Five Things I Wish I Knew When I Started Homeschooling


My kids and I began homeschooling halfway through the school year when I left my Montessori teaching job, and at first I invested all my energy into re-creating a small classroom in my living room.  I had visions of my children happily engaging  in my inspiring lessons. But instead of harmony and joyful learning, there was apathy and avoidance of anything that remotely resembled what they knew as school.

Humbled and defeated, I gave up my visions of my one-room schoolhouse. I wiped away tears of frustration (there were many!) and decided to just live and love without expectations.  Here’s what I discovered...

#1: Nothing happens without connection (two types)

Interpersonal connection: If we want our children to care about and pay attention to what we think is important (aka, academic learning), we FIRST need to pay attention to what matters to them. Children deserve to know (not just think, but know) that we value them for who they are right now, regardless of what their potential is or how well they perform. 

When they’re secure in the knowledge that they have nothing to prove to us, we’ve removed a huge roadblock and their natural curiosity returns. But beware: this human drive emerges shyly, like a skittery mouse peeking out from its burrow.  At the smallest hint of danger, it goes back into hiding.  Our unconditional love and acceptance must not be a facade, but a true transformation from within. And this can only happen if we’re willing to sit with our fears and misconceptions about education and success.

Intellectual connection: When I realized my children weren’t ready to learn what I wanted to teach them, I decided to learn what they wanted to teach me.  I sat down to play with them and noticed that I would feel bored and start drifting towards my own priorities if we were doing things that didn’t align with my interests.  And it struck me that they must feel the same way when we’re pushing academics that don’t connect with their interests.  I realized that I either had to share new knowledge in ways that appealed to them (through stories and experiences), or I had to wait for their questions. 

That led me to my second discovery…

#2: Learning happens when you least expect it

It took me almost two years, but I’ve finally accepted that most of my “Montessori lessons” aren’t going to take place around the rug or homeschool table, Instagram-style.  Instead, they’ll happen... 

  • In the middle of a crowded store (“Mommy, how did people figure out which foods were poisonous?”); 
  • As I’m trying to parallel park on a busy street (“Mommy, why did people think the Earth was at the center of the Universe?”); or 
  • When I’m putting the groceries away while cooking dinner and thinking about a topic for my blog (“Mommy, where do babies come from?”).  

I’ve learned to capitalize on these golden opportunities, and I’ve removed as many barriers to learning as possible.  I now have no qualms about plunking down the five-chain next to a plate of pasta when my little one wants to learn to skip-count halfway through lunch. I’m happy to cancel a playdate and sit for hours beside a fire extinguisher as my eight-year-old explores states of matter with candles and matches.  And I’ve learned to say yes, or at least “Tell me more about your plans”, to pretty much anything my children are curious about.

#3: You can’t control your children, but you CAN control their environment

When I channeled my time and energy away from fretting about my children’s education, and towards preparing an inspiring learning environment, spontaneous learning happened.  We are the keepers of their environment; we have the privilege and obligation to choose what enters their minds and their hearts.  

Preparing an environment doesn’t mean putting rows of cards on shelves; it means choosing books, objects, and activities that will kindle their curiosity.  And just as importantly, it means restricting or banning obstacles to their healthy development.  One caveat: Murphy’s law of homeschooling states that the more time and money you spend preparing a material, the less interested your children will be.  Focus on experiences, not teaching tools.  

#4: Adults need deschooling more than children do

Deschooling is the period of time in which new homeschoolers refrain from structured academic learning and focus instead on following the child's interests. The goal of deschooling is to break free from the mindset that tells us there's a specific time, place, and method for learning. The rule of thumb in homeschooling circles is that children need one month of deschooling for every year they’ve been in school (including preschool).  

If we apply that same rule to adults (and why shouldn’t we?), then we’re looking at 16-20 months of reassessing our views on education.  This timeline has proven accurate in my case, and while I worked on myself, my daughter taught herself to read, write, and add with her brother’s help, while my son taught himself more astronomy and engineering concepts than I’ll ever learn, and developed masterful language skills through reading and listening to audiobooks.  We’ve cooked, gardened, read entire novels in one sitting, made bubble solution, played with balloons, looked at clouds, and made fire in a pot.  And slowly...clumsily… organically...a homeschool emerged.  A homeschool that looks nothing like yours or anyone else’s. Because no two homeschools are alike.

But, you ask… What about “academics”?!

Sometimes there’s a need to lead your child in more structured learning, of the type most of us experienced in school.  That kind of learning is dependent on everything I’ve been writing about.  

When you let them have experiences and think for themselves, they’ll realize they need certain skills to keep making progress. And since they see you as a non-judgemental resource, they’ll come to you for guidance. Because you’ve spent your time focusing on the learning environment, you’ll be able to connect them to the tools they need. And since they know that you care about their priorities, they’ll be more receptive to yours.  

It’ll be messy and non-linear, but it will happen. And in contrast with conventional schooling, it will happen without bribes, threats, or punishments.  But only if you let it.

And here’s my final piece of hard-earned wisdom…

#5: Nature is the great normalizer

In Montessori, normalization refers to the state of peace and harmony children reach through engaging in work that aligns with their developmental needs.  My children have spent countless hours playing in nature and I’ve come to see the wild outdoors as the original prepared environment.  In nature, even the most jaded children demonstrate curiosity, respect, and a desire to work unbelievably hard to meet their goals.  

The irony in writing this essay is that you will need to learn all this through experience.  So my goal is simply to let you know that you’re not alone through the process.  Honor each phase of your journey, give yourself grace, and let yourself feel.  Embrace what’s working and let go of what isn’t.  Trust yourself and your child; we’re homo sapiens, the knowing human.  It’s in our nature to learn.

Are you ready to move from confusion to confidence in your Montessori homeschooling journey? Then join me in The Montessori Homeschool Hub, the only membership and group coaching program designed to help homeschooling families reap the benefits of the Montessori approach without the need for prior teaching experience. Harness the power of Montessori and at-home learning!


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