Interview with Hand Lettering Artist, Kiley Bennett of Kiley in Kentucky

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Today’s exciting for me because I get to introduce you to one of my best friends! Her name is Kiley Bennett and many of you might know her better as the amazingly talented hand lettering artist of Kiley in Kentucky. She was born and raised in Kentucky and is currently living in a small college town in Illinois with her hilarious husband Daniel and her sassy cat Bea. She is a full-time lettering artist and teacher, Tombow USA brand ambassador, and released her first book Super Simple Hand Lettering this past January.


Kiley and I met on Instagram. Our friendship started just by commenting on each other’s Instagram stories and when we were both working on our first books, we began talking more frequently, encouraging one another in that process. Eventually, we started chatting over GroupMe in a small business group Kiley started. Because of our similar businesses and personalities, our friendship really hit it off on a personal level too. She has become one of my nearest and dearest friends and I would love for all the people in my community to get to know her sweetness and learn from her experience as a full-time lettering artist!

So, aside from a few questions from me, I’ll let Kiley take it away…

When did you start hand lettering?

It’s a long story, so get ready! I discovered hand-lettering on Pinterest! When Pinterest first began (I’m talking back when it was invitation only and you had to get on a waiting list to join) I was seeing a lot of art – specifically lettering – on Pinterest and was very inspired to try my hand at it. I have always had the art itch, loving to draw and paint growing up, and lettering felt like a new challenge that I wanted to take on!

At this point, I didn’t know THE FIRST THING about lettering. I bought a pack of Micron Pens and a sketchbook and tried to copy things I saw online. I was quickly discouraged by how little progress I saw in my lettering practice, and I gave it up within a couple of months. Hindsight is 20/20, because it’s obvious to me that I didn’t progress at all because I wasn’t educated on lettering in the slightest. I didn’t know what lettering was (downstrokes? What are those?!), the right tools to start out with, or the basic foundations of creating lettering in any form.

Fast forward 2-ish years and I was a receptionist at an ad agency in New York City, surrounded by typographers, graphic designers, and lettering artists. I learned what a brush pen was and thought ‘now that I can do.’ I be-bopped over to Dick Blick on my lunch break, bought a pack of Tombow Dual Brush Pens, and the rest is history. At the time, I was very inspired by Amanda Arneill. She is the fairy godmother of brush lettering, in my opinion! I’m still incredibly inspired by her lettering and the brand she’s created, but these days I am thankful to have developed my own style that I love and continually draw inspiration from. I keep my outside influences to a minimum because that is the key for me when I’m in creation mode! I originally fell in love with lettering because of how relaxing and satisfying it was, but now I love it because it has given me this life I love! I work from home in my own studio, I make my own hours, I have an incredible community of friends and students around me, and it feels like a DREAM.

When did you realize you wanted to pursue a career as a hand lettering artist?

A little while into my lettering practice, I felt confident enough in my ability to make cute hand-lettered gifts for friends and family and felt as if I should start selling on Etsy. Etsy worked for a little while, but I quickly discovered that I did not enjoy the fulfillment and customer service side of having an online shop, but I did enjoy giving advice, sharing tips, and showing my friends how to use a brush pen. Having taken numerous online courses for business and Etsy from other creatives in my industry, I knew there was a market for online education in the creative world. I also knew that teaching would be a much better fit for my personality…and that creating online classes would give me an even more flexible lifestyle. It almost wasn’t even a decision. I just went for it! I came out with my first online class less than a year into having an Etsy Shop, and since then I have shut down Etsy and produced three more online classes.

You are clearly passionate about passing along your love of lettering! You just came out with a brand new online course to help others get started. Tell us about that!

28828247_938058963034260_3732958530609177644_oMy new class is called Learn to Letter and it’s a class for the complete beginner. I decided to structure this class much like I would an in-person workshop so that those who can’t make my in-person workshops (due to travel, circumstance, time conflicts, etc.) could purchase my online course and learn from the comfort of their home in a pressure-free, go-at-your-own-pace way. I’m so excited about this class because it is what I needed all those years ago when I bought my pack of Micron pens and didn’t know what to do with them. I can’t even imagine how different my life would be now if I had discovered the brush pen two years earlier than I did. I’m also proud that my other class, Love How You Letter, is a natural next-step for any lettering artist. Once you learn the basics of lettering (or even well after), the next thing I believe any artist should focus on is developing and nurturing their unique style. Love How You Letter does just that!

What is your number one piece of advice to people just starting out with hand lettering?

You’re going to be bad before you can be good. I got discouraged and gave lettering up completely because I wasn’t a professional within two months. Even when I started using brush pens, it took me at least 6 months of daily practice before I was confident in my skills. For some, it takes even longer! If you’re not where you want to be right now, don’t sweat it. Practice, be consistent and stick with it. You. Will. Improve. It just takes time.


