Join us for the all-new Beginner’s Modern Calligraphy Online Course, happening now! →

Learn More
    • Facebook
    • Instagram
    • Pinterest
    • RSS Feed
    • YouTube
    • Premium Membership
    • Beginner Calligraphy Course
    • Intermediate Calligraphy Course
    • Calligraphy Worksheets
    • Beginner Watercolor Course
    • The Calligraphy Book
  • Blog
    • Pointed Pen Calligraphy Worksheets
    • Pointed Pen Calligraphy Drills
    • Video Courses
    • Brush Pen Calligraphy
    • Handwriting
    • Hand-Lettering
    • Mail Printables
    • Printable Artwork
    • Procreate Worksheets
      • Cleaning Cloths
      • Erasers
      • Glass Jars
      • Inks
      • Kits
      • Mechanical Pencils
      • Nibs
      • Oblique Pens
      • Paper
      • Protectants
      • Rubber Stamps
      • Rulers
      • Straight Pens
      • Washi Tape
      • Watercolors
      • Wax Seals
  • Help
  • Cart
Log in

Your cart is currently empty!

The Postman's Knock written in calligraphy
Subscribe for $1/week
Sign In
  • My Account
    • Account Details
    • Addresses
    • Payment Methods
    • Order Receipts
    • Subscriptions
    • Printables + Worksheets
    • Video Courses
  • Help
Log in
The Postman’s Knock
  • About
  • Blog
  • Shop
  • Help
  • Premium Membership
  • The Calligraphy Book
Subscribe for $1/week
Sign In
  • 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!

    • Click to share on Pinterest (Opens in new window)Pinterest
    • Click to share on Facebook (Opens in new window)Facebook
    • Click to share on WhatsApp (Opens in new window)WhatsApp
    • Click to share on X (Opens in new window)X
    • Click to share on Bluesky (Opens in new window)Bluesky
    • Click to share on Threads (Opens in new window)Threads
    • Click to share on Reddit (Opens in new window)Reddit
    • Click to share on Mail (Opens in new window)Mail
    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

    • Click to share on Pinterest (Opens in new window)Pinterest
    • Click to share on Facebook (Opens in new window)Facebook
    • Click to share on WhatsApp (Opens in new window)WhatsApp
    • Click to share on X (Opens in new window)X
    • Click to share on Bluesky (Opens in new window)Bluesky
    • Click to share on Threads (Opens in new window)Threads
    • Click to share on Reddit (Opens in new window)Reddit
    • Click to share on Mail (Opens in new window)Mail
Sketchbooking

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.

Join TPK’s free mailing list

This field is for validation purposes and should be left unchanged.

Follow TPK on social media

  • Facebook
  • Instagram
  • Pinterest
  • YouTube
  • RSS Feed
  • Mail
Previous post: Simple Southwestern Envelope Art Tutorial
Next post: How to Learn Calligraphy in Two Months

All-time favorite posts

  • The Beginner's Guide to Modern Calligraphy

    The Beginner’s Guide to Modern Calligraphy

    1.5m views
  • 8 Tips to Improve Your Handwriting (Plus a Free Worksheet) | The Postman's Knock

    8 Tips to Improve Your Handwriting (Plus a Free Worksheet)

    864.2k views
  • Painting with Watercolors for Beginners

    Painting with Watercolors for Beginners

    823.3k views
  • Free Brush Pen Calligraphy Worksheet

    Free Brush Pen Calligraphy Worksheet

    483.1k views
  • How to Write Faux Calligraphy (Video Tutorial + Free Worksheet)

    363.8k views
  • 11 Calming Calligraphy Drills Printable | The Postman's Knock

    Celebrating Six Years of the “11 Calming Calligraphy Drills” Worksheet (Free Download)

    291.6k views
  • Lovely Loose Watercolor Flowers Tutorial

    Lovely Loose Watercolor Flowers Tutorial

    205.2k views
  • The Ultimate DIY Modern Calligraphy Starter Kit

    The Ultimate DIY Modern Calligraphy Starter Kit

    186.6k views

Latest posts

  • Stand-Up Tree Holiday Card Tutorial
    Standing Tree Holiday Card TutorialNovember 24, 2025
  • flourished holiday ornament
    Introducing the 2025 TPK Holiday Calligraphy Worksheet SetNovember 17, 2025
  • November’s Coffee Date: Creative Gift IdeasNovember 11, 2025
  • Simple calligraphy envelopes
    3 Easy Ways to Address an EnvelopeNovember 5, 2025

Browse by category

Browse by date

19 responses

  1. linden Avatar
    linden
    November 1, 2023

    This worksheet is one of my favorites. I love the creative prompts – they’ve helped me to “see” letters in new ways. I’ve completed the worksheet more than once for the same letter. Some of the prompts are comfortable to complete while others are more challenging,

    The completed worksheets are great to refer back to when selecting a lettering style for a project.

