Penelope Trunk

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Penelope Trunk
Adrienne Roston

(1966-12-10) December 10, 1966 (age 57)
Other names
  • Adrienne Greenheart
  • Adrienne Eisen
Alma materBrandeis University
  • Entrepreneur
  • writer
  • blogger
Years active1996–present
Known forSix Sex Scenes

Penelope Trunk (born Adrienne Roston,[1] December 10, 1966;[2][3][4] legal name Adrienne Greenheart), is an American writer and entrepreneur. Trunk published works in the early 2000s under the pen name Adrienne Eisen and later under the name Penelope Trunk, a name she adopted in her public life.

Trunk founded several startup companies and provides career advice through her blog[5][6] She has written columns about the workplace and the job market for several publications, including the syndicated column, "Brazen Careerist", featured on Yahoo! Finance, and "The Climb," which ran in The Boston Globe.[7] She has also appeared on news programs such as 20/20 and in segments for CNN and NPR.[6]

Inc. magazine referred to her as "arguably the world's most influential guidance counselor" in 2011.[8] She was included on TechCrunch's list of "30 Women Who Have Revolutionized A Male-Dominated Industry" in 2015.[5]

Early life[edit]

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.[9][10][11] On the Women's Professional Beach Volleyball Tour she was ranked 17th in the US.[12]



In the early-90s, Trunk was introduced to hypertext by a boyfriend who curated content for use in CD-i format.[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.[14]

In 1996 she published the hypertext novel, Six Sex Scenes as Adrienne Greenheart, and was credited under her pen name, Adrienne Eisen, from 2000 onward.[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][20] The reader starts the story in a section titled "Therapy", and is presented with a series of options at the end of the section in the form of hyperlinks that lead to other sections of the story, similar to a Choose Your Own Adventure book.[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! Finance.[6][7][21] Her blog posts were syndicated to more than 200 newspapers.[6] She has also appeared as a guest commentator on 20/20, CNN, and NPR.[6]

Trunk blogs and provides career advice through her personal website,[6]


In 2001 Trunk published Making Scenes with Alt-X (a subsidiary of University of Colorado), which is a book based on pages previously published on her website.[22] The novel was republished by Emily Books in 2012.[23]

Trunk's second book, Brazen Careerist: The New Rules for Success, was published by Warner Books.[1]


Trunk founded the companies and eCityDeals.[5] She co-founded Brazen Careerist, a social networking site aimed at millennials entering the job market,[24][25] now called Brazen Technologies.[26]

Since moving to Darlington, Wisconsin, Trunk co-founded Quistic, an online learning company.[27][28]

Personal life[edit]

Trunk has been married twice and has two children.[10] She moved with her family from New York City to Madison, Wisconsin in 2006, before relocating to a farm near Darlington, Wisconsin.[1][29]

Trunk is very open about her life and has received media attention for tweets about her divorce and miscarriage. The New York Times included Trunk's tweets about her divorce in a 2008 article about the airing of "dirty laundry" on social media.[30]

In 2009, Trunk was preparing to have an abortion, but suffered a miscarriage during a company board meeting.[2] She tweeted about the incident, which received widespread media attention.[2] She was also interviewed on CNN about the incident.[2] It was around this time, Marin Cogan recalled in an article for The Cut, that Trunk's blog began to take on a darker tone, less appealing than the one that had made her the "Sheryl Sandberg long before Sandberg wrote Lean In". Cogan came to feel she and other early career women had been "mistaken in assuming that Trunk’s brazen careerism was a feminist project in any meaningful sense."[31]

Trunk describes herself as having Asperger syndrome.[32]

Name changes[edit]

Trunk's name at birth was Adrienne Roston. She posted to her blog in 2007 that she legally changed her last name to Greenheart (which at times she spelled GreenHeart) because she "[didn't] want to be associated with patriarchal naming conventions."[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. She later adopted it in her personal life.[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.[14]



  • Six Sex Scenes (as Adrienne Greenheart, later Adrienne Eisen) (Alt-X, 1996)


  • "Making Scenes" (as Adrienne Eisen) (Broadvision, April 2001, ISBN 978-0970351708)
  • Brazen Careerist: The New Rules for Success (Warner, May 2007, ISBN 0-446-57864-9)
  • The New American Dream: A Blueprint for a New Path to Success (Hyperink, July 2012, ISBN 1614649928)
  • The Power of Mentors: The Guide to Finding and Learning from Your Ideal Mentor (Hyperink, October 2012)


