• A Decade of Improving My Calligraphy Skills

    You often don’t realize how much your skills have improved until you re-make a project! For today’s blog post, I took three envelope calligraphy concepts that I made in 2013, and I tried them out again. What I found was a remarkable difference in skill, confidence, and aesthetic. I’m betting that if you try re-making…

    For over a decade, I’ve focused on improving my calligraphy skills through drills, just-for-fun practice, and real-life projects. Today, I decided to make a direct comparison of 25-year-old Lindsey’s calligraphy skills to 35-year-old Lindsey’s calligraphy skills. I found three sample envelopes I created as a beginner+ pointed pen calligrapher in 2013, then I re-created them with my 2023 capabilities. I’ll show you the results through a series of photos and critiques below! Then, let’s talk about your own remarkable ability to evolve your skillset — and how comparing your current work to a project from the past could win you a $100 gift certificate.

    My Envelope Calligraphy Re-Dos

    1. Whimsical Green and White Envelope

    This 2013 envelope has a playful, whimsical intent. The recipient’s name is written in large calligraphy on a slightly domed baseline, while the address is written in sans serif lettering at the bottom.

    A critique of the 2013 Whimsical Green and White envelope:

    • There’s almost no stroke contrast, signifying that the creator (me) didn’t understand how to vary pressure exertion while writing.
    • Calligraphy letterforms look uneven and sloppy in an unintentional way.
    • The sans serif lettering used for the address deserves a cleaner, more careful creation process.

    For the 2023 makeover of this envelope, I began with a pencil draft. The original 2013 envelope could have benefited enormously from a bit of planning! While I want this envelope to convey a sense of casualness, I also want it to look neat and creative.

    To start, I went over the calligraphy using Bleed Proof White ink, a Brause Rose nib, and an oblique pen. I chose to use a Brause Rose nib because I wanted to achieve heavy, confident downstrokes. Notice how the “m” of “ms.” and the “d” of “cassidy” meet the top and bottom of the envelope with long, winding flourishes. I made that creative choice to help the calligraphy command more attention.

    The Sans Serif lettering was created using a Nikko G nib in a straight pen to ensure delicate, clean strokes. I hooked thin, loopy flourishes to the ends of some of the letters to add more fanfare to the street address.

    While the 2013 envelope demonstrates creativity and an understanding of basic pointed pen principles, there was a lot of room for improvement. The 2023 version of the envelope looks more confident and touts a higher skill level with its ample flourishes and embellished sans serif lettering.

    If you want to build up your skills to create an envelope like the 2023 Whimsical Green and White Envelope, work on your flourishing! Flourish With Me: A Pointed Pen Calligraphy Online Course will walk you through how to make fluid oval-shaped flourishes like the ones featured on the re-do envelope calligraphy.


    2. “30 Rock” Envelope

    Can you guess why I called this envelope the “30 Rock” envelope? (Remember, the envelope was created in 2013!)

    A critique of the 2013 “30 Rock” envelope:

    • There’s almost no stroke contrast, again, signifying that I didn’t vary pressure my exertion while writing (because I didn’t know how!).
    • Calligraphy letterforms look uneven and sloppy in an unintentional way.
    • The sans serif lettering used for the address deserves a cleaner, more careful creation process.

    As a beginner+ calligrapher, I was pencil draft averse. This resulted in several calligraphy projects with haphazardly-written, squished lettering. Over the past decade, I’ve learned the value of a solid draft. That’s why I began this envelope with two pencil drafts: one for the recipient’s name and one for their address.

    I began by using a white mechanical pencil to make a quick draft of a Kaitlin Style calligraphy name.
    Then, I made a sans serif lettering pencil draft on a ribbon-shaped piece of drawing paper.

    The 2023 version of the envelope has a bold, fun look. The calligraphy isn’t overcomplicated; it’s just all-lowercase Kaitlin Style written in Bleed Proof White ink using a Brause EF66 nib in an oblique pen. The crisp hand lettering was created with sumi ink and a Nikko G nib in a straight pen.

    Of course, the obvious element that makes the 2023 envelope sing is the choice of postage. When my husband saw this envelope, he said, “Wooow! That’s so cool!” Then, dubiously, “Wait, can you mail that?” The answer is absolutely. The postage stamps might be numerous, but they total 80 cents, which is more than sufficient for mailing a 1 oz. envelope via USPS.

    If you’ve never thought about adding artistry to your envelopes with postage before, I suggest reading How to Create Snail Mail Magic With Artful Postage Stamp Collages. In that article, you’ll learn about how to arrange postage stamps, how to use vintage stamps, and where to buy the best stamps.


    3. Banner Envelope

    This envelope endeavors to combine playful titles with pretty, Copperplate-esque calligraphy. Unfortunately, my calligraphy skill level wasn’t up to creating Copperplate calligraphy in 2013.

