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  • Welcome to TPK! This is your first of 2 free articles. For unlimited access to tutorials and articles, join TPK Premium for less than the cost of a latte.

    A Creative Calligraphy Challenge

    September 28, 2023

    by

    Lindsey Bugbee

    Beginner’s Calligraphy, Calligraphy, Calligraphy Drills, Dip Pen Calligraphy, Free Printables, Printable Goodies, Worksheets

    Today’s article includes a unique kind of calligraphy drill that will bring out your artistic side. The instructions are simple: print off the free worksheet, then pay special attention to the adjectives to make creative calligraphy!

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    A Creative Calligraphy Challenge | The Postman's Knock
    Don’t be afraid to experiment with your letters, even if they don’t turn out as intended! My “sloppy” “A” ended up looking like an “h” … c’est la vie.

    One of the secrets to success in any endeavor is to keep things interesting! Calligraphy is no exception, which is why I put together a Creative Calligraphy Challenge worksheet. The worksheet is intended to challenge you, stimulate your creativity, and encourage you to keep going with your calligraphy practice.

    How to Use the Creative Calligraphy Challenge Worksheet

    First, download the worksheet here. Print it out on 32# laserjet paper (or any other pointed pen-friendly paper), and gather your favorite pen/nib combination, ink, cleaning water, and a non-fibrous cleaning cloth.

    A Creative Calligraphy Challenge | The Postman's Knock
    The Creative Calligraphy Challenge worksheet is free.
    DOWNLOAD THE WORKSHEET

    Next, pick any letter of the alphabet. Write a version of that letter that fits each adjective on the worksheet. Remember that every letter should look different, even if some of the adjectives are similar.

    A Creative Calligraphy Challenge | The Postman's Knock

    Once you’ve completely filled out the worksheet with one letter, print out another copy and move on to experimenting with another letter. You can continue until you’ve made a worksheet for all letters of the alphabet (or you can just work on a handful of letters and call it good).

    How This Worksheet Will Help You

    Learning calligraphy can be stressful if you judge your creations harshly. This worksheet helps you to loosen up and realize that, at the end of the day, “calligraphy” just means artistic writing!

    A Creative Calligraphy Challenge | The Postman's Knock
    Try to make every one of your creative calligraphy letters unique from the others.

    I also like this worksheet because it encourages you to think outside of the box of calligraphy styles that already exist. You may create a letter that you really like, and you can make a whole alphabet that echoes the style of that letter.

    A Creative Calligraphy Challenge | The Postman's Knock
    The “spooky” “A” may be my favorite.

    The last way this worksheet helps you, of course, is by encouraging you to pick up that pen to write! Anything that gets you writing can’t be bad … after all, every time you write, your skill level improves that much more.

    How to Develop Your Own Calligraphy Styles

    The Creative Calligraphy Challenge worksheet helps you to create letters with a certain “vibe” — letters you might not develop otherwise. It mimics how I came up with my own calligraphy styles, most of which were requested by brides who had a certain look in mind (i.e. Kaitlin Style, Janet Style).

    Wedding Envelope Calligraphy
    Elegant “Janet Style” calligraphy was developed because I had a client who wanted a mostly traditional calligraphy style with just a hint a modern flourish. To take a look at all of TPK’s calligraphy styles, see this article.

    Coming up with your own calligraphy styles requires, first and foremost, an understanding of calligraphy basics. After that, you need creativity and a willingness to experiment. That’s something we focus on in TPK’s Intermediate Modern Calligraphy Online Course, where students are given assignments from faux clients.

    These calligraphy exemplars, designed for a “client” who wants a slightly bohemian feel for her wedding calligraphy, were created by students Lisa M. (left) and Nicola S (right).

    The vast majority of calligraphers create calligraphy as a relaxing, personal activity. However, many of us end up creating calligraphy for others — either loved ones or clients — at some time or another. (After all, you can’t keep your calligraphy skills a secret forever.) You have to have the flexibility to step outside of your comfort zone to achieve an effect that you might not have explored otherwise.

    Intermediate Modern Calligraphy Course student Laura M. designed this menu for a “client” who plans to open a Peruvian café.

    To that end, if you happen to create a letter that you particularly like as a result of using today’s worksheet, see where that style takes you! Come up with an alphabet exemplar (find instructions for making one here), then try making a couple of projects with your new calligraphy style. Then, if you want to dig deeper with your style development, explore adding flourishes, and add to your knowledge of supplies, consider enrolling in TPK’s Intermediate Modern Calligraphy Online Course. It’s 15% off through Monday, October 2nd (regular enrollment cost $40).

    LEARN MORE ABOUT THE intermediate COURSE

    Enjoy today’s worksheet, and if you’re on social media, I’d love to see what you use it to come up with. You can find the TPK Facebook page here, or tag @thepostmansknock (or hashtag #thepostmansknock) on Instagram! Thanks so much for reading, and happy writing!

