Meet Emily Pellegrino

Alright – so today we’ve got the honor of introducing you to Emily Pellegrino. We think you’ll enjoy our conversation, we’ve shared it below.

Emily, thank you so much for making time for us. We’ve always admired your ability to take risks and so maybe we can kick things off with a discussion around how you developed your ability to take and bear risk?

I grew up dreaming of becoming an artist, but was also very risk averse for a kid. Risk taking was never a pillar of my personality and I never set out to aim for entrepreneurship originally.

Once I saw that other calligraphers with no prior business experience were able to go full time with their side hustles, I knew that was it for me. If they could make it work, I could too.

Never in a million years did I think I’d be an entrepreneur offering calligraphy services.

While I worked my corporate job, I spent so much time learning as much as I could about entrepreneurship, pricing, adding services, web design, how to best reach my target clients so that I felt that the extra risk I was taking wasn’t that insurmountable. I knew I could not only survive as a full time artist, but thrive, and while creating work that meant something to people.

After being so burnt out on corporate, and feeling less intimidated by the stability I was sacrificing, I jumped in head first and never looked back.

Thanks, so before we move on maybe you can share a bit more about yourself?

I’m Emily Pellegrino and I’m a calligrapher and engraving artist in the Tampa bay area serving Orlando, Miami, and throughout Florida. I am a firm believer in the power of calligraphy to effortlessly transform ordinary words into works of art. My main focus is live calligraphy and personalization for luxury events and brand activations while also serving wedding clients through stationery calligraphy services and bridal gifting.

The most exciting part about what I do is the live events. Each one is so different, and being able to turn client’s names, messages, and requests into works of art that are made just for them right in front of their eyes. I never get tired of the process and seeing how guests react to watching the process. It’s definitely not instantaneous, but the few minutes it does take to create something is spent being mesmerized by each step from the initial draft, to the materials prep, to application, and final reveal.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

1) Ability to pivot if needed.

I started out only offering bridal calligraphy and not really attracting the clients that were willing to pay. I wanted to do more live event work because it seemed like so much fun but I only had one on-site calligraphy event under my belt. I had to make the decision to pivot into aiming for primarily event work which looking back was the most risky move to make.

2) Aim really high, really early, and work really hard to make them happen.

Putting myself out there is not my strength, so making these really big stupid goals for myself centered around putting myself out there motivated me to take action. I cant just make these stupidly big goals for myself and leave them hanging, right? Breaking them down into actionable tasks also made them feel less intimidating.

3) If you’re on the fence about taking the leap, whether its the first step, hitting that send button, or going full time on your dream. just take the leap. Chances are you will try to find every opportunity to make the safe bet or put off doing the thing. It took me 6 years of waiting around thinking it wasn’t the right time, and then when it actually wasn’t the right time I realized that 6 years ago was when I should have just gone for it. So I had to take a leap a little bit before I felt I was “ready”.

What would you advise – going all in on your strengths or investing on areas where you aren’t as strong to be more well-rounded?

I think your strengths can get you pretty far on their own, and are worth investing in so you can better leverage your natural ability, but there is always going to be someone whose strength is your weakness. For me, my weakness is putting myself out there. All else being equal, I would probably never choose to be the first one to introduce myself or be the social butterfly at the next group function. But what I’ve learned since starting my calligraphy business is that those are skills that can be learned and practiced. Putting myself out there is generally a weakness of mine and the fear of being seen held me back from my potential for so long. Investing the time and effort into building up your weaknesses so that they’re not weaknesses anymore can be far more rewarding than hiding behind your strengths, hoping it will get you just as far.

I joined a professional networking group this year and the first event I went to I nearly didn’t go at all. Even just being part of one of these groups was a huge step for me compared to where I had been most of my life thinking I wouldn’t need to face that fear of being seen. I had two options go or do not go. To move forward, I had to go. I didn’t feel like it, and was so anxious about not fitting in walking up to the doors, but I went.

Turns out it was an education summit for the vendors– not much networking at all. I felt far more relaxed and got to meet a few new people without putting so much pressure on myself to be entertaining or interesting. I felt much more confident going into the next event and like I had actually grown from the experience rather than waiting for confidence to somehow rain upon me.

Contact Info:

• Website: https://www.calligraphybyemily.com
• Instagram: @emilyrpellegrino
• Linkedin: https://www.linkedin.com/in/emily-r-pellegrino/

Image Credits

Angela Moon Photography
Ying Photography