Pen Pal Letters Between Generations of Me

Dear Teenage Jess,

It feels good to connect with you after all of these years, and boy did time fly! By now, you have discovered how much you love to draw and sing, and both the art room and the stage have become a second home for you. These two loves – art and music – will stay with you all of your life, bringing you comfort, helping you to build confidence, and being your therapeutic rocks to help you deal with what life throws at you.

I bet this feels super weird reading a letter from the older version of yourself! Never in my life did I think I would be able to go back in time and share some words of wisdom with anyone, let alone myself. Some pretty crazy things have happened in life, and especially in the last few months, that have made me want to reach out to you. I guess I want to prepare you, in a way, for what’s to come, but also tell you things I’ve learned that may help you in your journey through life. If you would like to write to me, I’d love to talk with you…maybe we can be pen pals.

From the tip of the brush, Jess

P.S. I’m 41 years old now. (Blah, but I’m dealing with it)

Photo by Karolina Grabowska on Pexels.com

Dear Me,

(or Jess? older Jess? future me? This is weird and I don’t know what to call you)

So…um…yeah, I will totally write letters back and forth with you, but I don’t think I’ll tell anyone about it. It took me a few days to believe that the letter was actually from me but in the future. Even my really best friends will probably think I’m crazy, and if my mom finds letters from someone who says she’s me from the future, mom will flip. She gets weird about stuff like ghosts and aliens, and it freaks me out, too, but I kinda believe this is real. Like, this is really me writing to me.

I think I should tell you about myself, but I’m not sure. You probably already know everything, right? But, if you’re 41, maybe you’ve forgotten stuff…seems like that’s old like my teachers at school. They’re nice though.

I really like to draw and sing. You were so right about that. I have taken double art classes instead of lame studyhall. My art teacher right now, Mrs. Bowers, is always excited about everything. I like being in her class because she makes me feel good and I have good grades. At the end of every day, I have choir on the stage. I sing alto. The stage feels good to me. I have gone to districts and regionals. Mrs. Kellerman is my choir director. She really helps us become good at singing, and someday I think I might want to be a music teacher. I’m not sure though because I only sing.

My parents are divorced, and I guess you know that. Dad was in the army and we see him during summer visitations and holidays, but he calls us a lot and asks us about school. Sometimes he is able to come to my softball games and my choir concerts. Matt, Carrie, and I live with mom. She’s waitressing at a restaurant in town, but hates it. She gets mad at us sometimes but I think she is just really busy with work and her ex-boyfriend is always calling and making her upset. I wish she was happier.

Okay, I think that’s it for now. Oh, I’m almost 17. What are some of the things you want to tell me? Are you married? Did you go to school in Boston for music like you thought you would? Where are you living? What’s the future like? I can’t wait to read another letter from you. Yeah…cool beans.

Sincerely, Jess

Photo by Karolina Grabowska on Pexels.com

Dear Younger Me,

I’m glad that you are interested in writing more back and forth. I have so much I want to tell you, but I have to be careful not to change your future with what I share – everything that has happened to me until this point on my journey to here still needs to happen in your life. You are going to have people who help you along the way, but others will feed into how you are feeling and influence your behaviors and actions – for good and for bad. Same thing with relationships, jobs, situations, and circumstances of life. It all has to happen because you will learn so much good stuff from them, even if you think it really sucks at the time.

I have to tell you about your art and music teachers. These women are wonderful parts of your journey and are planting seeds of confidence. They are teaching you that you are creative, that there are ways to express yourself and feel good about it, and give you a sense of belonging in your world. That last one is super important. Also, someday you will see them not only as your teachers, but mentors and friends, working alongside both of them as peers. It’s going to feel weird, but so awesome at the same time!

The divorce of your parents hit you really hard. You’ll learn, beginning in your 20s, just how much this impacted every aspect of your life. I can already see it in how you described school and your relationship with your parents. Luckily, you do have some family members who have stepped up – and will continue to all through your life – and guide you, teach you, and love you unconditionally. Your aunt and uncle, the ones who babysat you and your brother when you were young, are going to be so much more than an aunt and uncle for you. This will be a special bond. Mom will feel threatened by your aunt’s relationship with you, so be mindful: mom still has some healing to do to feel okay with how close you are to your aunt. Please do not say this to mom, just keep it in your mind when things are tough.

