I am in uncharted territory where Isaac is concerned.

He has hit that age - you know the one where all parents shudder about. While I was bracing myself for all the horror stories of teenhood, I never expected it to creep up on me as it did - not with Gillian but with Isaac of all people!

By day, he is your average student, quiet, seemingly well-behaved. But there is another side of him slowly emerging. The secretive, sensitive freedom fighter side.

It's been building up I guess. The lost phone and SIM card (barely weeks after I bought it), the lack of interest in work, the flagging grades (Bs and Cs), the total nonchalence about life, the defiant and blatant disobedience, the furtive early morning visits to the study room to use the computer despite my warnings not to. To which he turns a deaf ear of course. By the way, Isaac is never openly defiant or rude. Rather, he just blanks you out (poker face that he is, I can never tell if he is actively listening to my lectures!) and then quietly, in his own time, goes and does exactly what I explicitly told him NOT to. So I seethe and I nag.

Things finally came to a head two weeks ago.

KH and I were sick with H1N1 remember? So we were at home recuperating. It was a Monday. Isaac was supposed to be home by 2.30pm. School ended at 2.15pm and because we live a mere 15-min walk away, he should have been home latest by 3pm even if we factored in dawdling.

But nope. No sign of him. Not even a phonecall. By 5pm, I asked Gillian to call his buddy and our neighbour Bryan. The boys go back a long way. Bryan, or Bry as we call him, by sheer chance, went to the same kindy and today wound up in the same class as Isaac in school. His grandfather lives a few doors down the street and Bry is a common fixture around our house. Most evenings would see him hanging out here, sometimes dining with us and waiting till past 8pm for his parents to pick him up. I always say Bry is like an additional child of mine who wanders in, gets fed and then goes to another home for the night cos the next day, he's back haunting the yard again!

So Gillian called Bry. Bry says airily: "I dunno where Isaac is. I last saw him at 4.30pm in school."

6pm came and went. No Isaac. By then we were no longer fuming but just plain worried. Could something have happened? Was I going to get a visit from a policeman with bad news?

7.30pm and our friend finally, sheepishly walks through the door. Intact. Of course that didn't last long because I was ready to rip him into 28 pieces and scatter him for the wild dogs in some field in Punggol!

The interrogation started. Version 1 of his story went like this: I was at my classmate's house. No, you don't know him. No one was at home, only his maid. We finished our homework. Then we played some games on the Xbox and I got carried away and forgot about the time. Bry was with me.

Wait a minute. Bry? The holes in his story started to enlarge as I probed deeper.

Version 2 (what really happened) went like this: He went to Bry's house. They played on the Xbox and online as well. Gillian called and he told Bry to lie for him. They played until 7.30pm when Bry's parents came home and gave him a lift back to our house. And no, at no time during this whole escapade did he think of calling back to let us know.

So... not only did he not come home when he should have, he did not bother calling, and he lied. So many issues, which one to punish him for? How to punish? I didn't know where to begin. KH said shortly: cane him and throw him out of the house! Silly man. This is a strapping 12-going on 13- year old boy who is as tall as I am! It's ridiculous to cane him! And the "throw him out of the house" line is seriously getting old.

I didn't want to just punish. I wanted to delve to the bottom of this behaviour and I wanted him to see how wrong it was and to change. Already, he and his daddy have faced off on several issues. At least for now, I am still someone that he is quite close to, still affectionate with at times and will listen to (at least he still gives me the respect of acting like he is listening!). So caning and drama is out of the question.

Instead, I read him the riot act, took away his dinner and told him he can jolly well stand outside until I tell him to come in. So he stood outside, in his school uniform, schoolbag on his shoulder, from 8pm to 10pm. Guy got off cheap. If we lived in ancient China, he would have been kneeling on flagstones until his knees bled!

I was still troubled by the incident for several days and did a fair bit of soul-searching and reflecting. And recently, I had sort of an mini epiphany.

