December 10, 1966 
|Other names||Adrienne Greenheart|
|Alma mater||Brandeis University|
|Occupation||Businesswoman, blogger, writer|
Penelope Trunk (born Adrienne Roston; legal name Adrienne Greenheart; December 10, 1966) is an American businesswoman, author, and blogger. Her work focuses on the intersection of work and life. Trunk is the author of the books Brazen Careerist: The New Rules for Success, The New American Dream: A Blueprint for a New Path to Success, and The Power of Mentors: The Guide to Finding and Learning from Your Ideal Mentor. She blogged at Brazen Careerist before leaving that company. She now runs Quistic, her latest start-up venture—an education company—and maintains an eponymous blog featuring career advice. Trunk wrote a column for the Boston Globe that was syndicated in 200 newspapers across the United States.
Trunk grew up in Chicago's northern suburbs before moving to Los Angeles to pursue a career as a professional beach volleyball player. She is a graduate of Brandeis University. Trunk was a resident of New York City during the September 11 attacks. She moved to Madison, Wisconsin in 2006, before relocating to a farm in Darlington, Wisconsin.
According to Trunk, she spent ten years as a marketing executive in the software industry. She also says she started the companies math.com, ECityDeals, and Brazen Careerist. Trunk’s decisions about her own career have been written about in Time and The Guardian.
In September 2009, Trunk was replaced as CEO of Brazen Careerist. She stated, "When the company was clearly moving too fast for me to keep up as CEO, I badgered another board member to be CEO. He told me a number of reasons why that wouldn’t work – he had had two huge exits and he wasn’t planning to be CEO again, and another company wanted him to be CEO, and he wants to watch his kids play football. These are all good reasons that I overcame, and I got him to agree to be interim CEO."
Trunk began writing business advice when Fortune magazine published an open call for a woman to write about her own life as an executive and Trunk won the job. She has been a columnist at Business 2.0 magazine, Bankrate.com and Yahoo! Finance.
According to an article by Richard Rierson, "She has a reputation for giving advice that is counter-intuitive but effective, like take long lunches, ignore people who steal your ideas, and stop vying for a promotion." Writing in the New York Times, Marci Alboher called Trunk "one of the most popular career writers around."
In September 2009, Trunk was preparing to have an abortion, but while waiting out a state legal requirement, suffered a miscarriage during a company board meeting. Trunk's miscarriage was covered by numerous news outlets, including The Guardian. Trunk has two sons by her first husband. She homeschools her children. After she and her first husband divorced, Trunk married her second husband, a farmer. Trunk's accounts of physical abuse in the relationship with her current husband have been criticized on the feminist website Jezebel. Trunk says she has Asperger syndrome.
- "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)
- Trunk, Penelope (March 5, 2007). "My name is not really Penelope". Penelope Trunk Blog. Retrieved October 3, 2011.)
- Trunk, Penelope. "My birthday post". Penelope Trunk. Retrieved 8 August 2015.
- Prestegard, Steve (April 7, 2012). "The indescribable Penelope Trunk". Platteville Journal. Retrieved April 13, 2013.
- Smith, Jacquelyn (February 25, 2013). "14 Things Successful People Do On Weekends". Huffington Post. Retrieved April 13, 2013.
- Gartland, Matt (2012). "Penelope Trunk: Buzz doesn’t translate to book sales. Community translates to book sales.". Winning Edits. Retrieved April 13, 2013.
- Rierson, Richard (March 27, 2013). "32 – Penelope Trunk: Brazen Careerist Founder". Dose of Leadership. Retrieved April 13, 2013.
- Cogan, Marin (May 7, 2015). "Where Did Penelope Trunk Go Wrong?". New York Magazine. Retrieved 8 August 2015.
- Koetsier, John (October 29, 2013). "Penelope Trunk’s new startup is crazy, creative, insane, and genius — just like her". Venture Beat. Retrieved August 17, 2014.
- Ruth, Richard (February 12, 2015). "How Quistic Is Advancing Entrepreneurship". Startup Hook. Retrieved 8 August 2015.
- Kaufman, Leslie (April 18, 2008). "When the Ex Blogs, the Dirtiest Laundry Is Aired". New York Times. Retrieved 12 April 2013.
- Baedeker, Rod (December 7, 2009). "Big city blues: Could a more affordable life, away from the Bay Area, actually be better?". San Francisco Chronicle. Retrieved April 13, 2013.
- "Penelope Trunk, Columnist, Business 2.0". Time. September 12, 2001. Retrieved August 8, 2015.
- Trunk, Penelope (July 13, 2012). "From PR to profits: the problems with publishing". The Guardian. Retrieved August 8, 2015.
- Trunk, Penelope (September 23, 2009). "How to find the right job for you". Penelope Trunk Blog. Retrieved October 3, 2011.)
- Alboher, Marci (March 12, 2008). "An Antidote to Spitzer’s Style". New York Times. Retrieved April 16, 2013.
- Dee J. Hall (October 1, 2009). "Advice columnist's tweet: Too much information?". Wisconsin State Journal. Retrieved October 1, 2009.
- Trunk, Penelope (November 5, 2009). "Why I tweeted about my miscarriage". The Guardian. Retrieved October 3, 2011.
- Cowen, Tyler (October 29, 2011). "Assorted links". Marginal Revolution. Retrieved August 17, 2014.
- Bures, Frank (Summer 2012). "The Fall of the Creative Class". Thirty Two Magazine. Retrieved 8 August 2015.
- North, Anna (December 29, 2011). "Who Is Penelope Trunk?". Jezebel. Retrieved 13 April 2013.
- Louette Harding (July 30, 2010). "'I don't have an edit button': Twitter user Penelope Trunk on why she announced her miscarriage on the networking site". Daily Mail. Retrieved April 27, 2013.
- "Penelope Trunk Knows How to Pick a Husband". GOMI. January 10, 2013. Retrieved April 13, 2013.
- "Before you aim for someone’s job, look at the price they paid to get there". Penelope Trunk. May 9, 2013. Retrieved May 19, 2013.
- Schwabel, Dan (July 23, 2012). "Penelope Trunk on "The New American Dream"". Forbes. Retrieved 8 August 2015.