Pen Pal Project

Out with the old, in with the new

December 29, 2015


My office

Dear Reva,

I’ve just come in from shovelling the slush after the first winter storm in my new house. It took me about 45 minutes, and I am overjoyed.

Why? Because last year, living alone in my former matrimonial home, I had an incredibly long driveway, and nowhere to put the snow, and a series of colossal storms, and I found myself, on two occasions, physically incapable of clearing the snow in time to get my kids to school, even for part of the day. It was one of the very few times over the past twelve months when I felt completely helpless.

I was remembering that feeling as I cleared the walkway today, and I experienced a corresponding joy: the knowledge that a memory has lost its power to hurt you, because you have moved past the pain that gripped you in that moment.

I’ve had a few of these joyous realizations lately, the most profound from an unexpected source. Facebook, as you may know, generates a year-in-review montage for its users, providing a kind of highlight reel of life. I love this sort of thing, so I clicked eagerly on the link. And what I discovered, which will come as no surprise to you, or to anyone who follows the Pen Pal Project, is this: 2015 was a big year. Here’s a snapshot:

January: I ring in the New Year crying at a Mexican resort, where I have gone, by myself, to reflect on my recent separation, and a devastating first Christmas as a broken family. My nephew, Sam, is born. I don’t write a word.

February: We launch the Pen Pal Project. It is the only writing I feel capable of doing, but it gets me back into the habit.

March: My entire family (10 Hiltons, aged 7 weeks to 70) goes to Orlando, so that my kids can have a memorable March Break. I buy a new house.

April: I negotiate my separation agreement and sell my old house. I wonder if I will ever write anything except Pen Pal letters ever again.

May: I take my kids to New York for my son’s 12th birthday. It is the first time I have travelled alone with them. It is fabulous, and a major turning point for me.   I meet my NY editor and ask for an extension on my book. She graciously agrees.

June: I move. I love my new house. I set up my office and vow to get back to business as soon as the handymen leave.

July: I start writing on a serious schedule: one chapter every week with no exceptions. I do this for the next five months, with almost no exceptions.

August: I spend time at the family cottage with my kids and my parents. I plan some chapters for my new book, set at a family cottage.

September: I meet with a matchmaker. She tells me that I need to go online. I am completely freaked out by this idea. Anyway, I’m too busy writing.

October: I go online. I keep writing.

November: I start dating. I get my first U.S. review for The Hole in the Middle, and it is really good. I bawl my eyes out.

December: My first copy of the U.S. edition of The Hole in the Middle arrives in the mail. It is beautiful. I finish the first draft of my second novel, Just Like Family. My agent, my editor, and my trusted beta readers love it.

The other night, I had dinner with a new friend (a product of my online dating experiment), and told him about my highlight reel. “What an amazing year,” he said.

I had to think about this for a second. Because if you’d asked me in January, February, March, April, or even May, I would not have said that it was an amazing year at all. I would, in fact, have said that it was the worst year of my life.

In December, though, I smiled. And I said: “Yes. It really was.”

Happy New Year.



Pen Pal Project

Repeat after me: Change is not a crisis

December 15, 2015

My desk, 7 a.m.

Dear Reva,

I’m getting an early start this morning, and because it is so dark outside, and because I’m tired, I am completely disoriented. I have to keep reminding myself that I have already slept, had breakfast, packed one child (the one who isn’t sick) off to school and settled into my work day. The fact that I have to do this – remind myself of something so simple and obvious – is one of many examples in everyday life of how much of our behaviour is patterned and based on familiar external cues.

And this, in turn, is one of the answers to your question last week about why midlife changes are perceived as a crisis. I like this question, and have thought about it a lot in my own context. I used to describe my shift into a writing career as the result of a midlife crisis, partly because it got a laugh from the audience, and partly because I thought of it that way myself. But I’ve stopped doing that. I’ve decided that it is too reductive, dismissive, and even pejorative a phrase to describe what has been, in fact, a period of transformative growth and creative flourishing.

Having said all of that, change scares us at a fundamental level. We don’t think that we are good at it. We cling to the (misguided) idea that people don’t really change, and it comforts us, giving us a sense of control and stability. And, of course, change invites failure, which we fear most of all.

