Miss Kendrick (62), of Careys Bay, said her show Life: Fear to Freedom — Jenny’s Story was targeted towards anyone wanting to "conquer fear and find happiness".
The "taboo-breaking" show was part comedy, part motivational talk, she said.
She first thought of creating the show when she had a gender change in India in November 2017.
"This is my way of helping other people ... instead of fear ruling me, I rule fear."
The show section includes an "ask me anything" section.
Online bookings for the show at www.newathenaeumtheatre.com were essential to ensure Covid-19 social distancing measure could be met.
Life: Fear to Freedom — Jenny’s story. New Athenaeum Theatre at 7.30pm on September 12 and 13.