Letter to a teenager: Four writers offer advice to their younger self

Dear Tracey MacLeod

The first thing I'd advise the 17-year-old you in this picture is to stop plucking your eyebrows quite so viciously. Your attempt at Nico-esque world-weariness is never going to work when you walk around looking permanently startled. And maybe have a rethink on that fox-fur jacket. You're desperate to appear sophisticated; ever since you shot up to 5ft 10in at the age of 14, people have thought you were much older than you were, and you've tried to act the part. But you should worry less about fitting in and being cool, and start having a bit more fun. You're smart. You're funny. Enjoy being you, and stop trying to be someone else.

On the same subject, a word of warning – if we are permitted to interfere with history. You are considering a demi-wave. For God's sake, don't do it – you won't look like Siouxsie Sioux; more like Barbara Dickson. And it will take two years to grow out.

You're on your way out to a party, with some of the new friends you've been hanging out with since you went into the sixth form. Mainly clever, disaffected boys from the local public school, proud of their outsider status. Music is the shared passion. They play in bands, you play the guitar at home, and never seem to make any progress. Keep working at that – and maybe get some lessons. One day you will be a show-off with a mad desire to dominate every social gathering with a song. That would go better if you could actually play an instrument.

Behind that blank stare, some thoughts are beginning to stir. You think you might leave your small provincial town to go to university. It's a good idea; hang on to it. But maybe do a bit more research instead of choosing a town even smaller and more isolated than the one you're currently stuck in. Thanks to your new friends, you have moved on from the Crossroads-inspired desire to be a hotel receptionist. Now you're thinking of journalism as a career option. Again, perhaps you might want to do some research into that. And maybe even a little writing at some point? Just a thought. Try and pack a bit of knowledge into that frankly outsized forehead, while your brain still has some capacity to retain it.

The good news is that you will get away, and go on to experience things you haven't even begun to dream of yet. The bad news is that others won't be as lucky. Drugs are around, and will be around a lot more soon. You are right to be wary. Two of your closest friends won't make it to an age when they can write this kind of letter.

For God's sake, be a bit kinder to your mother. She doesn't deserve the withering contempt, the teenage tantrums and years of sullen non-communication. You don't know what she has been through, though you're going to find out soon enough. And be kinder to your father too. In fact, take off that stupid jacket, tell your friends you're staying in tonight, and sit down and talk to him. Laugh at his old jokes and silly voices. Listen to that record he wants to play you, the one he heard on the John Peel show, because he couldn't get to sleep, again. Hold on to him, and never let him go.

Yours, Tracey

John, dear boy,

Look at you at 19: that hideous Brideshead-on-a-budget jacket! That awful shaggy hair! That shoulder-bag! – and when did you learn not to prod your ladyfriends in the bosom with a baguette? But what alarms me more is that expression of cosmic puzzlement on your face. You were in your first year at Oxford, terrified that you had no business being there, desperate to convince people you were a serious intellect. But because you were a Battersea-Irish oik, you were equally desperate to be popular. So there you are, being fey and sweet with the laydeez, when you should have been in the Bodleian, working harder.

I wish you could get a First, and become a rival to Martin Amis (who was at your college four years earlier) but I'm afraid it won't happen. You don't have the graft and single-mindedness. Or, damn it, the talent. But you'll be OK, all the same, because you have a certain deranged optimism that people take for competence, and you'll be happier in noisy newspaper offices than writing a 10-novel sequence in a study.

At 19, you haven't much clue about what's important. You think life is about: a) being cool; b) making money; c) getting off with Laura/Gail/Joanna/Samantha as soon as possible (and in that order); and d) going to the Cyclades with Mike and Rob. You're wrong. What's important will turn out to be: a) raising children; b) discovering what you most like doing and having someone pay you to do it; c) falling in love a few times, if you're lucky; and d) going further afield than Greece, and not spending the rest of your life regretting you didn't explore the South China Seas in your early 20s.

You'll learn that it's OK, and not uncool at all, to have an ambition. Look at that job over there, that someone's doing right now. Tell yourself: that's what I want to be doing when I'm 25/30/40/50. To your surprise, it'll happen, if you want it enough. So will writing a novel/making an album/directing a movie, if you're sufficiently determined (just don't expect it to be Catch-22, or Sticky Fingers or Don't Look Now).

I wish you could learn a little restraint. You might try saying, "No thanks, I've had quite enough," and, "No, I really must be going now," and, "Is there a fee attached to this?" So many terrible mornings, so much emotional awkwardness, and so much penury could have been averted by being, you know, firm.

Don't panic about getting older. Life becomes much more enjoyable as you put a few years away. You'll understand the world and its curious inhabitants better, and relax into your (slightly paunchy) body and (slightly battered) soul. People will become more benignly disposed towards you and each other. And you'll discover, a pleasant surprise, that your sex life improves exponentially after 40.

Life advice in four words? They're from Blake: "Damn braces; bless relaxes."

