Does School Kill Entrepreneurship?

Quick link to today’s interview: Right-click to download the interview in MP3 format.

Most of the readers of this blog are entrepreneurs – out there in the world beating new paths, asking new questions, and questioning old answers.

And many of us are parents as well, trying to give our kids a good start in life.

One of the “givens” of that good start has been quality schooling.

So it was with some shock that I found myself, last fall, the parent of two “drop-outs.” Following our family’s year in South Africa, neither of my children could maintain their interest or their spirit in a conventional school setting. (And they went to a pretty alternative school, by most standards.)

As I struggled to make sense of their choices and keep in check my knee-jerk reaction to force them to go to school for their own good, I looked for guidance and advice from people who knew what they were talking about.

Luckily, through my 17-year-old daughter, I found Blake Boles.

Blake is an entrepreneur, educator, social activist, and force of nature. He runs, a travel and learning program for homeschooled teens. He’s written three books, including College Without High School, Better than College, and The Unschool Adventures Guide to Online Travel Fundraising (which is available for free at

I interviewed Blake about the connection between schooling, homeschooling, unschooling, and entrepreneurship. He shared a vision of Self Directed Learners (an all but extinct animal in our school systems) as a model for an entrepreneurial life.

If you have kids who are bored in school, or who feel like there’s so much more to life, or who feel bad about themselves because of their social or academic “shortcomings,” this could be one of the most important interviews you ever listen to.

Enjoy, and please comment. What did you agree with? Disagree with? Wonder about?

Right-click to download the interview in MP3 format.

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4 Comments. Leave a comment or send a Trackback.
  1. #1 • Catherine Gobron said on May 22 2013:

    We know Blake and really appreciate his work! Teens can choose to live their lives outside of school anywhere, but if you’re near Massachusetts. North Star can help. We have running a center for teens choosing to leave school to pursue their educations for 17 years. Many of our teens go on to start their own businesses and most go on to college. You can learn more at

  2. #2 • Howard Jacobson said on May 22 2013:

    Awesome, Catherine! I hope that someday programs like North Start will be the norm for the 97% of kids for whom school isn’t ideal.

  3. #3 • Gemma said on June 5 2013:

    Sammy wants to spell windoe. By the time miss tells him it’s ‘window’ Sammy’s forgotten what he was writing about. A group of people decide that a spelling is correct. Or not. Schools teach you how to make ideas by joining the pieces together. Teach you to tell stories by teaching you to spell. It’s great if you need a railway – it’s not so great if you want to know where the railway’s going.

    Grasping zephyr-like story forms is incredibly hard for the intellect. The other day Brian kept saying “that should have an umlaut” and I kept saying “If you’re going to say something, please make it relevant to my story” He kept bombarding me with stupid corrections. I didn’t need correctness at that point, I needed to connect. I needed to use the words to express an idea, that they were there at all was achievement enough.

    It’s the same for the entrepreneur. Most people can’t be entrepreneurs because they’re trying to make businesses out of the bits and pieces. It’s not easy because you don’t know where you’re going. The entrepreneur knows where he’s going – it may be that he doesn’t know which pieces to use!

    PS you never scorched my homepage. GL

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