On Braces, Broad Shoulders & Big Brows...

What would you say if you could snuggle a bit of encouragement into your 16 year old self today?

I’ll go first..


Piercing a second hole in your ear will NOT be worth the embarrassment of suddenly passing out on the floor in the middle of a crowded mall.

Someday your linebacker shoulders will look killer in a halter-style dress.

Feeling hurt when you’re left out of a get-together with girlfriends stings just as much at 29 as it does when you're in high school.

Your desire to impact others will never go away, so you might as well start now.

Those younger girls look up to you… Do your best to show them what it can look like to be a sassy combo of smart + funny + cute, but most of all - kindness is the key.

Sleepovers with girlfriends are far less frequent as an adult.  Enjoy them while you still can.

Stop wasting money/time trying to find the perfect acne remedy… Your skin will clear up (for good!) just days after you stop eating sugar.

For the love of tweezuhs: PLEASE, STOP OVER-PLUCKING ZEE BROWS.

She probably didn’t mean to hurt your feelings, and if she did - It’s either because she feels awful about herself or is not someone you want to be friends with anyway.

Frosted nude lipstick is not a good look on someone with your skin tone.  Stick with the berry brights.

When your closest guy friends can’t stand the boy you’re dating, it’s because they probably know you a lot better than you know yourself.

Wear your FREAKING retainer unless you want to have braces again.  (Two more times!)

Just because someone let him stand outside of an Abercrombie with his shirt off does not make him a model.  (Even if he really is a model, it won’t help the fact that he’s not a nice guy.)

You may get teased now, but someday you'll be glad you learned to brush aside the brand-names and embrace vintage at an early age… Oh, and thanks for hanging on to the good stuff.

Spend as much time with your grandparents as humanly possible.  Ask them every question you can think of, and write down all of their answers. 

He IS out there, little lovebug.  Start praying for him now, and you be infinitely blessed later.  (I can't WAIT for you to meet him!)


The more I thought about what I'd tell her, the more I realized:  

In most cases, the things we wish we would have known are what make us who we really are.
— Jessie Pepper

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I certainly wish there were someway I could sit Mini-Jessie down for a hug-fest and a hot cup of her someday-favorite tea but since that clearly isn’t an option, I’ve chosen to go another route...  

Passing along the things we’ve learned - from major mistakes to minor missteps, and many many heartbreaks in between - can be a precious gift to give the gals coming along behind us. 

Will you do me a petit favor this week?  

Find yourself a younger gal (you’ll know the one that needs you when you see that look in her eyes) and tell her that she is darling and lovely and JUST right and that everything will work out ok.  And then tell her, if it doesn’t?  That you’ll help her see it through, because we’re all in this together and that’s what we girls do.

In the meantime... I'm going to try and dig up a photo of those braces and big brows to show you sometime soon. ;)

With Broad-Shoulders (That Protect A Brave Heart),

XOXO - Jessie Pepper

Ps. - Have you ever thought about writing a note to Little You before?  I'd love to hear what you would have to say, and can already tell I'm going to be hanging on your every word. :)

SHARE THE LOVE // Thinking of a little lady that could use these words today?  Pass along this message and let my hiccups and hardships lend themselves to doing some good. ;)

On Avoiding Tomatoes & Ducking Doubt...

Currently standing on the proverbial stage of my mind, wondering how the dang hecklers got so loud this week.  

These Pepper Letters are definitely not supposed to feel like a gripe-fest, but I DO feel like we can be honest with each other here - and I am so grateful for that, my little Pepitas.


Really too embarrassed to even utter - much less actually transcribe - some of the self-criticism that has been clattering around in my head for the past few days...  

Do you ever have those moments?  

(Praying you’ll say no, but predicting that the answers might be a bit disheartening.)

A real performer would tell me to ignore the occasional rotten tomato being thrown from the crowd, but when one finally manages to splatter across my face... I find it tough to pretend like I don’t feel the sting.  

My own method of pressing on involves trying to encourage others at every turn, and embracing the things that I know to be true.  

Seeking out our clearest sources of confidence can stave off even the most disparaging doubts.
— Jessie Pepper

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Over the past few months, I have been learning quite a lot by asking dear friends AND strangers to answer the following question: 

What is something that makes you feel most confident?

The answer almost always reflects a personal victory or honest appraisal of their best characteristics (YES!), and not only do I feel blessed to find out more about their sweet souls, but am excited to use this “research” to continue encouraging discussion about something that we can so easily forget.

Now, I’m going to tell you something that would make me BURST with happiness…  

I would love to know what makes YOU feel most confident, and you can share your own answer to the question above by simply replying to this message or commenting below.  I can’t tell you how much I treasure the responses that I get from you each week, and am already feeling better because you let me share these candid words and a little snippet of my life with you here today. 

Blessed By Your Precious Hearts,

XOXO - Jessie Pepper

Ps. - Speaking of “candid words" (because I've never been very good at editing): You may have seen me mention what I WAS planning to give up for Lent this year, but it only took about sevenpointfourtwofive seconds to realize that my words couldn’t go without hugs for that long.  

(Lord knows that I try to give my words whatever they need… And THAT, my friends, is how you end up with a weekly love letter.)