Dear 21 year-old Me,

This summer in your life is the most rocky. You are in a perpetual state of panic and stress, you feel almost electric under your skin, you feel like you are two steps away from exploding. The world is against you, and you are walking this world alone with tortoise-shell glasses perched atop your pretty little nose and five inch Louboutins under your feet.  Damn, you are so strong in your mindset and confident in your public presentation yet so fragile in the art of understanding yourself that it almost constitutes an acute oblivion. But you don’t know it.  Because you’re always right, and the world is wrong.  And everything in your life is somehow wrong at this point.  Everything is broken. Absolutely everything.

You are young, you are reckless, and most of all, you have lost: you have lost your job and I hate to break it to you, but you are about to lose the relationship that you’ve been frantically trying to save in a few weeks.  You are in what you consider to be hell on Earth: you are a 21 year-old precocious banker in San Francisco who is simultaneously trying to mend your failing two-year relationship.  Let’s be frank, you fucking hate San Francisco.  The thought of those two words sour in your mouth.  You hate it so much you commission a shirt at the beginning of your San Fran stint that declares this antipathy against the land flanked by the notorious Golden Gate bridge.  And then at your end of your summer you commission another shirt, this time somehow even more acerbic, in loopy cursive in the form of rope that underlines that hate.  I fucking hate San Francisco.  Your anathema is swelling and alive; you might as well compose a diatribe against it and submit it to the Los Angeles Times, because the seething emotion on that subject would compel someone to publish it.

But this summer is a turning point for better times, believe it or not.  And I know you won’t.  Twenty-five year old me has little sway over these deep-set thoughts in your mind -you wouldn’t take this advice even if it floated in a bottle right to you with a silk ribbon on it as you sat along the Santa Monica beach wondering where you went wrong.  You are exhausted, you are overwhelmed, you are slowly spiralling and you think this is just a lull but everybody else can see that you’re plummeting to rock-bottom.  So I won’t give you advice, because you won’t take it, but I’ll recount the lessons that you soon learn, in case that will prod you to see things differently.

Love finds you again.   The months after San Francisco are tough even though you put on a smile and laugh through this delirium; you will become lost and the days and nights go by in a blur. you will become defeated.  you don’t know anything anymore and you’re so exhausted that you don’t even bother questioning why.  But I promise you that in a year, love finds you.  It starts right as San Francisco wraps up, surprisingly, with a text to a house party from an individual whose invitations you frequently decline.  But for some odd reason (or no reason at all), you decide to go this time. And there at that house party, you strike up a conversation with a stranger who is so different from you and profoundly bewilders you, and you immediately become friends. he is one of the kindest people you have ever met. and in the following weeks, he invites you to his own house party and this time you strike up a conversation with another stranger who has nothing and yet also everything in common with you. and he frustrates you because he wasn’t as good at The Game as you were, but there is just something about the way he laughs and the way he moves that broke you in a way that didn’t break your heart.  and it intrigues you enough that you follow him home and take his hand as he leads you into a modern day promenade. and this is innocent enough in the beginning until one day,  you work up the courage to tell him one day that this can’t keep happening because you’re in too deep and you’d rather break this now rather than later.  And when love finds you again, you’ll barely recognize yourself.  And that’s a good thing -it’s the perennial vestiges of growing up as you learn that a relationship takes work together, to ponder your long-term ambitions and the person you want to become, and learn that the act of challenging each other can be rewarding.  Not everything is a fight, Kayla, and that will be a lesson that takes so so so long for you to learn: not everything becomes won or lost.  You can only build or stop building.

Oh, and as some valuable advice, disclose that you broke your arm in Vietnam instead of lying about all injuries for two weeks out of embarrassment.

You are not invincible. There are so many days when you want to save the world, but you fall into bed thinking that you haven’t done enough.  Yet you’re completely exhausted and the guilt weighs incredibly heavy on yourself.  It’s okay to disappoint people, you know, especially yourself.  It’s okay to take a break even when people consider you to be their source of strength, and you don’t have to try to please others or impress them.  When a reporter tells you that you need to set a better example for young girls who want to follow into your footsteps, you will tell her that women aren’t perfect and that this is the way that you have decided to champion women’s representation in professional sports.  And even when you occasionally ponder whether or not this was the best answer, please know that there is no better answer in this unchartered territory; you are at the forefront, this cause’s inherent and unwilling leader, and you will make mistakes, but that’s a good thing.  We can’t always be the heroic feminists that we wished had been there when we were growing up,  and know that this doesn’t make you mediocre, this doesn’t make you apathetic, this doesn’t make you lazy.  It most of all doesn’t make you incompetent.  It makes you human.  So get some rest, kid.  You’ve got your heart in the right place, and I’m proud of what you have achieved even if it’s not the moon and more.

Cherish your years in hockey. It goes by in a blink of an eye, even if it doesn’t feel like it on the days that all your friends are posting pictures of their New York escapades, you’re sitting on your balcony alone facing the CN Tower and missing home.  And even though you laugh at me now about this, you get to play sports for a living and so few people get to say the same thing!  The friends and support network that you build in Toronto are indispensable and you don’t appreciate it until after you leave.  So go out with the boys for drinks and dinner more often, and savour the white and blue veraciously. It’s a surreal experience with its own set of challenges.


how i know i will have made it

1. i fly first-class and don’t have to make budget compromises to do that

2. i get to swim in a bath house in budapest

3.  i experience cape town. i climb the tabletop mountains.

4. when people think of me, the first that comes to mind is kind

5. i show up in a magazine or newspaper in the society pages

6. if i get married, i plan a wedding that i’m proud of.

7. i sit in a sailboat and bask in the sunshine.

8. i read a book in martha’s vineyard.

9. i trespass on backyard beaches in the hamptons.

10. i master French.

11. i give a talk on any topic at a conference.

12. i forgive.

13. i fall in love at least once.

14. i learn from it at least once.

15. i read regularly.

16. i learn to be less bitter.

17. i become a source of strength for my friends.

18. i learn to dress well.

19. i remain healthy.

20. my family remains healthy to the best of my ability.

21. i am successful in my career, and become an icon in my field.

22.  i smile everyday about something that’s happening in my immediate life.

23. i take risks. i learn not to be so afraid of moving on, letting go.

24. my house is tastefully decorated

25. i help the environment.

26. i am confident in my decisions.

27. i am thoughtful in my direction.

28. and to be continued and to be refined….

what i wouldn’t give to tell you that this ends well,

to stuff some optimism in you in these trying times

to try your hand at something other than typing out heartbreak

arms across your chest preparing you for the blow.

what i wouldn’t give to tell you what i don’t know.

man, i don’t know.

god, i don’t know.


what i would give to not regret

what i would give to sleep soundly

to sleep early

to sleep with the promise of a new fresh day

to sleep without desperately hoping for a new fresh different day

to sleep knowing that you are out of my reach

but i won’t stop reaching for it anymore.