How to teach risk taking

During the industrial age, when parents moved from farms to factories, it became more cost-effective to put kids in school than put them to work. So parents bought into the idea of state-run school. At that point, school became the most expensive babysitting operation on the planet.

In the pre-industrialized world, only the kids with a governess got an education. And those governess types were so quirky and fun because it was an alternative choice to be a governess instead of stay in the town you were born in, get married and have kids of your own. (Think of going airborne with Mary Poppins, or singing with the von Trapp kids and Maria.)

In today’s school system teachers choose teaching because it’s safe and predictable. You can generally get a job teaching where you were born, and (before Scott Walker busted unions) teachers could rely on a lifetime position.

The problem is that today’s workplace rewards risk takers. It rewards entrepreneurial thinking and people who are trained to think independently and creatively – information synthesizers. Why is it good to have people who took a safe route training people for an inherently unstable workforce?

The parents most willing to stay home and teach their kids all day long are probably the parents who do not fit in well in corporate America. That’s why they are willing to leave and stay with kids.

What if we had only the workplace geniuses running homeschooling? Would that be better? Are we aiming to train our kids so that they can successfully navigate the workplace that dominates adult life instead of leaving the workforce? What is the best type of person to teach children given the world they will need to navigate?

22 replies
  1. Tanya
    Tanya says:

    I’m really enjoying this blog conversation. It gives me new things to consider too as we begin our home education journey.

    My common sense tells me it would be better to have people actually working in their chosen field to teach a particular subject or skill. However, I had a few college instructors who were not professors, but rather were working part-time as a side to their day job in their field, who were terrible instructors. Since that experience, my thinking has always been that the teacher should be both – working in the field as well as possess some mentor/instructional qualities. Some can teach (I like the word mentor better), and some can’t; but in the end, I do think it should be someone active in the field.

    And as for the question, “How do you teach risk-taking?” I don’t think you can teach it. I think it has to be experienced. So, the teacher’s role would be more of a supportive, mentor role while the student experiences it in real life in different situations.

  2. Karen M
    Karen M says:

    The problems with the teaching profession are manifold and if I were running the world, the first thing that I would change is the model that we use to pay and promote teachers. Starting salaries are very low and a lot of the benefits are back-loaded, i.e. pensions. Once you get into teaching, it is very hard to get out so you have the situation of burned-out teachers who want to quit but can’t because they have too much invested. Very, very few people are suited to life-long teaching careers. We need to make it easier for someone to choose teaching by offering higher starting salaries and also make it easier to leave it after 10 years and go do something else with their lives without risking their retirements. How do we do this? No idea.

  3. Paul
    Paul says:

    I think people VASTLY overestimate the technical skills or raw knowledge base necessary to teach a kid, at least through 8th grade or so. I mean come on, we’re not talking rocket science here. If you as a parent don’t already know 8th grade material well enough to teach it, it probably wouldn’t hurt to learn it in the first place. Adding fractions isn’t that hard.

    So is the ideal teacher? Probably someone who has a specific interest in educating the kid. Someone who actually cares about the kid. Maybe even someone whose own future outcome could be dependent on the education level of that kid. Someone like… a parent.

    Once you the parent are the primary educator, you can teach your kids whatever you want by doing it yourself. Want your kids to learn about entrepreneurship? Let them watch you start a business. Want them to learn about risk taking? Let them watch you take risks. At the end of the day, you can’t shove any particular knowledge down a kid’s throat. You have to make them want to take it in, and then let them internalize it themselves. Exposing them to whatever you want them to learn, and doing it in an environment that makes them excited about the material is, I think, the best way to do that.

    All of that being said, my only child just turned 1, so I have no f’ing idea what I’m talking about.

    • Penelope Trunk
      Penelope Trunk says:

      I think that’s true — you can teach your kid whatever you want by doing it yourself. But that’s really limiting. My son loves soccer and I don’t know how to play it, and I have no interest in driving to soccer games.

      My other son loves entrepreneurship, and I could model by doing do it all day long — by sitting in front of my computer. But that doesn’t seem good. It seems, in fact, particularly bad.

      I’m not sure about the modeling thing. I think education needs to be more broad than the kids learning from what I do. And anyway, I feel like a nutcase a lot of days, and I wish I were different a lot of days. What about that? I don’t want them to get that. So i need their education to be more than that.


