On the Cusp of Kindergarten

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Dear Little One on the Threshold of Kindergarten,

I can hardly believe this moment has arrived. You’re fast asleep—your beloved toys scattered around you, a sprinkle of kindergarten magic resting on your pillow. I can just imagine that hidden binky tucked away, ready to comfort you if the mysterious sounds of the night stir you from your dreams. Each morning, I find it and tuck it back under your pillow, because I know it brings you a sense of safety. If we’re being honest, I cherish that secret binky too, for it means you’ll remain my little boy just a little while longer. I promise to keep your secret safe if you keep mine.

Tomorrow marks a significant milestone for us: kindergarten. Just typing those words takes my breath away. I’ve anticipated this day for the last six years, and now it’s just hours away. While I’m confident you’re ready for this new journey, I can’t help but wonder how I will manage.

I’ve often thought about how I would caption that classic “kindergarten, here he goes” photo. Should I go for something witty about what your teachers might be in for, or express my disbelief about how fast time has flown? Yet, as I reflect on this moment, the words that truly resonate with me are simply: Thank you.

Thank you for being my greatest gift. Thank you for transforming my life and helping me discover my purpose. Thank you for making me a mother and for teaching me to value the small moments, while also learning to let go.

You will always be my proudest achievement and my first glimpse of true, unconditional love. It may sound cliché, but watching you grow is like seeing my heart beat outside of my body.

Parenting is an intricate journey. At first, you have this utterly dependent little being who relies on you for everything. Those early months can feel overwhelming, filled with routines and doubts. I once read a mother say, “One day, I will put you down and never pick you up again.” I remind myself of that daily, trying to savor every fleeting moment of your childhood. I know that soon enough, all the sleepless nights and tantrums will fade into memory, leaving me beside an emerging young man. That’s when the real challenge of parenting begins—learning to let go.

Letting go is hard. It requires both faith and courage, and I often find myself lacking in both. The last six years have been a beautiful blend of my free-spirited journey into motherhood, filled with photos, blogs, and adventures. But as you step onto that bus tomorrow, your story will begin to unfold. You will take a significant step towards becoming the remarkable big kid you are meant to be, and a step further from being my little boy.

I will miss our daily escapades—your hand in mine as we navigate the grocery store or our cozy couch snuggles while watching “Curious George.” Yet, I know this transition is worthwhile. I eagerly anticipate hearing about the friends you’ll meet, your new teachers, and all the ways you’ll learn. It’s a bittersweet day indeed; that bus ride signifies you moving closer to being “all grown up,” and all I can do is watch, hope, and pray that I’ve equipped you with the tools to face the vast world ahead.

You’ve got this, champ! If there’s anyone ready to take on life, it’s you. “Oh, the places you will go!” You embody all I ever wished for in a son—intelligent, funny, and a born leader. You possess a unique style and confidence that I hope you carry with you always. So, as you board that bus tomorrow, I won’t cry because my little boy is leaving; I will shed joyful tears of pride for the incredible person you are becoming.

Tomorrow, you will wake up a kindergartner! I hope this school year opens the door to amazing adventures. May you forge new friendships and discover exciting lessons! Always remember Mommy’s rules: Be kind, question everything, and above all, be yourself (minus the “poopy butt” talk and obsession with imaginary guns).

Love you to the moon and back and even more than all the stars in between,
Love, Mommy