1) At dinner one night, I asked him: if you were asked to play a game which you had no hope of winning, against other better players, would you play? Would you be game for the experience? He went silent. Bingo. So I went on. This is why you don't do well in History, Geography, Lit right? These are subjects which I expected you would do well in, given your command of the language and your interests in these areas. So it was a surprise that you did not do well. But now I think I know why. You don't do well in these areas because this is new to you. It's unfamiliar. The rules of the game have changed. Its not enough to know the facts you need opinions and intelligent analysis. So you're not sure. You're not sure how to can play the game. So instead of learning the rules and playing to get experience, you'd rather sit the game out. You'd rather not play if you can't win. That is it, in a nutshell. Isn't it?

After a long while, he nodded reluctantly. I think I found out why he does not want to engage with the subjects - he prefers to avoid those that are harder, a bit more of a challenge and if they are not immediately something he knows he can do well in. But in avoiding and procrastinating, he is simply digging an even deeper hole of failure. I don't have an answer on how to motivate him, but I told him that whatever I can help with history, geog or lit, if he wanted, he could ask me, and certainly he should ask his teachers and never be afraid of seeking help or looking stupid because that was the only way to do better.

2) Looking at his behaviour over the past weeks, it is clear that he wants to flex his muscles of self-autonomy. Yes, his behaviour right now does not seem to merit my trust. Yes, he is looking less than responsible at the moment.

But as a mother, did I make it easy for him to gain my trust? I don't think so.

I keep telling him the usual: trust has to be earned. But I forgot one thing - that for trust to be earned, some has to be given out first. Like a small pile of capital that is wisely invested and grows. That is trust. How could I say I trust him if I were constantly tracking him, nagging him about his work, about why he is late from school, what he did, where he went etc. How much faith am I putting in him to make good (or even bad!) judgements when he hardly has the opportunity to do so?

I have to learn to let go. Let my children go, bash out their own paths, get scratched along the way. I have to get rid of rescue mode.

Last week, I finally bought a new cheap basic phone and a new SIM card and gave it to him. I told him: With this phone, I'm going to put some trust in you. I will trust you not to lose your phone and to take care of it. I will trust that you will know when to come home. I will trust that you will be responsible enough to call if you are delayed for whatever reason. Beyond that, I will not keep calling you, or tracking you, or calling your friends to find out where you are. About your grades, well, I don't want to sound like a broken record and I don't want to keep chasing you and bugging you about it. Honestly, I'm getting real tired of all this and I'm sure you are too. So I will leave it to you. You know what to do. While I really despise the feeling of 'regret' in life, if you have to have a taste of it, you just have to. You make your own road.

Well, its been more than a week so far. And I am getting regular calls and messages from him: I'm on my way home, geog teacher held the class back. Or walking home now, back by xx time.

I don't know if he is telling me the truth about why he has to stay back or why he is delayed etc. I find it hard to sit on my hands and NOT ask or probe. Not easy keeping to my end of the bargain. But I'm happy that he volunteers the information. And the talk about his work might have struck a chord somewhere. Bry came by the other day to say that Isaac scored Distinctions in Maths and Science. So maybe the lack of push helped?

And speaking of Bry, I had a quick chat with him too regarding the lie for Isaac. He looked abashed when we spoke but I think he got the message.

I think as parents, we might find it hard to let go. When our baby is learning to walk, how we baby-proofed the house, watched in proud anxiety as he took his wobbly first steps. But eventually, he learned to walk and we no longer watch the boy walk in nail-biting tension.

Teenhood is similar I think.

I am slowly learning how to let go. It's hard. And very scary! I still have the maternal-anal retentive feeling of wanting to rush in and smooth things, make it better, easier, do it more efficiently etc. But I think I would not be doing him any favours if I did.

If he screws up, or makes a major boo-boo in life, it will be bittersweet for us but it will be part of his journey, and it just has to be that way, whether I like it or not.

I'll just be standing in the wings watching, with that same heart-in-the-mouth-will-he-screw-it-up feeling. And if he does fall, just help him to his feet and do what I do now to all my babies - put a plaster and give a hug to make it all better.