Crowdsourced Kindergarten Advice + Encouragement

My beautiful, sunshine-filled, energetic, sensitive and brave five-year-old daughter is starting kindergarten next week. WHAT?!?! HOW?!?! You’ve probably heard the (paraphrased) Elizabeth Stone quote, but I  feel it so tangibly right now: “[To have a child is to] forever have your heart go walking around outside your body.”

I feel like I’m growing up alongside Lucy — the same person I’ve always been, but also a different version of myself now as a mother. The same me, but evolved and refined. continuously learning and growing and adjusting. Gosh – this is a new and very bittersweet season for our family.

I know my IG community is filled with wise parents who have already gone through this big transition to kindergarten and ‘real school’, as well as mamas like me who are going through this experience for the first time! I asked the question below and was so comforted by the wise, encouraging, loving words I  received from other parents.

“What do you wish you would have known or what advice/encouragement do you have for someone as their kid goes to kindergarten?”

The responses ranged from practical and tangible (ie books, etc.) to emotional, but there’s a lot of goodness in these words and I  wanted to compile and share!


Order Matching Bracelets! Just search ‘The First Day of School’ bracelets and you’ll see a bunch of options! Lucy loves jewelry and I knew would love this. I ordered this bracelet set and we’ll each wear one bracelet to us of each other throughout the day.

Take ‘First Day of School’ Photos BEFORE the actual first day of school. This is absolutely something we’ll do! I know that I’ll want photos documenting this big milestone, but also know that asking Lucy to pose for a photo and putting pressure to ‘capture the moment’ on an already emotionally overwhelming (early!) morning is a recipe for disaster. We’re going to do a first-day outfit try-on the day BEFORE school, and take ‘First Day’ photos then! P.S. This is a really cute customizable first-day-of-school sign!

Write a short encouraging note and put it in their lunchbox or pocket – reminding them you love them and will see them soon!

Print a Family Photo and put it in their backpack. Lucy loves displaying/carrying photos of us as a family so I have a photo printed she can keep in her backpack. Even if she doesn’t get to see it during the day, she knows it’s there. I’m also going to send her a little magnet in case she’s able to hang it inside her little classroom locker.

Read Books about Kindergarten/Going to School. Some top recommendations were:

Get in the classroom – find a way to volunteer in the classroom or school early in the school year.

Make Drop-off a Short and Positive Experience – obviously, it’s normal and okay to be sad! But try to put on a brave face for your child during this very new experience! Remember lots of parents are crying in their car or at home, too.

Write a letter – write your child a letter (and save it) on the first and last day of school.

Make Friday a CHILL night at home. They will be wiped after a long week — get in the habit of making Friday a low-key night at home as a family. We already have a Friday movie night tradition most weeks, so will definitely be continuing this!

Play on the school playground before school starts or after school on a regular basis to make it a super comfortable place.

Let them try free lunch! Saves money, and time in the morning, plus gives them extra independence that they might be craving.


Keep after-school plans and activities to a minimum, especially during the first few weeks. This was a piece of advice SO many people told me – so definitely something we’re planning to keep in mind!

It’s totally normal for kids to fall apart at night after holding it together all day.

It could go either way – kids might not remember or share anything from their first day(s). And others will be eager to tell you all of it. Hold space for wherever they are at.

“Friends will happen. She will not be alone. It’s hard to watch kids struggle but it’s good for her to experience the process of making new friends, even when it’s hard.” Here’s a book recommendation about making friends: Growing Friendships: A Kids’ Guide to Making and Keeping Friends 

If your child has a bit more separation anxiety, remind them that you always come back. Sing a song together or have a mantra to repeat before school. I’m reminded of a little song my mom sang to my sisters and me for years: “Sometimes my mommy takes me over to another friend’s house [or school] to play. Sometimes she’s only gone a little while, and sometimes she’s gone all day. But my mommy comes back, she always comes back, she always comes back to get me. My mommy comes back, she always comes back, she never will forget me.”

Be extra patient with her (and yourself) ❤️


“Like most things: The anticipation is worse than the actual event.

“It’s okay to let go.”

“It’s okay to be sad. This is a HUGE and new experience.”

“Kids’ confidence, independence and willingness to try new things will grow so much. Their personalities will blossom. Getting to watch them grow in new ways is SO special.”

“ITS FUN! It’s so good. You will be amazed at what they accomplish and become.”

“They are in great hands. They are cared for, supported, challenged, and educated by people who love their jobs and love kids.”

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