Small changes can throw us off for months or even years. Think about how long it takes to settle into a new house, for example, or a new route to work. Long after we should have rewired our brains, we still find ourselves looking for the forks in the wrong drawer, or getting off at the wrong subway stop. And it makes us tired, because every time we have to substitute a real decision, one that requires our attention and consideration instead of allowing us to operate on autopilot, it takes energy.

But here’s the good news. According to Charles Duhigg, author of The Power of Habit: Why We Do What We Do in Life and Business, “Routine basically gives us the mental freedom to think about what’s actually important…Almost every single species that has survived has the ability to take routines and make them automatic. That way you have cognitive power to invent spears and fire and video games.”

In other words, all of those routines are liberating space in our brains that could and should be used to contemplate change.

My own view is that we are far too wedded to the notion that change is threatening, and that it prevents many of us from reaching our full potential. There is no question that change is difficult (we will all spend a lot of time looking for forks and getting off at the wrong stop, no matter how adaptive we are), but it is also extraordinarily energizing.

This is not to say that I wake up every day and think, “Excellent! Another day of adapting to unfamiliar experiences!” I find change tiring too, even though I have come to appreciate and even seek it. But the rewards of change are as large as your own imagination.

This week, the first copy of the US edition of The Hole in the Middle rolled off the presses and arrived in the mail. Here is a picture of me, right after I opened the envelope. Do you see the same thing that I see? Wonder, astonishment, joy, and more than a little disbelief?


us edition copy

That’s what change looks like.



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Pen Pal Project

Second Novel Syndrome

December 1, 2015

My office

Kate Hilton, The Hole in the Middle, Best Selling Author, The Scar Project, Book Club, Breast Cancer

Dear Reva,

This is an important date for me. December 1st was the deadline for my second novel, a project that caused me untold angst. And I’m happy to report that I made it! I handed in my first draft to my agent on Friday.

Here is something you will rarely hear me say, and which I should say (which we should all say) far more often: I’m really, really proud of myself.

Second novels, as you may know, are notoriously challenging. Writers who have been fortunate enough to experience a success with their first book often struggle with their second, so much so that the phenomenon has nicknames, including The Sophomore Slump and Second Novel Syndrome. In the writer Anne Lamott’s words, “The beginnings of a second and third book are full of spirit and confidence because you have been published, and false starts and terror because you now have to prove yourself again.”

And that’s without getting divorced and moving in the middle of the book.

Now I will wait to hear from my agent, who will tell me honestly what she thinks. And I will either rewrite at that point, or we will submit the manuscript to my Canadian and American editors. And pretty soon, I’ll have to start thinking about my next novel (although I have some ideas taking shape already).

I love that you passed me a note in class for your last letter. I should say that I make a point of promising the men I date not to write about them here (although the person I’m currently seeing says, “Why not?”). But let me offer some observations in the abstract.

Dating at midlife is simultaneously easier and more complicated that it was in our twenties. It is easier because we know ourselves better and because we are looking, for the most part, for simple companionship. It is more complicated because we all have baggage. It is easier because people are comfortable in their bodies and know what to do with them. It is more complicated because people have significant responsibilities, and need to shoehorn dating into an otherwise full life.

But overall? It’s pretty fun.



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Pen Pal Project

Brave New World

November 17, 2015

Dear Reva,

Macgyver.  Not my new online boyfriend.
Macgyver. Not my new online boyfriend.


You’ve been on my mind all week, since I learned of your arthritis diagnosis. In the same week, a dear friend lost her sister to cancer.

A couple of letters ago, I talked about the shiny upside of midlife, the ushering-in of a life stage rich in professional opportunity and success. Here, though, we have the dark side of the midlife coin, where things start to go wrong with kids, marriages, aging parents, and our own surprisingly fragile health.

You will, of course, address this challenge with your characteristic grit. But I so wish that you didn’t have to. I know you will tell me if there is anything I can do, at any time, to help you.

I have news of my own. I’ve started…dating.

