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Sarah Hampson at an earlier age.

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Dear 20-year-old Sarah,

First things first. Wear your bikini more. Forget about those body flaws you think you have. They're nothing. One of the cruellest ironies for women is that we're most self-conscious and critical of how we look when we're our most effortlessly beautiful. If I could redo a day at 20, I would wear my bikini to do the laundry. On second thought, I might fold sheets in the buff.

I'm in a groundhoggish mood. It's winter. A time to go underground and think, preferably in front of a fire, then poke your head up to see where you're headed. And with that comes a review of where you've been.

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Dear 25-year-old Sarah,

At this crucial juncture, there are a few key things I would tell you to do differently. About men, in particular. Look for kindness above all. We underestimate its importance in relationships and confuse it for a sign of weakness or effeminacy. That is a mistake. It is essential. And don't be fooled by charm. That's not kindness. It's a tactic. Like wearing your best suit and skyscraper heels to a business presentation.

You know that good-looking guy in the fancy car who whisks you off your feet – the master of the grand gesture? Your knight in shining armour, right? Wrong. Take a moment to consider whether he would bring you tea in bed in the morning. The small gestures are more important. And think about whether he's like an old pair of sweatpants. Your man should be like those fat pants that you never throw away – comfortable, cozy, forgiving and reliable, wash after wash.

The trouble with these kinds of rewind-the-tape exercises is they make me feel that all life in middle-age holds is a dainty cup of tea and a layer cake of frothy pontifications. But we all partake in them from time to time, in our heads, if not on the page. We tell ourselves, if only I could redo a certain day, or year, or decision, my life would be different.

Of course, there are moments we want back – the time before a tragedy, when we feel we could have avoided some horrible life-altering accident if only we had done one thing differently. Or the time we had something to say to someone we love, and didn't, and then it was too late. But generally, is the groundhoggish mood helpful?

Dear 30-year-old Sarah,

What I have to say is really simple: Stop comparing your life to others. So your friend has a nicer house, one with stainless steel appliances and a shower designed for dogs. So she and her husband and children go on amazing holidays, and she has a smaller waist, and she doesn't have to do the great balancing act of being a working mom. There's always something that you feel diminishes your life – or, alternatively, makes you feel superior. Do not do this. What people project on the outside is not always a true reflection of their inner lives. (I learned this from a seasoned divorce lawyer.) What you have is not who you are.

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I press the rewind button to rethink my hinge moments – those times when you made a decision that changed the course of your life. We all have them. And it's only normal that we entertain the what-if-I-hadn't-done-that possibility. Sometimes, those moments sent you to a desert, a place it took years to find your way out of, and other times, they led you into a beautiful garden. And there's value in ruminating over them.

For one thing, you can see a pattern of how you think – what makes you do things. I know a change-management consultant whose work is all about tracing the decision patterns of a company – what the culture is that creates the environment for certain ways of thinking, and the need to trace those decisions, that pattern, for better outcomes.

One of the great things about getting older and living the second half of your life span is that you have a great view over your emotional landscape. It's the 30,000-foot perspective that lets you see which paths you took and why; which were good, which weren't; which were intentional and which ones you just happened to stumble upon. You can see what got you here. And if you pay attention, if you trace those paths, you can learn to recognize patterns, for good or for ill.

Dear 45-year-old Sarah,

Things are not great. But here's the thing: The moment you are in is only a moment. A surprise you cannot imagine – a person, an opportunity, an idea, some revelation – is just around the corner. One of the things you are beginning to see is that this is the nature of life – a whirling energy of chiaroscuro beauty you cannot easily predict.

Hope you're enjoying the cup of tea I'm brewing over here. It's either that or a tumbler of Scotch – neat. Once I get into a groundhoggish mood, I can wallow in it, especially if I'm having said Scotch while soaking in my bathtub. The what-if scenes play in my head like a movie, and I see myself in an alternate life – living in the English countryside, if I had decided to stay in London when I was in my early 20s, say, or being a painter living in a garret, if I had chosen to indulge that urge.

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But the truth is, I don't really like to stay in rewind for long. And that's because the root of the rewind wish is that if you could do things over again, differently, you would be happier, wealthier … you fill in the adjective. We think we would be better off somehow. And that's a bit like people's fantasies about their past lives, if they believe in reincarnation. They usually imagine they're a reincarnation of a queen rather than a scullery maid.

I'm not saying I fully believe in the adage that "Everything happens for a reason," that acceptance of things that have happened to us, good and bad, is the only way to find peace. That's a coping strategy that invites passivity. We have agency in those hinge moments. We make the decisions. And we have the power to make even more of them happen. But I also know that there are many things beyond our control and that railing against them, feeling angry about them, is useless. You are here in the present with stories to tell, and a character you have had some hand in shaping.

I will tell you this, counterintuitive as it may seem: Hardship is a better, more memorable, teacher than happiness. It shows you that when you allow for happiness, when you learn what it really is, you know to savour it – like, well, that piece of layer cake you have eaten to the last crumb.

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