  1. ^ a b c Hopper, Ben. "Plugged into Madison. Blogger on careers took her own advice and moved here". The Capital Times. Madison, Wisconsin, United States. p. 1. Retrieved May 3, 2023 – via The voice belongs to Penelope Trunk, a columnist and blogger for Boston Globe and Yahoo!, and a recent arrival to Madison who has a book on careers coming out this month. . . Trunk, who was born Adrienne Roston and lived in New York before moving to Madison in August, says there were a number of reasons she chose here. . . The approach is neatly encapsulated in her new book, also entitled "Brazen Careerist: The New Rules for Success," which comes out May 25 from Warner Press.
  2. ^ a b c d "'I'm in a board meeting, having a miscarriage ... ' Is this a tweet too far?". Irish Independent. November 2009. Retrieved May 3, 2023.
  3. ^ Trunk, Penelope (December 10, 2009). "My Birthday Post". Retrieved September 3, 2023.
  4. ^ Trunk, Penelope (December 10, 2010). "My Birthday Present to Myself". Retrieved September 3, 2023.
  5. ^ a b c Vuittonet, A.D. (September 20, 2015). "30 Women Who Have Revolutionized A Male-Dominated Industry". TechCrunch. Archived from the original on September 23, 2015. Retrieved May 3, 2023.
  6. ^ a b c d e f Schawbel, Dan (July 23, 2012). "Penelope Trunk on "The New American Dream"". Forbes. Retrieved May 3, 2023.
  7. ^ a b Lain Kennedy, Joyce (June 11, 2007). "Brazen career advice for Generations X & Y". Visalia Times-Delta. Tribune Media Services. p. D1. Retrieved May 3, 2023 – via The independent-thinking Trunk has been a software executive, entrepreneur and professional beach volleyball player. She writes a column, "The Climb," which runs in the Boston Globe, and a syndicated column, "Brazen Careerist," featured on Yahoo Finance.
  8. ^ Warrillow, John (February 25, 2011). "What Does It Take to Become an Entrepreneur. Psychopathy? Brazen Careerist blogger Penelope Trunk shares with contributor John Warrillow who is and who is not cut out for entrepreneurship". Inc. Retrieved May 3, 2023.
  9. ^ Elejalde-Ruiz, Alexia (November 8, 2007). "Have a bawl; Sometimes, you just need to cry -- but do you know why?". Chicago Tribune. Retrieved May 3, 2023. "It's this baby boomer myth that if you play like guys, you'll succeed," said Penelope Trunk, a Wilmette native who runs a blog called the Brazen Careerist.
  10. ^ a b Trunk, Penelope (Spring 2011). "Can We Talk?". Brandeis Magazine. Brandeis University. Retrieved May 3, 2023. Penelope Trunk, aka Adrienne Roston '90, is the founder of three startups — most recently Brazen Careerist, a career management tool for next-generation professionals.
  11. ^ "Adrienne Roston's Beach Volleyball Profile". Women's World Beach Volleyball. Retrieved May 3, 2023.
  12. ^ "Adrienne Roston". Beach Volleyball Database. Retrieved May 3, 2023.
  13. ^ Picot, Edward (May–June 2002). "Self-publication without tears? – Writers with their own websites". PN Review. Manchester, United Kingdom. pp. 54–56. Retrieved May 3, 2023 – via ProQuest. I launched the web site because I was writing interactive stories for CD-Rom, before there was the Internet (outside of the university setting) and I saw the Web as a way to distribute my writing much more easily than on CD-Rom.
  14. ^ a b c d e Mackrous, Paule (2010). "With Penelope Trunk : What happened to hypertext writer Adrienne Eisen?". Magazine Electronique du CIAC. No. 37. Centre International d'Art Contemporain de Montreal. Retrieved May 3, 2023.
  15. ^ Bernstein, Mark (May 1, 1998). Hypertext 98 - Proceedings of the Ninth ACM Conference on Hypertext and Hypermedia: Patterns of hypertext. ACM Press. p. 23. doi:10.1145/276627.276630. ISBN 0897919726. S2CID 317442. Retrieved May 3, 2023.
  16. ^ Greenheart, Adrienne. "Six Sex Scenes". Mark Amerika. Archived from the original on October 18, 1996. Retrieved May 3, 2023.{{cite web}}: CS1 maint: unfit URL (link)
  17. ^ Greenheart, Adrienne. "Six Sex Scenes". Mark Amerika. Archived from the original on April 19, 2000. Retrieved May 3, 2023.{{cite web}}: CS1 maint: unfit URL (link)
  18. ^ Eisen, Adrienne. "Six Sex Scenes". Mark Amerika. Archived from the original on August 21, 2000. Retrieved May 3, 2023.{{cite web}}: CS1 maint: unfit URL (link)