You mentioned briefly about what inspired you when you got started lettering, but I’d love to hear about what inspires you now!


As I mentioned previously, when it comes to lettering, I really try to keep my eyes on my own paper (literally and figuratively), because that’s what fosters creativity for me. However, since my hobby became my career, I’ve had to find new hobbies! One of those hobbies is painting. I love using gouache and acrylics to create abstract art, dabble with landscapes, and just explore color and pattern and movement with paint. I do not sell my work, nor do I teach painting, so it’s definitely just a hobby, and I like to keep it that way. I created a separate Instagram account to share my paintings (@loandroseco) if you’d like to check them out! Having a creative outlet aside from lettering has been key in keeping my ‘lettering fire burning.’ I could easily suffer from burnout if I didn’t have something else to turn to!

If people want to get to know more about you and learn about your online courses, how can they find you?

You can find all my classes and links to my YouTube Channel, Instagram, Facebook Page, and mailing list at!

If you would like 10% off either of Kiley’s online courses, click HERE to choose between Learn to Letter (for total beginners) and The Love How You Letter Class (for experienced letterers). Use the code lauren10 at checkout!

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April Wins and Learns


Well hey there! Happy May! This monthly “Wins and Learns” blog post is getting out a little later than I’d normally like. I’ve been frantically getting prepped for local events the past couple weeks, so I had to prioritize and get through all that before I could sit and reflect on this past month. But, I’m sitting out on my deck as I write this, it’s warm… spring finally decided to show up in Minnesota… that, my friends might possibly be the biggest win of them all! 😉


  • My retail sales continue to grow! I’m so thankful for Etsy, for my consigners, wholesalers, and local customers. I wouldn’t be able to do what I love without all your support! You keep me going and motivate me on to keep going – especially on the hard days. Thank you!
  • I had my first real product shoot with the lovely and talented Steena Anne! I have to admit, I was pretty overwhelmed, but Steena has such a great eye for what looks good, there was no need for me to be overwhelmed. She took charge and I love that she was able to capture the beauty of my creations and the love behind each one of them. Check out my Etsy or Facebook cover photo to see a collection of some of my favorites from this shoot!
  • I released my second Procreate brush pack: the Natural Brush Pack. These five brushes were created (by yours truly!) to look more like real-life brush pens. I’m really excited about them and I’m encouraged to see others start to get excited about them too! I’d love to show you these brushes, so watch my latest YouTube video to learn more. And of course, you can go right ahead to Etsy or Creative Market to download!
  • I started making foiled prints! I finally took the plunge, invested in new equipment, and I’m now kind of in love with foiling. (Shoutout to my bestie, Kiley Bennett for giving me such a great deal on her foiling machine and foil collection!)
  • I had to reorder more “Be Kind” enamel pins. Why is this a win? Well, I honestly created these pins as a passion project, not expecting to sell many, but I’ve nearly sold out in just two months and I’m pretty jazzed about that!
  • I had my third pop-up event at Pottery Barn in Edina, MN and it went so well! My first event there was around this time last year and all I had were prints and cards. It was so fun to realize how far I’ve come since then. I now have a book, pins, wood banners, custom stamps… I praise God daily that I get to do this for my day job. ❤


  • I need to learn to compartmentalize better. As my shop grows, so do my opportunities to create more and connect with people who enjoy my work. However, on the flip side, as my shop grows, so do my responsibilities and I’m presented with new challenges. I won’t get into all the details, but let’s just say I haven’t been great about handling the unexpected and difficult circumstances that arise and I really don’t want to give those moments any power to ruin my day!
  • I need to set more realistic expectations for myself. I’ve been getting better at this in the past couple weeks, but there is still a lot of room for growth. I tend to set unrealistic expectations for what I will accomplish each week and I’m continually reminded I’m not Supergal! I can’t do it all!
  • I learned that I need to take a break from local workshops after my Bible Lettering workshop on May 19th in Eden Prairie, MN. I’m struggling to get people to sign up. I know it’s not because of the content and I am confident that I’m priced correctly for the amount I spend on materials and the amount of work I put into each class. I just need to take a step back and come up with a marketing strategy. So far I’ve reached all my students organically on social media and through word of mouth. It’s pretty incredible that I’ve made it this far without having a marketing strategy, but until I have a plan in place, I won’t be scheduling any more workshops.


Thanks for reading! I don’t receive a whole lot of feedback on these monthly posts, but I enjoy including you as I look back on the past month and process the highs and lows and the wins and learns. I hope you’ll learn something from my personal experiences each month and if you do, please send me a message! I love hearing from you!

❤ Lauren

P.S. I’d love to stay connected with you a little better! If you join my mailing list, I’ll send you 2-4 emails throughout the month to let you know about blog posts, shop updates, new releases, and more! I’ll even send you a free PDF print to print and display at home!