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Okay, guys – I’m really excited. This Friday, I get to spend 30 minutes on Skype with Penelope Trunk, the author of the entertaining, controversial, and extremely insightful career blog Penelope Trunk’s Brazen Careerist.
Why you should be reading Penelope Trunk
About a month ago, a Rotary friend of mine sent an article by Penelope called Why Your Job Won’t Make You Happy. After reading this article, I learned quickly that Penelope’s musing is going to surprise you, inspire you, educate you, make you laugh your ass off, and eventually, offend you. This is career advice like you’ve never seen it before! It is no surprise she has 56,050 subscribers. Personally, I find myself falling a little more in love with her every day she posts. can’t get enough of this blog.
I’m thrilled to have the opportunity to chat with Penelope this Friday, but this isn’t just for me… this is for you! If you don’t know Penelope’s writing and businesses, here is some info about her along with some of my favorite articles. Check them out and then…
Ask Penelope Your Burning Questions!
This is a rare opportunity so take advantage of it while you can! Leave your questions for Penelope in the comments section of this blog post. The best ones will be asked on Friday during the recorded interview.
About Penelope Trunk’s Brazen Careerist Blog
“This blog is about career advice. And about me.
My career never had a straight path, but I am always learning and trying new things, and that’s what makes my career fun. And sometimes scary.
I had a crisis in college when I realized that all entry-level jobs sucked, so I decided to play professional beach volleyball instead. Then I went to graduate school for creative writing and had a boyfriend who taught me HTML. This miraculously made me qualified to run an online marketing department for a Fortune 500 company in the mid-90′s. I stayed in software marketing for a while and then founded three internet companies. I’m at the third one today: Brazen Careerist.
Throughout my career, I have always been a writer. Often unpaid, always obsessively interested in which media is best for which writing. As an entrepreneur I got a column in a national magazine and started spewing advice in places like Time magazine, the Wall Street Journal, and the London Times. Then I got a six-figure book deal. Today, my column runs in more than 200 newspapers, but my blog is where my heart is, because I’m enthralled with the idea of managing careers through a community.
What I think my life is about is figuring out how to find success at the intersection of work and life—one happy, synchronized adventure. It’s a difficult task, and I don’t want to do it alone. My blog is a community where we all do it together. (And my company is community career management on a much larger scale.)”
Betty Jean’s favorite articles (so far) by Penelope
- Bad career advice: Do what you love
- Why an MBA is a waste of time and money
- Forget the job hunt. Have a baby instead.
Leave your best question for Penelope Trunk in the comment section here!


Hey Betty Jean! I’m so excited to hear your interview with Penelope.
I have two questions:
1. Why do you think adults in their mid-twenties to thirties are experiencing a much harder time with discovering careers that actually bring fulfillment? Is this a generational phenomenon?
2. What advice can you give to personal development entrepreneurs?
Brett recently posted..Why Downward Counterfactual Thinking is Good and What the Heck It Is
Great questions, Brett!!!!!! Thanks for contributing! You’re the best!