Lessons On How To Let Go


The beginning of a child’s school-going years present a major transition in his or her life. For the first time, your little one will be expected to follow a stranger’s authority (the teacher), to focus on a task of learning that he may not prefer, and/or to mingle with other children who are as yet strangers to her. And all this without the reassuring presence of Mummy or Daddy around.

It’s therefore not uncommon for children to experience some measure of separation anxiety when they begin school, ranging from teary eyes and some clinging to full-on “No I don’t want you to go!” rants, screams and kicks. I even know a friend whose daughter started crying about not wanting to go to school the next day every evening for over a week!

These are tough times – both for your child and for you, the parents. It can be extremely disheartening to see your child in this state, and to feel powerless to be of much help. How do you balance comfort with encouragement, consoling with challenging? What can you do, knowing that this is a natural phase of independence that your child may need to go through himself?

There are no easy answers, really, because every child is so unique, and the fears and struggles he or she may have can be very different. Do know, however, that you are not alone. So many other parents are in the same “boat” as you, each one learning how to let go, learning how to encourage growth, learning when to be a safe harbor for their child’s emotions and yet to challenge them to sail alone.

We’ve asked three mothers to share with us what those first few tough days of school were like for their child.


 Lyn, 34, is a full-time working mum, with two daughters aged 5 and 3 years. Her younger girl, B, started school (Nursery) this year.

Lyndis girls

1. How did you prepare your child for the first day of school? 

She had been tagging along occasionally since last year, when we sent our elder girl, K, to school. She would offer her hands to be checked as part of the health-check routine, as well as attempt to enter the school!  So we thought that she was quite ready to start school. Still, we diligently prepared her by reading books about preschool to her, and she kept telling whoever would listen that “B is going to school next year, you know.”

I was quite heartened and thought that it would be a relatively easy transition for her. Besides, she has always been quite sociable. So I thought there would be minimal separation anxiety when the first day of school came.

2. What was the first day of school like?

Alas. On the first day of school, she wailed!  Like many of the other children who were starting school for the first time, she experienced separation anxiety and cried buckets.  Thankfully, the school had arranged it such that the first two days of school were only 2 hours long, instead of the usual 4 hours! The teachers sang songs and tried to engage the kids and orientate them to their new surroundings.

I wasn’t very emotional, having gone through this before with K – I felt more embarassed than anything, that she was crying so loudly!

3. What challenges did you face during the initial days and weeks? How did you cope?

My little B was a persistent wailer. Every morning for 2 weeks, she would still cry when I left her in school.  During the first week, she would also cry sporadically during class. She would be okay after a short cry, and apparently participated and enjoyed school, based on what the teachers told me.

Every day, I would smile, say a cheerful “See you later!” and hand her over to her teachers calmly (no matter how dramatic her cries were). No extended hugs, teary (on the parents’ part) goodbyes, or lingering at the door after she went in. The school advocates this form of short and sweet farewell, and I agree. Cold turkey works best, I believe. I might have appeared callous, but I think creating a matter-of-fact transition is the fastest way for a child to adapt. After all, it’s nursery! The best period of school in a kid’s life with fun, games and hardly any stress!

In the evenings, we’d chat about how fun school was, how much her teachers enjoyed having her in class, and how great it was to have friends to play with, and how there was absolutely nothing to cry about.  After ten days, she stopped the persistent five minutes of crying at drop-off. She took longer than expected to adapt, but I was glad that she eventually saw the light and is now going to school cheerily.

4. How do you feel now that your child is attending preschool?

I am glad that she has got a wonderful kindergarten to go to, where the teachers are competent, caring and experienced. I think this will probably be the most carefree period of school that she will have, where she can learn at her own pace, pick up the wondrous gift of reading, and have lots of fun with innocent little friends.


 Kelly, 37, is also a full-time working mum, with three boys aged 8yo and 4yo, and 15 months. Like Lyndis, she had the benefit of experience with her eldest son to fall back on, when it was time to send her no. 2, Joseph, to Nursery this year. But things were not that easy…


1. How did you prepare your child for the first day of school?

In all honesty, we didn’t prepare him for school much.  He had been at home most of his four years, except for Sunday School times in church, which he had attended since he was 18 months old.  We did try to indirectly tell him a bit about school, for example, bringing him along when we fetched his big brother to/from school, and reading him books about school.

2. What was the first day of school like?

 Joseph woke up in the morning quite eager to go to school.  He wore his own school uniform, and socks and shoes.  He was pretty excited about taking the bus to school….until he realised that daddy and mummy were not going to be on the bus with him!

The school bus came late and without hesitation, he was shoved up the bus before I could even say a prayer or kiss him goodbye! Shawn, my hubby, was already waiting in the school for the bus arrival, so I quickly joined him there.

