When my firstborns started pre-school years ago - and I am almost embarrassed to say this - I stood under a tree and wept.

One twin - led into class by a young, kindly teacher - had been sobbing and howling: "Mummy!" The other, unfazed by new surroundings, had happily skipped into class, without even a backward glance.

Two different responses, but cue those heart pricks all the same.

"So melodramatic," said a friend when I texted her from beneath that tree.

My husband and I had prepared the children quite adequately for school, I thought. While I was thrilled about this new milestone, I hadn't expected these almost irrational waves of sadness.

It was a bizarre blend of pride and anguish. On the one hand, sending them to several hours of independent learning was an exciting prospect. On the other hand, drop-off felt like a painful wrench.

It seemed like just yesterday when we first held those tiny infants born under 2.6kg, admiring every smile (muscle twitch) and gurgle. "Well, time to snip those umbilical cords," I muttered to myself wryly, resisting the urge to peep at them through the windows. I still did.

The first day of school can be surprisingly hard for first-time parents. Perhaps it is the realisation that your child is not a blanket-holding baby any more.

The challenge is in letting go and letting others - beyond familial or naturally trusted caregivers - and people whom you may not know, have a hand now at nurturing the child. Parents recognise that the process is good for their children, but raw emotions may flood them all the same.

Will she be bullied? Will she be the perpetrator? Will he have friends? Will the teacher treat him fairly? Will the school accept their quirks and idiosyncrasies?

Some have an easier time transitioning, but the experience may be more traumatic for parents of little ones with greater theatrics.

A close friend related her deep distress at how her son had wailed and rolled on the floor for many weeks, or months, at daycare drop-off. This child has since blossomed into a well-adjusted and highly respectful child whom teachers love.

Friends - and Google search results - had offered me some advice on how to manage the first week of school. There were the usual tips such as reading your child books on starting school, and familiarising the child with the new route and programme.

I found it useful to offer visual depictions of the school routine to my children, drawing kiddy maps to help them envision activities of the day. I even talked them through photographs snapped of different school spots, such as the assembly hall where they gather each morning, classrooms and playground - all shot when teachers had allowed anxious first-time parents to linger.

Speaking of lingering, some experts recommend that not hanging around may actually help the child settle in faster. Keep your goodbyes short and sweet, they say, then will yourself to walk away.

I now see merit in this advice, as a more experienced third-time parent who is exponentially more chill with each year (or kid). My youngest child recently settled into her Sunday school drop-off programme very quickly, with just a short burst of tears, after I had steadily walked away.

Working closely with the child's teachers can help too. Naturally, we all wish for nurturing and seasoned professionals who can anticipate our child's every need, but a relative who is a pre-school teacher says she appreciates it when parents show that they trust her, and share information that helps her understand the child better. This can include crucial medical issues such as food allergies, eating habits and even favourite songs.

Sometimes, it is easy to get on the defensive when working with the school, especially if any issues arise. I remember feeling perplexed in the early days whenever a teacher suggested there was something I - an adult who supposedly knows my kids best - should or should not do, to help them acclimatise better.

But several parent-teacher meetings later, I have learnt to be positive and use feedback constructively to help my child and I, as a far-from-perfect parent, improve. My children's teachers last year were especially stellar in maintaining close communication with parents, and we all grew from that.

It does get better.

Last month, I chuckled while watching a hilarious viral clip of United States mum-blogger Susannah Lewis depicting her sweat-suited self melting down on her son's first day of kindergarten. "He's not ready! He's only five! His teacher doesn't know he needs 14 kisses every 45 seconds," she wailed.

Cut to the first day of school in subsequent years. Her head bobbing to George Michael's Freedom, the now well-groomed Susannah is zooming away from school and answering a phone call, agreeing immediately to a manicure, a pedicure and, heck, even Vegas.

It is caricature, but it is true. The first day of school for any parent can be a bittersweet pill to swallow, and the tears may come. But a few years later, the tune may change and the distress will dissipate.

With the holidays ending and school reopening, expect to see memes of exuberant seasoned parents (and glum teachers).

Tomorrow, I send my youngest child, the baby of our family, to school for the first time. It is hard to believe she has grown so quickly and is now headed to nursery. But it does feel easier this time.

There will be other children who are attending school for the first time. They may be apprehensive, even panicky upon reaching the new premises. And trailing behind them? Nervous, anxious parents who are in transition too.

If you are sending your child for the first day of school, perhaps with wet eyes, I offer you gentle assurance that you are not alone. Your child will settle in with time, hopefully sooner than you expect, and he or she will be fine.

And you, parents, will be too.

•Denise Lim, a freelance writer, was formerly a communications specialist with a financial institution.