A Letter To My Sixteen Year Old Self by Jess Witkins

A smile never increases in price or decreases in value.

Today it’s my privilege to host a guest blog by Jess Witkins, cofounder of the Life List Club. The last time Jess graced my site, you readers made her post “A Thanksgiving to Remember” one of the most read blogs ever to appear here. After you enjoy her letter here, jump over to Pam Hawley’s site to read my submission on Coed Shopping, a glimpse of the togetherness my wife and I enjoy when we go to the grocery store. Well, you didn’t come here to read long intros, so let’s proceed to Jess:

A Letter to My Sixteen Year Old Self

Hello Life Listers!  How’s the holiday season treating you all?  Are you just as overwhelmed and anxious about the holiday season’s flux of “get it now” and nostalgia combined?  I am.  But then I came across a Freshly Pressed post by Traci from Adventures on the Road titled “Dear Me:  A Letter to My 16 Year Old Self.”  Traci’s post made me think.  What if we could have received a letter from our future selves letting us know not to sweat the small stuff and take courage and go for your dreams?  Wouldn’t your teenage self have put a lid on the raging hormones long enough to stop and say, “Ok, I’m with you on this.”?  I think I would have.  But then we don’t have the privilege to get that letter.  I’m sure I did the reverse; write a letter to my future self.  I even wrote out my eulogy on one morbid night that shall not be blogged about.  That’s what happens when you journal continuously from the age of 13.  But if I could go back, I think I’d write something like this:
Dear Jess,
Please stop obsessing over what other people think of you.  You are smart.  You are kind.  You are quirky, even though you hate that term.  You will grow and learn things at your own pace so take pleasure in the discovery of it all.  You beat yourself up too much.  Try giving yourself some credit for a change.  Ten years from now you’re going to help co-found a group of bloggers who will support you and remind you again and again that you have the tools necessary to fulfill your dream, you just have to keep working at it. 
Take chances.  Right now, you’re fearless.  You’ll do anything for a laugh.  You’re the overachiever and dare devil of the group.  Don’t lose that.  No matter what boys upset you or what friends leave your life.  You are the main character of your life, so go where you want to go.  Otherwise, you waste too much time trying to get there.
Don’t be so worried if you don’t go out every night!  At 26 you’ll be PLANNING nights in where you can stay on the couch with a glass of red wine and a good movie.  A little solitude helps renew you, so stop panicking that no one likes you or that you’re a bad friend if you don’t attend every party and get together!
Don’t be sad if you lose some friendships.  The best ones will stay with you because they’re honest and open no matter what.  The friends you have at my age do not judge you and you can call them at anytime.  You do the same for them. 
Good news!  You will dress more fashionably and grow boobs in college!  Don’t go too wild now!  You crushed way too much high school.  Tone it down now, expand your mind not your growing list of possible last name changes!  When you’re my age you’re going to decide to never change your name anyway. 
Be thankful.  I know it’s hard to watch others get things so easily while you have to work for them.  You’re going to appreciate that hard work ethic when you become a manager of 40 some associates at a leading department store.  Your actions speak for themselves and you can be proud that you earned every vacation, every continuing education course, and every bag of groceries.  If you work just as hard on your writing, one day I think you’ll make that goal too.
Your love life?  I can’t give too much away.  After all, a lady doesn’t kiss and tell.  I’ll just say, you’re going to screw up big time the first time around, but you learned from that and you changed who you are now, so maybe that’s ok.  You’ll be the heartbroken one next time after a failed bi-racial relationship, but you’ll have taught your parents a lesson about acceptance that you’ll be forever grateful for.  You’re in a serious relationship now and I think he’s worth keeping.  Only time will tell…
Can’t wait to see what you’re up to in another 10 years! 
Stay true,
26 Year Old Jess


What would you say to your 16 year old self?


