Blake Boles & kids who don’t fit in the school “box”

Hey, what’s up, everybody? This is Seth, and I’m here today with Blake Boles. If you’ve been following me for any period of time, you know that I’m an executive function coach from Colorado. I help struggling students navigate this thing called school.

My buddy Blake here — who I’ve known for years, though I honestly don’t even remember exactly how we met, probably through the World Domination Summit or something like that — comes from this world of unconventional work and alternative lifestyles. A lot of the people in that community are bloggers, podcasters, authors, or entrepreneurs who don’t follow traditional life paths. Over the years, Blake and I have crossed paths here and there, and now he has a new book coming out that I really wanted to talk with him about.

The reason I invited Blake on today is because the ideas in his work are so aligned with the kinds of struggles that many of the families I work with face. I wanted to ask him some genuine questions that I think my audience will really appreciate.

Blake, what’s up?

“Good to be here.”

Tell everybody a little bit about your work and your website.

Blake explains that his main website is BlakeBoles.com, where he shares his writing, podcast, and projects. He also runs a travel company called Unschool Adventures, which organizes trips for teenagers who don’t attend traditional school. He has written books about self-directed learning, unschooling, alternative education paths, and how students without conventional diplomas can still become successful, functional adults.

Then Blake introduces his new book:

“Why Are You Still Sending Your Kids to School?”

He explains that the title is intentionally provocative. The book is aimed at parents whose children clearly are not a good fit for conventional school, but who still believe they must stay on the traditional educational path.

Before diving deeper into the book, I wanted to frame the conversation for my audience. Most of the parents who follow my work have kids who are 2e, neurodivergent, or struggle with executive function — things like planning, organization, time management, and follow-through. But there’s also a much broader group of kids who simply don’t fit into the traditional school system.

In fact, I had just received another email that day from a parent asking whether they should move their 10-year-old to another school because the child simply doesn’t fit “the box.”

One thing I’ve learned is that finding the “right school” can feel like a complete crapshoot. Families often move their child into what looks like the perfect fit on paper — maybe a private school, Montessori school, or charter school — but once the child gets there, it turns out not to be what they expected.

On the other hand, I’ve also seen kids stay in schools with poor ratings but end up with an amazing teacher who truly sees them, understands them, and helps them thrive.

So many families have been deeply conditioned by the traditional narrative:

Go to school → go to college → get a job → retire.

But for many kids who struggle with executive function or who simply don’t fit the system, school can become a source of real suffering.

Blake responds by pointing out that neurodivergent kids are definitely part of the audience for alternative education, but there are also many children who don’t technically fit that label and are still miserable in school. Some are simply bored. Others are crushed by the bureaucracy and rigidity of the system, leading to anxiety and depression.

Some kids move too quickly for school. Others need more time, more autonomy, or the freedom to deeply pursue one interest instead of constantly switching subjects.

According to Blake, there are countless reasons why a child may not be a good fit for school, and he suspects that the number of kids who truly are a natural fit for conventional schooling may actually be smaller than most people think.

So what are the alternatives?

Blake explains that some families explore progressive schools like Montessori or Waldorf programs, but many of those schools begin to resemble traditional schools once students reach middle school and high school.

He personally tends to focus more on radically alternative models built around self-directed learning. These include programs like Sudbury schools, Agile Learning Centers, and Liberated Learner Centers — small, innovative learning communities that are appearing all across North America.

Blake also discusses homeschooling and unschooling, which is the area where he has spent the most time. In this model, parents take advantage of flexible homeschooling laws to support a child’s interests, passions, and curiosity through self-directed learning.

At that point, I asked Blake to define self-directed learning more clearly.

He explained that self-directed learning means “following the child.”

However, he points out that this becomes difficult for many parents when the child’s interests don’t align with what society typically values. For example, parents are often happy to support self-directed learning when a child is deeply interested in physics, art, or something obviously productive. But things become more complicated when a child wants to spend eight hours a day playing Minecraft.

Still, Blake argues that games can teach incredibly important skills. A game, broadly speaking, is an activity where a child voluntarily takes on challenging tasks simply for the reward of progressing to even harder challenges afterward.

That’s why engagement matters so much.

Children immersed in something they genuinely care about are learning how to focus, overcome obstacles, and pursue mastery. Even if a child obsessed with Minecraft never becomes a professional gamer or programmer, they are still learning what it feels like to become deeply immersed and motivated.

This led into a discussion about how schools measure success. Traditional schools mainly measure subjects like math, science, language arts, and social studies through tests and essays. But there are countless valuable skills and interests that aren’t captured by those systems.

Blake reframes the entire conversation around one word:

Engagement.

When a child is fully engaged, that is where the real growth happens.

He references the idea of “flow state,” developed by Mihaly Csikszentmihalyi — the mental state where someone becomes so absorbed in an activity that they lose track of time and everything else fades away.

As parents, that can actually feel scary because it may seem like the child no longer needs you in those moments. But Blake believes those states of deep engagement are incredibly valuable and worth nurturing.

I told Blake that if I could wave a magic wand and completely redesign how schools are evaluated, I would stop measuring schools based primarily on test scores and instead ask:

“How engaged are the students?”

If engagement became the primary metric, schools would look radically different.

Eventually, the conversation shifted toward what happens after the “high school years” for students who follow alternative paths.

Blake explains that many unschooled or alternatively educated students still go to college. However, they often do it on their own timeline and through less conventional routes.

Many take advantage of community colleges, which Blake describes as incredibly valuable yet underrated systems. Students often begin taking community college classes at ages 16–18, accumulate transferable credits, and later transfer into four-year universities as juniors.

Others take gap years, move directly into careers, or simply delay college until they genuinely feel ready for it instead of “following the herd.”

Toward the end of the interview, I asked Blake what he believes is the main benefit of his book for parents.

He explained that many books focus narrowly on homeschooling or one specific alternative model, whereas his book lays out a broad range of options on relatively equal footing.

He also explores topics that many alternative education books avoid — including parenting research, higher education, and the economic concerns parents naturally have about unconventional educational choices.

Ultimately, he hopes the book helps parents feel less afraid of taking an unconventional path when traditional school is clearly harming their child.

I really loved the way Blake phrased that:

“What’s going to serve the child best?”

Finally, I asked Blake what one concrete step a parent could take if they feel like school simply is not working for their child anymore.

His answer was simple:

There is probably an alternative educational option near you that you don’t even know exists yet.

So the first action step is to go explore. Visit an alternative school, learning center, or educational community for just an hour. Bring your child. Observe how it feels. Even if you never make the switch, simply knowing that options exist can bring tremendous relief.

I closed by thanking Blake for the work he does and for helping so many families rethink what education can look like.