So, January rolled around and the town moms page was abuzz with excitement —  kindergarten registration is open.

Wait. What?

It’s only January! The school year is nine freaking months away. How is it already time for this decision, this process — this milestone? He is only in preschool 2.5 hours a day, twice a week, and we haven’t even had parent-teacher conferences yet.

How do I know if he is ready for kindergarten?

Having a supposed-to-be-September-24 baby who turned into an actually-August-15 baby (who was also accidentally born a New Yorker because… surprise!) is one of many factors swirling in my mind. He is smart and sweet and chatty and curious — all things that will help him in school and life. But he was also in Early Intervention for the three years following his premature birth, seeing OTs, PTs, and beyond. And he spent an additional year in EI for speech as well as separate private speech therapy through our doctor and our town. Eventually, it all clicked, and now you can NOT get him to stop talking. But, still, none of the milestones from birth to age 3 came “on time” or easily.

So, this kindergarten decision is kind of a big deal! And one I didn’t feel equipped to handle on my own.

Since he is my first to be part of the public school system (after going to an amazing in-home daycare his whole life), I approached his wonderful preschool teacher with my one billion questions. I was prepared for any response she was going to give me on this one, including maybe waiting to send him to kindergarten for another year. He’s a “cusper” — a summer baby who was supposed to be a fall baby. Given his late birthday and whatever her assessment was on his development, I knew that may be a recommendation. While my budget was not ready for this suggestion — one more year of full-time care! — my heart and mind were. I think my gut felt he was ready for kindergarten, but I was open to an expert opinion.

She let me know he is doing great, and she has no hesitation with sending him to kindergarten in the fall. I’d seen all the progress he’d made since starting there in September, and his excitement for going every Tuesday and Thursday. He’s been saying for months that when he turns 5 he gets to take the bus and go to the big kid school. And every time he said that, I would ask myself, Is he ready?

And then I realized. This isn’t the last time I will be asking myself this question. This is maybe the first. Of many, many moments where I will ask if he is ready for something. But the better question may really be, Am I ready?

My employer hosted an event featuring author and CEO Suneel Gupta. As he closed his remarks, he talked about the “game of now,” suggesting none of the extraordinary leaders were ever really ready. Paraphrasing his message: Don’t wait for courage in order to take action; take action, and let courage catch up along the way.

So that is what my son will be doing. And that is what I will be doing, too. 

Is he ready for kindergarten? Well, to kindergarten and beyond!

Colleen Lubin is a native of Arlington, MA, who dragged her New Yorker husband back to the Boston area after years of splitting the difference in Connecticut. She has 15 years of experience in training, development, culture, and belonging in higher education and recently moved into the marketing industry. Colleen is a fierce advocate for women and families navigating infertility, loss, and postpartum challenges. Colleen uses honesty, authenticity, and humor to break down the stigma, raise awareness, and support the infertility community on her blog and Instagram at @notquiteknockedup. Colleen is a mom of two miracles, Liam and Logan, born in 2018 and 2020, who keep her both young and tired. She loves listening to '90s hip hop and R&B, trying new recipes, Peloton-ing, sleeping as much as possible, and eating New York bagels. She does not love writing about herself in the third person, calling customer service, or bagels from anywhere but New York.