Jan 20

Beatrix: Four

Hi B,

This morning you yelled for 20 minutes about how we had to tape your banana back together. Because it had been opened improperly.

This is the best age you’ve ever been. Since my last letter to you, you’ve started Junior Kindergarten. It’s been really incredible to watch you grow into it. Your birthday means you’ll always be one of the youngest in your class, but most people don’t know it. You’re a tall, strong kid. You’re extremely verbal. You have a stronger command presence than most adults, for better or for worse.

Your emotions are so unguarded these days, and it catches me in my chest sometimes. Your sis was the same way. Your giggles are the best. And when your feelings are hurt, there’s no attempt to hide it. Just this abject pouting sorrow that takes over your whole body. It’s so extreme it would make us laugh if it weren’t so serious. You don’t know what to do with all these feelings either. Sometimes when you think you’re in trouble you’ll start frantically looking around for things to throw or break to try to get in more trouble. I don’t think you even know why.

And still this age is the best. You want to talk about T-cells, and lava, constantly. You make me recite major portions of The Princess Bride in exchange for eating your dinner. You have individual run-on sentences that can go for 10 minutes or more. And you collect everything. You are one of the only kids in your class who knows what the word “hoarder” means. You pick up a pine cone, or a good leaf, or the stick from an old cake pop and tell us, “I have to add this to my collection.” Never “want to.” Only, “have to.”

When you were littler, your sis was someone who would come and go and I think you didn’t really understand the pattern to it. You understand more now. Enough that when it’s time for Lil to go back to her other home for a week, you really feel it. And each time Lil comes back to our place, you two spend the first evening re-negotiating how to be together. You just don’t know what to do with yourself every time she comes back. After a day you settle back in to being sisters and that’s pretty great, too.

Your mom and I talk a lot about that. About how you two get each other in a way that no one else does. Lil is your big sis and big sisters are always annoyed with little sisters, but she takes care of you and you look up to her. She is one of the only people in the world whose authority you accept. Watching the two of you read books together, or paint, or listening to you talk her ear off. Well that’s my hobby now on alternating Saturdays.

On Monday you head back to school after the break and not a moment too soon. Two weeks without structure has made you loopy, and maybe the rest of us, too. After the banana incident you threw a pine cone. You know it’s serious when you’re disrupting your collection.

I love you, ridiculous creature.


Sep 19

Lily: Nine and a Half

Hi Kid,

Tomorrow you start grade 4 and it feels like everything is changing. You’re in the same school with the same friends, but even since my last letter to you so much is different.

There’s the obvious stuff. Your mom moved. You’ve grown half a foot. But what keeps catching me when I’m not paying attention is how much you’ve grown up. There are these moments when you’re talking or even just sitting on the couch reading where you could be 10, or 12, or 14. I don’t know what it is exactly, but I’ve had this sense of it several times over the summer and it knocks me over. It makes me feel happy and sad at the same time. It feels very fast.

Missy and I have this joke that, if you ever got a tattoo, it would be a heart with the world “Rules” on it. You are a kid who likes to know the rules, and to help other people remember them. B will often come up when the two of you are playing and say, “Lily, can you be in charge?” Your teachers have come up with every euphemism they can to express it on report cards and at parent teacher nights. At one point your grandma said you were being bossy. Missy and I shouted from the next room, “confidence & leadership skills!” It’s part of your brand, is what I’m saying.

But I’ve been thinking about your relationship to rules, and what it will be as you grow up. Because I’ll tell you, kiddo, I was also really good at rules. I broke a few in pretty big ways, but overall rules felt like a game I knew how to win. And I got a lot of positive feedback for following those rules well. You get a lot of it, too.

What I want to tell you, though, Lil, is that they aren’t all good. You can be too good at following the rules. And it can stop you from seeing that you’re playing the wrong game. Sometimes the rules let you succeed, but they keep other people from ever having a chance. That’s not a good game to play. Those are rules worth breaking. Sometimes the rules say you have to stay somewhere, or with someone, that makes you unhappy. I know this is hard to imagine, but the rules can be so loud, kiddo. People follow those rules. I’ve followed those rules. But I hope so much that you won’t.

