How to Be a Total Failure by 25

How to Be A Total Failure at 25 (aka 25) centre’s on a young woman who, whilst going through a quarter life crisis, encounters a casual loop on the eve of her 25th birthday. And upon fighting to get through it, she reflects on what her life was like 10 years ago, and ponders on what her life will be like 10 years from now. Throughout her journey, she battles with major questions of self confidence, the resilience it takes to build the life she wants, and the possibility that her life may not turn out the way she’s always dreamed.

CONTENT AND SENSORY ADVISORIES: Suicidal ideations, references to toxicities of social media and copious amounts of sarcasm

RUN TIME: 60 minutes, Double-Billed with Black and White


How to Be a Total Failure by 25

  • Producer/Playwright/Actor: Cassandra Henry
  • Director: Ethan Persyko
  • Stage Manager: Lisa Sciannella
  • Projection Designer: Evander Dewar
  • Sound and Lighting Designer: Natalia Cortes
  • Movement Coordinator: Robert Feetham
  • Dramaturg: Summer Mahmud
  • Actor: Ingrid Liu
  • Actor: Ojonugwa Mansu


Part of the 2024 Festival

  • May 15 at 6:00 PM

  • May 16 at 8:30 PM

Cassandra would like to thank 

The 15 year old who started it all

The 35 year old who has yet to finish

And the 25 year old who still keeps going 

And to my mother, for every single thing 

This production is made possible through support of Metcalf Foundation’s Booster Program.


Native Earth Performing Art’s Aki Studio

250-585 Dundas Street East
Toronto, ON M5A 2B7


Native Earth Performing Arts and Artscape strive to provide equal treatment to and equitable benefits of its services, programs and facilities in a manner that respects the dignity and independence of people with disabilities.

  • The Dundas Street entrance provides barrier-free access to the building
  • Two elevators are located in the South Lobby
  • All floors have accessible washrooms and stalls, as well as accessible drinking fountains
  • Signage throughout the building is written in Braille
  • A hearing enhancement system is available in Aki Studio and the Ada Slaight Hall


Cassandra Henry

Cassandra Henry (She/Her) is an emerging actor, playwright, producer and singer. A graduate of York University’s theatre program, she has developed her craft of acting in theatre and singing in musical theatre from the age of 10. Having studied, musical theatre, classical music, the Laban movement, the Alexander technique and the The Batdorf Technique, she has learned the practice of creating a character from the inside out, creating unique voices for characters that contribute to meaningful and memorable performances for all audiences, with the emphasis and drive of creating representation and inclusivity for BIPOC and neurodiversity in theatre and film.