I am constantly writing about the connection between education and careers because that’s pretty much all I think about. How could I not because they are so clearly connected. Look, if you are just wanting your kid to love learning, independent of the need to have a career, then you don’t have to worry about education at all. The human brain is made to learn. Kids will learn no matter what. So you can stop thinking about education at all.

But if you want to prepare your kids to have a fulfilling adult life, a mere love of learning won’t cut it. Educator Isaac Morehouse points out that if we taught kids to ride a bike like we prepare them for careers, it would be a disaster.

First, we’d never buy them a bike. We’d do all the bike riding preparation by having kids learn things that do not involve bike riding.

Then we’d put them on the bike and the second they fall off, we’d tell them they failed and we’d start worrying they’ll never ride successfully.

Morehouse’s piece goes on and on with great examples of how poorly we prepare kids for careers. (But also, inadvertently, he writes that finding a career is like riding a bike. And then it becomes logical that I have photos of riding bikes on every single trip I’ve ever taken with my kids.)

So I’m giving you a list of books I’ve read recently that have great ideas for thinking about careers in new ways so that you don’t have to wait until your kid is 22 before they start to investigate careers.

More than Happy: The Wisdom of Amish Parenting, by Serena B. Miller.
Our farm is in the middle of a huge Amish community. We do a lot of business with our Amish neighbors and see their culture first-hand. There are many things I love about living in such close proximity to people who make such different life choices than I do, but one of the most interesting things we see is how hard the kids work. The kids are all major contributors to the family, even very young kids.

Whenever we go to our Amish neighbors, it spurs a conversation about whether our family should depend more on the kids for labor. I see how good my kids feel when they are an important part of a difficult farm job. Before I moved to a farm I would not have considered putting my kids in a cattle lot and telling them to sort calves. Before I lived near an Amish community I would not have believed kids could look happy and confident working all day in the fields.

The Misfit Economy: Lessons in Creativity from Pirates, Hackers, Gangsters, and Other Informal Entrepreneurs by Alexa Clay and Kyra Maya Phillips
So many of the things your kids do all day might well be considered work in their generation. For example, gaming is now something kids can get paid to do. Crafting is a path to an etsy shop, and learning to download free movies is a path to a coding career. This book teaches us to recognize that play and mischief and work might be the same thing.

Yes, Maria Montessori said this, but she wasn’t thinking of the same type of play that you’ll read about in this book. In fact, I think it’s safe to say that this is a career manual for the kids who got kicked out of Montessori.

How to Raise an Adult: Break Free from the Overparenting Trap and Prepare Your Kid for Success, by Julie Lythcott-Haims
When you prepare your kids for a career it’s so much like teaching them to ride a bike. You can put them on the bike and give a push, but they either pedal or they don’t. They balance or they don’t. They practice or they don’t. You can’t do this stuff for them.

That said, I find that helicopter parenting is enticing since I’m around my kids all day. And because I give career advice for a living. I say I’m hands off, that kids are independent learners, and so on, but actually I watch what they are doing all the time, and so often I find myself putting options in front of them that address my own agenda.

It turns out that this sort of parenting leads to depression in kids (and, I have to guess in parents as well since really, we should be living our own lives). Lythcott-Haims shows us how to walk that fine line between neglect and helicoptering.

And so really, (even though I’m giving you a list of books to help you think about new ways to help your kid find a career) it’s not your job to get your kid a career. And it’s probably your job to get out of the way so your kids find careers on their own.




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33 replies
  1. Erin
    Erin says:

    I loved this: “And so really, (even though I’m giving you a list of books to help you think about new ways to help your kid find a career) it’s not your job to get your kid a career. And it’s probably your job to get out of the way so your kids find careers on their own.”

    I often wish I’d had more freedom earlier in life to fail a lot in a safe environment. When my daughter wants to take a risk, I try to just let her. And, if she screws up or gets hurt, I try to be ready to catch her and help her move on.

    • YesMyKidsAreSocialized
      YesMyKidsAreSocialized says:

      I agree that it is wise to get out of a child’s way so they can find their own career and to not be the one planning their career. But, I think it is wise for parents to recognize a child’s aptitude and encourage them in areas that they do shine and show promise while still encouraging them to try new things.

      If one has a child who shows aptitude in math or science or the arts, the path to prepare a child would and should look very different except for still embracing the mindset of trying out or testing new avenues if a child is open to this. Some children know what they want and don’t want to be steered away from their passions.