      • Paul
        Paul says:

        Eh, I think it’s only limiting if you let it be. Back to the defining words thing, I guess. If you define entrepreneurship specifically as starting a new company, then yea, that’s tough to teach by example and still be a parent. But when I say that I want to teach my kids entrepreneurship, I don’t mean the nitty-gritty of how to start a company. I just mean that I want to teach them to think like entrepreneurs. In my mind, that just means that I want them to constantly be on the lookout for ways to innovate, for mutually beneficial exchanges, and in general, for ways to get paid for making someone else’s life (or the world) better. I might not be able to teach the former by example without abdicating parenthood, but I can certainly do the latter. Hell, I bet your kids learn more about entrepreneurship in a week living on a real operating farm than most kids do in 18 years of life.

        As for specifically teaching risk taking, I think you need to define what kind of risk takers you want your kids to be. Taking risk for risk’s sake is pretty worthless. If that’s all you want, just start them early on cocaine. When I think to myself that I want my kids to be risk takers, what I really mean is that I want them to learn to understand the risks involved in any endeavor, to look for situations where the payoff far exceeds the risk, and to be able to hedge the risks that do exist. THEN I want them to have the balls to take those risks. But, IMO, the value judgement part is far more important than the balls part. It’s easy to have balls when the upside is high and the downside is low.

        As for the crazy thing, your kids are going to learn from your example whether you like it or not, you may as well be intentional about what they learn.

  4. Online
    Online says:

    The best person to teach a kid is someone who cares about them and is resourceful in getting assistance when they are over their head. Unfortunately, the demands in education today reward those who can shuffle resources to meet testing accountability requirements and punish those who care for children.
    The fact that the schools are by design unstable at present, are forcing our children to learn to deal with lots of different types of stress than they might have in years past.

  5. Lori
    Lori says:

    again, it’s not about *teaching* risk — it’s about creating an environment where kids are encouraged to direct and manage their own learning, where they are investigating things that matter to them, and where they get used to making mistakes and taking risks.

    ” What is the best type of person to teach children given the world they will need to navigate?”

    the point isn’t to try to anticipate the world your kids will live and work in — the point is to help your kids develop their own talents and their thinking and learning skills so they can be successful no matter *what* the world looks like and no matter what they want to do. and it’s what *they* want to do that’s important.

    • Penelope Trunk
      Penelope Trunk says:

      Well, I think I’m an expert on risk taking. I’m great at it, if you call taking risks and making them pan out as being great at it. But the life of a risk-taker is very tumultuous and unsettling because you never know how things will turn out.

      So, you could say that modeling risk taking for kids is not good for them. Kids need stability. But if stability is the best environment for kids then they will not see that the adults in their life are okay with the abject failure that risk-taking entails.


      • Lori
        Lori says:

        no offense, pen, but you keep thinking it’s all about *you*. and you would play an important role if you were hs’ing, but their education is about *them*. the fact that you are a risk-taker and modeling risk in your personal life is good (or bad, depending on how you see it), but what i meant by “creating an environment where kids are encouraged to direct and manage their own learning, where they are investigating things that matter to them, and where they get used to making mistakes and taking risks” was creating a learning environment for them .. a schedule, a workspace, a way of learning, a family attitude about thinking/learning/making/doing.

        my husband and i are risk-takers – we start businesses, write books, build things, get involved in big projects. i wouldn’t describe our life as “tumultuous and unsettling” though, even though – as you say – we never know how things will turn out. and we’ve had some total failures – doing big things means accepting failure. but underneath, our home life is pretty simple and relaxed. stable. our kids would not be surprised to hear some new venture bombed, but they wouldn’t ever think they were going to lose the house. so i have to disagree with your statement that stability is incompatible with risk-taking.

        you say that stability isn’t the best environment for learning to accept failure/take risks – but, on the other hand, a tumultuous, unsettling home life associated with risk-taking might make a kid crave stability.

        back to my point – when we’re talking about homeschooling and helping *kids* become risk-takers, we need to create a learning environment that allows and encourages them to make mistakes, try new things, innovate, fail, bounce back, collaborate, etc. – apart from what we’re doing with ourselves, we have to create the circumstances that allow them to explore their talents and build up their thinking and learning skills. personality, temperament, or reaction to home life might determine whether they want to veer toward risk or away from it. that will be their choice. we can only prepare them as best we can to be successful at whatever *they* want to do.

