Margaret Shepherd: 5 Things I Wish Someone Told Me When I First Became An Artist

Yitzi Weiner
Authority Magazine
Published in
7 min readJun 5, 2024

Don’t be too modest. Do the very best you can, on every job, in case someone else who needs your work sees it. Revise your designs, then proofread carefully. Sign your work boldly. Price it firmly. Publicize every interesting job you have done. Pitch new clients on your talents, and don’t forget to remind your existing clients of what else you can do for them.

As a part of our series about “5 Things I Wish Someone Told Me When I First Became An Artist” I had the pleasure of interviewing Margaret Shepherd.

Margaret Shepherd is a professional calligrapher, author, and educator. Throughout her 45-year career, Margaret’s calligraphy is currently featured in the Smithsonian Museum and the Rare Books Department of the Boston Public Library, and has previously been featured inside multiple colleges and law firms. She has taught classes and given live calligraphy demonstrations to artists across the world, stemming from Boston all the way to Uzbekistan. Margaret’s newest book, Learn American Calligraphy (Skyhorse, 3/4/24) is a fascinating guide to the history, culture, and design of calligraphy in America.

Thank you so much for doing this with us! Can you tell us the story of how you grew up?

I had an idyllic childhood in Ames Iowa, a quiet university town. My dad was an economist; whenever he needed to explain something, he would draw a graph. My mother was a sociologist. I enjoyed learning to draw and paint, with an artist neighbor, but then I flunked cursive writing in third grade. Later, working on the high school yearbook, I re-acquired an interest in all things visual — and all things bookish.

Can you share a story with us about what brought you to this specific career path?

While I was learning the basics of calligraphy at college, the alumni office asked me to produce name tags for a faculty reception. The next day, half of them had saved their hand-lettered names and posted them on their doors! The light bulb went on in my head — there was a demand for this, suggesting how to make a living while exploring my own creative work.

Can you tell us the most interesting story that happened to you since you began your career?

I once was writing names onto name tags at the last minute for a gala event that celebrated an awards ceremony. The usual calligrapher had not shown up so even though I was a guest that evening, I had volunteered to fill in. With my head down in my work, I looked up to see that Yo Yo Ma, the famous cellist, was waiting patiently for me to get to his name in my list. But he did not just wait; he got involved; he asked about how I worked and how I got around the problem of mistakes. He admired the letter style and pointed out the pleasure of having something handmade. Without distracting me, he chatted with the other guests about the music evening. And he made everyone around him feel noticed.

I was blown away by his inquisitiveness and his courtesy. In a situation when he was the star and everyone around him was just a supporting player, he went out of his way to be supportive. It certainly made me believe that real celebrities are people who play down their own importance and who can make everyone else feel important.

What are some of the most interesting or exciting projects you are working on now?

I’m lettering large-format memorials to the founders of First Church in Boston — literally First, founded by the same people who founded Boston in 1630. It plays to my interest in combining traditional letter forms with ultra-modern page design.

Who are some of the most interesting people you have interacted with? What was that like? Do you have any stories?

I’ve had wonderful mutual learning sessions with other calligraphers who did not speak English. In Vietnam, I communicated with my class of art teachers mainly by writing the letters large and, just like in my youth, adding little graphs and diagrams. You can write the ABC’s without talk, talk, talking about them. Show them.

I got a month of Arabic calligraphy lessons from the Imam of Bukhara, Uzbekistan, without any translation of the language. Letters are all about what you can already see: proportions, spaces, and shared strokes. (His name was Gafurjon, but I don’t think tutoring an American woman did his reputation any good.)

Where do you draw inspiration from? Can you share a story about that?

I am never not looking at letters and thinking about them. For instance, I created a self-guiding tour of the most significant letters in public you can see on foot around Boston; from marble carvings to neon signs. It’s like a 2-hour basic course in materials, and history, and design.

How have you used your success to bring goodness to the world?

Effort. I’ll teach anyone, no matter how klutzy because that was me back in the day.; One of my favorite students was a 60-year-old beginner whose hands shook. I keep working because I never know who’s going to read what I write and get inspired to try out some new letter art.

My books are particularly popular with beginners, I think, because I’m a slow learner myself and can remember how to explain things in small steps. My first book Learn Calligraphy is still in print, 45 years later, and my newest book Learn American Calligraphy explores new territory.

What are your “5 things I wish someone told me when I first started” and why.

These are particularly relevant for freelancers.

1 . Tame the ups and downs of your variable income. At first, you need a part-time job, reliably repeating client, well-paid spouse, trust fund (!); just some stream of work and income that means you are not always in panic and needing contingency plans to make ends meet. If a job offers any benefits, that’s icing on the cake, and you can hope the experience will help you grow. For me, I got lucky; I wrote a condolence letter to the family of a calligrapher who’d died recently, and they replied “What can we tell her clients?! They are begging us to find another calligrapher.” That was when I started 2 decades of lettering names and thesis titles onto diplomas for MIT, for 3 different graduation ceremonies a year.

2 . It’s better if your drudgery feeds back into your dreams. You could work in a coffee shop and take home a minimum wage… Or you could address envelopes and put names onto place cards for a wedding planner, ending up with — maybe — the same minimum amount, but with better skills. Getting paid to practice is the best work for beginners.

3 . Don’t work for free. The world outside doesn’t know anything about how artists survive, and especially not about what calligraphy is worth. If you work for free, you lower the status of your art for everyone in your field. You imply that this is a hobby. And the client will not value what you have spent your time on. (Also charge for your time — consultation, travel, buying special materials, rush service, etc) I did a logo for a group that was advocating equal pay for women; at first they thought I’d be happy to work for free (for “the exposure”) but even they recognized the irony.

4 . For useful exposure, distribute a small poster/card to everywhere you think people who need your work might enquire. For me, that was the local printer. Try a hotel that hosts events such as weddings and meetings. Or schools that need good connections with donors through events and publicity. Digital PR and sales are not my specialty but I do know that you have to keep reminding people. Visually. Otherwise you will get the weirdest mis-interpretations: “do you use stencils?” “Isn’t that a dead art?” or “but nobody writes by hand anymore.”

5 . Don’t be too modest. Do the very best you can, on every job, in case someone else who needs your work sees it. Revise your designs, then proofread carefully. Sign your work boldly. Price it firmly. Publicize every interesting job you have done. Pitch new clients on your talents, and don’t forget to remind your existing clients of what else you can do for them.

6. Remember about copyright. You are hired to design something for a specific purpose. Freelance clients should not take your design and re-use it without your permission.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I’m an advocate of having people of every age learn about arts and crafts as a window into other people’s lives. When I give a talk about calligraphy and hand-writing, I usually hear heartfelt anecdotes afterwards about how much the listeners love handwritten letters or texts, how much more handwriting means to them than a typed document. Instead of moaning about how “handwriting is a lost art” it would be better to move the study of calligraphy into the art curriculum or history or area studies.

We have been blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she just might see this.

When I eat breakfast I need the newspaper, on paper, in front of me and nobody talking. Sorry!

But I have to say I just love Obama’s signature. That graceful B and generous O. I’d love to see him write and talk about how he does it.

What is the best way our readers can follow you on social media?

http://margaretshepherd.com

Instagram: https://www.instagram.com/shepherdmargaret5/

Facebook: https://www.facebook.com/profile.php?id=100063293675293&ref=ts

This was very inspiring. Thank you so much for joining us!

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Yitzi Weiner
Authority Magazine

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator