[5] Trunk was born in Wilmette, Illinois and graduated from Brandeis University in 1990, before moving to Los Angeles to pursue a career as a professional beach volleyball player.
[13][14] Once the internet became public domain, her boyfriend taught her HTML and in 1993 Trunk created her own website where she posted her hypertext works.
[15][16][17][18] Written in the first-person, the semi-autobiographical story focuses on the love life of a young Jewish woman, interspersed with flashbacks to her childhood, both of which are fraught with dysfunction.
[19] Trunk has written articles related to career advice, entrepreneurship and the evolution of the workplace for publications and news agencies such as The Boston Globe, The Wall Street Journal, Business Week, Glamour, Marie Claire, Business 2.0, BNET and Yahoo!
The New York Times included Trunk's tweets about her divorce in a 2008 article about the airing of "dirty laundry" on social media.
"[33] In a 2010 interview with Magazine Electronique du CIAC (a publication by Centre International d'Art Contemporain de Montreal), she said she changed her last name from Greenheart to Eisen because she "had a big job and my company just forced me to change the name on the hypertexts.
"[14] She claims that her name change to Penelope Trunk was prompted by Time Warner when she was hired to write for them.
[14] She also told Magazine Electronique du CIAC that her original first name, Adrienne, causes her emotional discomfort and reminds her of negative experiences during her childhood.