    A critique of the 2013 Banner envelope:

    • There’s very little stroke contrast, resulting in calligraphy that has a monoline look.
    • The calligraphy letterforms endeavor to look neat and elegant, but they were written haphazardly and don’t flow like they should.
    • There needs to be more space between address lines to ensure a more legible reading experience.
    • The banner could be cleaner and more carefully illustrated.

    Just like with the other two envelope re-dos, I began with a pencil draft and guidelines. Luckily for me, I have two tools that didn’t exist in 2013: TPK’s (free!) Perfect Calligraphy Envelope Generator and Nico Ng’s Lettering Composition Ruler. I used the Generator to make perfectly-spaced calligraphy guidelines, then the lettering composition ruler came in handy for the banner.

    The 2023 version of this envelope has an assertive feel to it. The calligraphy is still embellished, but it’s more skillfully written with plenty of stroke contrast and some clever unions (like using the tail of the “z” in “Ortiz” for the top of the “F” in “Folsom”). Loopy flourishes ground the calligraphy to the top and the bottom of the envelope for a look that isn’t afraid to take up space.

    The calligraphy for this envelope was written in Janet Style calligraphy with Bleed Proof White ink and a Brause EF66 nib in an oblique pen. The lettering in the banner was created using a Nikko G nib in a straight pen.

    The flourishes are the star of the 2023 version of this envelope, and they steal the show in a way that I would have been terrified to attempt a decade ago. It’s satisfying to see how the letters themselves look infinitely more polished, the result of years of practice (and understanding the importance of pencil guidelines)!

    It’s important to meet yourself where you’re at and stay optimistic. When I created the 2013 version of this envelope, I applauded my own creativity and worked within the skill level I had at that point.


    I hope that this article serves as a reminder that no one starts off as a calligraphy expert. Remember, too, that my 2013 envelopes model a beginner+ level. I created them at a time when I was just starting to feel comfortable sharing my pointed pen calligraphy work with others.

    Second, it’s important to recognize how far you’ve come. Sometimes, we have to attempt the same projects we made as beginners in order to see a meaningful change. Giving yourself the opportunity to make a direct comparison can show you exactly how far you’ve come. Usually, that’s farther than you think!


    If you read the TPK Blog, chances are, you enjoy a certain creative pursuit: maybe it’s calligraphy, or it could be hand-lettering or watercolor. You started out as a beginner, then you put in the time and the practice to get better.

    Ultimate Beginner’s Watercolor Online Course student Dorothy F. created the peony on the left as a watercolor beginner. After getting more watercolor practice, she created the comparatively polished peony on the right. (For more inspirational photos of Beginner’s Watercolor Online Course student work, see the Celebrating One Year of Beginner Watercolors! article.)

    Today, when I revisited envelope calligraphy concepts from a decade ago, it became clear how much my pointed pen skills had improved. It made me think about the many people whose skills have also evolved. So! Let’s have a fun and uplifting contest. I’m going to give you five weeks to re-create a project that you made as a beginning artist. Your medium can be anything: calligraphy, watercolor, illustration, lettering, etc. Re-make the project at your current skill level. Then, take a photo of that first project (or use a photo you took after making that project), and take a photo of the re-made project. Email both photos to me at [email protected].

    Place Card Calligraphy
    Here’s another example that showcases how hard I worked at improving my calligraphy skills. These place cards don’t look like they were made by the same person, but they were!

    On Friday, September 1, I’ll share your before and after photos on the TPK Blog, and we’ll all vote on whose skill level has changed the most. To be clear: your project doesn’t have to be the prettiest project to win. Instead, it needs to show a remarkable evolution in skill level. Here are the contest rules to follow:

    • The project can be anything — an envelope, a painting, a handmade card, whatever.
    • Your before and after photos must be of the same project, though stylistic changes can be made to reflect your skill level. (Think about how I approached the envelope concepts for today’s article, adding flourishes, etc.)
    • The “before” photo can be from any year as long as you were 16 years old+ when you created it. (In short, don’t choose an illustration that you made as an 8-year-old as your “before”.)
    • You must email both your photos to me at [email protected] by Tuesday, August 29th.
    $100 TPK Gift Certificate Giveaway!
    Re-do a project you made as a beginner for this contest, and you could win a $100 gift certificate!

    The person whose skill level transformation gets the most votes will win a $100 gift card to TPK, which will be mailed to you in a gorgeously embellished envelope. I strongly encourage you to enter the contest for a couple of reasons. First of all, I know that you’ll surprise yourself at how much improvement you’re making in your artistic pursuits. Secondly, it’s really neat to see what people in the TPK community at large are making. I recently rediscovered this blog post (a showcase of TPK reader-created art projects used to enter a contest), and the entries are utterly and completely cool. I’m so excited to get to see your work!

    Thanks so much for reading, and cheers to putting your thinking cap on your head and your favorite writing utensil in your hand.


    Lindsey's Signature | The Postman's Knock