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The Hindsight Letters on CBC Radio’s “Being Jann”

30 Jun

The very lovely Jann Arden and I! (me with crazy eyes, clearly star-struck)

Hello again, wonderful Readers!

I have some more exciting news to share: Yesterday I had the opportunity to visit the CBC Radio studios once again. This time, I had the pleasure of sitting down and chatting about The Hindsight Letters with Canadian Singer-Songwriter Extraordinaire, the very lovely Jann Arden!!!

The segment will air on Saturday, July 16th at 10am on Jann’s super cool program, Being Jann. The episode is a Mom-themed show jam-packed with hilarious stories, great tunes and even a chat with Melissa Gilbert from Little House On The Prairie. I will be posting on the day of the broadcast to keep everyone up to date on the details.

I’m so honoured to have had the opportunity to share the story of The Hindsight Letters with such a wide audience as “Being Jann”s. Thanks so much to Sara Tate, Iris Yudai, and of course, Jann Arden for including me in the broadcast. And most of all, thanks so much to all the HL readers for joining me on this journey. Hopefully I’ll make you proud!


Letter 55: Being A Teenager Is Awesome

20 Jun

Dear me at 15,

I’m writing you this letter to tell you about an epiphany I had a few nights ago:

Being a teenager is awesome.

Now, I know this sounds contradictory to all the Letters I’ve written to you prior to this one. And it kind of is. Most of my Letters have been addressing all of the anxieties, grievances, confusion and general turmoil that tends to accompany one’s adolescence. But I’m here to tell you that there’s actually a whole lot of awesomeness that’s involved in being your age. And I want for you to recognize it and take advantage of it before it’s too late.

You see, the other night, I was downstairs in your future kitchen, having just put your future daughter to bed. It was one of the first hot days of summer, and the sky had that wonderful warm glow that happens just after the sun sets. I myself was settling down for the evening; teeth brushed, jammies on. But looking at that summer sky, I was overcome with a feeling of anticipation. Excitement. Freedom.

Something about that summer night sky sent me right into a full-force teenaged summer flashback. I was right back into your life again.

I was putting on my makeup and my cutest little punk rock outfit with Amy in the upstairs bathroom of my parents’ house. I was taking the Don Mills bus down to Cliffwood Park. I was singing Sublime into the wee small hours with a 40 oz of Cherry Wine Cooler in my hand and not a care in the world. I was relishing in time wasted without responsibilities, surrounded by friends, feeling the warm summer breeze on my skin. Enjoying the first real kisses with my first real love. Laughing and dancing and falling down.

And as much as I tried to remember all of the uncomfortable, awkward and even downright traumatic things that happened during my teenaged years, I just simply couldn’t. All I could think about was that uncontrollable laughter. The time that Amy and I had a food fight with Betty Crocker frosting at the Lake House in the middle of the night. The way that we were literally rolling around on the ground, holding our stomachs, smears of chocolate in our hair, sore from giggling so hard and trying even harder not to wake Mom.

The luxury of time. Planning for hours about what outfit would be worn to which show. Organizing snacks, travel arrangements and must-see-acts to each years’ Warped Tour with the intensity deserving of a year-long journey. Going to a concert and dancing until hot and sweaty, hair ruined, make-up running, and not caring, because I was having the time of my life moving to the music that truly moved me.

The connection with friends. Such a deep, intimate connection. Sharing every detail of your life with someone, good and bad, unafraid of judgement, and knowing that person cares enough to listen and understand. The feeling of connecting intensely with someone who isn’t either related by blood or legally bound to appreciate you.

The hope for the future. Everything is an unknown. The possibilities are endless. There’s so much to experience. So much to see. So much to look forward to.

My dear girl, you will do a lot of wonderful things in your life. Most of your dreams will actually come true. But I’m here to tell you, in many ways, the dreaming can be almost as good as the fruition. Dreaming about the things you want, not knowing, wondering, questioning, imagining all the possibilities- that’s an incredible feeling. And it’s a feeling you’ll experience less often, the more experiences you gain.

I know that being a teenager can be frustrating. You feel like an adult. You just want to get your life started, already. You want to be in control of your own independence and no longer under your parents’ rule. But, in many ways, you have more freedom now than you will as an adult. All your expenses are covered. There is food on your table without you having to prepare it. Your bills are paid. Your laundry is done. The only person that you need to focus on right now is YOU.

I know that you’re itching to be responsible for your own life. But there is something really, really great about being able to be irresponsible.

You have the ability to write your future. To decide who you want to be and be it. Try on some different hats. Don’t be so serious all the time. Stop worrying about the details of the sequence of events that will follow from every single step of your life. Stop worrying. Stop being so darned responsible and just BE for a while.

