Dear Anna [Jan 2, 2018]


When I originally mentioned on Instagram that I write myself letters all the time and open them later at a set date (kind of like a time capsule with wishes of sorts) I got some questions about what to include in such a letter.

As nervous as this oversharing makes me feel, I think someone will find value in it, and perhaps inspiration to pen their very own letter. So here goes…



Hi Anna,

I hope this letter finds you well. It’s the second day of 2018 and I am optimistic for us. I am writing this with much hope and excitement about the future that awaits us.

All being well, you will have opened this letter on December 31, 2018 (or January 1, 2019 – it’s your call) in a completely different , though being the same person in all the ways that really matter. Whatever the outcome – however your reality differs on new year’s eve 2018/new year’s day 2019 – know that I love you and I am immensely proud of the woman you’ve turned out to be. Sure, I have a laundry list of wishes, but darling above all else, I hope you are happy and pleased with the choices you’ve made.

In 2017 there was much procrastinating. You dragged your feet on many things and ended up with regrets. I hope you have less of those at the time of reading this letter.

Before anything else I have to ask…did you publish that chapbook of poetry? And what about “Notes to My Unborn”? We’ve been meaning to do that for some time so I hope you got it done.

I hope you made it to Africa and Australia. You talked a lot about those two continents in 2017. And all those other countries you had on that list in your notebook. I hope you made it to at least three (3) of them (not including South Africa and Australia).

Did you ever start that bog Jamaican Girl Abroad? And did you sustain it? I hope it’s yes on both accounts, because I really think it has tremendous potential.

As far as passions go, I hope you’re still writing and painting. You are really talented and should be making a living doing what you love.

On the note of following passions and pursuing dreams, I hope you had the courage to walk away from Ibex Global soon enough. I know you love your agents but that job sucked your soul, plus you always complained you felt like your brain was atrophying.

We said you’d start the MBA in March 2018 or June 2018. I hope you stick with it just to prove to yourself you have what it takes to bring a task to completion. But know that if you changed your mind about pursuing it I don’t love you any less. Whatever you decide will be the right decision. And that will be that.

Ultimately I hope 2018 was a year that saw you taking more risks, dreaming bigger, and trying new things. I hope it brought you at least one epic love story. If you tell me all this was true for you I’ll be happy.

My darling, I hope you were fearless in the pursuit of ALL the things that set your soul on fire. I pray the end of 2018 finds you reading this letter with pride, happiness, and a sense of having lived your best year yet.

As for the challenges which I’m sure will come, I pray for your strength and resolve in overcoming them. I hope you will have learnt invaluable lessons from every seed of misfortune.

As I’m closing this letter I can’t wait to see the woman you will become in the next 364 days. Whatever happens, I will always love you unconditionally, and I am immensely proud of you.

Jan 2, 2018

Hi, I’m Anna

A girl who traded in her cushy 9 to 5 to pursue a life of travel and passion. Words are my superpower (and also how I pay the bills these days). I love pasta, binge watching Grey’s Anatomy and anything that allows me to flex my creative muscles. I talk travel, dream chasing and living on purpose here on the blog.

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  1. Janae

    I’m tearing up reading this post, this looks like something I could also consider doing going forward….. Btw did you find love?

    • Anna

      Thanks love. You should absolutely try it.
      And no I didn’t. At least, not yet. But I’m optimistic about what 2019 holds 🙂
      Happy new year to you!

  2. Sachie

    Lately I have been burdened with a few things that made me feel like I really needed help,on another level. Now I think,I know what I need to do. #inspired

    • Anna

      Awesome sauce! Happy to help love :-).


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Hi, I’m Anna.

I traded in my cushy 9 to 5 to pursue a life of travel and passion. I talk travel, dream chasing and living on purpose here on the blog. Hope I can inspire you to chase a dream of your own!