Today we’d like to introduce you to Emily Pellegrino.
Hi Emily, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today.
My first experience with calligraphy was when I was in college. I just wanted to make some wall art for my room. From then on, I’d spend hours mimicking lettering art I’d seen on Pinterest as a creative outlet.
A few years in, I got quite good just from observing other artists enough to land me a few unpaid projects for friends even without formal training. When I got married, I used my new and improved calligraphy skills to do all my signage, place cards, and an acrylic menu. Which I look back on and you can REALLY tell just how far my work has come.
I decided to start my calligraphy side hustle in late 2022, I struggled for months trying to get my side hustle off the ground with no paying projects for the better part of a year. (Yikes!) After struggling to land paid work from bridal clients, I retired those services until recently in the summer of 2023. But in the meantime, I added on a bunch of new services including engraving, wood burning, and leather foiling and completely upgraded my portfolio to attract more of the work I wanted. I also began noticing other artists like me were offering on-site work and was intrigued by the idea. I added it to my services before I did any live events.
Equipped with an upgraded portfolio and a tablespoon of qualified overconfidence, I decided to do a complete overhaul of my website branding and position myself as a Live Event Calligrapher on my website. Dress for the job you want right? Three months of investing time, effort, and energy exclusively into SEO by October last year, I started showing up on Google enough that brands were finding me.
During my first season offering live calligraphy, I was getting booked by clients like Tory Burch, Friexenet, and Patrón (and inquiries from several more well-known brands that didn’t end up working out with my full-time job schedule), and almost all my weekends were fully booked out well into January this year. I remember my jaw dropping to the floor opening up those emails work and then immediately telling my close coworkers. I have been doing live calligraphy events ever since!
We all face challenges, but looking back, would you describe it as a relatively smooth road?
My path to calligraphy success has been a really weird, disjointed, non-linear one that doesn’t fit the one most calligraphers take. Most will say they started with wedding place cards, calligraphy signage, and envelope addressing, a friend of theirs asked them to do XYZ for their wedding invitations. I didn’t. And because of that, I thought I wasn’t good enough.
Not because I had a crappy website and was intimidated by posting on social. I did a few odd jobs in calligraphy for free years before I started the business and spent years putting it off thinking I wasn’t good enough to start. The biggest challenge I’ve had to overcome being in a creative career, as an artist, calligrapher, and event professional, has always been doubting myself.
I think for many calligraphers like myself and young artists in general impostor syndrome is their Achilles heel. It’s what prevents many more artists from ever putting themselves out there, to begin with, delays others like myself, and can easily make professionals doubt their skills. That alone held me back from pursuing calligraphy as a creative business for nearly 5 years.
Putting myself out there does not come naturally to me, and for a long time, I wrestled with it. After dreaming about the idea of offering calligraphy services for literal years, I got to a point where I decided I wanted that to be my life more than I wanted to stay in my comfort zone.
Fast forward to now where I’m regularly working with notable brands, big fish clients, and the most creative event professionals in the industry, even now I STILL feel impostor syndrome kick in.
I will say I have learned to focus on the positive feedback and take a look at how far I’ve come since the beginning. I am exactly where I thought I would never be in a million years. The wild, out-there, probably-never-going-to-happen kind of goals I had in 2021, are my day-to-day life now all because I took the first step out of my comfort zone.
The thing I have to tell myself the most these days is, “You’ve come this far. You don’t just deserve to be here, you have been perfectly capable of being here the whole time.”
Appreciate you sharing that. What else should we know about what you do?
I’m a calligrapher and on-site artist for brand activations, luxury events, weddings, and corporate gifting.
I specialize in creating artful calligraphy with a timeless design aesthetic that blends modern with traditional calligraphy for clients aiming for a timeless look. Brands, event planners, and marketing agencies will often hire me to customize products, personalize take-home favors, or as a unique interactive element to entertain guests in between cocktail hour and corporate dinners.
I currently offer calligraphy personalization for both on-site activations, and in-studio projects including bridal calligraphy, hand lettering, bottle engraving, leather foiling, and wood burning.
I fell in love with calligraphy because of its effortless ability to immortalize meaningful words as art. My love language is words of affirmation which means that I am very sentimental when it comes to thank you notes, birthday cards, love letters, and when people say nice things about me.
Because of this, I deeply believe that words as important as wedding vows, a 50th anniversary message, a baby’s birth date, and all the moments in between, deserve to be remembered in an equally beautiful art form– in calligraphy.
How do you define success?
Ever since I was little I wanted to be an artist and LOVED horses, but I didn’t think you could do both (turns out you can and that is my new dream now). I always wanted to grow up and be successful enough as a creative to afford to own or ride horses, while painting or drawing them all day long. The 8-year-old in me would define success as being able to own a horse instead of a car to get me places.
Now, my definition of success has slightly changed but still along the same lines, I want to make a good living doing what I love while having the time to also explore my creativity… and continue drawing horses like the horse girl that I am.
Being able to spend a random Tuesday morning getting coffee with my mom because my work hours are flexible and cover the bills plus extra– that’s a success.
Contact Info:
- Website: www.calligraphybyemily.com
- Instagram: https://www.instagram.com/emilyrpellegrino/
- Linkedin: https://www.linkedin.com/in/emily-r-pellegrino/
Image Credits
Deanna Grace Photography, Angela Moon Photography, and Ryan Joseph Photographs