And the next time you hop on the Don Mills bus and head down to Cliffwood Park for the evening, do me a favour and give an extra big hug to your friends. Dance a little more. Laugh a little harder. Love those moments as intensely as they deserve and I promise you, you won’t regret it.

And as for me, tonight I’ll raise a special glass of Cherry Wine Cooler to you, my friend. The night is ours. Now hop on that bus and go make me proud.


If you liked that post, you’ll surely like this one and this one!

*GUEST SUBMISSION* Letter 52: Jealousy Ain’t Pretty

30 May

Lauren writes:

Dear me at 15:

Jealousy ain’t pretty.  Since you hit the double-digits, you’ve found a way to analyze, dissect, and find ways to be jealous of pretty much everyone who walks down the hall in high school.  This girl’s hair is longer and more manageable than yours.  That girl has two thighs that are separate and don’t make brushing noise when she walks down the hall.  This girl has a boyfriend and sucks face with him in front of the lockers (however, that boy has atrocious acne and is a supreme jackass, so she can keep him).

My dear, it is time for you to learn a valuable lesson:  Don’t be so jealous!  It doesn’t do anything to empower you. Staring at This Girl’s long, shiny hair won’t make yours any more luscious.  You just start to pick on your own hair that much more viciously, becoming that much more frustrated, making you feel that much more doomed to live your life with a frizzy Jennifer Aniston “shag.”

Not only will being jealous cause your self-esteem to plummet; it also wreaks havoc on how you view your friends.  When your good friend (who grew up to create The Hindsight Letters) sang in the talent competition with a voice that brought half the audience to tears, you couldn’t even be happy for her.  Instead, you wished you had a voice that didn’t make mirrors crack (and let me tell you right now, you never will.  End the dream now.)  When you saw how excited everyone was for her, and how no one could stop talking about how wonderful her performance was, you felt the Green-Eyed Monster take over you more and more.  When she was later was walking in the hallway, surrounded by congratulatory fans, you pouted in the corner, fuming.  Now really, is it so hard to tell her how wonderful she was in the show?  Deep down, you ARE happy for her.  And you know that wishing won’t make your voice angelic, your grades better, or your boobs bigger.  Being jealous of those things won’t help you get them.  Not to mention, having most of the things your are so jealous of (see “bigger boobs”) won’t make you happy.  The things worth having in life are the things you have to work for.  When was the last time you took a singing lesson, hmm?

So stop looking on with a critical eye, put down the padded bra (you’re not fooling anybody), and go hug your friend!  High-fives and grins beats pouting and premature wrinkles any day of the week.

And relax, by the time you hit 19, you’ll have filled out and discovered the magic of flat irons.

Lauren still can’t carry a tune, but she did grow out her hair and is thrilled for all of the things her talented and brilliant friends have accomplished.


If you liked this post, you’ll surely love this one and this one!

Letter 44: You’re Not A Badass

28 Mar

Me (right) and my best friend (left) at 17.

Dear me at 17:

You’re sitting in the back room of a Queen Street tattoo parlour. Your boyfriend is by your side, holding your hand. You’re waiting for the piercer to come into the room and punch a couple of holes in a couple of very sensitive body parts.

You’re already regretting your decision, and it hasn’t even been made yet.

Let me tell you something here:

You are not a badass.

I’m sorry. I know you really want to be. But let’s face it: You’re an Optometrist’s daughter. You live in the Canadian suburbs. You like to eat chicken fingers and your Mother drives you to school every day in her blue Dodge Caravan. You’ve grown up in a neighbourhood so safe that you were able to meander your street with your jump rope late into the summer evenings. Neighbours would wave at each other as they took out their garbage.

Your family isn’t perfect. You’ve had your setbacks. But you’ve never once had to wonder whether there would be food on the table, or how you would purchase your next pair of sneakers. In fact, though they are blissfully unaware of its usage, the money to purchase your ill-fated piercing was given to you by your parents.

I’m sorry, honey, but I don’t think it’s possible to do anything remotely badass using Mommy and Daddy’s cash.

This whole badass deal began at the end of Junior High. You had been torturously bullied for being the token “good girl”. You wanted so badly to change your image. So you went about doing it the only way you knew how: running, full force, in the opposite direction. You chopped off your hair. You wore crazy clothes. You tried your darndest to become a “punk rocker”. Along with this came the piercings. First, all over your ears. Then your nose. Then your eyebrow. Now this wholesome little number.