I was never very adept at dating, truthfully. In fact, I managed to avoid dating entirely in high school, then Macgyvered a few university hook-ups into relationships, and then went to law school and married a classmate. And now I’m going out for coffee with strangers, and remembering why it was easier to do this in university, surrounded by packs of friends and fortified with bad beer.

It is also, I have to say, a total paradigm shift to date without any objective other than companionship. I’m not looking for a father for my children (they have one, and I’m done birthing babies). I don’t need a financial partner. And I’m not trying to assess potential, as we all had to do back in our twenties. We’re fully formed adults now, most of us having been through at least one brutal life experience. We know who we are.

And we’re online.

My god, Reva, the brave not-so-new world of online dating, that has such people in it! I am learning so much, about myself most of all. Because I am an extremely nice person, I will say no more than this: it is a whole book of its own.

And it would be a shame to waste good material.

With lots of love,


Pen Pal Project

By The Numbers

November 3, 2015



Dear Reva,

It was so wonderful to see you the other day. I love our letters, but it is such a rare treat to be able to talk. I always leave our conversations with my head full of ideas – dangerous, because that’s how we ended up committed to writing letters to each other every week.

My office is on the third floor of my house, with a view from the desk of a century-old maple tree. After five months in the house, I’m quite attached to my tree, even though it offers concrete evidence of the passage of time. It is still clinging to a few yellow leaves, but not, I think, for much longer.

Five months. The number surprises me, actually. I am not a numbers person, as many friends have observed, but even I accept that a ‘by the numbers’ approach to any experience can be revealing. I used to love the Harper’s Index, for example. (From the July 2015 edition: Portion of Americans in 1984 who believed that ‘most people can be trusted’: 1/2. In 2014: 1/3.)

I started my new life as a single person on November 1, 2014. Here’s my year, by the numbers, or at least some of the numbers. A girl’s got to have a little mystery here and there, or at least that’s what they tell me.


Houses sold:                                      1

Houses bought:                                 1


Vacations taken:                                4

Without children:                              2

Completely alone:                              1


Number of Hiltons between

the ages of 7 weeks

and 70 who went to

Disney at March

Break:                                                 10


Dinner parties hosted:                     2

In the previous year:                        25


Plays attended:                                 9

In the previous year:                       0


Games of tennis played:                   70+

Number of doubles partners

who let me cry on the court,

for at least half of those games:      3


Kickboxing lessons:                           4

Massages required to

heal effects of

kickboxing lessons:                           4


Days spent in mediation:                 2


Werewolf costumes purchased:      1*


Meals with trusted girlfriends:        71


Books completed:                              1 (almost)


Pen Pal letters written:                    22


Not a bad year, all in. Here’s to a year ahead with a few more in-person meetings. You almost have me convinced about the tattoo….






* a shameless inclusion for the sole purpose of solving my photo problem for this letter.


Read Reva’s last letter here:


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Pen Pal Project

Election Day

October 19, 2015

Dear Reva,

Vote-CanadaThe fall is racing by in a blur of turkey dinners and Halloween decorations and soccer games and homework and karate lessons and puberty and literary events. And political chatter, of course, because today is the Canadian election. Have you voted yet?

On the subject of the election, I’ve obviously aged into a new demographic in the past four years: I know a statistically significant number of people running for office. As I commute across the city every day, I see people on lawn signs that I knew in law school, or in university, or in a previous career. Other friends are holding fundraisers or running campaigns.

We’ve arrived. We are officially entering our professional power years. So, what are we going to do with them?

This was, I recall, one of the reasons we started The Pen Pal Project. I haven’t spent much time talking about my career in these pages, not because I haven’t been focused on it, but because I’m superstitious about work-in-progress, and because other life events seemed more letter-worthy. But you asked in your last letter about how I write, how I keep the threads of the story from unraveling in my head when real life is grabbing at the ends and pulling.

So it seems like the right time to mention that my second novel is due at the beginning of December, and it appears that I will hit my deadline. This means two things. First, that I am writing furiously and am displaying frequent hermit-like behavior, with an occasional exception made for the aforementioned literary events (I still feel like a fan-girl, but not like an imposter, which is progress). And second, that amid all of the personal chaos of the past year, I have managed (almost) to write a book.

