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Diane LeeWord Wrangler & Law Student
  • About
    • + 62 Micro Memoirs in 2025
    • + 12 Essays in 2024
    • + 26 Essays in 2017
    • + Essays: Mothers & Daughters
    • + Historical Posts
  • Alienated Grandparents
  • COVID-19
    • + Never Forget What They Did Podcast
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Self awareness Article

Dear Me: A Letter To My 16 Year Old Self

On 25 January 2014 by Diane Lee

This post was first published on 19 November, 2011. I am more at peace with the concept of work, and now enjoy it for the benefits it gives me. I turned 50 last year, and I still give away my heart a little too easily to unworthy men – some things never change! 

Dear Me,

letter to my 16 year old self

Wow. You are almost 50. So glad you made it out of the 80s alive, with your brain cells fully intact and no hint of a STD. But wasn’t it an interesting decade? I would say to you though, in order to make those years a little easier, be careful who you choose for a partner. Good looks don’t necessarily equate with a good character. You will realise that the boys you overlook (because you were really quite superficial back then) will be the ones you should have given more than the time of day to. And guard your heart. You fall in love much too easily and for all the wrong reasons.

Make sure you don’t lose that adventurous spirit of yours. There is a curiosity in you that burns bright. Fan that flame. It will lead you to all sorts of interesting adventures. Trust your gut. You have good instincts. You know when something is not right: don’t question that feeling, go with it. Your path is not planned, despite our wishing it was so. Don’t feel guilty for taking the scenic route through life: it is an enjoyable way to travel.

You will achieve more educationally than you ever thought possible, but that’s no surprise. We always knew we were smart. Don’t worry too much about what you study – you will make the right decision, even if it doesn’t feel like it retrospectively. Just enjoy the process of learning.

Don’t get caught up with family stuff. It will do your head in. You will never be able to win, so don’t even try. You will have your own family, in your own way, and this will be enough for you. You will struggle for many years dealing with family stuff, but please don’t. Let it go. It’s just not worth tying yourself up in knots over. I know your teen years were hard and awful, but they will pass, and soon enough you will be your own person, living your life, on your terms.

Men and work will be your two greatest challenges, probably for the same reasons. They seduce you with their promises of a better, more exciting life, but it is all smoke and mirrors. Work will be a series of jobs that you will find ultimately unsatisfying. You would be much better off concentrating on developing your writing and your art. And I would strongly recommend you becoming a photo-journalist; that way you can combine your two loves: photography and writing. Look out for The Italian in your late thirties. You will know him when you meet him. Do not give that man a second chance, for he will break your heart.

Travel sooner. There is a whole world out there waiting to be explored. Make sure you pack another change of clothes when you do go though, because you will have trouble in China with lost luggage. I’ll take it one step further: never trust an airline that says locating lost luggage is an easy process. It’s not. Especially in China.

Look after your health. By about 30, you will struggle with your weight. It will sneak up on you, so buy yourself some scales and weigh yourself regularly. Take up running. You will be surprised how much you enjoy it. And you might as well skip that smoking phase. You won’t sustain it past your 20s.

Oh, and you won’t regret getting that tattoo. Don’t listen to anyone who says you will.

Lots of love and respect,

Me xo

PS you are an incredibly resilient person and have a killer sense of humour. I love that about you. Don’t ever lose that.

This post was inspired by an excerpt from Dear Me: A Letter to My 16 Year Old Self in today’s paper.

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8 comments

  • Cate 19 November 2011 at 10:14 AM - Reply

    And you are lovely. And you will meet an awesome lady called Cate…

    • The Diane Lee Show 19 November 2011 at 1:42 PM - Reply

      I remember reading your letter to 23 year old you, Cate, and thinking that’s brilliant! Cate’s post is here by the way: http://catep36.blogspot.com/2011/05/letter-to-myself-yes-ive-gone-nuts.html. And you are right – you are awesome 😉

  • Gary Lum 19 November 2011 at 1:29 PM - Reply

    Is that really you at 16. You have such a nice smile.

    • The Diane Lee Show 19 November 2011 at 1:38 PM - Reply

      Thirteen… it was the best I could do in a pinch 😀

  • Millie In Hanoi 6 April 2017 at 12:09 PM - Reply

    That tattoo of yours is something that’s a part of you now. It’s something that I first noticed on you and I thought ‘wow, this girl is cool.’ It’s a part of you just like every event in the past. And you own it. You rock.

    • Diane Lee 6 April 2017 at 2:16 PM - Reply

      Thank you, Millie! That particular tattoo is a new one! I have one on my hip that was done when I was 26… I had that one fixed last year, and one added to the back of my neck at the same time…! Four in total, with the fifth on its way…!

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