The secret is to know that we can write new rules. For ourselves. For our relationships. For the whole world if we need to. It’s helpful to know the rules. But it’s also helpful to look at where they’re steering you. To realize that they are not always good ones. We have to make our own decisions about what’s right. And it’s helpful to know that you can break those rules if they’re steering you wrong. You can break them if you need to, kid. I will love you no matter what.

In other news, you had an amazing summer. You hiked, swam, biked, and caught frogs. You made claymation movies, and chimichurri. You had your first ramen, first bubble tea, first manicure, and first charcoal ice cream. I’m so excited to see what grade 4 brings, and so grateful for the time we had together this summer.

One quick note before I go: I think this may be the last of these letters – at least publicly. You and I have talked about it a couple times. You know these letters exist, I’ve never kept them a secret from you. But you and your friends are getting more digitally literate now. I don’t think there’s anything too embarrassing in them, but I also know how complicated it will be to navigate the next 10 years.

You told me last week it would be fine to keep writing them. I might do that. But privately, now. You don’t need me telling your story to the world any more. You’re starting to be the one holding the pen.

I’m so proud of the person you’re becoming. It’s all happening faster than I can really handle, but that’s the way of things and I wouldn’t change it. I love you, Lil.


Jun 19

Beatrix: Three and a Half

Hi kiddo,

This weekend you turned three and a half and you are treating it as a very big deal. You have been asking what three and a half year olds get to do that three year olds don’t. We have been suggesting that three and a half year olds have fewer tantrums than three year olds, to limited effect.

But it’s true, you are a much bigger kid now. Since my last letter, you’re out of diapers, out of your crib, riding a balance bike, and getting ready to start kindergarten in the fall. That went by really fast, B.

It’s warmer now, even if summer is taking its time getting here. Last year you would hide behind our legs when the neighbours were out on the street. This year you march up to them and tell them about fire hydrants and flowers, whether they asked or not. You’re still an introverted kid like your parents (and your sis!) but you’re finding your confidence. Don’t let anyone ever tell you those things are incompatible. One is about who you choose to be around, and one is about who you choose to be.

You have big feelings these days. The other day in the car I was too slow to respond to you pointing out a backhoe on the shoulder, and you got upset that I was “not respecting your words.” And sometimes when you’re crying you’ll shout, with this incredible 3.5-year-old self-awareness, that you don’t know how to calm yourself down. But it’s not just the hard emotions – your happiness is dialed way up, too. Your giggles are incredible, and they come out most when you’re with Lil. So is your curiosity. You notice things. You notice everything.

The other day we were walking you home from preschool, and you were up ahead with your mom. I was watching you go, this strong, confident, healthy kid. And I had some of my own big feelings. I thought back to the scary bits. When your mom was pregnant and we found out that she’d been exposed to a virus that could cause us to lose you. When you were a baby and the docs were getting worried that you weren’t gaining weight. I was talking with grandpa about it yesterday. About how parenting is amazing and transformational and also sometimes really scary. I’m so grateful for you and lil and your mom. I’m trying to live in a gratitude place instead of a fear place. But sometimes it’s cause for some feelings.

Thank you for being the incredible kid you are, B. Thank you for all of the big feelings. I love you, and I’m so proud of what a big kid you are now.


PS – There’s a charity that we support that works on ending violence against women. This year they asked me to write up some thoughts about Father’s Day and how being a dad of daughters makes me think about those issues. I wrote them something, and I’ve included it here below in case, when you grow up and read these, you’re curious.

When you’re a dad of daughters, people expect that to be why you give. I get it. Dads don’t talk about it a lot, but the depth of the love we feel for our kids is so intense. And to see one of them hurt, a skinned knee or a bruised cheek, it causes this sharp physical pain in us. At least it does in me.

And so people figure, sure, he’s supporting women’s shelters because he has daughters. He can see them in that position. He would want to protect them.

If that’s what drives you to give, that’s so excellent of you. And thank you for stepping up. But it’s not really why I give.

Because the truth is, I can’t see it. I can’t imagine my daughters, grown, and running for their lives. I can’t picture them abused and fearful and trying to protect their own kids with nowhere to go. I can’t see my happy, safe, healthy daughters in that. When I try to, my brain sort of shuts it out.