It occurred to me recently that the crux of identity is in the doing. That is to say, we are what we do. I’ve spent more time than I’d care to admit over the course of my life asking the question Who am I and what is my purpose? Lately I’ve had very little time for that kind of reflection, and have been fixed on present-tense questions, such as How am I going to get through this? Different.

The interesting thing that happens when things fall apart is that your life boils down to certain essentials. You see a much smaller circle of people, you participate in a much smaller range of activities, and you engage in a narrower set of intellectual pursuits. You do not have the energy to perform. You are doing only what is essential for your survival, and it reveals an incredible amount about your identity without any effort on your part.

I’m a writer. I discovered this because even in the worst moments of my life, I kept writing. Characters pushed themselves into my imagination, and even when I was too tired to write their stories, I could still find the energy to write my own, here in these letters to you. So I’m electing to spend my power years writing. What are you going to do?








Pen Pal Project

I Can See The Moon

October 6, 2015, my office


Dear Reva,

I passed a big milestone this weekend.

It’s been a year since my husband told me he was leaving. At the time, it came as an extremely unpleasant surprise, and today it still remains something of a mystery.

I’m not going to say that my house burned down and now I can see the moon (as the saying goes). No one wants her house to burn down, and you can see the moon just fine by stepping outside once in a while (except when there is a rare and beautiful eclipse, in which case you can’t see it at all). I don’t think that change, even necessary change, requires a catastrophe to bring it about, nor do I believe that every catastrophe is for the best, necessarily.

But if your house/life burns down, the process of rebuilding is intensely conscious. The life you had before the disaster took shape organically, over many years, and it reflected both the compromises of partnership, and the preferences of your younger self. The life you now contemplate will express your present identity. So what should it look like?

Adversity isn’t identity, and no one would want it to be. We are infinitely greater than the sum of our negative experiences. But it is human nature to reject the idea of pain without purpose. I think that our sense of a true self, of an identity, often comes into focus through our attempts to understand painful events.   (On this topic, I was very moved by Andrew Solomon’s thoughts on how the worst moments in our lives make us who we are.)

When you emerge from the shell of your former life, you feel as you imagine a newborn must feel: dependent, disoriented, frightened, and battered by overwhelming emotions and sensations. But then, as your agency returns, you begin to observe your own actions with interest. Freed of patterns and routines, how do you choose to spend your time? With whom? Which activities do you anticipate with pleasure, and which ones with dread? And from these basic cues, you can begin to build a life around your identity, instead of crafting an identity to fit your life.

I wouldn’t have chosen the fire, but it has generated a new life that is wholly mine. Because if your house burns down, why content yourself with simply looking at the moon? Why not shoot for it?



P.S.  God, yes, it’s messy.

P.P.S. Really looking forward to seeing you in person (!) at the International Festival of Authors party.  Both of us in the same room at the same time: an event almost as rare as a lunar eclipse.  We will need photographic evidence.

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Read Reva’s last letter here.

Pen Pal Project

You’ve changed

September 22, 2015

My office

Dear Reva,

neon sign change

You’ve changed.

Has anyone said that to you recently? What was your reaction? Did you think the person meant it as a compliment or a criticism?

I ask because I’m interested, in life generally, and in the book I’m writing, in how we construct our identities. And I think that many of us resist the idea that we change. Sure, we change the music we like and the fashions we admire, but our fundamental personalities don’t change, right? Identity isn’t fashion. Identity is fixed.

In fact, the opposite seems to be true. The current neuroscience research suggests that we are constantly evolving, or, as Dan Gilbert puts it in his delightful TED talk: “Human beings are works in progress that mistakenly think they’re finished.”

I accept that this is true intellectually, but until recently, I’ve resisted it on an emotional level. I’ve always found the idea that people change to be quite threatening. What if you invest all your energy into a relationship – a marriage, a friendship, a work partnership – and that person changes? How can you control that? How can you protect your investment?

You can’t, obviously, which I learned the hard way on several fronts.

