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Happy Friday and welcome to another edition of Heart to Heart! This week we are learning more about hand letterer and author Kiley Bennett from Kiley In Kentucky. Kiley wears a lot of hats. In addition to being a letterer and author, she also co-hosts a podcast, teaches hand lettering classes both in-person and online, is a Youtuber, blogger and a Tombow Ambassador. Let's learn some super fun facts about Kiley first....

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Who was your favorite music artist/group when you were in high school?

I loved Ingrid Michaelson in high school. She spoke to my teenage soul! I still listen to one of her albums when I need a little burst of nostalgia.


Which Disney character does your life mostly resemble?

This is not a very exciting answer, but I love Belle from Beauty and the Beast. She is well-read, does not care what others think of her, and is fiercely protective of her tribe. All admirable traits!!


What is the best knock-knock joke you know?

Knock Knock….
Who’s There?
Yoda Lady.
Yoda Lady Who?
I didn’t know you could yodel!


If you could be an Olympic athlete, what sport would you compete in?

Figure Skating!!! It is so beautiful and fun to watch. And of course, I love the costumes.


What is one meal you can’t live without?

A Grilled Chicken Sandwich with chips and a dill pickle. I could eat this meal every day!


Ok, now the Heart to Heart stuff….


Tell us about yourself….

First, I bet you wouldn’t have guessed, but I’m a born and bred Kentuckian. I love coffee, my cat, Beatrice, and my husband (not necessarily in that order). Currently, we live in Southern Illinois while my husband attends grad school. I run my business, Kiley in Kentucky, from my sweet little home office, and travel (for work or for fun) any chance I get! When I’m not lettering, I like to paint, stay sharp on the piano, and visit vineyards, breweries, and local hiking trails wherever I live.


How and when did you start lettering?

I began lettering in mid-2015. I had a desk job at an advertising agency in New York City and I desperately needed a hobby to keep me sane! My interest in lettering began when I taught myself how to use Adobe Illustrator, and thought I might want to make fonts of my very own. I bought a brush pen at Dick Blick on my lunch break one day, and I guess, never put it back down!


What are your favorite lettering tools?

My favorite pen is the Tombow Fudenosuke Soft Tip brush pen, but I LOVE the Apple Pencil (to use with Procreate) when I want to digitize or make graphics for my website.


What has the road been like since you’ve started?  

It’s a winding one. The first year of my lettering practice was spent just trying to ‘like’ my own lettering. The second year was all about figuring out my own style, and figuring out a path for myself in the lettering community. Now, in the third year, I’m refining my skills, adding new ones to my arsenal, and trying not to lose sight of what’s important to me as an artist, teacher, and a business owner.


What has been a constant in your life that motivates you?

I have an incredibly supportive husband who is my biggest fan and motivator. He sees the highest highs and the lowest lows, and never seems to tire of my emotional self! But, before him, I relied heavily on my family and friends for support and motivation. I’m lucky---I have only the best of the best in my life.


You just published your first book, congrats!!  Can you tell us everything about it?

Yes!!! My book is called Super Simple Hand-Lettering: 20 Traceable Alphabets, Easy Projects, Practice Sheets, and More! I was approached by a publishing company in mid-2017 about writing a book for beginners, and said yes right away. Super Simple Hand Lettering is a reflection of my teaching philosophy….I teach lettering the way I taught myself and I provide so much variety in the traceable alphabets and exercises. I think the book makes learning to letter FUN and helps you to learn faster since it’s so interactive.


You also co-host a podcast, who is this podcast for and what is it all about?

The podcast is called Misses Ambitious! I co-host it with my business BFF, Blaine. We began the show in March of 2017--we are celebrating one year---and have two episodes a week on iTunes. The podcast is for aspiring or beginning business owners who want encouragement and advice for starting a small business. We do not claim to be experts, so we interview guests that are in different stages of business to provide even more wisdom and support for our listeners. Also, we like to keep it real. It is not all rainbows and unicorns, and we are very open about that!


What other doors have opened up for you that you are proud of?

I recently filmed a class with Brit + Co in San Francisco, which was an incredible experience, and really affirming for me...I’m a chronic second-guesser and self-doubter! This year, it seems as if opportunities for speaking at conferences or lending my ‘brain’ for non-lettering use (encouragement, mentorship, etc)  have been popping up left and right and I am very excited about the prospect of using my experience to help another creative business owner in a way that will be impactful!


Tell us how your hashtag #magicalunicornladyboss came to be.

That is the hashtag for the Misses Ambitious podcast community! We came up with this hashtag because it sometimes seems as if being a successful business owner might as well be as easy as finding a unicorn in the wild. It takes a lot of special ingredients--magical ones--to strike the balance and achieve success! And of course, all women in business are lady bosses to us!


What’s the biggest piece of advice you’d like to give to the lettering community?

Don’t compare. Don’t compete. Stay in your lane. Embrace your own brand of uniqueness and don’t let fear of failure keep you from playing the game.

If you'd like to follow Kiley and learn more about her, visit these links below:


INSTAGRAM: Kiley In Kentucky

FACEBOOK: Kiley In Kentucky

PINTEREST: Kiley In Kentucky

WEBSITE: Kiley In Kentucky

Kiley's Lettering Class - Love How You Letter  (use code mandy10 for an additional 10% off!) 

Kiley's book - Super Simple Hand Lettering  

Kiley's podcast - The Misses Ambitious Podcast 


Take a look at some of Kiley's beautiful work!