    Warmly,

    Lindsey's Signature | The Postman's Knock

    *This post contains affiliate links to Amazon

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About the author

Hi, I’m Lindsey Bugbee, the illustrator, calligrapher, and author behind The Postman’s Knock (TPK). Since 2012, the TPK Blog has been a vibrant creative space filled with tutorials and lessons on modern calligraphy, hand lettering, and illustration. After publishing The Calligraphy Book, I wanted to elevate the quality of content even further—so I launched TPK Premium. You can join here to receive access to some of the internet’s best creative inspiration and project tutorials.

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19 responses

  1. A Avatar
    A
    October 31, 2023

    This worksheet is wonderful! I had so much fun creating diffrent “styles” of letters. Thank you, Lindsey!

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  2. FT Avatar
    FT
    August 1, 2019

    Thank you for the free worksheets, they are amazing and it’s useful for beginner like me. Many thanks.

    Log in to Reply
  3. Jenny Avatar
    Jenny
    October 3, 2017

    Thank you, Lindsey! This worksheet is amazing for beginners like myself. I had a lot of fun filling it out:)

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      October 8, 2017

      So happy that you enjoyed it! I think that it presents a fun little challenge, for sure. 🙂

      Log in to Reply
  4. Bre Avatar
    Bre
    September 6, 2017

    Thank you for the free worksheet. I posted it in a lettering group I am in, and everyone seems to LOVE it! I am always so thankful for teachers like yourself who have free downloads for beginners.

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      Thanks, Bre! Kind words like that make the energy it takes to create the downloads totally worth it. 🙂

      Log in to Reply
  5. Andrea Goo Avatar
    Andrea Goo
    September 6, 2017

    Since I can’t print on calligraphy friendly paper, I print on ink jet paper, then use my light box. I put the worksheet down first and laser jet paper over top, with blue painter’s tape to keep them both from moving. This work around has really done well for me.

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    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      (A great tip!)

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  6. Andrea Goo Avatar
    Andrea Goo
    September 6, 2017

    This will be fun to work on!

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      I have a feeling that you’ll come up with some cool letters, Andrea!

      Log in to Reply
  7. Linda Avatar
    Linda
    September 6, 2017

    Thank you, Lindsey! Can’t wait to start this. What a great idea!

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      I hope you liked filling it out! It’s challenging but fun. 🙂

      Log in to Reply
  8. farmchickdownhome Avatar
    farmchickdownhome
    September 6, 2017

    I love this! Can’t wait to sit down and “play”– Thank you so much for giving my brain and hand a kick start!

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    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      You are very welcome! I enjoyed filling it, too, despite being the worksheet creator. 🙂

      Log in to Reply
  9. Lieve Avatar
    Lieve
    September 6, 2017

    This looks great, thank you !

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      My pleasure!

      Log in to Reply
  10. Eréndira Espinosa Avatar
    Eréndira Espinosa
    September 6, 2017

    Hi, Lindsey! This is a so creative way to give us that little push into swimming pool to discover our possibilities that I’m surprised. Thanks a lot. I will begin today.

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      September 20, 2017

      I hope you enjoyed it!

      Log in to Reply
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A couple of days ago, I posted a clip from Lesson A couple of days ago, I posted a clip from Lesson 1 of the new Beginner’s Modern Calligraphy Online Course (seriously, join us — enrollment is a *steal* at $5/month, and you get complimentary tutorials [that happen to complement the course] — link in bio)! People seemed to like the story in that clip, so here’s another fun story from the same lesson. Sorry, I can’t confirm who the client was! That was a project with an NDA (Non-Disclosure Agreement). 🤐 Still: a very fun, very cool experience ... I’m grateful that calligraphy has given me cool adventures and connected me to such an amazing community. ✍️

#calligraphystory #moderncalligraphy #learncalligraphy #beginnercalligraphy #pointedpencalligraphy #calligraphy
Lesson 1 of TPK’s Beginner’s Modern Calligraph Lesson 1 of TPK’s Beginner’s Modern Calligraphy Online Course doesn’t actually start with the pointed pen! ✍️ Instead, we ease into it with faux calligraphy and then pencil calligraphy. Here’s a little preview of what the pencil calligraphy lesson looks like. ✏️

If you’ve been wanting to learn calligraphy, join us in this course. It is an absolute *steal* because it’s included with your TPK Premium membership ($5/month - cancel anytime). Once the course concludes in January, you can choose to purchase lifetime access to the videos; or just continue on with us to the next course. For more information, visit the link in my bio!