      Letting kids fail seems to go against mainstream parenting. Not only do I allow my kids to fail, but I encourage them to fail. Failures are still successes in our family. It is all about one’s mindset. My 6 year old is self-teaching piano and she is going through the books all on her own, I know I will need to prepare for more formal lessons for her in the future if she keeps showing aptitude and progressing and has the desire.

  2. malaika
    malaika says:

    “I would not have believed kids could look happy and confident working all day in the fields.”

    loved this. It makes me happy that you write about how farm work and agriculture can be parallel paths to fulfillment alongside the office job.

  3. Jim Grey
    Jim Grey says:

    I think there’s a lot of usefulness as parents to expose our kids to things that might light their fire and to talk with them about needing to support themselves one day and finding a direction that will do that.

    My youngest son was interested in video editing for the longest time, but struggled to get anywhere with it. Then I noticed that when he was bored he cooked up algebra problems and worked them out on pencil and paper. So we had a talk about mathematics as a direction, from practical to theoretical. My eminently practical son is looking at accounting, to see if he likes it.

  4. Tracy
    Tracy says:

    I like the bike analogy for careers.

    My son learnt to ride a bike in quite a different way than I did as a child. I had a bike with training wheels and only learnt to ride when they eventually fell off, one by one. In contrast, he started with a balance bike, which meant he could propel himself along independently from a young age and slowly get used to lifting his feet up on the downhills. So by the time he was 5, when he tried a proper bike with pedals, he didn’t have to try to learn to balance and push at the same time, and as a result was off and cycling in seconds – I didn’t have to teach him. It was yet another case of my parenting preconceptions being shattered, for the better.

    So applying that to careers that would mean my role is:
    1) Help him take advantage of modern techniques and technology that genuinely help develop skills (aka buy him a balance bike)
    2) Give him access and opportunity (aka take him somewhere he can ride, increasingly challenging)
    3) Provide smiles, thumbs up and other forms of silent encouragement (aka stfu)

    • Zellie
      Zellie says:

      That’s how my son learned too! He couldn’t even pedal a tricycle at age 3 but was off on a 2-wheeler at age 5.

      • liz mom of 5 under 10
        liz mom of 5 under 10 says:

        One of my sons used a balance bike for a bit and was riding a 2 wheeler by age 4. My next son used the balance bike twice and then hopped on the 2 wheeler and taught himself on our deck in a couple minutes. We just bought him his own 2 wheeler and he turned 3 this past March!

  5. YesMyKidsAreSocialized
    YesMyKidsAreSocialized says:

    Thanks for the book recommendations and I agree with the career analogy. Why wait until after college for them to figure out life? My kids have the freedom to explore the world now (with age appropriate boundaries) and figure out who they are and what they enjoy in life with very little have-to’s and zero “shoulds”.

    I speak with so many parents in their mid-late thirties who still don’t have an idea of what they really want to do in life and struggle to find meaning. When one is controlled by such external forces like school for the majority of childhood, adolescence, and pre-adulthood it makes sense that once those restraints cease to exist that one can feel a sense of no identity.

    Unschooling allows children the freedom to be independent and make real choices about what, when, and how they want to learn so they will have a strong identity early on.

    (Here are a few books that I like by Alfie Kohn:

    -Unconditional Parenting: Moving from Rewards and Punishment to Love and Reason

    -Punished By Rewards: The Trouble with Gold Stars, Incentive Plans, A’s, Praise and Other Bribes

    And this book is great:
    -Raising Your Spirited Child: A Guide for Parents Whose Child Is More Intense, Sensitive, Perceptive, Persistent, and Energetic)

    • Bostonian
      Bostonian says:

      Control seems to me to be the key question as well, YMKAS.

      Despite how much some folks here might slag off universities, your husband made good use of one when he went back to one for a mechanical engineering degree. Ideological expostulations notwithstanding, he could not have the exciting career he has now without having gone to university for his degree.

      As a counter-example, when I taught at universities I met numerous kids who had no business being there. They were floundering, aimless delayed adolescents whose appearance at university was the inevitable destination of the channel they were pushed down by their parents and schools. If they held on tight they might get a credential at the end that someday could be some help at maintaining a middle-class existence. Or, just as likely, they would fail to acquire anything but debt.

      The key difference between the examples seems to be control. At the same university your husband used as his tool, many other students could be the ones being used.

      A young man in my house has declared he wants to be a mechanical engineer. I have done what I can to explain the things he’ll have to do in order to make that a reality. We have pursued his homeschooling with an eye on the entrance requirements to MIT.

