I’m fascinating by the research about what makes a good entrepreneur. Because it turns out that entrepreneurs come in lots of shapes and sizes, but the common thread among successful entrepreneurs is they are great at mitigating risk.

I am good at that, too. I’m the founder of four companies, but I went through 50 business ideas before I found one that seemed like it would work. I wrote business plans and pitch decks, and intricate Excel documents to show detailed, month-by-month five-year profit and loss estimates. And then, if it looked too risky I dumped it all and started over.

I am also really careful who I go into business with. It’s always someone who has skills that I don’t have. I keep a running list of people who would be good business partners for me. And I wait until I have a perfect match between the type of business I want to build and a top-tier partner who would want to do that business.

That said, most people would look at my life and say I take more risks than I mitigate. And maybe that is true. And maybe the truth is that I spend my whole life thinking about risk. I’m willing to take more risks because I’m good at thinking how to mitigate risks.

When I started homeschooling it felt like a very risky thing to do. I had never in a million years considered homeschooling and then, in a matter of months, I was doing it. Here’s how I mitigated the risk for myself:

Self-directed learning
At first I worried about curricula. And, like many parents, I started teaching things I liked: my kids know a lot about Picasso and Matisse. But then I realized that the vast majority of research about education reform proves self-directed learning is more effective than any curriculum. So I decided to let my kids choose what they learn, and my kids choose how they structure their days.

It’s difficult to allow, but it’s a way I mitigate the risk that I would fail to choose something that my kids would be passionate about. In fact, my kids have settled on many things (fan fiction, 3-d animation) that I don’t know one single thing about and could never have helped them learn.

Life insurance
The first time I got serious about life insurance was when I was at the World Trade Center when it fell. I was sure I was going to die, and the only thing I thought about was the people I love most. Would they be okay? Nothing else entered my mind.

But when I started homeschooling things seemed more serious when there is no school structure controlling a child’s life. I decided I needed a place to get life insurance to get the kids through their homeschooling childhood if I’m not there. Not that the money would replace a mother, but I’m all about mitigating risk. And I see the family’s future through the same sort of risk-management lens as my companies.

I don’t know what I thought I was doing when I started writing this blog. When I first started writing about education I wasn’t even admitting that I was going to homeschool. I guess I mostly was appalled that the education reform discussion did not seem to include any of the research I was reading. I wanted people to know.

By accident I discovered a community of people who were thinking like me, trying to uncover the truth about the best way for kids to learn. My decision to homeschool felt much less risky because I had this community to lean on every time I felt like I was on too risky a path with homeschooling.

I also mitigate my risk by including guest posts on this blog, like the posts from Sarah and Erin. Both write a lot about how they make decisions that are independent of mainstream but not so crazy that they worry they’ve lost their minds. I like those posts. But I don’t love the photos that Sarah takes of her family. So I convinced Erin, who is great at taking pictures of her own family, to take pictures of Sarah’s family. (There’s one there up top.)

I realized that my endeavor not only got me better pictures for the blog, but they also created a nice tie between Erin and Sarah, and this reminds me that we all help each other to be more brave in our education decisions because we have a community to mitigate risk.

This post is sponsored by Haven Life, but views expressed are my own.

7 replies
  1. Jim Grey
    Jim Grey says:

    Sure seems to me like people who take a lot of risks — even people who are good at mitigating them — are going to have things go wrong more often. Not that having things go wrong is always inherently the worst thing. Sure seems to me that a life where the entire risk mitigation strategy is to avoid risk would be the worst thing. How stultifying such a life must be.

    • Anna
      Anna says:

      Things “going wrong” might be the very *opportunity* a risk-taker might appreciate. This is in contrast to someone who eliminates risk (as much as the person is able) because the person has no interest in problem-solving the way the risk-taker does. The latter would be a dried up life as far as I am concerned, *for me*. But the latter would allow a care-taking type (i.e. of others) of person to continue taking care of people without interruptive problem-solving needs. I think it comes down to the goals of different personality types. A care-taker, helper type, such type 2 in the Enneagram, is very different than a puzzle-solving type 5 in the Enneagram. It can translate also to Myers-Briggs really well. A sensing type sees “what is there” and might not mitigate risk as well as an intuitive type who sees possibilities. Someone who extroverts their intuition would not mind risk even more than an intuitive type who introverts their intuition.

      My husband (an INTJ – introverted intuition, verses me who is and INTP which has extroverted intuition) is more conservative with certain kinds of risks (like financial) and puts some really serious speed bumps on my willingness to venture out with $$. So hopefully we hold each other in good tension and balance. My financials have never looked better, but I am shopping a lot less (which to me can be a negative if it goes too far like that). We eat out more though than I would on my own. So that reveals what he is willing to spend money on. Food isn’t really risky. You eat it and it is done.

      Just some thoughts, if a bit rambling…

  2. Craig
    Craig says:

    My 3 girls were home schooled and it was the best thing I have done! I connected with them on another level and at the same time I knew what they were good at and what needed improving.


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