The optimism of one woman’s 20s meets the disappointment of her 30s in I Used To Go Here, a new film from Chicago filmmaker Kris Rey.

“I wanted it to feel nostalgic, but I didn’t want it to feel like it took place in the past,” Rey told Nerdette.

Set and filmed in Chicago and Carbondale, Illinois, I Used To Go Here follows Kate, played by Community star Gillian Jacobs, as she returns to speak at her alma mater at the invitation of an old professor, played by Flight of the Conchords comedian Jemaine Clement.

“She’s trying to figure out, ‘Where did I go wrong?” Rey said. “‘I followed all the rules and checked all the boxes. How come I didn’t achieve what I thought I was going to achieve?’”

We talked to Rey about the inspiration for the film, her recent name change from Swanberg to Rey and what she tells young filmmakers.

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“Go for it,” she said. “The stakes are not that high. You can always start over.”

Press play to listen to the conversation, and check out the trailer for I Used To Go Here, available for rent on Apple and Amazon Prime streaming services.