To some extent, you achieved your end goal: You’re no longer the resident goody-two-shoes of York Mills Collegiate Institute. But this is more accurately because you switched schools. The bullies of YMCI have long since forgotten about you and moved on to some other poor unfortunate soul. But there you are, still sitting in that piercing room. Still trying to prove something to some invisible critic apparently stalking your every move. Who are you trying to fool?

You are sweet. You are naive. You are pretty. You love your family. You are a homebody at heart. You still sleep with the same stuffed animal you’ve had since you were three. Your favourite movie is “Little Women”.

You listen to punk rock because you love the music. You walk to the bus blaring NOFX “Perfect Government” and it sometimes gives you chills. But you also can’t bring yourself to sing along to all the f-bombs. It makes you blush. And though you sometimes try to talk the rich/poor political punk rock jargon, you will never be an anarchist. At the core, you feel way too blessed.

You don’t believe it right now, but these are all wonderful things. These are the qualities that will help you to build your truest and most meaningful friendships. These are the qualities that will draw your husband to you. These are the qualities that will make you an excellent mother (if I do say so myself).

Now listen, I’m not telling you to quit the punk rock scene. You Love the music. You spend hours sewing checkered ribbon onto your outfits and dance the night away at Slackers concerts and feel happier than you’ve ever felt. Those moments will forever be your favourite adolescent memories.

I’m just saying, quit punching holes in places you shouldn’t. Grab your coat, take back your parent’s money, and walk away. Don’t pierce yourself there. It’s going to hurt and look gross and you will most definitely regret it in your later years.

Quit trying to be a badass when what you actually are is a textbook Good Girl at heart. No matter how many piercings you get, that heart, and all the good inside it could never be disguised or hidden away.

And in its own special kind of way, I’d say that’s pretty badass.


If you liked this post, you’ll surely love this one and this one!

Letter 42: Boy/Friends, Unicorns and Loch Ness Monsters

14 Mar

Dear me at 19:

You’ve just come home from a really tasty sushi dinner and a rockin’ concert by a Swedish Girl Band . You’re standing in your bathroom, staring in the mirror as you wipe away your mascara. You’re completely puzzled by the night’s events. You’re rehashing the evening, moment by moment in your mind, trying to figure out what the heck went so terribly wrong.

Allow me to clear something up for you: He likes you.

He doesn’t want to be your friend. He doesn’t want to be your “big brother”, even though that’s his self-proclaimed nickname and how he has positioned himself in your life thus far. He is into you. Big time. And, here’s a really big newsflash: To him, tonight was a capital D-A-T-E.

Looking back on the evening, I’m sure you must be piecing it together. He was wearing a dress shirt. His hair was different. He’d offered to pay the bill at the restaurant (though you declined). He made up a weird excuse for the two of you to go back to his apartment and asked to show you something in his bedroom (which you thought was super weird). And he lingered. Most importantly, he did a big time pout at the concert after you made a joke about your boyfriend (the one whom he knew you were dating). He’d stopped bopping his head. He was practically monosyllabic.

“What the heck is going on?” you might ask. “I thought we were friends.”

Let me fill you in on something here: The concept of the Boy/Friend is equally as fictional as the Unicorn, Loch Ness Monster and Santa. (Straight) Men and women simply cannot be friends. Sure, it might start out with the best of intentions, but sooner or later, someone decides to change the rules.

Whether anyone likes to admit it or not, there is always an unspoken sexual tension between (straight) men and women. Sure, we might try to act like high functioning, important and intelligent beings but ultimately humans are essentially a few chromosomes away from Chimpanzees. We are hardwired to procreate. The survival of our species depends on it. This makes it very difficult to forge meaningful friendships between members of the opposite sex. Because, no matter how hard we try to think of the opposite, we always just wind up thinking about sex.

Countless films, books and pieces of music have been written about exactly this narrative. Boy meets girl. Boy and girl become friends. Boy or girl falls in love. Tension ensues. Now, in the movies, this is almost always an excellent thing. Harry realizes that he loves Sally and they live happily ever after. What could be better than two friends falling in love?

Unfortunately, the real world is a lot messier. A lot of the time, the feeling isn’t mutual. And that’s the situation you are now in. You like your friend. You think he’s a great guy. You think he’d be a great boyfriend. But there just isn’t that indescribable spark on your end. That certain something special that makes you need him. And the fact that he feels that for you unfortunately doesn’t change anything.

Most unfortunately, this is where the road must end for you and your Boy/Friend. He is hurt. You are confused. And things are just going to get even more complicated. The best thing you can do is to tell him how you feel and allow him the space to quietly walk away, should he so choose.

