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My 5 biggest Montessori teaching ‘fails’ turned into great parenting lessons

Becoming a Montessori teacher was my second career after five years in business and, to be honest, the transition was harder than I thought it would be. I made a lot of important mistakes that first year in the classroom.


These mistakes were hard and incredibly humbling, but taught me so much—about teaching, about children and, now as a mother, about raising a child.

Lesson 1: You can learn a lot from observing your child

When I was first hired, they asked me to sit and observe the classroom to see how the children worked and how the teachers guided them.

Sitting and watching is harder than it sounds. I had so much nervous energy and I feared that the other adults would resent me for not helping when things got busy.

An anxious looking little girl walked by and I enthusiastically introduced myself. She looked at me in horror and walked silently away, as quickly as her little legs would carry her.

It turned out the little girl was selectively mute and rarely spoke, certainly not to bubbly strangers she had never met before.

I should have watched first.

Watching before acting takes practice, especially if it looks like a child may be about to break a rule, but you can learn so much from observing.

Whether it’s an interaction your child is having on the playground or a rule it seems like he’s about to break, taking 30 seconds to look a little closer can save you from all sorts of misunderstandings.

Lesson 2: Building (and reinforcing) connections can help when there’s trouble

Montessori classrooms include mixed age groups, so 3-6 year olds are all together.

Most of the difficult interactions I had my first year in the classroom were with the five and six year olds and the reason is clear to me now—I didn’t recognize the importance of building connections with these children.

The three and four year olds were generally new enough to the classroom that they viewed me as a teacher and listened to me. This was not the case with the older group. They knew I was the new one and it was their job to test the limits. I tried to be stricter, which does not come naturally to me, to show the children I was serious.

Then one day, another teacher gently suggested I sit and have lunch with one of the little boys who was giving me the most trouble.

She told me building connections was the key.

So I sat with him and we talked. He told me about his dog. I got to know him. I built a connection. I still had difficult days with him, but when I did, I knew it was time to focus on the connection.

You, of course, already have connections with your own children at home, far deeper ones than are developed in any classroom. But reconnecting can still be important, especially if you’re apart during the day. So if your child is testing limits or refusing to listen, try spending a few minutes just being together.

Lesson 3: Ask for help when you need it

I spent a good part of my first year in the classroom being intimidated by the lead teacher. I would see how good she was with the children, how they always listened to her and I would hope she didn’t see me struggling.

I watched everything she did and tried to copy it, but I never asked her for help. I was scared to open up and tell her I was overwhelmed.

I should have asked for help.

When I found myself in transition again, as a new mama, I felt the familiar feelings of intimidation and doubt.

Watching a mom effortlessly float through the grocery store with three children while I could barely manage to juggle the shopping cart and my one baby, I thought What am I doing wrong?

But this time, I asked for help. And you know what? It made all the difference. It took a few months, but once I started, I couldn’t stop. I asked moms at storytime questions about nap timing. I asked my former boss questions about independence. I asked my own mom questions about development.

No one ever laughed at me or refused to offer advice. Not once. It turns out people are glad to help, but sometimes they just don’t see that you need it until you ask.

Lesson 4: Allow your child to feel their emotions

One day I was on the playground at school and a very sweet little boy was feeling down about something. He was sitting under the playscape by himself. I talked to him a little bit and then suggested he go play with one of his friends, a little guy he’d told me many times was a “joker.”

“Why don’t you go play with John, he’s always funny, I bet that’ll cheer you up,” I said.

“No. I don’t feel like being funny,” he replied.

Children have many moods and emotions, and that’s okay—we don’t need to “fix” them.

I was trying to cheer him up, but just like adults, children need to sit with their feelings sometimes.

It’s too much to expect them to be happy and fun all of the time. It would have been better if I had just asked him if he wanted me to sit with him or if he needed anything, instead of trying to fix it.

Lesson 5: Believe in yourself

This was the hardest lesson for me to learn.

