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.