#learncalligraphy #pointedpencalligraphy #moderncalligraphy #pencilcalligraphy #blackwingpencil #pencilart #letteringart #handlettering #modernlettering #artisticletters #artisticlettering
I’m editing videos for the new Beginner’s Mode I’m editing videos for the new Beginner’s Modern Calligraphy Online Course (🎉 JOIN US! link in profile for enrollment info!!) — and wanted to share this story from Lesson 1. In that lesson, we’ll chat about how to develop your motivation (this story is part of me sharing mine); and we’ll ease into our pointed pen experience with faux calligraphy and pencil calligraphy. Step by step, you’ll develop skills that will serve you for a lifetime ... and surprise and delight those around you, just like my “rent check envelopes” did! ✉️

#mailart #moderncalligraphy #learncalligraphy #storytime #calligraphy #snailmail #snailmailrevolution
Some recipes aren’t just instructions — they’re memories on a page. 💛 I spent some time illustrating one of my favorites, and it turned into the sweetest (literally) keepsake. Calligraphy, watercolor, and a little patience bring the story of a dish to life.

If you’d like to try illustrating your favorite recipe, too, I shared the full process (with helpful printables) on the TPK Blog — link in bio. ✨

#illustratedrecipe #calligraphyart #watercolorillustration #creativeproject #keepsakeart #slowcreativity #handletteringlove #moderncalligraphy #calligraphyinspiration #watercolorart
As much as cooking is an art, illustrating a recip As much as cooking is an art, illustrating a recipe takes it one step further. ✨ In TPK’s latest tutorial (link in bio), I’ll show you how to create an illustrated chocolate lava cake recipe using watercolor. You’ll find helpful PDFs and step-by-step instructions so you can follow along — or use the layout to bring one of your own favorite dishes to life.

Frame it as keepsake art, or give it as a thoughtful handmade gift this holiday season. 🎁

#illustratedrecipe #watercolorart #calligraphycommunity #foodillustration #arttutorial #watercolortutorial #creativeprojects #handmadegifts #keepsakeart #thepostmansknock
✨ One of the most beloved assignments from Lesso ✨ One of the most beloved assignments from Lesson 5 of Hand Lettering 101 was this playful project: design an artistic alphabet where no two letters look the same.

The idea? JUST PLAY. 🎨 I used watercolor and a paintbrush, but many students grabbed markers, pens, or anything colorful on hand. The results were incredible — @adriennelovesletters gave it her own flair, Isabel C. made it three times, and Laura M. created a stunning version too. (You can peek at more inside the TPK Premium Discord!)

If you’re ready to try this project yourself, you’ll find the Hand Lettering 101 eCourse waiting in the TPK Catalog. Just head to the link in my bio to be taken to the TPK website. 💌

#handlettering #watercolorlettering #moderncalligraphy #letteringpractice #creativeplay #calligraphycommunity #artinspiration #calligraphyart #watercolorart #letterlove #tpkpremium #handlettering101
Had the best time writing the latest tutorial on t Had the best time writing the latest tutorial on the TPK Blog — “Drawing Lesson: Elegant Swallows” (🔗 link in bio). If you’ve never drawn birds before, swallows are an excellent place to start. Their shapes are simple once you break them down! ✍️ 

In the tutorial, you’ll find:

🪶 Step-by-step visual instructions for drawing swallows in four different movements
🪶 The “Hand-Drawn Swallows Cheat Sheet” PDF
🪶 A detailed tutorial for making the mail art shown here

On another note, I want to extend a huge THANK YOU to TPK Premium and Premium Plus members ... your support allows me to write cool detailed tutorials like this one. 🙏 You all are amazing, and I’m so proud of our community.

#mailart #snailmail #illustration #illustrationtutorial #drawingtutorial #drawinginstructions #birdart #swallowsart #calligraphy #moderncalligraphy #pointedpen
In June, I kicked off the Hand Lettering 101 eCour In June, I kicked off the Hand Lettering 101 eCourse with TPK Premium members, and wow — it’s been such a joy to watch the transformation.

Over six lessons, students went from that “where do I even start?” feeling to confidently creating their own alphabets, playing with flourishes, and putting together gorgeous compositions. I loved seeing those little lightbulb moments along the way.

Here’s the great news — you can still take the course.
When you sign up, you’ll get instant access to:
📚 All six lessons (9+ hours of video demonstrations + printable PDFs)
🖌 Fun, approachable projects that build your skills without feeling overwhelming
🎯 A “before and after” assignment that’s always such a satisfying reveal

If you’ve been wanting a gentle, step-by-step way to get started with hand lettering, this is it. You can DM me for the link, or search Hand Lettering 101 on the TPK site (link in profile).

#handlettering101 #handlettering #moderncalligraphy #letteringlove #calligraphycommunity #learntoletter #creativelettering #letteringcourse #onlineartclass #artpractice
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