Question: “Hi James, I’ve relied on writing in my career and personal life, and it has served me well. But it’s hard for me to imagine that I would have learned it as well or as thoroughly if writing exercises hadn’t been forced on me in school. I can’t imagine a situation where I would have chosen to take a class that required writing more than one or two essays. But since they were required, both at school and in college, I muddled through them and in the process became a pretty good writer.

Do you ever worry that your kids won’t pick up proficiency in things that will serve them well but aren’t very appealing on their surface? Writing essays = not appealing. Being able to write well for the rest of your life = priceless. At least for me this has been true. And as much as I didn’t enjoy certain aspects of school, I am seriously grateful for being forced to write. This is the constant struggle I have between the philosophy of letting children be free, which I adore, and the reality that some things that will likely make life better and easier in the long run are unattractive in the short run. I’d love to read your thoughts on this!”

One Free Family - Letting Go of ExpectationsAnswer: Whew, this is a tough one. I have to admit, I’ve had similar thoughts myself. Over the past 7 years I’ve made a career out of being able to communicate clearly, and I have to think some fairly large portion of my skill development (particularly the written part) comes from my time in formal schooling. By unschooling my kids, am I damning them to a life where they simply never have the option to do the type of work that I have? Am I hamstringing their career choices by not putting them through the same rigorous writing regimen that I was put through in high school and college?

Let’s take a step back for a second, because there is a lot in this email that needs unpacking. “But it’s hard for me to imagine that I would have learned it as well or as thoroughly if writing exercises hadn’t been forced on me in school. I can’t imagine a situation where I would have chosen to take a class that required writing more than one or two essays. But since they were required, both at school and in college, I muddled through them and in the process became a pretty good writer.”

First things first: you almost certainly would not have practiced writing the way you did if you weren’t drilled the way you were. I probably wouldn’t have either. You and I weren’t intrinsically motivated to write essays, and the promise of a potential writing career someday would have unlikely served as strong enough motivation to put us through the paces necessary to develop the same skills we wound up developing.

But what if writing was never portrayed as something you had to do? What if, instead of writing a 5 paragraph essay on the Whiskey Rebellion, you occasionally dabbled in writing fiction, or persuasive essays about causes you cared about? What if a thoughtful mentor asked you pointed questions about what you were trying to convey, and offered feedback about how you could have done so better? Maybe you would have acquired similar skills, but maybe not. I actually think there’s a more important question, though:

What if all that time spent writing when you didn’t want to actually distracted you from some other dream you may have had? I think that, for people like you and me, it’s easy to retroactively go back through our schooling and pick out areas where we developed skills that wound up being useful later on. I also think this is true of many physicists, or accountants, or other people who wind up acquiring skills that are rather difficult to hone thanks to the steep learning curve and rather thankless process of skill refinement.

So we turn into grown-ups, and we notice a demand for our hard-to-acquire skills. We see that we can be compensated well for these hard-to-acquire skills, so we put them to use. And it feels pretty good. After all, it’s fun to be good at stuff, and things could be a lot worse than being paid to do something you do well. It also affirms our life’s journey. There’s some solace in knowing that all that time spent doing things we didn’t enjoy has led to some payoff, rather than considering it a waste of time.

While you and I have “turned out okay,” we’ll never know how we would have turned out without our formal educations. What if there were other dreams we may have had, had we had the space to think of them as a reality? Perhaps I would have become a professional video game player, or a travel photographer, or followed any other number of unknown paths that are typically less traveled. But okay, we can’t know that.

And I actually love how my life has turned out, so wouldn’t putting my kids through similar educational paces be the least risky path for them? I’m not so sure. Let’s look beyond our own experiences for a moment, since we have no guarantees that our kids will have the same interests and aptitudes that we have.

For every person like you or I that achieves some level of marketable mastery in the classic school subjects, there are a number of people who wind up working careers where their schooling is largely useless. I wonder how these people reflect on their time spent writing essays, or doing geometry. I wonder how they felt when getting Cs on essays, and how that impacted their confidence to pursue other endeavors. I wonder how they felt in math classes where they “just didn’t get it,” and how they felt when they saw their peers being praised for academic success as though it was the only thing that mattered.

And now this part: “This is the constant struggle I have between the philosophy of letting children be free, which I adore, and the reality that some things that will likely make life better and easier in the long run are unattractive in the short run.“

I agree with the idea that some things that will likely make life better and easier in the long run are unattractive in the short run, but the important question here is, “Who should decide which unattractive things one does?” Basically anything that our kids decide to pursue will contain to shortage of challenges to overcome. But…

Have you ever noticed the difference between someone who is overcoming a challenge forced upon them, versus the person who is overcoming a challenge they’ve taken on themselves? The former is often resentful, simply going through the motions until they’ve either done the bare minimum to get by or the bare minimum to avoid parental disappointment. This was me growing up. I wound up learning a lot of these skills as a survival mechanism, and some of them stuck with me into adulthood. While I experienced occasional satisfaction in a job well done, I still wonder how my peers who were doing the same work with none of the rewards felt.

Now consider the latter – the person who is working to overcome challenges they’ve taken upon themselves. I’ll give an example from my own life: my son. I watched him try and succeed in the popular video game Overwatch. He was six years old, playing with mostly teenagers and young adults. He had never played a game of that type before, but was determined to improve. He watched videos, talked about his strategies with me, and practice hard every day. He lost hundreds of matches of Overwatch, and sometimes lost very badly. There were some aspects of the game he did not enjoy – like having to place his character in certain less exciting positions, or patiently waiting for an enemy attack, or trying to improve his aim by doing drills. He occasionally got really frustrated, and turned off his console in disgust. He sometimes got bored, and forgot about the game for a week. But after 6 months of incredibly hard work, he achieved the “Diamond” level, which meant he had out-ranked 85% of the 35 million people (again, almost all adults and teenagers) who had purchased the game. Now his Overwatch-specific skills may or may not translate into a career someday, but that’s beside the point.

At the age of six he learned more about the process of achieving mastery than I did in the first 22 years of my life. He learned it by living it. He learned it because it meant something to him. He also eventually moved on past it, and rarely plays the game these days. The next time he encounters something that fires him up that way, he’ll have the confidence to know that he can go from a rank novice to a near expert if he applies himself. Maybe that will be writing, maybe it will be math, and maybe it will be another video game. Who knows? What I DO know is that the market is looking for people who can achieve mastery of things.

In the modern world one can make a living doing almost anything as long as one is willing to put the work in to master it. If we give our kids freedom, chances are good they won’t pursue mastery in the same things we did. This is a very good thing!

Raising autonomous children means giving them the strength to stand firm against societal expectations and pursue the life they would pick for themselves. I also know that happiness often means listening to one’s internal voice, and walking away from things that aren’t fulfilling for us. I delight in giving my children the opportunity to push through hard times when they are motivated to, and to walk away from things where that motivation isn’t present. And if they need to send me their emails for a proofread later in life, I’ll consider that a price worth paying.

James is an unschooling father of three, an entrepreneur, and a Free State Project mover living on the Seacoast of New Hampshire. When he’s not spending time with his own children, he tries to get adults throughout the country to re-think the adult-child relationship through speaking engagements, staff trainings, and his podcast, One Free Family. He continues to experiment with the ideas of child autonomy and self-direction at Camp Stomping Ground, a summer camp he co-founded in 2014.