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Conversations with Olivia Dijamco

Today we’d like to introduce you to Olivia Dijamco.

Olivia Dijamco

Hi Olivia, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I started my caricature journey being trained in Florida theme parks, learning techniques from a variety of artists I have been so blessed to meet and learn from. Those early years gave me a foundation in speed, style, and capturing personality on the fly.

From there, I spent some time traveling across the country, drawing at state fairs and large events. I shifted my focus to local markets and city holiday festivals after I had my daughter, building relationships and refining my style in a more intimate setting.

Today, I keep a handful of regular public pop-ups, but most of my work is contracted private events—weddings, conferences, grand openings, and celebrations where I get to draw stories and memories into every sketch.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It definitely hasn’t been a perfectly smooth road. When I first branched out under my own name, it took about a year to really figure out which markets worked for me. I lost plenty of vendor fees simply because I didn’t yet know how to research or read an event properly.

But through a lot of trial and error, new display setups, and constant adjustments, I learned what worked and what didn’t. That perseverance is what brought me to where I am today—regular return events, coordinators and city officials reaching out directly to me, and a setup I’m genuinely proud of. And even now, I’m still tweaking and improving it every chance I get.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I’m a caricature artist based in Central Florida, and my work spans everything from live event sketching to custom commissions and digital illustration. I got my start drawing live caricatures in theme parks—learning from some really amazing artists that I had the honor and pleasure of drawing next to at Legoland Florida, Disney World Theme Parks & Resorts, and Universal Studios.

I specialize in live caricatures at private events like weddings, conferences, grand openings, corporate parties, and community celebrations. I also take on digital and traditional commissions, bringing people, pets, and characters to life with a mix of humor and stylized realism. Over the years, I’ve drawn thousands of faces across theme parks, state fairs nationwide, local markets, and city-run events.

I’m most proud of the fact that my work has become entirely referral-based. Event coordinators, city event officials, and returning clients reach out directly because they trust not just the art, but the experience I bring—professionalism, speed, and a setup that’s been refined over years of learning what actually works in the field.

What sets me apart is my background: theme-park-trained, fair-season-tested, and market-hustled. I’ve learned from a wide range of artists and environments, and that’s shaped a style that’s both approachable and elevated. My sketches are quick, bold, and expressive, and I love capturing someone’s personality in just a few exaggerated lines. More than anything, I care about making the moment memorable—turning a simple drawing into a story someone gets to take home. And honestly, my Google reviews say it all for Olivia Lynn Sketches.

What matters most to you? Why?
What matters most to me is that people genuinely love the art I create of them. I find something beautiful in everyone I draw—there’s always a spark, a light, a little piece of personality that stands out the moment they sit down. If I can capture even an echo of that on a blank page and hand it back to them in a way that makes them smile, then I’ve done what I set out to do. That connection is the heart of my work.

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