Good luck, love John Walsh

Dear Deborah Ross (rather than "Debee", which you once tried to call yourself, wholly unsuccessfully, thank God)

Firstly, what are you doing in that terrible bikini? Go inside now and put some clothes on, girl. Have you no shame, you big lump with hair that looks like it's been done with an electric toothbrush? Tell me, is it nice to hear from me after all these years? I think it must be.

Anyhow, hello, how are you? And what's on your itinerary today? Let me guess: a bit of lying, a bit of shoplifting, a bit of bunking off, a bit of smoking (more than a bit – you're on 20 a day by the time you are 16) and a bit of drinking Dubonnet from the Thermos you take to school and your mother thinks is soup? You are bad. In fact, it's 1976, you're 15, and I've just looked at your school reports and your school absolutely hates you. As your maths teacher writes: "Deborah evinces a great dislike for thinking, and does not produce any homework." And as your form tutor writes: "Deborah is an incorrigible gossip and seems unwilling to control this." And as your woodwork teacher writes: "Deborah has good knowledge of most woodworking tools and knows how to use them." You always did make a bloody good letter-rack, Debee. (No, it's still not working.)

You are bad, and you drive your mother and father mad with worry. You're a nice, middle-class Jewish girl from Golders Green, yet if you're not being chased by truancy officers you're being picked up from some police station or other. Look, don't take this the wrong way, but I'd give up the shoplifting if I were you. You're crap. Also, if you've yet to tell your parents that you are going to Lauren's to revise when, in fact, you are going to party, don't. They'll find out and your father will pull you out by your hair. But I don't want to rebuke you for any of this. I don't. From where I'm standing in my late forties (I know! Can you believe it?) what I'd most like to say to you is this: you go, girl. You go.

You're in trouble all the time, I know. And you do fret dreadfully about your looks. And you would like boys to hanker after you. And you would like your hair to be sleek and smooth. But – and this is what I really want to tell you – you will never feel more authentically yourself. You know who you are, and have the courage to be it. Enjoy yourself because, by the time you get to your A-levels, you will have started knuckling down, and just become more phoney somehow. I think we both know the form these letters usually take – cheer up; keep with the piano – but what I'm saying to you is this: celebrate yourself now. And this: I like you and will never like you as much again.

Anyway, all the best, Debby (I think you tried that too, at one point).

Love Deborah

PS: One day you will have a grumpy son, a mortgage, a dog who eats chair legs, a roof that needs expensive repairs and knees that sag. So much to look forward to!

To: Michael Bywater

From: Michael Bywater

ME: What were you thinking of?

ME: What? Who are you?

ME: You.

ME: No, you.

ME: Me? You.

ME: But ... oh, never mind. Never seen you before in my life.

ME: You will, Michael. You will. Now: what were you thinking of?

ME: What?

ME: There you are in the Market Square [in profile, wearing glasses], 14 years old, campaigning for Hubert Humphrey for President. of America. You're not an American. You hate politics.

ME: It was Colley's idea.

ME: It's typical you. Faking it, day after day. Because you're scared. Because you didn't listen to my mother.

ME: Your mother?

ME: OK, yours. Same thing. You listened to the stuff where she was talking nonsense and you didn't listen to the bit where she was talking sense. When she said "You're a show off" and "Nobody's looking at you" and "Who do you think you are?" and "Stand up straight" you listened. When you got into trouble at school, boy, did you listen. You got the idea that everything was conditional. That terrifies you. That's why you won't practise the piano: in case someone hears you playing wrong notes. That's why you'll not realise when girls like you. You go on performing and doing your tricks until they become your friends, at which point it's too late. You're a good-looking kid, you know. Slim. Cute ...

ME: Are you some sort of –

ME: No. Just telling you what you should already know. You're a nice-looking, curious, enthusiastic, clever kid. And you're idle.

ME: No I'm not. I –

ME: You are. There are worse things to be. But you're idle. An idle polymath. You go by fits and starts. Never finish things. Leave it to the last minute. You're going to hit problems from that, you know. Listen: you're not good enough to be a professional musician and there's no shame in that. You could be a doctor but you might be too lazy. Our mother said you should be a barrister – God knows you've got the gift of the gab – and she's right. And you'll regret it later.

ME: Don't tell me what I'll –

ME: Because you know what? Money is important. More than you can imagine. It's the most important thing. You'll rack up debts. Don't. Debt means someone else owns you. Don't fall in love with the first girl who smiles at you. Don't marry until you have established yourself. Remember the world takes you at your own valuation. Don't be so scared of other men. Make good friends.

ME: I'll make what friends –

ME: Shut up. I haven't long. Learn how to say "I can't do that" and "I can't afford that". Realise you're not special and the world doesn't owe you anything.

ME: Oh thanks. So you screw up your own life and then you –

ME: No. I screwed up your life.

ME: Thanks.

ME: Well ... take my advice then. And remember the most important thing.

ME: Well?

ME: Women like it too.

ME: Whatever.