Unless you have people in your life who have gone through it, I bet yours does, too. You tell yourself a story about how it wouldn’t happen to your daughter. How you would protect her, because that’s what loving dads do. I hope that’s true for her.

But it shouldn’t happen to anyone. Everyone deserves to be safe, and loved, and protected, but not everyone is. I can’t let my brain shut that out. I can’t treat this as someone else’s problem. I need to make this my problem, too.

On father’s day, I’m thinking less about how this gift might help my own girls. I’m thinking more about the conversations I’ll have with them as they grow up. When they learn how awful the world can be. When they look to me and ask what I’ve done to help. I want to have a good answer.

Feb 19

Lily: Nine

Hi kid,

It snowed today. Snow on top of two-week-old sheet ice. So we took the two of you sledding. B had her fill after the first run and wanted to go play in the snow-covered playground, but you and I got a couple more in. You’re so much braver than you used to be, going down those hills. I remember when you would insist on riding down with one of us, and when you couldn’t carry the sled back up the hill. I remember you crying when you’d get a face full of snow. Now you have this wonderful, nose-crinkling laugh.

Not that you’ve lost your conservative streak entirely. We went to Mexico earlier this month, and you had a minor meltdown the week before. You were worried that it wouldn’t be as good as the place we’d taken you last year. That we had reached peak vacation that very first time and everything else would be worse. You loved our trip this year, of course, and on the way home we made lists as a family of ways this place was better and ways that one was. We wanted you to see the adventure and variety and possibility in all of it. But mostly, as I write this, I wonder what you’ll think as an adult, reading it. Will you recognize that anxiety, or will it feel like a far away thing? I don’t honestly know which future my money’s on.

A thing I wrote in my last letter is still true: you’re not 8 any more. 9 feels very different. Different emotions, different fashion, different language. And sometimes as your dad I can get swept away in it. It’s so excellent to be able to introduce you to new things, and talk with you about what you think. I love our conversations, and love that there are still things I know about that you find cool. But it’s also tricky because you’re still a kid. Things like a suspenseful video game (even without any violence) can really freak you out. You’re such a big kid until we hit some element where you aren’t. And then I ask myself if we screwed up. If we brought things to you that you weren’t ready for, yet. I hope that we are finding the right balance there, and that we keep finding it. I want to keep being someone who has new things to show you.

Missy and I are doing up our wills. We both plan to be around for a long time, to be clear, but it’s still the right thing to do. And one of the things we talk about a lot is what it would mean for you and B, if we weren’t here. The way you are with each other is the most special thing, Lil. It fills me to bursting. The photos app on my phone is stuffed with pictures of the two of you holding hands while we walk somewhere. I know it will change profoundly as you grow up, but I hope you’ll never lose that closeness. When you were B’s age, you used to want a “Princess Lily” story every night before bed. Now when I put B to bed, she always wants a “Princess Lily and Princess Beatrix” story. You are very much your own kids, but your stories are intertwined.

Missy finally got B down, and you’re out like a light. I’m going to go sit with M and pour some scotch before we go to sleep.

I love you I love you I love you, Lil. Thank you for sometimes finding me cool.


Dec 18

Beatrix: Three

Hi B,

We took you to the West end tonight for dinner with Lil. You’ve learned the days of the week and everything now, so you knew it was unusual to be seeing Lil on a Tuesday. But you were thrilled. We’re starting to do more of that – restaurants, baby sitters – stuff that was hard for you when you were a baby is getting a little easier.

In the time since my last letter to you we’ve opened our office space. You love it. The training space has a stage, and you and Lil have dance parties. You sit in all the chairs, and ask if you can use your mom’s trampoline. There’s a gym down the street with a play area that you can’t get enough of. Which is great for your mom and me, because when you don’t get out and run in the morning, you go a bit feral. Your mom often spots it before I do: “these kids need to go run around.” By the time we get back from the office/gym double bill, you’re wiped. This is good.