  19. ^ a b Picot, Edward (Nov–Dec 2002). "Some versions of hyperfiction". PN Review. Manchester, United Kingdom. pp. 52–54. Retrieved May 3, 2023 – via ProQuest. Perhaps more typical, from the design point of view, is Adrienne Eisen's 'Six Sex Scenes' — the story of a young Jewish woman's dysfunctional love-life, with frequent flashbacks into her equally dysfunctional childhood. Again, this is written in numerous short sections; but in this piece, instead of the organisational scheme being laid bare at the outset, we are merely presented with a many-forked path and left to explore it as we may. The story always starts with a section entitled 'Therapy', but at the end of this section we are presented with a list of possibilities: 'You Suck/Bored/ Mind Disorder/My Room with a View'. If we choose 'My Room with a View' from this menu, we are taken to another section with another list of alternatives at the end: 'Mom Says to Aim for a Nice Arc/Reading/The SPIN Woman/The Wisdom of Puberty'. Whichever section we choose to view next, at its end we have to choose again from another list, and so on.
  20. ^ Porco, Alessandro; et al. (2012). From Text to Txting: New Media in the Classroom. Indiana University Press. pp. 102–103. ISBN 9780253007209. Retrieved May 3, 2023 – via Project MUSE. Some examples of hypertext novels that keep to Coover's classic ideal are the hyperfictions of Adrienne Eisen, Judd Morrissey, and Judy Malloy. Eisen's works contrast the tactics of many normative hypertexts in the sense that there are few links and the narrative is usually framed within the first-person account of a particular character and his or her life situation. While the reader has some choice with respect to what text portion to read, these choices are quite limited so that getting through all the links is not a burdensome project as it is with the more complex hypertexts that initially defined the genre, notably Michael Joyce's afternoon, a story.
  21. ^ "BNET names new editors, columnists". Talking Biz News. February 25, 2010. Retrieved May 3, 2023.
  22. ^ Zaleski, Jeff (February 18, 2002). "Making Scenes". Publishers Weekly. Vol. 249, no. 7. pp. 72–73. Retrieved May 3, 2023 – via ProQuest. Like a boxing match, hypertext-the original format of much of this novel-demands quick, punchy prose that will keep the reader riveted between mouse clicks. Sex helps, too. But while this first print effort by veteran hypertext writer Eisen has generous helpings of both, it serves mostly as a cautionary tale about the difficulty of moving Internet-ready writing to the page. The unnamed narrator is a stunning young woman who wants to play professional beach volleyball-at least until she decides to become a model, and then a graduate student.
  23. ^ "Making Scenes. Adrienne Eisen". Emily Books. Retrieved May 3, 2023.
  24. ^ "An Antidote to Spitzer's Style". The New York Times (online). March 12, 2008. Retrieved May 3, 2023 – via ProQuest. As for Ms. Trunk's new company, it is still in a beta launch mode. But I have a hunch I'll be visiting often since it appears to be a place where people are already starting to congregate to talk about what is new in careers. So far, about 60 career bloggers (vetted by one of Ms. Trunk's partners, Ryan Paugh) have joined the network.
  25. ^ Phelps, David; Yee, Chen May (January 2, 2011). "U want job: Help for 'Gen Text': Many young people are short on the skills and etiquette needed to go into an interview". Star Tribune. p. A1. Retrieved May 3, 2023 – via ProQuest. Their very familiarity with social media mores and trends can make them attractive hires for companies looking to market to young people, said Ryan Paugh, the 27-year-old cofounder of Brazen Careerist, a Web-based community for business networking.
  26. ^ "Fast 500 Winners". Deloitte. November 16, 2022. Retrieved September 4, 2023.
  27. ^ Ward, Tom (March 30, 2016). "How Andy Cohen Got To The Top: 3 Career Launching Tips". Forbes. Retrieved May 3, 2023.
  28. ^ "Penelope Trunk, Co-founder & CEO, Quistic, Author, Blogger". The European Business Review. April 16, 2016. Retrieved May 3, 2023.
  29. ^ Nishi, Dennis (January 18, 2015). "It Pays to Ask Smart Questions at a Job Interview". The Wall Street Journal. Retrieved May 3, 2023. Don't wait until the end of the interview to ask about the job and what the employer is looking for in a candidate, says Darlington, Wis.-based career expert Penelope Trunk.
  30. ^ Kaufman, Leslie (April 18, 2008). "When the Ex Blogs, the Dirtiest Laundry Is Aired". The New York Times. Archived from the original on 13 November 2013. Retrieved May 3, 2023.
  31. ^ Cogan, Marin (2015-05-07). "Where Did Penelope Trunk Go Wrong?". The Cut. Retrieved 2023-02-23.
  32. ^ Trunk, Penelope (March 10, 2018). "Stop telling me that I don't have Asperger's". Retrieved May 3, 2023.
  33. ^ Trunk, Penelope (March 5, 2007). "My name is not really Penelope". Retrieved May 3, 2023.

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