Friday, 2 October 2026

The Last First Day: What my Son Starting Preschool Taught me about Letting Go.

 


There is something different about doing something for the last time.

Today, my youngest started preschool.

Five years ago when my daughter started school, everything was new. She was my first and every milestone was a first for me too—first steps, first words, first time eating ice-cream, first time playing with bubbles, and her first day of school. There was an excitement in watching her grow and a curiosity about what came next.

My son is my second…and my last, and I’ve discovered that milestones feel different when you know there won’t be another little one coming behind.

I was fortunate enough to spend this chapter of my life home with him, and for the past three years he has been my little sidekick observing me through all of life’s changes. Every…single…day. We have kept each other company and watched each other grow. Today, I left him somewhere without me.

I’m excited for him. I want him to make friends, learn new things, and have experiences that don’t include me. I want his world to expand beyond the bubble we have created and the safety and familiarity of home, but I hadn’t quite anticipated that watching his world expand would mean accepting that I would occupy a slightly smaller place in it. There is something surprisingly heartbreaking about that.

This experience has made me think about how many of life’s beautiful transitions carry a quiet grief with them. We can be excited about getting married and starting a new life and still be sad about saying goodbye to the independence of our single lives. We can desperately want to start a family and have more children and still occasionally miss the freedom and carelessness of the people we were before having kids. We can know that it is time to leave a job, a place, or even a version of ourselves behind and still experience the leaving almost like a breakup.

Perhaps that’s because moving forward always asks something of us. In order to begin something new, we often have to accept that something else is ending, but life has taught me that those feelings don’t cancel each other out. They can and do coexist.

I don’t have to be less excited for him because I’m sad for me. I don’t have to want this chapter back in order to grieve that it’s over. I can know that he is ready, that we are ready, and still feel the loss of something that has been extraordinarily precious to me. There won’t be another first preschool drop off, another three years like these. And all those ordinary days, the ones that sometimes felt incredibly long while I was living them, have quietly become something I can never go back to. We spend so much of life looking forward to what’s next that sometimes we don’t realise we’re living something for the last time until its over.

All week we wondered how today would go. Would he cry? Would he want us to stay? Would he settle? Would be okay without us? This morning, he was excited to go. There were some tears when we left…him…and me…and apparently a few more after we were gone. The hours between drop off and pick up seemed longer than it was and then it was time to see my precious baby again. He was happy to see us, excited to show us what he had done at school. A handprint, his “paw print” as he proudly called it.

I had spent so much time wondering whether he was ready, and it turned out he was more ready than I was.

This morning, I left my last baby at preschool. This afternoon, I picked up a little boy who has lived several hours of life I knew nothing about. He cried a little and then he carried on. He played, participated in class, helped the teacher, and made something with his own little hands. Without me. And he was okay.

And maybe that is how letting go happens, not in one enormous goodbye, but in a thousand little ones.

Their world gets a little bigger while ours changes shape. And somewhere between holding on and letting go, we both become someone new.

~


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