How I Started Handlettering + A Few Tips To Get You Started

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Above is one of the very first lettering pieces I ever did. It was a little doodle series I was working on to give as Christmas gifts to friends and family. To be honest, I didn't even think of it as lettering. I just thought it was a sweet, homemade gift. It wasn't until the following summer of 2014 that I really dove in and decided that I wanted to learn lettering. So here's my story.  

Once Upon A Time... 

(just kidding)

I will forever remember that fateful day in June, 2014 when I literally declared to myself (but it felt like I was declaring it to the world) that I was going to learn handlettering.

It was the topic I was Pinning the most on Pinterest at the time, and I was starting to follow letterers on Instagram like crazy. I was eyeing all the lettering books, devouring any beautiful type I found out in the "wild" and just loved any and everything that had to do with lettering. To say I had officially become obsessed with this new art was an understatement. 

Then one day it smacked me in the head like a ton of bricks. I realized,

"Wait a second... why can't I become a letterer?!"

Duh! All this time I never stopped to consider that this could be a new skill I could acquire... Which sounds so silly, but a few years ago, "lettering" wasn't a thing (like it is now) and it definitely wasn't something people did for a living. Sure, there were calligraphers - but I remember calligraphy was something my mom wrote on our birthday cards. 

So I decided I was going to learn and start lettering. 

However, even though that felt like a pivotal moment for me - I realize looking back, that lettering has always been a part of my life. 

You see, I was that girl in school that always had really nice handwriting. I remember practicing my print letter forms so I could have that "cool print" (90's kids, you know what I'm talking about). After awhile, I had it down. I loved hearing "Wow, you have such cool handwriting" and being proud of how nice my everyday writing was (in like, 4th or 5th grade).

I was also that girl that wrote a lot of letters (like, physical college ruled paper, a la snail mail), and folded them in all those funky but again, "cool" ways (see here for examples). At the top of all my letters I wrote my friends' names all chunky, funky and bold lettered. I absolutely LOVED decorating the letters and putting emphasis on words I wanted to stand out.

I remember my mother gave me this book, Letter Art by American Girl for examples of different lettering styles that I could pull from (they were all awful; think incorporating pumpkins or bows into every single letter kind of thing) but it was so fun! I actually just recently discovered this book and was tickled pink when I realized that lettering has been a larger part of me then I ever realized. 

There were other such instances throughout my life that showed lettering really was a passion of mine. I could ramble on about them, but to move this story along, it wasn't anything I took seriously. Up until that summer, like I mentioned before, I was just the "girl with nice handwriting" or "ask Rosalynne to write on our car wash/cheerleading/youth group/etc. poster" person. But that's as far as it ever went. Until the summer of 2014.

June of 2014, I started my personal lettering challenge. 

I decided that I was going to letter everyday for 30 days, because I was determined to somehow figure out this lettering thing. To be candid: I didn't know where to start or how to learn. I didn't know of classes or books, I just knew I saw things on Pinterest that I loved. So everyday I would look on Pinterest, and use the artwork that I saw as my place to start. I did this until I started to get a hang of it, and slowly discovered how to create letter forms, shapes, composition, etc. that would all come together.  All this was in my personal sketchbook (because I knew it wasn't my original work to share) and it was how I started figuring it all out. 

A lot of the beginning involved tracing other lettering pieces that I found on Pinterest. I wish I knew back then that I should have credited the pieces I was lettering in my sketchbook, so I knew who the original artist was and wouldn't get confused and think it was one of my own - but that's part of my learning curve at the time.

In the beginning, I bought a lot of different pens from Blick. I studied typography, brush lettering and calligraphy. I really just explored, played around, and didn't pressure myself to only share work that was perfect. It was a beginning! And I was so excited to start. 

If you follow me on Instagram, or want to see some of my oldest art over the years, check out the hashtag #handletteringbyros. I'm not always the best at using hashtags, but you can see some of my earliest lettering pieces that I posted and the progression over the last three years! 

The most important thing I learned was this: you have to start where you are, with what you have. I believe that sharing your beginnings is hard, but so beautiful. I'm so thankful I shared those first few pieces so I could admire how much I've grown over the years. 

And it's funny to me, how God works. I thought I was just learning something that I found interesting. Little did I know that it would be something that I turned into a career! Lettering is something I absolutely LOVE and I cannot imagine my life without it. Even if I didn't letter for my work, it would still be something that finds a way into my everyday life.

You see when you love something, you find yourself doing it frequently. Jessica Hische says, "The work you do when you procrastinate is probably the work you should be doing for the rest of your life." Lettering was the thing I was doodling while taking notes in class, while writing out todo lists for my life. You name it and I was drawing letters on it. 

So moving along in my story - I did the one month challenge, and in all honesty - I didn't even finish it! But it did spark a passion for letters and I continued to keep lettering slowly over the next year. I remember for Christmas, my husband and I didn't have a lot of money for gifts for the family, so I decided to letter quotes for all my favorite people. I'm so glad I did this because my sweet friends and family still have these quotes and frames hanging up in their homes and offices, today! :) 

The following year in 2015, I was finishing up my senior year of design school, and that's where I found myself screen printing for a class project - this is what led to the birth of my apparel business. But that's another story for another time (coming soon). So stay tuned for that! This was the year that my lettering really started to take off, as my business was stemming from this newly found art form that I loved!

And then as they say - the rest is history. 

I hope you enjoyed this story and behind-the-scenes of my lettering journey! It's crazy to me that I've only been lettering on-and-off for about 3.5 years. I still have so many more years of growth and experience to gain... But that's one of the things I love most about lettering: you never "get there." There is always more to learn, new techniques, new tools, and different ways you can apply it. So I have a feeling I will be lettering many things, for many years to come. 

I get asked a lot about lettering and how to learn. So below I've outlined a few tips that can hopefully encourage you and help you get started! 


  1.  Don't be afraid to start where you are. We all started at day one. Please don't look at someone who's been lettering for 5 years and get discouraged. They all started from no experience once upon a time, too. 
  2. You don't need fancy tools, pens, devices to letter. I literally used a pencil and a Sharpie for years. Only as time went on did I discover new pens, and eventually buy an iPad Pro. These aren't what make me a good letterer - they are just ways I play around with my lettering. 
  3. Probably the most important one - Practice Makes Perfect. Seriously, practice every. single. day. You'll see improvement if you do this. 
  4. Find inspiration in the world around you. Sure, you can follow other letters and look on Pinterest - but I caution against this because you don't want to intentionally/unintentionally copy. Yes, that's how I started, but I kept those sketches private. And from experience over the years, I've learned that it's better to go look through vintage labels in antique stores.

    Hope this helps! Below are a few more photos from over the years, or like I mentioned before, feel free to look through my #handletteringbyros tag to see tons more! 

    1 comment

    • Posted on by Courtney Stoll

      Your story is an inspiration! How far you’ve come in such a short time is inspiring to so many ? I hope that I find the same amount of motivation to work on my goals for my business as you show in yours. America is such a beautiful country (your photos are incredible), I hope to live there someday! Thank you for sharing!

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