What I know from your sister is that 3 can be a rough age. A lot of transition – when you were two you were still in your crib. By this time next year you’ll be in school. But it’s also a wonderful age – the best age you’ve ever been. You borrow adult-isms in your speech in funny ways. You’ll walk up to me while I’m cooking and say, “Daddy, any progress here?” You are a really funny kid in general, actually. People sometimes think it’s unintentional but your timing is too good, and too consistent. You know you’re funny. And after a meal you’ll say, “Hands up if you want dessert.” You’ll wait, stifling a grin, until we all put our hands up, then you’ll raise your foot. Then you’ll cap it off with, “I raised my foot.” Comedic genius.

Your new language and expressiveness means that you’re also more articulate about missing your sis when she’s not at our place. That part stings. But it’s part of your world, and we know that this is you figuring it out. My hope is that as you get older, you two will have more conversations and contact without needing us to mediate. That you’ll call or skype or text each other. The sometimes-distance doesn’t stop you from fighting like siblings at times, but overall you two are so close and so excellent to each other that it makes my heart hurt. You love your big sis, no surprise there, but she was also so proud to show you off to the kids at school when we picked her up today.

I love you, B. We all do. Happy birthday, my big girl.


Aug 18

Lily: Eight and a Half

Hey kiddo,

I’m writing this letter at the dining room table with the back door open. It’s the first night in weeks that it’s been cool enough to let the outside in, and it’s marvellous. Missy and I have wine. It’s been a really good, but really hot, summer.

Okay so first off some updates from my last letter. We did get office space, and you’ve seen it and approved it, which is a relief. We’re still doing demolition on the stuff that was there before, and it will be another month before we can use it, but we’re so excited to see it coming to life. Lil, I can’t even tell you – we feel like it’s going to change so much of what our business can do.

We also got you started with lock picks. So far you’ve got me still holding the tension wrench while you work the rake. But you mutter a little “yesss” when you get it open and that’s honestly the whole point.

You just finished a week of video game design camp and you loved it. Sometimes it’s hard to get updates out of you about school or camp, but every night this week we got reports. “Today we’re working on graphics, tomorrow is debugging but I don’t think our game has any bugs.” On the last day your camp did Demo Day, and M and I thought it was a hoot. We were over the moon proud of you, of course, but having a bunch of 8-11 year olds do demo day sounds strikingly similar to having professional engineers do it in a startup, and that was delightful. Well, it was delightful for us, anyhow.

There’s this thing that I think all parents are trying to figure out right now around digital literacy, and we’re right in there with them. We love that you’re learning about tech, equipping yourself to make it work for you. That’s crucial for us, and has opened so many doors in our lives. But you’re also eight and a half now, and that feels a lot different than eight. You’re still a kid, but you’re not a little kid any more. You sound more and more like a tween every day. And while we haven’t seen you pulled too deeply into the social pressures of online spaces yet, we know it’s coming, and it freaks us out a little. We want you proficient, but insulated. We want you to explore, but stay safe.

I don’t remember where I saw it, but long ago at some formative moment in my life I encountered the phrase, prepare the child for the path, not the path for the child. It seems wise to me and I try to remember it when I worry about things like this. Obviously we still stay close to you, watch for tripping hazards we can see that you can’t, whether you’re online or just running around on the street. But more often these days we’re trying to have conversations with you. To let you figure it out and then check with us, instead of waiting for us to say yes. In my last letter to your sis I talk about raising warriors a lot, or possibly dragons. I think this is what that looks like, but that doesn’t make it less scary.

You’re back with your mom this weekend after a week with us. I miss you. The house always feels so full and right when you’re here. But I got pics from your mom of you sitting on a (stationary) motorbike and you look pretty pleased. I’ll want a full report next time I see you.

Love you kid,


Jun 18

Beatrix: Two and a Half

Hi B,

I’m writing this letter on an airplane and the first thing that strikes me is how rare that is these days. When your sis was your age, I was still at Mozilla, and I was in the air a lot. Her mom and I had already split up, and I scheduled my travel to avoid missing time with her. But it was still pretty hard. Not because I don’t love the travel. I really do. I hope you will, too. But emotions always feel bigger for me on airplanes. Movies affect me more. And I end up writing letters.

I’ll say the things I always say: you’ve grown so much since my last letter. You’re a funny, brave, sensitive, full contact kid. You want to do everything Lil does, be everywhere she is. You have this thing you do where if you’re about to tackle someone or something, you stick out your jaw and bare your teeth like you’re going into battle. It’s excellent.

