40 Day Blog Jog - Day 10 - Penelope Trunk

Don't be put off by Penelope's very proffessional sounding resumé. She's funny, a great writer and her frank discussions about Asperger Syndrome is refreshing.

Penelope Trunk is CEO of Brazen Careerist, a career management tool for next-generation professionals. This is her third startup. Each company Penelope built was focused on a community. Her own career path has had twists and turns and in a world where straight, safe career paths are nowhere to be had, Penelope appreciates the power of managing oneself through community.

Penelope's career began in Los Angeles, where she played professional beach volleyball. She then went to graduate school for English. During that time she learned HTML which allowed her to get a job in the marketing department at Ingram Micro.

After a stint in the Fortune 500, she went to a few smaller software companies and then started her own company, Math.com, a math-tools resource for the teaching community funded by Encore Software. She sold that company for a small sum, and founded eCitydeals, an online auction service for city governments, which was funded by Shelter Ventures, and was shut down in the dot-com bust.

During this time, Penelope wrote a column for Business 2.0 magazine about her experiences as a startup founder. She relocated to New York City and after only a few months at her next startup, she found herself a block from the World Trade Center when it fell.

She decided to be a full-time writer so she did not have to leave her apartment. And she focused on giving career advice instead of writing about herself. At that point, generation Y was entering the workforce and they were looking for advice to tell them how to steer a career that accommodates their lives: old career advice was irrelevant to them.

Penelope started writing career advice for a new generation of workers. Today Penelope is the author of a bestselling career advice book for generation y and the number one career blog.

She explains why old advice - like pay your dues, climb the ladder, and don't have gaps in your resume - is outdated and irrelevant in today's workplace. She has a reputation for giving advice that is counterintuitive but effective, like take long lunches, ignore people who steal your ideas, and stop vying for a promotion.

She is dedicated to helping people find success at the intersection of work and life, because that's what she wants for herself. She thinks of career advice as a group effort. And she launched her company, Brazen Careerist, to create a large-scale community for young people manage their careers for the new millennium.