      This is school talk, but it’s also career talk. He can ‘ride the bicycle’ all he wants to – and it will help with entrance as well as understanding – but he will still need to go to university to get a degree if he wants to pursue that profession. Like your husband did.

      Recently my son also declared he wants to go to school in seventh grade. He wants to go to a difficult, competitive, uncaring school famous locally for both the achievements of its graduates and the number of its dropouts. I was surprised by that announcement.

      I wonder whether this choice is an example of “the freedom to be independent and make real choices about what, when, and how he wants to learn.” It might also be an example of a kid being drawn along by his peers. Or a kid who is sick of his grumpy old dad. But mostly I believe it is the action of a kid who is at a crucial period of developing self-determination trying to figure out the best course toward his goals.

      How old does one have to be to use school as a tool, rather than being used by school?

      • YesMyKidsAreSocialized
        YesMyKidsAreSocialized says:

        Your son sounds quite remarkable and it seems like he is well-informed of the steps needed to get on the path he would like for his life. You asked an interesting question, “How old does one have to be to use school as a tool?” I would answer that I personally think it has less to do with the age of a person, and more about the mindset that one has.

        I agree that many people enter college/university for the wrong reasons, following the crowd, doing what they are expected to do, or parental control. But those who have the right mindset and have some goals are the ones using university as a tool, they are the ones getting internships in their field straight away every summer, joining rocketry clubs etc.

        7th grade seems like a great year to test the waters of school to see if he feels he needs to dumb down to make it through and fit in, and is he willing to make that trade off? Or if this is a Phillips Academy of sorts, will he find a group of outliers like himself to help get through the control that is being exerted over them so that he can thrive. Since 8th is when things “start to count” if one wants to go down the traditional path of university right after 4 years of high school, 7th is like a “free” year of trying things out.

        In a lot of ways our families seem to do things very similarly. We also talk about career paths and how to get there. My oldest also wants to be an engineer–not sure on specialty since she is having fun designing video games right now. I am clear with the path she will need to take, but I try to look for short cuts to help her get it over with… for instance, bypassing high school completely and going straight to university if she wants. Right now, there are very little have-to’s, but we emphasize hard work that people put in to be successful. Right now she is into programming. For video game design, it’s not click and drag like Scratch, it’s typing in code and staring at a screen all day, not much fun until you see the end result that makes it worth it. Intrinsic motivation is what is innate to her. The payoff for hard work and self-teaching this very difficult subject is seeing successful results after having a frustrating beginning where mom is zero help and she has to tinker to get things to work right.

      • Katarina
        Katarina says:

        This is a tricky question, especially with MIT. They make a point of saying that they don’t want kids to choose a path to impress the admissions office. But then I see self-made brilliant people get turned down and relatives of faculty who are smart but not distinguished get in. Places like MIT look for people who fit their idea of an MIT person. The student who got turned down is thriving at another prestigious school and with a hefty scholarship. This is hard to navigate but I agree that kids have to buy in and want to make their education count in a competitive way if they have their eyes set on competitive schools. It is simply the name of the game.

        • YesMyKidsAreSocialized
          YesMyKidsAreSocialized says:

          Caltech and others have been known to gravitate towards kids with alternative paths. I know on a personal level one tween who was accepted to Caltech and USC but chose to continue self-directed learning for now.

          I can’t speak for Bostonian’s son and MIT but it seems like they are well aware of the trade offs that have to happen in order to get there.

          • Katarina
            Katarina says:

            I hope I didn’t sound like I am implying that they don’t know that. My comment was meant sympathetically, not instructionally.

          • Bostonian
            Bostonian says:

            I’m not talking about some kind of kremlinology or second-guessing. MIT is a top engineering school that happens to be local to us (my wife works blocks away, and it’s an easy bike ride from our house). By the time my son applies for university, he will likely have had multiple learning experiences there, and he already knows many people who work or study there, or who are graduates. MIT exercises authority in our community.

            MIT has uniform admissions, no matter what the student will be studying – majors are declared during freshman year, not prior to admission. Its admissions suggestions are also very clear. Their page What to Do in High School includes good suggestions for anybody who imagines they would like to study engineering there or elsewhere. If one is homeschooling, without a pre-set curriculum, it gives one a good idea of some of the material one should try to master if one’s intended path involves such a university.

            For example, their suggestions include “Math, through calculus.” That’s not something you can quickly cram in at the last minute. If you expect to master math through calculus in High School, you have to start accelerating with regard to the standard curriculum years in advance.

