn when he paints a portrait of one of them.

In the year 2000, Orion is a young software developer who’s hit it big with his tech company in Cambridge, Massachusetts. Despite his long-term relationship, success, and newfound riches, he feels an emptiness in his life, leading him into dangerous territory.

A man recalls his intimate friendship with his former English professor, who resolved to fuel his unsatisfied desire for playwriting during the time they were apart. In their reunion decades later, instead of the brilliant play he promised, the professor shows his former student a disturbing product of his mental instability.