Letters To My Former Self

Letters To My Former Self


Lora Leslie DeMoss, LCSW

“Life is one big transition.”

-Willie Stargill

I’ve been thinking a lot about life transitions and perspective lately. Each phase of life seems challenging and some days even feel impossible, but somehow I’ve made it though each transition stronger and better for those challenges. It’s easier to look back on those periods when you aren’t in the thick of it and consider a different perspective. So I thought I’d take some time and reflect back on the different transitions in my life and write some letters…


Dear Little Lora,
You are growing and learning so much every day. That’s hard work! You are figuring out the world around you and where you fit. That’s hard work too! You have so many emotions and not quite all the right words to explain those feelings. Everything feels so personal, and that’s okay. You’re learning skills that will make you a better friend and person – it’s okay to share, it’s okay to not share too! It’s okay cry and it’s okay to feel angry. You’ll find the tools to make these feelings easier eventually.

Take the next few years to let your brain grow! You will have some big adventures coming up, and those big adventures come with even bigger feelings. It’s going to be tough, but you’ve got parents to take the lead. They get to love and support you and make that hard work feel not quite so overwhelming! They will help you navigate all these big moments. They will help you label all your feelings, and hold you when you need them. Just be sure to give them a little grace, they are learning and growing too! Yep, even adults are still figuring stuff out!

Good luck!
Talk soon.


Dear Middle School Lora,
Life feels pretty crazy right now, doesn’t it? Acne and puberty are super annoying and make you feel like a stranger in your own body, right? As crazy as it all feels, remember that you are beautiful and special! All those big feelings you were learning to understand over the last few years just feel even bigger now. I get it, it is hard. I promise, it will get easier. Life won’t feel as heavy in a few years, and you will have developed some more skills to managing these big emotions. I know, I know, I told you before that you’d develop these skills…but life will keep throwing you new stuff, and you’ll keep rolling with the changes, and you’ll find new and more refined ways to cope! Cool thing is, we never stop growing and learning! Remember, I told you even adults don’t have it all figured out. That’ll be a big revelation to you when YOU are an adult!

Enjoy the freedom you have to just be you. To make friends. To find hobbies. To sleep in! Don’t try to take on the world quite yet…you’ve still got some learning to do!

Talk again soon!


Dear Teenage Lora,
Holy moly, so we thought the last few years were tough…high school is a real ride, eh?! Everything feels dramatic and big, and kinda like the end of the world, and nobody really understands. Your friendships feel like they are filled with drama and your peers are adventuring into new and risky places. It’s all a bit intense! Boys and relationship drama is ALWAYS on your mind, but girl, let. it. go. I promise, these guys won’t hold a candle to your future husband – he’s pretty amazing!

Everyone keeps telling you that the choices you make now impact your future, and while that is totally true, you still have so much life ahead of you, and many opportunities for mistakes and growth!

You’re working hard in high school to get into a good college, but don’t forget to slow down and enjoy this time! Enjoy being a kid, enjoy the security of living at home and not having lots of responsibilities yet! Even if it feels like the world is impossibly heavy! Try not to obsess about the future…and just like before, you have a world of adventures ahead.

Enjoy the ride!
Talk to you soon!



Dear Adult Lora,
How about these adult responsibilities?? So fun huh? Lolololll yeahhh…we didn’t take that advice about slowing down and enjoying high school and college enough, did we? The stress of adult responsibilities pushed you into a place of striving for perfection, and then somewhere along the way we realized perfection isn’t the goal! But what is the goal? Have you figured that out yet? Or have you realized your goals are ever changing and growing – just like you are!

Working hard in high school to get into a good college, and then working hard in college to get a good job paid off…but sure did leave you feeling a bit out of sorts when there wasn’t an obvious “next.” The cool thing is you still have so much time to enjoy the now. Enjoy the present. Try to find that work/life balance, but give yourself grace for the times where the balance is “off.” Let your daughter get messy, get messy with her! (I promise, a little dirt and mud is good for her!) Find time to just “be” with your husband, don’t let the day to day responsibilities take place of finding time to connect.

It’s okay to reflect on where you have been, and to think about where to go…but remember to soak up today. Your daughter has already grown and changed so much in a few short years, you can’t get this time and these moments back.

Enjoy the process!
Talk again soon!
Wow! So all those letters in each of these periods of time sure do have some similarities! Seems each stage of life felt tough, and each stage was challenging in its own way, and my advice was always to slow down. They always say hindsight is 20/20 and now I’m excited to take this perspective and make a change for future Lora.

What would your letters to your past self say? What would you say to your future self? Take some time and reflect!

Here’s a few prompts to help you in your letters to yourself:
Think about yourself at a particular age – 8. 12, 16, 25… think about how you have changed and grown since that age. What would you do differently? What would you change? What do you pride yourself on?
Be honest, but also be compassionate and empathetic.
What’s a piece of advice you wish you had been given back then?
Stay focused on one or two issues – don’t go too broad or you could write for days!
Write it all down – then read it a few days, weeks, months later. How has this reflection impacted your day to day?
Enjoy the process 🙂



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