Your mom and I talk a lot about raising warriors. You’re coming up in a world that can be so harsh, so nasty. I watch a lot of the adults in my life build up tougher skin and draw harder, angrier lines to protect themselves from it. I see myself do it. But if we’re not careful that toughness will cost us our tenderness, B, and those lines will make it harder for us to see each other. When we talk about raising you as warriors, we mean that we want you to have agility and perception, resourcefulness and strength. We want to teach you to defend yourself from all this without letting it harden you. “Warriors” is a hard word because combat is not at all the only tool we want you to have. War is never something to wish for, and even when you win you lose. I guess we just want you to be prepared for anything. I think every parent does.

Every night before bed you want a Beatrix and Lily story. The plot lines have been getting more esoteric as I run out of new stories to tell. There was one story that was just a thinly-veiled recipe for making oatmeal raisin cookies. But you listen, perfectly still, to each one. One of your favourite guest stars is Hyacinth, the dragon. If I ever omit her in a story you make me go back as epilogue and write her in. Hyacinth has purple scales, and big powerful wings, and only breathes fire when it’s to help people who need her. She is magic, and protects the world, and likes watermelon. Maybe your mom and I should say we’re raising dragons.

The plane is landing soon, so here’s a few final fun facts about you. You’re starting preschool soon, and next September you’ll start big kid school. You’re learning to ride a balance bike. And avocado makes you projectile vomit. It’s really something.

I miss you, B. You’ll be asleep by the time I get home tonight, but I’ll be there when you wake up tomorrow. I love you.


Feb 18

Lily: Eight

Hi sweets,

I miss you. A few weeks ago we all went to Mexico. You had a blast and so did we, but after a week of uninterrupted time together, it’s always hard to go back to the some-days-on, some-days-off schedule we have. B, who has even less patience, feels it every time you’re away, and still shouts your name every time the doorbell rings.

I was talking to a friend the other day who’s going through a divorce, and they asked about it. About how it felt to move out, to not be in the house your kid lives in half the time. Your mom and I split earlier than many folks our age, so I’ve answered that question for a lot of friends over the years. My answer is always the same: it’s awful. It’s awful and it doesn’t really ever stop being awful. That doesn’t mean it can’t also be the right call — I know it was for us. And I know that you have two amazing and loving homes and I am so happy with how comfortable you are in each of them. How much each of them is really yours. But I still feel the gaps so deeply, even years later, and wouldn’t wish it on any parent.

I’m not moping, though. We see each other a lot and I love that time. The other day we were talking about crushes, over pizza. You explained that a crush is “when you love someone so much but they don’t love you back or maybe even know.” I asked if you’d ever had a crush. (You have.) You said no. (You’re incorrect.) But, you said, “even though I’ve never had a crush I think some people have had crushes on me.” Well I wouldn’t know about that, kiddo, but it’s clear to me already that 8 is not the same as 7 1/2.

Speaking of 7 1/2, since my last letter to you a lot has changed with our business. The book came out, and became a best seller. You don’t care about book sales, but you find the title hilarious and keep asking to see it again and then giggling. Swears are a hot topic in the house right now and we’re talking a lot about how to use words carefully and why words can upset some people more than others.

Melissa and I love the work we’re doing for RSG. We get such an energy off of it, and off the impact we have. We truly feel like we’re making work better, Lil, and that’s exactly what we wanted to do. We’re starting to make offers on office space and I hope that my next letter will be able to treat that as a done deal.

Speaking of next letters, I’ve been thinking about these. The first kids in your class are starting to get their own smartphones. In a few years I imagine the tide will have fully engulfed your peer group, and I don’t want these letters to be a thing that someone uses to tease you. Right now my plan is to keep writing them until you’re 10, and then get your opinion about what to do with them. I didn’t know, when I started writing them, whether I’d keep it up or not. But every 6 months as your birthday (or half-birthday) comes up and I think about it, I can’t imagine not writing one. I imagine 10 will feel that way, too.

For your 8th birthday you asked about learning to program, and learning to pick locks. I’m gonna go figure out whether it’s legal to buy lockpicks in Ontario or whether we need to first teach you how to make your own. In a few days you’re back at our place. I’m really looking forward to it.

Love you kid,