            Now, I haven’t tried to turn my son into some sort of mathematical dog-and-pony show, as some do. I am pleased he hasn’t shown any sign of being a prodigy. But he does understand, from observation of our society, professions, and realities such as the admissions recommendations of MIT, that if he wants to pursue the path he fancies for himself, he must work to learn math, and he has. He has enjoyed algebra and geometry very much, and looks forward to continuing study.

            Their suggestion of study of two years of a foreign language also impressed on him how useful it would be to begin studying now. He will have two years down and be well on his way to fluency by seventh grade. I can’t wait until I can share some of my favorite Spanish-language literature with him.

            We don’t see MIT just as the prize in some grand worldwide competition – which it also, undeniably, is – but as a key resource local to us which already provides us with guidance, teachers, and inspiration.

          • YesMyKidsAreSocialized
            YesMyKidsAreSocialized says:


            I trust that as a fellow INTJ you know your stuff when it comes to MIT, even I have researched admissions to MIT quite extensively over the years and it isn’t even within biking distance. So I have no doubts you and your son know what the minimum admissions requirements are.

            I’m a little worried though, about what happens if he doesn’t get accepted to MIT, will he be ok?

            Sharing an alternative path, my husband went to college in his thirties to study mechanical engineering. He went to a lowly state school in CA, it wasn’t even ranked because they don’t offer PhD’s in engineering there. But he was able to get student engineering positions where he could work as many hours as he wanted doing real engineering work while going to school full-time. He then got hired with the aerospace company he was an engineering aide at for two years. From there he worked himself into management a few years later and then SpaceX nabbed him a few years after that. SpaceX prizes itself on the fact they recruit the top 5% in the field. Where one goes to school is only a part of the equation. So just in case MIT doesn’t happen he can still be successful anywhere with the degree he wants. I know several people who were recruited by SpaceX when they were attending Embry-Riddle as an example.

            I’m rooting for you guys! :)

        • Bostonian
          Bostonian says:

          YMKAS, if my son holds to his path, applies to MIT six years from now, and then learns he has not been accepted, I expect he will do the same thing he did when he wasn’t cast in a lead role in this summer’s musical, despite his smashing audition performance. He will throw himself down on the couch and cry his eyes out. And then, the next day, he will start talking about the positives (e.g. but look how many lines I have). He will accommodate himself and do the best with what he’s got.

          Katarina, you have it right: charting one’s course is exactly the point. We were sailing this weekend, and my son was setting our course by the buildings and bridges visible from the harbor. MIT makes an ideal point of reference for him right now. There’s a lot of time between now and university, and his intellect and technical skills will develop along with his versatility, creativity, and leadership. Don’t worry about him, because I don’t.

          • YesMyKidsAreSocialized
            YesMyKidsAreSocialized says:

            B, I didn’t realize he was already beginning 7th grade! I thought he was a little younger than that. Wow, so he begins B&M school this fall?

          • Bostonian
            Bostonian says:

            YMKAS, my son just turned 11 and will be (homeschooling) in sixth grade this fall. He will be in seventh grade (putatively, brick&mortar) next fall, one year from now. He will most likely apply to university in the fall of his 12th grade year, six years from this fall. I just counted that on my fingers, and I’m pretty sure it’s correct.

          • YesMyKidsAreSocialized
            YesMyKidsAreSocialized says:

            Ha! Yep, my math was starting on the tail end of things.

            Your son sounds like such a sweetie pie. :) I hope he has a great time with the theatrical part he did get! Happy birthday to him.

          • Melissa
            Melissa says:

            Your son can also apply again. It took me multiple tries to get into my university of choice (not MIT, but it has similar initials).

            If it’s the right school for him, it’s definitely worth waiting (a year or so) for.

      • Katarina
        Katarina says:

        Just wanted to say that I appreciate your comments very much and have a similar story with my 7th grade son. I do think that setting the bar for MIT is a great means of charting one’s course. I don’t think it makes sense to do it any other way. I am just lamenting that their process isn’t exactly as fair or rational as they make it out to be. I know from first hand experience that a relative has an advantage and that someone who even exceeds their expectations may not get in, simply because they don’t perceive the person as “their type.” This was language that was used in talking to me. My bottom line is that it is useful to my son to have their bar set before him (as well as the bar of all the engineer relatives he has, including 3 from MIT) but I also believe that for the dear student (homeschooled, but I don’t think that was held against him) who is a phenomenal scholar and person who didn’t get accepted, there are just things that are out of our control. That particular student is happier where he is for other reasons, anyway. All of this is to say that when kids hit the age of pursuing their goals, it is deeply rewarding to see them finding the path and making decisions, no matter how tricky the circumstances may be. I’m sure that your son will lead a very exciting next six years and whatever lies ahead will be his own wonderful story. (BTW, my husband also teaches engineering at a “prestigious” school so he is a bit skeptical about the whole admissions process, too.) Please forgive anything I say here that might sound preachy or annoying. My intention is to chime in with support and admiration. Sometimes I may fail to achieve that tone.