To answer some of your questions: 1) the messages I’m telling you are scattered all throughout my letters, 2) I am married, 3) I chose a local college (you’ll understand), 4) I’m living in Central PA, and 5) the future is all about growth, which makes it pretty cool.

How’s your little sister, by the way?

From my world to yours, Jess

Photo by Miguel u00c1. Padriu00f1u00e1n on Pexels.com

Dear Future Jess,

I don’t have a whole lot of time to write today. I just started working at a restaurant with my mom, and I feel pretty gross from washing dishes all day. She started at this restaurant not too long ago. She hated the other place, but loves this one. She worked here when she was young and is happy to be back. I smell like a kitchen. Do you remember that smell? The people I work with are really nice, but I don’t like the owner. He watches everyone like a hawk, and I wonder if I’m doing something wrong. One of the chefs has really long, blond hair. He’s super nice and went to school with my mom.

I just saw my art and music teachers today. It might be a little weird knowing my teachers as my friends sometime, but whatever you say! Am I allowed to call them by their first names?

My Uncle Jim and Aunt Nadine must be the ones you are talking about. They babysat us when mom had to work weekends. I stayed at their house not too long ago. There was a bad flood and I couldn’t get home, so I stayed with them. I won’t say anything to mom about what you said about my aunt, but what do I do when I think it’s happening? Will mom be sad or mad?

Okay, I have to do my homework and call my boyfriend, then I have to go back to the restaurant and pick up mom after her shift because she let me drive her car, so I’ll talk to you later!

Sincerely, Jess

P.S. My little sister is adorable! She is all over the place, getting into everything. I babysit sometimes.

Photo by picjumbo.com on Pexels.com

Dear Younger Me,

I’m so proud of you for starting your first job! Believe it or not, but you’ll actually work with your mom and the blond-haired ponytail guy in other jobs in your future.

I think it’s time to really get down to what I want to tell you, my words of wisdom from the future, so to speak. Here it goes:

  1. Your self-worth starts with you. You are enough. You are going to have a false sense of self-worth and value until you are close to my age right now. (I’m on the mend, I promise, and helping other women see their value, too) You are going to think that school is where you find your value, even far into your teaching career (you will choose teaching because you think it holds your value), but at some point, that will dream will be broken, and you will be left picking up the pieces from that mess.
  2. Love unconditionally. This will be a tough one, especially for your relationship with your mom. You love her. You will always love her. Despite all of the stuff you will hold against her, you love her. Be mindful to show her that unconditional love because someday you might regret allowing the resentments have more power over you than love did.
  3. Take time to create. You are a creative soul, so make time to connect meaningfully to creation. This could be making art, singing, being in nature, chatting with friends, daydreaming, thinking, writing, putting yourself first, talking to yourself, it doesn’t matter! Whatever form of creating looks like for you when you need it. Creating will help you process information, quiet your mind, and improve your wellbeing.
  4. Forgive. Forgive others and forgive yourself. Both may be challenging, but it’s the only way to break through what you are carrying on your heart and move beyond it.
  5. Give yourself permission to feel emotions. You will find yourself avoiding how you really feel and instead engaging in self-sabbotaging behaviors. This will be detrimental to yourself and the people around you. There are people to support you, listen to you, and teach you the tools you’ll need to sit with your emotions, process them, and be comfortable with how you feel. You’ll learn that you can use your feelings to intuitively make decisions to live your life as your authentic self.

I hate saying this, but as soon as you opened this letter and started reading, you unlocked a powerful sense of something that will erase our communication with each other. There’s nothing you can do to reverse it. You might be wondering why. The only way I can explain is that you absolutely need to experience everything that will happen in your life. It will develop you into the person I am now. That might sound a little selfish, but it has to happen. Without those experiences, lessons will be lost, relationships avoided, feelings left undiscovered, a career that impacts thousands of young minds won’t happen. Most importantly, if you hold these words close to your heart and live by them, you will not learn to be you and be comfortable with you. This isn’t just for you, but it will affect everyone in your life as well, so it’s for the best. For both versions of us.

Please remember that I love you. You are loved. Your parents love you, your family loves you.

With love, Jess

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