        • Florence Gardner
          Florence Gardner says:

          I find I’m totally with you Lori in this conversation. It’s a relief to read this perspective articulated so clearly (and making it so I don’t have to try!). I left a longer note on the post about summer “enrichment” along similar lines about creating the environment for risk taking, riffing off of your quote from Eudora Welty, which is all about finding that inner daring.

  6. Randi
    Randi says:

    I am a relatively new mama (I married a wonderful man and his 3 beautiful babies, ages 10, 7, and 5 almost 2 years ago), and the idea of homeschooling has flickered across my mind repeatedly as I’ve adjusted to this new life as Mama.
    I can’t tell you how disappointed I was when I stumbled across your blog today. You see, I am also a public school teacher — a reading specialist at an elementary school with an 80% poverty rate — and I’ve devoted the last 13 years of my life to pursuing excellence in my field. But you describe me, a perfect stranger to you, as a contributor to a broken system and have the audacity to claim you understand my motives for teaching as choosing what’s “safe and predictable”.
    My husband and I enjoy a two-income lifestyle, a home that we own in a lovely suburban neighborhood, and the benefits of post-graduate levels of education. I like to believe that we worked hard for those things, but the reality is we were born into them. Our families were well-educated, white-collar people who expected us to become well-educated, white-collar people. We can drop everything to homeschool our children, if that’s what we prefer. But I work with children all day long whose families couldn’t do that for them, even if they wanted to! And those kids need good teachers in a school that they don’t have to pay to attend. Although, you may prefer to consider it merely “the most expensive babysitting operation on the planet.”
    I have a LOT to say about the choices their parents have made along the way, and a LOT to say about the brokeness of the public education system, but none of that matters to the six-year-old who needs to learn how to read. What matters to him is that the Department of Justice states, “The link between academic failure and delinquency, violence, and crime is welded to reading failure.” What matters to him is that “85 percent of all juveniles who interface with the juvenile court system are functionally illerate” (just google literacy and crime stats). What matters to him is that I show up every day and do my job with excellence and integrity so that he has access to a different kind of life — a life that his family is unable or unwilling to provide for him (how to fix THAT problem is an entirely different issue!).
    There is absolutely nothing “safe and predicatable” about working with our nation’s at-risk or less-privileged youth. I’m happy for you that your children are not among them. I’m happy for me that mine aren’t either. How blessed we are! There is nothing “safe and predicatable” about choosing to role up your sleeves and be an advocate for change WITHIN a broken system.
    Public schooling isn’t for everyone, and if you’ve got the resources to pursue an alternative, great! I am right there with you on the issues that plauge the public system. There are problems that need to be solved! But how arrogant to assume that it is the teachers who perpetuate those issues. The truth is, most teachers are noble public servants, doing their absolute best with the meager tools they’re given, with a heart for children, seeking to produce a literate citizenry capable of self-government… ensuring that your kids live in a world that is safe and democratic. Maybe my husband and I will end up homeschooling our children, but I will look for advice on the matter elsewhere.

    • Mark W.
      Mark W. says:

      @Randi – I was educated in a public school and got a good education. I agree with many things you have stated here. However, the one thing I really have to disagree with is – “And those kids need good teachers in a school that they don’t have to pay to attend.” Somebody has to pay. I don’t have children and yet I still have to pay school taxes since I own a home. If I rented, I would still be paying school taxes indirectly since the money would be coming from the landlord.

      • Randi
        Randi says:

        Notice I didn’t call it a free education — somebody is certainly paying for it! I just think it is a beautiful thing that in this country a child’s access to basic education is not dependent on his family’s ability to pay for it! It is a collective effort (thank you, tax payers!) because our nation values an educated citizenry. Having children of your own has nothing to do with it. You don’t think your own quality of life isn’t intimately connected to the kinds of students being turned out of your local school system (see stats above related to crime and literacy rates)? And if you don’t like what your local school system is doing, you vote, you volunteer, you serve on your school board – because it matters to you, not just to any kids you may have, that your school system is working. I would much prefer that my tax dollars go toward education in the hope that fewer of my dollars go toward the justice system! Have you compared how much it costs to run a school to how much it costs to run a prison?! You’re paying for that, too, you know.

    • Paul
      Paul says:

      Come on, be honest. Can you really, with a straight face, say that most of your teaching compatriots fit the mold of you rather than the mold that Penelope described? I’m glad you’re a great teacher. There are lots of them. But in my experience there are FAR more terrible teachers than there are good teachers.