clip_image004Bio:  Jess Witkins claims the title Perseverance Expert.  She grew up in a small Wisconsin town as the much younger youngest sibling of four, she’s witnessed the paranormal, jumped out of a plane, worked in retail, traveled to exotic locations like Italy, Ireland, and Shipshewana, Indiana, and she’s eaten bologna and lived to tell about it!  She deals with it all and writes about it!  Come along on her midwest adventures; Witkins promises to keep it honest and entertaining.  Go ahead, SUBSCRIBE, you know you want to. Follow on Twitter:  @jesswitkins


About David N. Walker

David N. Walker is a Christian husband, father and grandfather, a grounded pilot and a near-scratch golfer who had to give up the game because of shoulder problems. A graduate of Duke University, he spent 42 years in the health insurance industry, during which time he traveled much of the United States. He started writing about 20 years ago and has been a member and leader in several writers' groups. Christianity 101: The Simplified Christian Life, the devotional Heaven Sent and the novella series, Fancy, are now available in paperback and in Kindle and Nook formats, as well as through Smashwords and Kobo. See information about both of these by clicking "Books" above.
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20 Responses to A Letter To My Sixteen Year Old Self by Jess Witkins

  1. Pingback: What Would You Say to Past-You? « Sonia G Medeiros

  2. Hi Jess/David.

    I can barely remember what I was like at 16! Ignoring all the serious stuff I would have said (which I would have ignored anyway) I think there are two things:

    1) Do what you really want to do, even if your scared of it.

    2) Buy Apple stock.



  3. StoriesAndSweetPotatoes says:

    Aw, wonderful Jess! I don’t know that I could write a letter to my younger self just yet.


  4. When I was 16 I knew everything, and my parents were pretty stupid. Funny how that changes through the years. Thanks for honoring my site today, Jess.


  5. Jess, your post makes me think how I thought I had everything figured out when I was 18. Then at 24, I thought I didn’t know anything when I was 18, and now I have it all figured out. In my thirties, I had the same experience. So now, I’m humbled and jaded enough to have figured out that we’re always learning. It doesn’t end. And I certainly don’t have it all figured out yet!


  6. Catie Rhodes says:

    I would tell myself a lot of things, but it would all boil down to one message: Don’t be so scared! It’s okay to fail. It’s okay to be weird. Just let it fly and see where life takes you. You can’t control everything.


  7. It’s funny how many similarities our notes would have!

    I would probably tell myself that having a boyfriend doesn’t make you more of a person and that it’s okay to be yourself and have your own interests.

    It’s amazing that it’s taken me 11 years to figure that out!


  8. Marcia says:

    I often wished we could all send letters back to our younger selves…oh, the heartache and angst we’d avoid. But I guess it’s all a part of living and learning.
    I was hoping you had posted a picture of your 16-yr old self…but I’m glad to know the 26-year-old you. You have accomplished a lot and are obviously a brighter, smarter and more curvy YOU! Love this post, Jess!


    • Jess Witkins says:

      hahaha, yah I would’ve liked to post an older photo, but they’re all at home. One of these days I’ll have to scan a bunch for blog posts, cause it is fun to look at older photos. The fashions!


  9. I love this! I caught that post too. Good stuff! Ah, to be 16 again…no thank you. 😀


  10. hawleywood40 says:

    So much of this rings true to what I’d say to my 16 year old self (even now at 41!) that I got a little misty-eyed reading. You have so much to be proud of and so much insight to share! This makes me want to dig into my Facebook archives for a note I did to my 20ish self on my 40th birthday – I hadn’t started my blog yet so it never got shared there, and might still be worth a future post.


  11. “Good news!  You will dress more fashionably and grow boobs in college!  Don’t go too wild now!  You crushed way too much high school.  Tone it down now, expand your mind not your growing list of possible last name changes!  When you’re my age you’re going to decide to never change your name anyway.”

    Hahaha! Awesome! I guess this is why they say “if we only knew then what we knew now!” And you know a lot!


    • Jess Witkins says:

      LOL. I’m so happy that part spoke to you Renee. You are such an awesome partner and friend, fryber as Clay calls it. LOL. Yah, I definitely wished I’d known some of THAT way back when.


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