    Log in to Reply
Older Comments
1 2

Leave a Reply Cancel reply

Sorry! Only TPK Premium members can comment on articles and tutorials. You can become a member here. Already a member? Sign in.

✨I’ve been making these little calligraphy Chr ✨I’ve been making these little calligraphy Christmas trees for years. They’re a go-to whenever I need a quick gift tag, envelope flourish, or something festive that doesn’t require a whole afternoon.

They look fancy, but they’re really just simple strokes stacked in different patterns. Truly: once you get the rhythm down, you can make a tree in under 30 seconds. 🎄 

If you want to try them (there are six styles!), the tutorial is on the TPK Blog, and it’s called
“6 Simple Ways to Make a Calligraphy Christmas Tree.” Feel free to google it, or visit: thepostmansknock.com/6-simple-ways-to-make-a-calligraphy-christmas-tree/

It’s very beginner-friendly, video-based, and a great way to get some creativity in during a busy season. I hope you love it as much as I do. 💛

#calligraphy #moderncalligraphy #holidaycalligraphy #calligraphyart #creativelifehappylife #christmascrafts #holidaycrafts #giftwrappingideas #diychristmas #christmascards #calligraphytutorial #finetec #metallicwatercolor #papercrafts #creativepractice #thepostmansknock #holidayinspiration #blackandgold #christmasideas #holidayideas
🎁 These printable gift tags are one of my favor 🎁 These printable gift tags are one of my favorite free printables on the TPK site. Just download, print, cut them out, and — if you want to — reinforce them with a bit of cardstock.

Inside the PDF you’ll find four designs: Festive Frida, Flourished Tree, Pine Boughs, and Merry & Bright. They’re all hand-drawn, and they make even the simplest wrapping look bespoke and artistic. 🎨 

Pro tip: If you’ve got a bit of extra time, add a pop of watercolor or some gold dots; and consider mounting the tag on a contrasting piece of cardstock for extra oomph.

They’re free to download at: thepostmansknock.com/free-super-cool-hand-drawn-printable-gift-tags/ (or visit the link in my stories today). Happy holidays!

#handdrawn #gifttags #printablegifttags #freeprintables #holidayprintables #christmascrafts #holidaygifts #papercrafts #snailmailinspo #mailart #creativegiftwrapping #diyholiday #diygifttags #artistsoninstagram #illustrationartists #thepostmansknock #tpkcommunity #calligraphycommunity #stationerylove #creativecommunity
There’s something extra fun about a card that do There’s something extra fun about a card that doesn’t just open … it comes to life. ✨ This little stand-up tree might look fancy, but it’s totally approachable — relaxing to make, satisfying to embellish, and (my favorite part) it folds up perfectly to pop in the mail. 💌🎄

If you’re looking for a holiday project that feels creative and doable, this is *such* a good one. The printable template does half the work for you, and you can customize the rest with flourishes, white ink, ornaments, or whatever feels festive to you.

The full step-by-step tutorial is waiting for you on the TPK website; just head to the link in my bio and tap “Blog.” I think you’ll have as much fun making this as I did. ❤️

#calligraphy #calligraphytutorial #holidaycalligraphy #flourishedcalligraphy #moderncalligraphy #calligraphycommunity #calligraphypractice #calligraphyart #letteringcommunity #letteringart #papercraft #papercrafting #diycards #handmadecards #holidaycards #christmascards #christmascrafts #snailmail #snailmailrevolution #snailmaillove #creativecommunity #stationerylove #makersgonnamake #thepostmansknock
I love it when I can make simple pointed pen pract I love it when I can make simple pointed pen practice on cardstock ... and it magically turns into a festive card! Find instructions + a printable template for making this “Loop-de-Loop” tree in the TPK 2025 Holiday Calligraphy Worksheet set. 🎄 (Link in bio, then navigate to the Blog!)

#pointedpen #calligraphy #calligraphypractice #pointedpenpractice #holiday #christmastree #treedrawing #doodles #goldwatercolor
Every November since 2016, I’ve looked forward t Every November since 2016, I’ve looked forward to sitting down with a cup of something warm ☕️ and sketching out ideas for the TPK holiday worksheet. This year was no exception, and I think you’ll be pleased with the motifs! They’re designed to bring calm, beauty, and (sneaky) pointed pen practice to your holiday season. 🎄Visit the TPK Blog (link in bio, then navigate to Blog) for details!
The other day, I was thinking about sending out ho The other day, I was thinking about sending out holiday cards, and I immediately dismissed the thought with, “I have zero time to calligraph envelopes for those.” ✍️

... But is that true? I put it to the test for the latest article on the TPK Blog. Using some time-saving tricks I’ve learned over the years (like using a watery ink, a bouncy calligraphy style, and minimal pencil guidelines), I timed myself making three envelope concepts. Two of them took 5 minutes or less. The most time-intensive took 5 minutes, 30 seconds. The envelopes still turned out looking elegant, especially with the help of some artistic postage stamp collages. 💌

For clear step-by-step tutorials detailing how to make these envelopes and sourcing pretty postage, visit the TPK Blog (link in bio, then navigate to “Blog”)!

