ASK JESSIE PEPPER: How to know if you're on the right track...

I’m back! And I come bearing gifts!

You may have noticed that Pepper Letters took a bit of a breather since the first of the year, but after Twenty Fourteen's 52 love notes in a row, I had a feeling you’d forgive me. ;)

The good (GREAT!) news is that I’ve got a little something that I’ve been excited to send your way for weeks, and I couldn’t have done it without the encouragement and permission from a few of YOU, my sweet Pepper Girls...

A few months ago, I curiously tossed this question at you in the close of a letter: “If you could sit down with a mentor, older sister or trusted friend right this very instant, what would you ask her?"

The heartfelt replies that I received were honest, scary and beautiful all at once.

Even though it gave me a glimpse at how vast our oceans of hurt can be, just knowing that you are comfortable enough to share some of your stormiest struggles was a total gift, in my eyes.

It felt so important to respond with more than just a few clickety-clacks on the keyboard, so I decided to record special videos messages to each one of you who reached out with a personal prompt. The earnest chats that followed have been confirmation that we are more than just ships passing in the night… Many of us fill our sails with the same spirit, experience the same title waves of emotion and like to enjoy the same bouts of swimming and splashing whenever we can.

When we share both the bleak and bright parts of our lives in community (alongside women we trust), it can truly wash up some of the most glittery treasures this magpie has ever seen.

Today, I’m sharing (with express permission!) one of the special videos that I recorded, and my hope is that you’ll continue to share your heart with me here so that I can do my best to be the sister I was created to be.

A quick recap:

What does YOUR version of the right life look like? I'm guessing that you're seeing glittery glimpses in the stories of those around you, but I'm here to say that YOU, my Dear, are destined to shine your own kind of bright. [Click to tweet.]

Set your timer for 25 minutes. (Extra points if you've got a hot cup of tea handy.) On a crisp-clean piece of paper, write down what the daydream version of your brightest life looks like.

+ Whose hearts will you touch?
+ How will you make a difference?
+ What will you create?
+ What does the perfect day look like?
+ How do you go about feeling healthy & happy?

The best version of yourself will start to surface, and knowing what this looks like can be so handy in guiding you toward the actionable items needed to follow that "right track" that you're seeking. (Which is only spot-on because you've drawn it on the map yourself.)

Have faith, listen to your heart, and I can't wait to hear about your incredible adventure of getting there. :) 

XOXO - Jessie Pepper

(Looking for extra help with navigation? You know I'm always standing by when you need me!)

Vulnerability allows us to start the work of shining light into dark places, and I am infinitely blessed by this bright little garden of growth we’ve created... Feel free to share your thoughts in the comments below, and let's see what might flourish by exploring life with new friends! 

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

[Tweet it!]

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. ;)