Is it possible for a Man and a Woman to forge a meaningful friendship and keep it at just that? Maybe. Possibly. I mean, I’m sure that in the span of history, at some point, it might have happened. It could also theoretically be possible in the future. But in the meantime, I would suggest switching your hunt for the Boy/Friend to a mystical creature that’s a little less complicated.

At least at Loch Ness you might get a tan.


If you liked this post, you’ll surely love this one and this one!

The Hindsight Notes: Teenaged Theme Song

4 Feb

The Hindsight Notes is a recurring section created for all you readers wanting to participate in THL, but lacking time to write a full letter. Each Note is composed of a question. All you need to do is answer it, in the form of a comment (below).

This week’s topic is: Your Teenaged Theme Song.

We’ve talked about your Teenaged Playlist, now we’re going to narrow it down even further. We want to know: If you had to pick one song to be the Theme Song of your Teenaged Life, what would it be? Why? It could be simply because it was your favourite song. Or because you identified with the lyrics. Or because the title sums up your teenaged years (i.e. The above song. Or maybe that’s just me…).

We know it’s hard to drill it down to one song. But we want you to try anyway.

As always, I’ll start us out:


If you liked this post, you’ll surely love this one and this one!

Letter 33: The Wicked Witch Of Windfields Junior High

10 Jan

Dear me at 13:


You have just successfully won the lead role in the school play. You will be Dorothy in “The Wizard Of Oz”. You were the only Grade Seven student to audition for the lead role amidst a sea of Grade Nines. And you managed to get the part.

Me as Dorothy, during the Big Performance

You should be proud of yourself. Take a moment to bask in the glory of this achievement. Because unfortunately, you’ll soon be wishing you could click your own little ruby slippers together and be anywhere but up on that stage, rehearsing for the big performance.

When the school play was initially announced, and you started to think about auditioning for the lead, you fantasized about how playing Dorothy would redeem yourself socially amongst your peers. After your unfortunate loss in the campaign for student council (something that we discussed in a previous letter), your circle of friends seemed to be shrinking by the minute. You desperately needed a win. Surely securing the lead role in the school play would give you some street cred. The Grade Sevens would think you were cool because you would get to hang out with the Grade Nines. The Grade Nines would think you were cool because your skill level was at par with theirs. Your popularity would skyrocket. A clear win-win.

So you auditioned, sang your little heart out, and nailed “Over The Rainbow”. When the music faculty first announced the results, you alone were named Dorothy. Ripples of dissent began to reach the teaching staff. The Grade Nines were outraged that a Grade Seven was cast in the lead. A chubby, tone-deaf Grade Nine girl named Jessica W. began leading the uprising. She was mean and loud and very convincing in her argument. You were told in a meeting that there would now be two Dorothies. You would each get to do two performances. Bureaucracy at its best.

You thought to yourself, “It’s not that bad. Maybe Jessica W. and I will bond over our common goal. Maybe we will encourage and learn from each other. Maybe we will become BFF’s”.

I love your optimism.

Jessica W. does not. Evidently, at some point her focus shifts from being the Best Possible Dorothy to making your life A Living Hell. Every time your turn comes to practice your solo, she snickers in the background. She all but forbids the other actors from talking with you at all, outside of practicing lines. She makes fun of the costume your Mother made you.

You seek sanctuary in your fellow Grade Sevens. However, they too are not pleased with your win. Having been cast as munchkins, flying monkeys and dancing trees, the other 13 year olds are feeling equally silly and insecure and are too frightened to risk associating themselves with you. You have unwittingly upset the delicate hierarchy of Windfields Junior High. There are many days where you consider dropping out of the play entirely.

My dear, sweet girl.

You auditioned for this role because you love to sing. You love to perform. And “The Wizard Of Oz” has been one of your favourite movies since you were a child. Yes, when Jessica W. snickers during your solo it breaks your heart a little. But ultimately, the joy that belting out that tune gives you trumps any negativity that she sends your way. And it’s that joy that will lead you to see your commitment through to your two big performances. You will nail them both. You will bring your Grandfather to tears. And when you look back on the experience, you will be so proud of yourself for refusing to allow an insecure, jealous Grade Nine take that joy away from you.

So, my dear girl, sing your little heart out. Memorize your lines as best you can. Go to each and every rehearsal and hold your head high. Own that role, regardless of what Jessica W. or anyone else thinks. And the next time you hear someone let out a snicker during your solo, take it as a sign to sing louder. After all, when you sincerely focus on your own joy, it will always drown out the din of your critics.


If you liked this post, you’ll surely love this one and this one!