Jenna Rainey

CEO + ARTIST + EDUCATOR

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I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.

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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

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My Creative Journey From Calligrapher to Children’s Book Author

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5/16/2025

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Jenna 

If someone had told me a few years ago that I’d be writing and illustrating a children’s book, I probably would’ve laughed. Not because I didn’t think it was possible—but because it just wasn’t on my radar. At all.

But that’s the wild and beautiful part of a creative journey, right? You start in one place, and if you’re open to it, the path unfolds in the most unexpected ways.

So today I want to share a little behind-the-scenes look at my own creative path—from my early days as a calligrapher, to becoming a watercolor artist and educator, and now… creating a children’s book with my son (yes, Myles is involved in the best way). This project has brought me full circle in ways I didn’t expect, and I hope it encourages you to trust your own creative unfolding too.

It All Started with Calligraphy

Before watercolor, before courses, before books and YouTube tutorials—there was calligraphy.

I first fell in love with the way ink moved across paper. The rhythm of it. The intentionality behind each stroke. I’d spend hours practicing letterforms, studying spacing, and trying to create something that felt both structured and expressive.

Calligraphy taught me so much about patience and observation. It’s where I learned to slow down and look closely. (That skill still shows up in my watercolor work every single day.)

And even though I don’t share as much calligraphy content now, it’s still part of me. In fact, I’ve included little nods to my lettering roots in my children’s book. You’ll see it in some of the textures, the flow of the lines, and even how I thought about composition.

(That’s one of the coolest things about a creative journey—nothing is ever wasted. It all comes with you.)

If you’re curious about how I went from pointed pen calligraphy to writing and illustrating a children’s book, I made a video that walks through the full journey. I share early samples of my lettering, how calligraphy influenced the book’s design, and what the creative process has looked like from day one.

Watch the video below to see how my love for letters grew into something so much bigger.

Watercolor Became My Playground (Eventually)

Watercolor didn’t enter my life as a side hobby. It showed up during the early days of my custom stationery business—when I was deep in designing wedding suites, menus, and invitation sets for brides all over the country. (Yes, that season.)

At the time, watercolor was just one of the many tools in my kit. I was still doing a lot of calligraphy and design work, but watercolor quickly became the piece that felt the most alive. I loved how unpredictable it was. How it forced me to let go a little. (A lesson I really needed in that fast-paced, high-pressure client world.)

But here’s the thing: back then, it wasn’t play. It was work. Beautiful work—but still very tied to deadlines and client needs.

It wasn’t until I stepped away from custom design and gave myself permission to explore watercolor for me—not just for someone else—that it truly became my playground. That shift cracked something open.

I started experimenting. Sharing process videos. Teaching others what I was learning (and unlearning). And somewhere in that transition from “designer” to “educator,” I found my voice as an artist.

Watercolor is still where I go to unwind, to connect, to create without overthinking. It’s been with me through business pivots, personal growth, and now—bringing a children’s book to life. (Which honestly feels like the most playful project yet.)

A Shared Project With Myles

Clarence started as a simple sketch—just a rectangle with eyeballs—that Myles doodled one day. It was silly and sweet, and something about it stuck with me. We started imagining who this little character might be. What made him nervous. What made him light up.

We weren’t trying to write a book. We were just playing. Around that same time, Myles had a sensitive experience at school, and as we explored this little character together, something deeper started to take shape. It became a story about big feelings, finding your voice, and learning how to express what’s going on inside.

That’s when I realized: this wasn’t just a fun character. This was something I wanted to bring to life in a bigger way.

I never set out to write a children’s book, but once the idea clicked, it became one of the most meaningful projects I’ve ever worked on. (And the fact that it started with Myles? That’s what makes it really special.)

Curious how this whole children’s book journey started? 

In this video, I’m sharing the big news—and all the messy, beginning-stage thoughts that came with it. From developing the visual style to navigating the early creative process, it’s a behind-the-scenes look at how I was building something from the heart (and how it early on taught me so much about creativity, storytelling, and style development).

Watch the video below to come along for the ride—I’m so excited to eventually give this book to my son, and even more excited to share the journey with you.

The Full-Circle Moment

When I look at this project now, it feels like all the pieces of my creative life are finally sitting at the same table.

  • My calligraphy background gave me the love for detail and flow.
  • Watercolor taught me to embrace looseness and emotion.
  • Teaching helped me build confidence in storytelling and creative leadership.
  • And parenting? It opened up an entirely new layer of creativity—one I didn’t even know I had.

That’s why I always say: your creative journey doesn’t move in a straight line. It zigzags. It loops. It pauses. But it always moves. And it brings every part of you along for the ride.

This book—this shared project with my son—is the most recent chapter in mine. But it’s also a reflection of everything that came before it.

What This Journey Taught Me

If you’re in the thick of your own creative process (or you’re just starting out), I want to share a few things I’ve learned from this wild ride so far:

  • Trust the pivots – I never would’ve predicted this path, but each shift led me closer to something that felt true. Let your curiosity lead.
  • All skills are connected – Even if something seems unrelated, it probably isn’t. Calligraphy, watercolor, storytelling—they all feed each other in ways you’ll see later.
  • Let the project change you – Working on this book stretched me creatively and emotionally. That’s what big projects do. Lean into the growth.
  • You’re allowed to evolve – You don’t have to stick to one niche forever. If something new is calling, explore it.
Laughing joyfully in a tiled bathroom, a woman wears a knotted green top and jeans, exuding carefree, creative vibes.

Creating From the Inside Out

One of the biggest takeaways from this project (and honestly, my whole career) is this: the best work comes when we create from the inside out.

When we stop chasing trends and start listening to what lights us up. When we make space to hear those little whispers. When we allow our creativity to be personal—not just polished.

That’s the heart of my course, The Art Within. It’s where I teach the process I’ve used in every stage of my creative journey—from calligraphy, to building an art business, to writing and illustrating this book.

If you’re ready to go deeper into your own voice and style (or you just need a little help staying grounded in the process), this course was made for you.

Still Becoming

The truth is, I don’t know where my creative journey will take me next. And that’s kind of the fun of it.

I’m still learning. Still experimenting. Still making messes and starting over and getting excited about weird character shapes my son draws on the kitchen floor.

But what I do know is this: creativity grows when you give it room. When you let it evolve. When you stay open to what’s next—even if it looks different than what you planned.

So wherever you are on your own creative journey—whether you’re picking up a brush for the first time, or pivoting into something new—I hope this encourages you to follow the path that feels most like you.

It’s not about staying in one lane. It’s about staying honest, staying curious, and letting your creativity keep you moving.

And who knows? You might just end up writing a children’s book, too.

by Jenna Rainey 

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