Challenging 30 Day Letter Challenge

I’m finding it really difficult to plough through the 30 Day Letter Challenge. Really tough, actually. I’m up to Day 21, where I have to write a letter to someone I judged by my first impressions. Well, my first impressions are usually right, so it’s difficult for me to lend credence to what you are trying to make me do. If I think someone is a dickhead, I am usually proven right. I have this knack. I guess it comes through being so emotionally intelligent. I work people out. I understand them. That sometimes makes people feel uncomfortable and it’s something I find useful. I don’t get fucked over, or conned. I get people instantly and that is just the way it is.

So writing a letter in what is supposed to be a positive self-learning way, about how I misjudged someone by thinking they were one thing and them actually being another is quite difficult. Unless I’m supposed to just reveal how much I usually dislike people and how much I am usually right to dislike people…. Quite negative, don’t you think?

Which brings me to the point of this post. Most of the things I have written have either been negative, distressing or plain boring. The onw who broke my heart, the one who I miss the most, the deceased person, the one who caused me pain. Most of the letters, or at least the interesting letters have dealt with very negative themes, and rather then feeling writing about them as an outlet, they have simply highlighted things that I wanted to keep locked in. Feelings of hurt, pain, rejection. Understanding my own inadequacies as a boyfriend and father. Rationalising why someone did what they did, or why I did what I did. It hasn’t been therapy, it’s been pain. There is another argument that getting things out, no matter the context, is ‘a good thing’. But something should be left buried. Dead things should be left buried.

I’m going to commit to finishing the letters. I’m off work now for a week and I’m going to attempt to finish the Challenge in the next week. This will not be a one a day challenge, this will be an outpouring of shit to get this challenge done and put it behind me. Part of me wants to delete the category and pretend like it never happened, but I’m still deluding myself that there will be something positive at the end of it.

Let’s rattle on through this and see what happens at the end.

Here is an update on progress:

Day 1 — Your Best Friend
Day 2 — Your Crush
Day 3 — Your parents
Day 4 — Your sibling (or closest relative)
Day 5 — Your dreams
Day 6 — A stranger
Day 7 — Your Ex-boyfriend/girlfriend/love/crush
Day 8 — Your favourite internet friend
Day 9 — Someone you wish you could meet
Day 10 — Someone you don’t talk to as much as you’d like to
Day 11 — A Deceased person you wish you could talk to
Day 12 — The person you hate most/caused you a lot of pain
Day 13 — Someone you wish could forgive you
Day 14 — Someone you’ve drifted away from
Day 15 — The person you miss the most
Day 16 — Someone that’s not in your state/country
Day 17 — Someone from your childhood
Day 18 — The person that you wish you could be
Day 19 — Someone that pesters your mind—good or bad
Day 20 — The one that broke your heart the hardest

Day 21 — Someone you judged by their first impression
Day 22 — Someone you want to give a second chance to
Day 23 — The last person you kissed
Day 24 — The person that gave you your favourite memory
Day 25 — The person you know that is going through the worst of times
Day 26 — The last person you made a pinky promise to
Day 27 — The friendliest person you knew for only one day
Day 28 — Someone that changed your life
Day 29 — The person that you want tell everything to, but too afraid to
Day 30 — Your reflection in the mirror

Let’s get this show on the road…

3 thoughts on “Challenging 30 Day Letter Challenge

  1. Yeah,I’m having a difficulte time on the parent one because I don’t want to offend my mom or dad but they only appeared back in my life recently! My Grandma raised me from a baby until about 10! I’m now 15 and have trouble with guys because of being abandon by my parents and because my Grandma died August 15th,2008.Two days before my 13th birthday so I’ve had a crazy couple of years and still pretty depressed and don’t want to put my true feelings out on facebook where family and”friends” cand see it all! But I’m going to try to write the postitives
    Thank you so much,
    Courtney M.


  2. So happy you took the challenge! I agree that it is emotionally challenging. I hope everyone who takes it will learn about themselves a little and share with me the feelings it brought and whether or not it was helpful either in forgiving or moving on or just maybe happened to reveal something you didn’t recognize in yourself. Thanks again for your participation. Maybe you will try another? 🙂



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