        • YesMyKidsAreSocialized
          YesMyKidsAreSocialized says:


          What do you mean “their type” when referring to MIT? I have a hard time reading between the lines sometimes. Would you mind elaborating?

          • Katarina
            Katarina says:


            I wish I knew what “their type” means. I did ask, but I didn’t get a very clear answer. I guess it is almost like a job interview, at some point. They want to bring in people who seem like they have the personality to fit in. But I am only guessing. When I think about it, probably most elite private/competitive schools work that way to a greater or lesser extent. I spent a lot of my professional life in a state university setting and so I didn’t see that dynamic playing out. As the saying goes, whaddayagonnado….

  6. Jay Cross
    Jay Cross says:

    The best quote in the Morehouse post was…

    “Kids would hear the history of bikes, mostly from professors who hate bikes.”

    Dan Aykroyd captured the problem succinctly in Ghostbusters:

    “Personally, I liked the university. They gave us money and facilities and we didn’t have to produce anything. You’ve never been out of college. You don’t know what it’s like out there! I’ve worked in the private sector. They expect results.”


  7. Karelys
    Karelys says:

    Ugh I hate to feel like a groupie but whatever. I’m not going to tone it down. I whole heartedly love this post!

    Not only it makes me look back on my childhood and pick out times when this was true for me many times but it makes me look to the future and feel giddy and hopeful.

  8. Mark W.
    Mark W. says:

    I agree with the last paragraph – “And so really, (even though I’m giving you a list of books to help you think about new ways to help your kid find a career) it’s not your job to get your kid a career. And it’s probably your job to get out of the way so your kids find careers on their own.”
    However, I would add it’s your job to prepare yourself and be knowledgeable to act as a guide when your kid starts asking questions and is ready to have discussions about careers. It’s about quantity time from which quality time is derived and you know your kid well enough and you are present for him/her when they take the initiative. How and how much you want to bring up the subject of careers is when you start walking a fine line and is somewhat tricky.

    • jessica
      jessica says:

      Jeb Bush was asked directly about how he approached education with his own family (they went to private and boarding) in his Amazon prime interview.

      He said people think it’s quality, but it’s quantity (something he regretted).

      Funny enough his whole interview talks about the need mass disruption of education to break the system, but he fails to mention that it’s happening already through HSing.

      • Mark W.
        Mark W. says:

        I did a search using keywords Jeb Bush and homeschooling and found this quote from his campaign in 10/2002 – “I fully support empowering parents to determine what is best for their children’s education, and have always been an advocate of home school education. Parents in Florida have long had the right to educate their children themselves. Under my administration, the rights of home-schooled children and parents have been strengthened.”
        It sounds good on the surface. However, it says nothing about any regulations that may be associated with such a statement. I’ve read numerous articles where he has been identified as a strong supporter of Common Core. Many parents are pulling their children out of school due to the implementation of this nationalized education program. I’m not surprised he didn’t mention homeschooling as being disrupting and revolutionary in the education of young people. Also, based on his other political beliefs, I don’t believe he would be an advocate of child-directed learning. He appears to me to be more a proponent of structured learning.

  9. Mark W.
    Mark W. says:

    Also I wanted to add that I thought the two links within Educator Isaac Morehouse’s article were very good. I got more out of the links than the article.

  10. Justin
    Justin says:

    Looking back on how I was raised I think the two most significant factors, that will carry on with my children is: perspective and trying a lot of different things.

    Kids only know their own situation for the most part, exposing them to different perspectives would be a good way to start growing their gratitude muscle.

    As cliche as it may sound, I still believe that passion in what you do for a living is still the goal. Trying many different things will hopefully expose a hidden passion the child can pursue.

  11. Debbie
    Debbie says:

    “How to Raise an Adult: Break Free from the Overparenting Trap and Prepare Your Kid for Success”, fantastic. I feel like I read this just in time. My daughter is starting 9th grade. I knew how to not be a helicopter parent when stakes were lower (Elementary) but was freaking out for her as academic work got harder. Now I know how to pull back so she can step up. Thank you!

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