      Of course I also live in Louisiana, the world capital of terrible public education, so maybe my experience is not indicative of the rest of the country.

      • Randi
        Randi says:

        Experience is certainly a powerful lense. I work at a National School of Distinction and rub elbows every day with exceptional teachers who pour their hearts into public education. If I were from Louisianna, I might have different things to say.

        My point is that in an issue as complicated as ed reform, nothing is simple. And to paint with as broad a brush as Penelope has chosen to use (“In today’s school system teachers choose teaching because it’s safe and predictable.”) is, in my opinion, dishonest and counterproductive. And it doesn’t do anyone any good to pretend that the problem is that small or the solution easy. If Penelope wants to write about the brokenness of the system (and there is PLENTY to write about!), she should inform herself about the real issues and use her platform and influence to really wrestle with them. Otherwise, I think she’d be better off not saying anything at all! What she’s doing now is perpetuating misunderstanding. Who does that help?

  7. Lori
    Lori says:

    pan down to read this part:

    “…The Grommets of Maui, an island that had never produced a world champion surfer. A little boy named Dusty Payne announced his ambition to be that surfer. He formed a cohort that would compete and collaborate to perfect their skills. At 20, Dusty achieved his ambition. And so did every single one of the kids in his cohort –including the fifth one that can’t communicate or socialize because he suffers from Asperger’s Syndrome. The group pulled themselves up by their bootstraps until each one became a world champion. …

    How did they do it?

    1. passion to achieve and willingness to fail, fail, fail along the way. …”

  8. Lfey
    Lfey says:

    I love your blog and particularly this section! I have two things to say in response to your recent posts:
    1.I have been an entrepreneur, a home-school mom,a public employee, a private sector employee and a public school teacher.I was encouraged to get my teaching degree because I would “always be able to have a stable job”. That is what people told me. It is not true. Even those union protected jobs can be lost for a variety of reasons that have nothing to do with teacher competence. After more than 20 years in the workforce I can tell you that the only thing that gives you job security is being as creative, confident, reliable and competent as you possibly can. Being pleasant and having a sense of humor also helps — ALOT. This is true no matter where I was working or what I was doing.
    2. The people who should teach are the people who know what it takes to succeed in their subject area. But it does take a “certain kind of person” to succeed in the current workplace atmosphere that surrounds school teaching. I think most people who could do something else wouldn’t want to put up with the bull**** most teachers have to endure. Fresh out of college, I was a dedicated teacher and I knew my subject but I was not a great teacher until I had used my subject-area skills to earn a living outside of teaching. My students score high on standardized assessment and are successful in college. I think the experience of being a business owner allowed me to understand the types of skills, habits, and attitudes that are required to be successful outside of a school setting. My students are successful both in and out of school and the lessons I teach in my classroom are founded not only on knowing my subject but also in knowing how my subject fits into the non-school world AND understanding the skills needed to succeed in the pursuit if any number of goals.

    Oh and, if I could afford it, I would home school my daughter because it isn’t just teachers who are hurt by the attitude and policies that currently impact the public school workplace.

  9. Sarah
    Sarah says:

    This post and the ensuing comments fascinate me. Most of my friends consider me to be a risk-taker, some consider me downright crazy and there’s no arguing that I’m a little off-beat (or just plain weird). But then, so is my family. When my parents decided to home educate me it was a risk. They didn’t know of anyone who’d done well in life having been home educated, but they took the risk and it panned out. My parents didn’t specifically raise me to take risks, but they did raise me to question EVERYTHING. And, judging by my life experience so far, that’s the riskiest thing to do in this world.

  10. Latha
    Latha says:


    I love reading your blog and you have raised an interesting question.But you seem to be confusing risk-taking with drama. There are a lot of people with a well developed sense of self and security who can handle risks without drama.Perhaps that is what you need to be cultivating and nurturing in your kids rather than an abstract notion of risk-taking.

    Despite being raised by a sole parent and all our global travels and disruptions, my son has an extremely stable and nurturing environment. He knows (through consistent experience) that he can trust me and more importantly that I trust him to make the right choices (even though he is only 9) and that he can trust us as a family unit to make the choices that fit us and make it work.

  11. KateNonymous
    KateNonymous says:

    Where did you get your information about governesses? I ask because it’s totally wrong, and I hope that if you’re going to homeschool your kids, you’ll do some research into whatever topics you’re studying.

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