That first day was pretty messy as the teachers tried to channel the children into their respective classes.  Teachers were shouting names in between wailings.  When Shawn saw that Joseph was standing alone by himself, trying to make sense of the commotion, he tried to help by settling him at a desk and entertaining him with toys.  All was well until I popped my head in for a peep.  That was when tears started to roll and he started wailing for me…

3. What challenges did you face during the initial days and weeks? How did you cope?

After the first week of school, Joseph fell sick and stayed at home the whole 2nd week. That stay at home led to a horrendous start in the 3rd week.  He suddenly said he didn’t want to go to school.  We still sent him anyway after much coaxing and threats. We called the teacher to understand how he was coping in school.  He was not coping well.  He didn’t like the Chinese teacher, and was very clingy to the English teacher.

Hubby and I tried to make sense of his fear.  We wondered if it was because the Chinese teacher tended to be loud.  Or if anything had happened in school that had given him a scare.  The fear was so bad that he would wake up with nightmares, screaming “Mummy, I don’t want to go to school!” and he didn’t want to go to bed the night before!

Shawn and I were seriously at our wits’ end on what to do with him.  We couldn’t agree with each other’s approach.  He wanted to take him out from school because of such adverse reactions.  I was of the view that we should press on and not succumb to Joseph’s pressures.

At home, I thought there might be too many changes taking place that were overwhelming Joseph’s little life. So we tried to minimize any transitions – we let him sleep with mummy in our room (even though we had said he was a big boy and should sleep with his brother now); we walked him to school every morning instead of putting him on the bus, even though it was a good 20-30 minutes walk, at his speed.

Things are much better these days.  After the Chinese New Year holidays, he said he liked the Chinese teacher, but not the English teacher, which threw us for a loop.  But at least he is happier about going to school now… Thank God!

4. How do you feel now that your child is attending preschool?

I’m really not sure at this point – I’m still taking one day at a time for now, trying to convince him to go to school every day. I do hope he enjoys school life, beyond the academics, and that he will learn many new things there, and still be able to enjoy the rest of his childhood to the fullest.


A full-time nurse by profession, Grace, 32, has now been back at work in a public hospital for just over a year. She was able to enrol her daughter Isabel (Izzy) in the in-house childcare centre, which means she gets to see her during lunch and tea breaks. 


1. How did you prepare your child for the first day of school?

I was a stay home mum prior to Izzy attending school (infant care) so I was pretty much the only person she turned to for comfort in the first seven months of her life. I would leave her at my parents’ place and in-laws’ place for a few hours, so she could get used to my not being around physically – but I dont think it really helped very much, because she would wail non-stop until I returned! It was a pretty traumatic process for both of us, and especially when I felt the guilt started to creep in for wanting to return to work, versus continuing as a stay-home mum.

2. What was the first day of school like?

It was a huge ball of emotions for both of us! Izzy started bawling when we left and my husband had to gently but firmly guide me away from the school doors. Poor Izzy only lasted about 3-4 hours that first day. When she came home; her eyes were all puffy from crying. It was extremely painful to see her like that, but yet I knew that she had to learn to adapt to the changes.

3. What challenges did you face during the initial days and weeks? How did you cope? 

Izzy took quite a while to get used to school. It was really difficult to see her crying and reaching out to me whenever I passed her to the teachers. The thing that worried me the most was her feeding. She had been fully breastfed until that time, and refused to drink from the bottle. I couldn’t find a bottle which she was willing to drink from!

I must say, the infant care teachers were really wonderful! They always assured me that she would be fine, and not to worry. They also suggested many different alternatives for her feeding, including trying different types of bottles, and even assuring me that they would spoon-feed her if necessary. Making connections with two of the other mums whose kids were in the same infant care was also extremely helpful. We actually formed a Whatsapp chat group to support and encourage each other along in this journey.

I guess a breakthrough moment came when Izzy started waving and doing ‘flying kisses’ at me when I dropped her off in school in the mornings. It showed me how she has adapted to school and I was so proud of her! Now, she has even become ‘class monitor’ in school. Every time a parent comes to pick up a child, she will peer out of the gate to see whose parent has arrived and inform the respective child by shouting the name, or going to her friend’s side and telling him or her, “Home”.

4. How do you feel now that your child is attending preschool?

I feel excited! Izzy loves school and she has learnt so much from the interaction she has with other children. She is able to articulate more and more everyday and it is really fun to watch.


 Most young children will experience some measure of separation anxiety when they begin childcare or school. Depending on their personalities and how their parents and the school/centre handles it, they may experience more or less difficulty in adapting to the changes.

However, on rare occasions, a child may be so overcome by his anxiety that he needs professional help. If separating from you is causing your child extreme distress, to the extent of even causing physical symptoms like stomach aches, headaches, and dizziness in anticipation of the separation, you should bring her in for a proper evaluation by a professional child psychiatrist or psychologist.



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