Author and blogger on careers, entrepreneurship, and education, as well as founder of four companies, Penelope Trunk joins me to talk about her past and current projects. We talk about writing, unschooling, startup mentality, trends in career development, and how to be honest with yourself when it comes to your future. Her latest startup provides online courses that help people manage their careers.



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Meet the hosts

I'm an entrepreneur, thinker, and communicator dedicated to the relentless pursuit of freedom. I'm the founder and CEO of Praxis, an intensive ten-month program combining real world business experience with the best of online education for those who want more than college.


  • Two years ago, my twelve-year-old brother got cancer. He was in public school, sixth grade. He’s fourteen now and perfectly healthy but he missed a lot of class in the mean time. My parents fought the school, teachers and administrators alike, attempting to get my brother educated during his illness. That bad experience with the public school system led my parents to homeschool my brother for the past year. He works only three days a week, yet learns more than his public school peers. He still has one elective for which he attends public school, and he’s told us that, although he takes regular math classes, he’s conversant with his peers who take honors and advanced placement classes. The most obvious and striking difference was the change in his personality. When he attended public school he talked and acted like his peers. He used their slang, dressed like they dressed, and had the same opinions and attitudes. Since he’s been homeschooled he’s undergone the transformation into an individual. Even though he still interacts with his peers daily, he talks differently and chooses his own styles. He’s naturally individualistic but his time away from his peers allowed him to recognize what parts of him were influenced socially and become his own person. Ideally, the educational system would produce unique, thoughtful individuals but too often it produces cookie-cutter drones, spouting the same dull ideas. I’ve been fortunate to witness a young person escape that fate.

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  • I was homeschooled up until the 11th grade when it became necessary for my family to send me to a private school primarily because my father was worried he was not equipped to get whatever paperwork together to ensure I could get into a good college straight out of homeschool. The plan worked pretty well and I was able to attend the college of my choice. But the cost was high. I absolutely hated the standardized classroom of private school(I didn’t like college’s standardization levels much either but college was still fun). But my experience led me to want to make sure other students in similar situations would not be forced to go to a private or public school just to smooth the path to college if that is their desired outcome. To that end, how can this community help you, the homeschooling parent, the homeschooled student(who may still have friends or siblings), reach your educational goals? Any information, from the most grandiose abstract, to the most tediously specific, would be of great help. Except for corrections of my grammar, those belong on hate-filled screeds at the NYT.

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