When you go through divorce, people tell you that you’ve changed. Usually the person who no longer wants to be in a relationship with you will tell you that (and it isn’t intended as a compliment). But friends will tell you that as well. Some will mean it as an encouragement, as in the end of your marriage will allow you to grow further into the person you are meant to be. Some people don’t, as in, I can see why your marriage fell apart, because you are one of those people who changes, but I’m not, so my marriage is safe.

And because you are, in fact, changing, some of those people will remain friends, and some of them won’t.

Which brings me to the question you asked in your last letter: “Have you via your writing or otherwise ever not been liked?” Yes, I have. And it sucked.

But I’m getting better at dealing with it. Because I’m changing.



Read Reva’s last letter here:

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Pen Pal Project, Recent News

Say please

September 9, 2015

My office

please like me

Dear Reva,

Someone recently described these letters as ‘earnest’ in conversation. The conversation was, in fact, about something else, but I can’t remember anything about it other than this one comment. I don’t think he meant it as a criticism, even. But I am not very good with criticism, which is a huge problem if you tend to see it everywhere.

(To my friend, who reads my letters, and innocently chose the word ‘earnest’ to describe them: THIS IS NOT ABOUT YOU. Although one of the great differences between this friend and me is that he wouldn’t actually think it was about him, first because he knows me; and second, because he is a man; and third, because he is not a pleaser, which I most assuredly am.)

The point of this story is mysterious, I know. Maybe I just wanted to warn people off referring to me as earnest in the future. But because I’m an English major, I’m good at pretending to have a point, so here goes: at the halfway mark of our Pen Pal Project, I wonder if I have fallen into the trap of trying to make everyone like me in what was supposed to be a really honest conversation.

Don’t get me wrong. I am, in person, extremely likeable. You know that, because you’ve met me, but it’s important to me that other people, the ones who read these letters but haven’t met me, think so too.

There, you see? It’s like a tic.

For me, September has always felt like the start of a new year. It’s a time for resolutions and promises of self-improvement. And this year, I’m going to become less concerned with pleasing others, and more concerned with pleasing myself.

Is that okay?



P.S. It’s odd how often our minds are on the same topics, however scattered they may be (not adult colouring books, necessarily, but refugees and Ashley Madison for sure).  Thanks for your last letter. And for your piece in the Huffington Post today on how communities can start to shake off the sense of helplessness and rage that we all feel about the refugee crisis, and channel it into positive action. Well done.

P.P.S. Okay, that was earnest.  But it’s in a post-script, so it doesn’t really count.

Read Reva’s last letter here.

Follow the ongoing correspondence here.

Pen Pal Project

Time flies

August 24, 2015

My office

time flies

Dear Reva,

Time is indeed flying by. The evenings are getting cooler, I’m ordering school uniforms and lunches and registering for fall programs, and my book deadline is getting closer week by week. What a summer, though! Such long stretches of glorious weather. We’ve been lucky.

You asked if I was motivated to write The Hole in the Middle by an anxiety about the passage of time. In short, yes, I was. I had a disconcerting sense, as my 40th birthday approached, that I was spending my precious time on the wrong things, professionally speaking. I was in a job that was very senior and challenging, but my work was largely invisible. My role was to contribute to the individual legacy of my boss, and to the overall reputation of my institutional employer.

I began to feel that I was hiding in some way, and was in danger of never realizing my full potential. And I remembered that I had always wanted to write a book. And I asked myself if I still intended to keep that promise to myself, and if so, when.

Five years later, my life is transformed. I’m a professional writer with a bestselling book that will come out in the US in January. I’m halfway through the writing of my second novel. I’m not married anymore. I’ve moved. I’ve lost friends. I’ve gained friends. I have a pen pal. My boys are old enough to be proud that their mother wrote a book.

As for my favourite quote about the passage of time, I give you Robert Frost:

 Nature’s first green is gold,

Her hardest hue to hold.

Her early leaf’s a flower;

But only so an hour.

Then leaf subsides to leaf.

So Eden sank to grief,

So dawn goes down to day.

Nothing gold can stay.


Much has been written about this deceptively simple poem, but my own interpretation is that a life fully realized – fully lived – includes loss, change, and grief. And perhaps, understanding that reality, we can embrace change with less fear and less regret?




Read Reva’s last letter here.

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