#snailmail #mail #calligraphy #pointedpencalligraphy #happymail #snailmailrevolution #mailbox #postage #vintagepostage
After I chose this music to accompany this reel, i After I chose this music to accompany this reel, it dawned on me: drawing a calligraphy medallion is like, well, Belle’s arc with the Beast. 

At first, it’s a bit of a weird situation. Strange shapes, questionable structure, possibly some growling (à la “YOU WILL JOIN ME FOR DINNER. That’s not a request!”) when the inevitable ink smudge happens. You keep thinking, “I’m not sure why I’m doing this ... should I hop on Felipe and gallop away?” 🐎

But something shifts as the medallion starts to come to life. And when you finish that last detail and pull back, the music swells. Light bursts from your paper like it did from Beast’s digits as he transformed into a stunningly beautiful prince. ✨ You’re practically in a ballroom celebrating, and, wait, did your furniture just turn into an adoring crowd that’s celebrating your fortitude and skill?

(And now you know how my mind works 🧠 ... I love a good metaphor, no matter how weak it may be!) 

To learn how to make a calligraphy medallion, just search for “calligraphy medallion” on the TPK site (link in bio). You’ll find both free Blog tutorials and detailed premium worksheets.

... I’ll show myself out now. 🙈

#pointedpencalligraphy #calligraphy #handwritten #pointedpen #dippen #calligraphymedallion #calligraphydrill #calligraphypractice
My favorite autumn projects are the ones that remi My favorite autumn projects are the ones that remind you how cozy this season can be. 🍂 This project definitely fits the bill ... create it with a hot, comforting drink nearby and an excellent audiobook, and you’re in for a treat! ☕️ ✍️ The tutorial on the TPK Blog (link in bio, then navigate to Blog) is super detailed, with mini tutorial videos to guide you every step of the way.

#autumnart #watercolortutorial #arttutorial #handpainted #paintingtutorial #pointedpen #dippen #flourishing
The Postman’s Knock

About

  • About Lindsey
  • Get to Know TPK
  • Behind the Scenes
  • How I Learned Calligraphy

Legalese

  • Terms of Service
  • Privacy Policy
  • Refunds & Return Policy
  • GDPR Data Erasure Request

Printable Worksheets

  • Pointed Pen Calligraphy Styles
  • Pointed Pen Calligraphy Drills
  • Brush Pen Calligraphy
  • Handwriting
  • Hand-Lettering

Courses

  • Beginner’s Pointed Pen Calligraphy
  • Intermediate Pointed Pen Calligraphy
  • Beginner’s Watercolors

Help

  • Contact Lindsey
  • Calligraphy FAQs
  • Calligraphy Troubleshooting

Subscribe to the Blog

Join over 125,000 creative minds who receive inspiring, value-packed emails from TPK each week. As a free subscriber, you’ll get helpful tutorials, free worksheets, and creative ideas delivered straight to your inbox—plus the occasional sneak peek or special offer.

This field is for validation purposes and should be left unchanged.

Follow TPK on Social Media

  • Facebook
  • Instagram
  • Pinterest
  • YouTube
  • RSS Feed
  • Mail

© Copyright 2025 The Postman’s Knock – All rights reserved

Manage Consent
To provide the best experiences, we use technologies like cookies to store and/or access device information. Consenting to these technologies will allow us to process data such as browsing behavior or unique IDs on this site. Not consenting or withdrawing consent, may adversely affect certain features and functions.
Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
  • Manage options
  • Manage services
  • Manage {vendor_count} vendors
  • Read more about these purposes
View preferences
  • {title}
  • {title}
  • {title}
Writing Copperplate Calligraphy

Unlock Exclusive Perks with Premium Plus

Fuel your inspiration and creativity with TPK Premium Plus! Members enjoy three free worksheets or learning resources every month, unlimited video course access, member-exclusive tutorials, and a 10% discount on all Supplies Shop orders.

join today ($15)
All About the Brause Rose Nib

inspiration in your inbox

Let The Postman’s Knock Spark Your Creativity

TPK’s innovative newsletters are an artistic treat. Join the 125K+ subscribers who have already discovered The Postman’s Knock, and receive 10% off your first Digital Catalog order.

This field is for validation purposes and should be left unchanged.