I gave the children reminders about their behavior. I tried so hard to use the same language the other teachers did. But the children often didn’t listen. I repeated myself. They still didn’t listen. It was so, so frustrating.

I finally realized that when I doubted myself the most, when I felt the most anxious, the children were the least likely to do what I asked.

I had to believe they would listen.

I learned that repeating myself only made things worse. Repeating the same request over and over again just made it clear I didn’t expect the child to respond the first time.

It worked much better to say something once, clearly and confidently and then wait expectantly, maintaining eye contact, for as long as it took.

Looking back, I think what I really learned was that children are people, beautiful little complex people.

They look to us to set boundaries and feel safer when those boundaries are strong.

They look to us for guidance and connection, but want to maintain their autonomy too.

They are at once fragile and strong, just like we are, and it is such a meaningful job to care for them.

Without camps and back-to-school plans still TBD, the cries of "I'm bored!" seem to be ringing louder than ever this summer. And if you're anything like me, by August, I'm fresh out of boxes to check on my "Fun Concierge" hit list. It's also the point of diminishing returns on investing in summer-only toys.

With that in mind, we've rounded up some of our favorite wooden toys that are not only built to last but will easily make the transition from outdoor to indoor play.

From sunny backyard afternoons to rainy mornings stuck inside, these toys are sure to keep little ones engaged and entertained.

Meadow ring toss game

Plan Toys meadow ring toss game

Besides offering a fantastic opportunity to hone focus, coordination, determination and taking turns, lawn games are just plain fun. Set them up close together for the littles and spread them out when Mom and Dad get in on the action. With their low profile and rope rings, they're great for indoors as well.

$30

Balance board

Plan Toys balance board

Balance boards are a fabulous way to get the wiggles out. This one comes with a rope attachment, making it suitable for even the youngest wigglers. From practicing their balance and building core strength to working on skills that translate to skateboarding and snowboarding, it's a year-round physical activity that's easy to bring inside and use between Zoom classes, too!

$75

Sand play set

Plan Toys sand set

Whether you're hitting the beach or the backyard sandbox, this adorable wooden sand set is ready for action. Each scoop has an embossed pattern that's perfect for sand stamping. They're also totally suitable for water play in the wild or the bathtub.

$30

Water play set

Plan Toys water play set

Filled with sand or water, this tabletop sized activity set keeps little ones busy, quiet and happy. (A mama's ideal trifecta 😉). It's big enough to satisfy their play needs but not so big it's going to flood your floors if you bring the fun inside on a rainy day.

$100

Croquet set

Plan Toys croquet set

The cutest croquet set we've ever seen! With adorable animal face wooden balls and a canvas bag for easy clean up, it's also crafted to stick around awhile. Round after round, it's great for teaching kiddos math and problem-solving skills as well.

$45

Mini golf set

Plan Toys mini golf set

Fore! This mini golf set is lawn and living room ready. Set up a backyard competition or incorporate into homeschooling brain breaks that shift focus and build concentration.

$40

Vintage scooter balance bike

Janod retro scooter balance bike

Pedals are so 2010. Balance bikes are the way to go for learning to ride a bike while skipping the training wheels stage altogether. This impossibly cool retro scooter-style is built to cruise the neighborhood or open indoor space as they're learning.

$121

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I've always been a down comforter sort of girl, but after a week of testing the ridiculously plush and aptly named Snug Comforter from Sunday Citizen, a brand that's run by "curators of soft, seekers of chill" who "believe in comfort over everything," it's safe to say I've been converted.

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Our list of 100 baby names that should be on everyone's list this year includes more choices than in the past of names that are obscure and surprising. That's because there are so many more unusual baby names coming into widespread use and baby namers have become a lot more adventurous.

Expectant parents do not need to be told to move beyond Jennifer and Jason. Their thinking about names has evolved to the point that the most useful thing we can do is offer a large menu of intriguing choices.

Here are our picks for the 100 best surprising + unusual baby names now.


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