Conversations with Sasha Kalupahana

Today we’d like to introduce you to Sasha Kalupahana.

Hi Sasha, we’d love for you to start by introducing yourself.
I used to love art as a kid. Growing up in Sri Lanka, where I’m originally from, I participated in many school art events. I was especially good at sketches and portraits, a talent I believe I inherited from my dad; Sarath Kalupahana.

However, when it came time for college, I shifted my career path toward the IT field and eventually became a software engineer. After migrating to the U.S. for higher studies, I didn’t have much time or mental space to focus on art. But after spending about nine years in the U.S. and settling down in Florida, I felt a strong urge to reconnect with my artistic side. That’s when I discovered I could draw digitally on my Galaxy Tab.

As I explored digital drawing, I realized I needed guidance to use the apps effectively and produce high-quality artwork. That’s when I came across Chalani Wasala, a local digital artist from Sri Lanka, on social media. She’s a children’s book illustrator and runs her own art business. Her work and journey inspired me to pursue digital art seriously. I joined one of her workshops, where she guided me through everything, from using digital drawing apps to understanding how to turn my passion into a small business.

Since I’ve always been more skilled at portraits, I used her tips and guidance to specialize in digital portraits of both people and pets. I began showcasing my work on social media platforms to attract more customers, and now I’m slowly growing this into a local business during my free time. Eventually, I hope to build Sasha’s DigiArts into a full-time business.

Through every step, my partner Nívea Claro has been my unwavering support; always rooting for my growth and celebrating every little success with me. I’m also feeling incredibly grateful for my dear friend Jenna Balthazar, who constantly motivates me and encourages me to pursue my dreams of becoming an entrepreneur.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
No, it hasn’t been a smooth road for me. In fact, I still face many of the same challenges today; some more, some less.

To create any kind of art, you need a clear and relaxed mind. That’s when the best ideas flow. Since my parents depend on me, I didn’t have the freedom to focus on my hobbies or passions when I first arrived in the U.S. During those early years, my main priority was securing financial stability. I also went through many personal struggles along the way, which added more weight to my journey.

It wasn’t until 2024 that I finally gained some stability and freedom. That’s when I started focusing on myself and my art again. Still, the stress of my full-time job often leaves me without the mental space I need to fully immerse myself in digital art. I now do most of my artwork during weekends.

AI is one of the biggest challenges we face as artists. It’s advancing rapidly, and now there are hundreds of free AI tools that can generate digital art or turn people into cartoons in seconds. Even legendary artists like Hayao Miyazaki, whose work shaped generations, have had their styles copied and turned into free AI generators, often without credit. Most people don’t even know Miyazaki is who originally created the iconic Ghibli style. This has made it harder for genuine artists to get attention on social media, and even harder for us to earn a fair price for our work. That’s why I always try to include time-lapse videos of my process, so people can see the effort behind each portrait.

Scammers are another major challenge. What many don’t realize is that small businesses, especially new ones like mine are targeted constantly. As soon as I post a new artwork, I’ll often get messages from scammers pretending to be customers. They usually try to pay a large amount for a small piece, even after I quote a fair price. They act in a rush and often insist on paying before the work even begins.

Now, I have to be extra cautious when replying to orders, which can be stressful, especially when I fear I might miss real, genuine clients. But I’m lucky to be part of a supportive group that helps identify scams. I met all the members of the group through Chala’s workshop. We are all Sri Lankans, now living in different parts of the world, and we share many of the same challenges. We support each other through challenges and uplift one another to stay focused on our art and growth.

Appreciate you sharing that. What else should we know about what you do?
I’m an artist specializing in digital portraits, creating both cartoon-style and realistic versions. I run several social media accounts under the name “Sasha’s DigiArts”, where I showcase all my work. My art is gaining popularity every day on Instagram and TikTok.

I also accept custom portrait orders, which make meaningful and memorable gifts. People love having digital portraits of their loved ones and pets; either as a gift or to keep for themselves. Since my artwork is created digitally, it’s easy to share high-quality versions online or have them printed beautifully.

I’m especially proud of my realistic digital portraits. One of my recent favorites is a portrait of two beautiful dogs, Briggs and Wilson, which I consider my best work so far. I believe my realistic portraits stand out for their vibrant colors and emotional accuracy. They don’t just capture features, they capture presence.

Can you share something surprising about yourself?
I have the ability to eyeball and scale any given subject without using traditional methods. I did my first set of professional large acrylic portraits when I was in high school. I painted three scientists on a large canvas (about 4′ x 3′) using only an A4-size printout as a reference; roughly the size of a letter paper.

Typically, artworks of this scale are done using a grid method, but at the time, I didn’t even know that technique existed. I started drawing freehand directly on the canvas. Everyone was surprised to see how accurately and proportionately it turned out.

Pricing:

• Cartoon Style Potrait: starting from $50 ($15 per additional subject)
• Realistic Style Portrait: starting from $60 ($20 per additional subject)

Contact Info:

• Instagram: https://www.instagram.com/sashasdigiarts
• Facebook: https://www.facebook.com/people/Sashas-DigiArts/61567093231955/
• Youtube: https://youtube.com/@lifewithsashasl
• Other: https://www.tiktok.com/@sashasdigiarts

Image Credits
Sasha Kalupahana at Sasha’s DigiArts