Dear Me: A Letter to Myself


Recently on a trip to visit my parents, I was talking to my mom about my High School experience. It might have been the first time that I have ever really spoken openly with my mom about how bad my experience with High School was and why my grades and performance suffered so much. Ever since that conversation, it has got me thinking about the things I wish I could go back and tell myself in my younger years. If I could get a magic mailbox these are the things I would put in a letter to my younger self!

To the teenage me:

  • I wish I could tell teenaged me why I never felt like I fit in at school, or why so many people seemed to get pleasure out of making my life miserable. I’m over 20 years older than the girl in the picture above and I still can not understand it.
  • I wish I could tell teenaged me that seeking the approval of boys was NOT where it was at. I understand now that the positive attention was like a break in the storm of High School and each time I thought it was my chance to change things. Unfortunately, the hard lesson I had to learn was that it more often than not just made things worse. Something I hope to communicate with both of my children when they are older.
  • I wish I could tell teenaged me to open up to her parents. This is a hard one because I know now that I did not have the maturity to understand that my parents just wanted the best for me, and that opening up to them would be the best way to make decisions. This is where being a parent is hard, I know that my kids will feel the same way I did when I was a teenager (Parents Just Don’t Understand). But my goal as a mom who wishes she had been more open with her parents is to make sure that I am open and honest with my kids and hope that it makes the lines of communication easier. I want to tell them about my experiences, how they made me feel, and some of the bad decisions I made as a teenager that I wish I could go back and change.
  • I wish I could tell teenaged me to ask for professional help. In my senior year of High School, my family experienced the devastating loss of my Step-Brother to a car accident. He was also a senior. We went to different schools since we lived in different households. 19 years later and I still feel like I deal with the grief of that loss, so I know that I could have really used some grief counseling after that experience. Again this is something that I think could have helped me make better decisions and maybe I wouldn’t have had to learn so many lessons the hard way. At the very least it would have helped my anxiety be better controlled.

To the early twenties me:

Dear Me: A Letter to Myself

  • I wish I could tell the early twenties me that she is NOT FAT!!! We have all been there, right? Looking back at pictures of ourselves and remembering HATING our body at the time the picture was taken but then not understanding why? When I look at the picture above I know that I was sucking in so hard that it was physically painful. How much time have I wasted over the years worrying about the way my body looked instead of enjoying the years where I could eat whatever I wanted and not gain an ounce.
  • I wish I could tell the early twenties me to stop making such impulsive decisions. This is a hard one. And I am still at times too impulsive. But I made SOOO many decisions in my early twenties that were just NOT smart. Like moving 6 hours away from home without a real plan of action, and then several years later moving back again without a good plan of action. Moving to Tuscon, Az without a real plan. (Do you see the pattern here!)
  • I wish I could tell the early twenties me to SAVE HER MONEY! In my early twenties, I was so focused on when my life would start, and when I was going to be married and you know be a REAL adult. That things like saving money for the future, traveling, and learning how to actually live life to the fullest just were not on the radar. If I can help my kids learn anything from my past mistakes THIS is the one I want them to learn.

To the newly married me: 

Dear Me: A Letter to Myself

  • I wish I could tell newly married me to TRAVEL! There are so many trips that I wish we would have taken as a couple with only ourselves to worry about.
  • I wish I could tell newly married me to keep communicating. A couple of years ago my husband and I hit a rough patch. It was mostly due to our poor communication and years of letting the little things go unsaid until they added up and became very big things. I would go back and tell newly married me that it is ok to speak up and that it doesn’t make you a nag, or whatever fun names society likes to label you.

You may be wondering why write this, I can’t go back and change anything so writing this fictional letter to myself at these different stages of life really makes no difference.

This is true, I can’t go back and make better decisions, and I can’t go back and make my teenage years less hard. But the act of writing this was very therapeutic in its own way. So welcome to my public therapy session.

It also serves as a reminder to myself, a reminder of the struggles and what I think I can help my children avoid by being open with them about my younger years. As women especially we have been conditioned over the years to attach shame to our failures.

Telling my children about how bullying affected me, and the bad choices I made because I longed to fit in can only happen because I have realized there is no shame in sharing our struggles and the lessons we learned from them.

I highly suggest this exercise to you my fellow mommas. Write a letter to yourself at a particularly hard season. What do you wish you could tell that version of yourself? What part of those lessons do you want to share with your children? What do you hope they would learn from your mistakes?

Do you still feel shame from those mistakes? Embarrassment? Disappointment?

Those feelings won’t ever move us forward, they will keep us there reliving the hard moments over and over. But if we can realize that there is no shame in being human and making mistakes and sometimes taking the hard road, we could move past those moments. Leaving them and the shame in the dust, and emerging wiser, more confident, and able to pass the lessons on to our children, hoping that it can spare them even a little bit of the hard road.

Previous articleWe Recently Potty Trained. And Here’s What I learned.
Next articleI had “The Sex Talk” with our 7 Year Old
Jennifer is a Coastal Bend Native, born and raised in Ingleside. She began contributing to the Corpus Christi Moms Blog in 2018 and stepped up as the Community Engagement Coordinator in 2019. She is happiest when she is crafting, writing, or doing anything artistic. She loves music, especially ANYTHING from the 90's, and is often seen dancing around the kitchen to Nsync while cooking dinner. She is married to Derik and has two kids, Connor and Keeley (pronounced Key-Lee). Jennifer still feels like a novice when it comes to parenting and enjoys letting other moms know they are not doing life alone. She also admits she watches copious amounts of Netflix, but balances that out by reading to and with her kiddos as much as possible each day.