We were lucky to catch up with Sarah Calandro recently and have shared our conversation below.

Alright, Sarah thanks for taking the time to share your stories and insights with us today. Can you talk to us about how you learned to do what you do?

Yes, I feel like I could talk about this all day — this topic of learning oil painting, or more so, learning to “become” a painter.

You know what our culture thinks about artists? You’re either naturally talented or you’re not. You wake up one day, pick up a brush, and can paint a masterpiece — or you can’t. But ironically, we don’t expect that we’d be able to sit at a piano for the first time and perform Beethoven flawlessly, nor do we expect to execute heart surgery with no training. These are things we wouldn’t dare try without years, even decades, of training and practice.

But drawing and painting? For some reason, we expect our first painting to be worthy of space on a wall somewhere for all to see. We think we should be great before we know how. And if we’re not, that must mean we don’t have it in us.

I started drawing in high school, then studied architecture in college, where my drawing skills really took shape. I wouldn’t say it came easy, but it did feel natural, especially as compared to my peers. I dreamed of one day being a painter, but never made the time to try. I think I assumed that one day I’d figure it out with ease and my drawing skills would pull me through.

Then, in my mid-20s, I got inspired, gathered supplies, and painted… a really ugly painting. It was frustrating and embarrassing. Months, even years, would pass before I’d try again with the same result. At some point, I started to avoid thinking about painting altogether. I couldn’t fathom the idea that maybe I just didn’t have it in me.

Right before my daughter was born, I couldn’t push the idea aside any longer and felt (somewhat dramatically) that I had to figure this painting thing out. And to do that, I’d have to accept that I didn’t already know how. I’d have to start at the beginning, make bad paintings, and put in the time — I mean, really put in the time.

So I found teachers, took workshops, and set up space in my home. And eventually, I had an idea: to commit myself to painting 1,000 paintings before I turned 40. This changed everything. Success became not about how good a painting was, but instead that I showed up. If it was bad, it still counted.

I think the shift in mindset helped me tolerate the discomfort of it all — the not knowing when or how or even if it would get easier and the paintings would get better. Over time, I was able to stop judging my paintings (and myself) so harshly, and start showing up more frequently to try. The process got easier, my skills improved, and my bad paintings started to become good ones.

What I wish I’d known from the beginning, is that painting isn’t about talent. It’s about practice. And the only way around the frustration and the discomfort is to accept it and move straight through it.

What could you have done to speed up the process? What skills were most essential?

No one in my family knew anything about the art world. I was on my own, relying on ego and “natural talent” to guide me. Maybe if I’d been exposed to traditional drawing and painting earlier—or even known just one working artist—I would’ve had a better sense of what it really took. Maybe I could have avoided the roller coaster of trial, avoidance, and frustration.

But I didn’t. My path was different, and that became part of my story—learning how to learn and being humbled by the process. And honestly, I wouldn’t change it. That struggle gave me a deep appreciation for the craft and taught me just as much about myself as it did about painting.

As for skills, there are so many. The essentials: drawing, understanding values, color mixing, and knowing your materials. Then there are things like how to light your easel, set up and light a still life, hold a brush and palette knife, control your medium, and push paint around the canvas. At some point you start working on composition, brushwork, edgework, and explore more subtleties in applying the paint to create mood and emotion. The learning never really stops.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Sarah Calandro, an artist and art educator. I’m originally from Baton Rouge, LA and now live in Richmond, VA with my husband, daughter, and yellow lab. My background spans architecture and over 10 years as a software experience designer before fully committing to painting. Though I’ve always been passionate about visual art, it wasn’t until I was deep into my 1,000 paintings project that I truly embraced my identity as an artist.

I believe practice is the key to growth, and I bring that mindset to both my painting and teaching. I’m still working toward my goal of 1,000 paintings, refining my skills in still life while focusing on my favorite subjects—people and animals. I love the process and reward of capturing a likeness.

I see teaching painting as a design challenge. To learn to paint, you have to rewire the way you see, train your brain and eyes to interpret the world differently, and then translate it through your hands onto the canvas. It’s a complex process and can feel really daunting. So as a teacher, I strive to break down these complex skills into clear, actionable, and timely steps that meet students where they are.

My hope is for my students to get into a continuous cycle of growth—where they accomplish something new, feel proud of their progress, and become curious about what’s next—so they feel motivated to guide their own journey and eventually create the work they’re truly proud of.

My paintings are available through my website and two local galleries in Richmond, VA, and I also take on private commissions. I offer private coaching and lessons both online and in person, and occasionally, I’ll teach group classes and workshops.

What do you find most rewarding about being a creative?

I would have never expected I’d be saying this, but the first thing that comes to mind is that it’s brought me closer to God. I grew up in a Catholic family, attended Catholic school, and gradually moved away from religion as an adult. Over time, I found solace in a daily Ashtanga yoga practice—a ritual where I can connect with God each morning through movement and breath.

I notice that the more I paint, the stronger my spirituality becomes. Painting feels like a form of prayer, an act of surrender. It allows me to let go of my ego, to release expectations, and to trust in what unfolds on the canvas.

I’ve begun to feel like the art I create isn’t truly “mine,” rather, it’s a gift from something beyond me and beyond this world — and that realization is incredibly rewarding. I think this has drawn me back toward God and religion in a more traditional sense, too. It’s as if I understand something now that I didn’t before, and there’s meaning in that.

Another unexpected gift has been the community I’ve built through painting. I wasn’t searching for it, but through art, I’ve met so many generous, open-hearted people who have profoundly impacted me. Before painting, my community was primarily the tech space, where the culture was dramatically different. And looking back, I think that culture shaped me into someone I didn’t really want to be. I subconsciously developed a cynicism about people in this world, and their values and motivations. But then I stepped into the artist community and saw something entirely different.

The artists I’ve met have changed me. Their generosity, patience, and authenticity have inspired me to be more giving, more present, and more open. I never expected that painting would deepen my spiritual connection and bring me such meaningful relationships — and I’m profoundly grateful.

We’d love to hear the story of how you built up your social media audience?

When I started my 1,000 paintings project, it was right before the pandemic—when everyone was online all the time and social media for artists was thriving. At the time, I had a one-year-old, and my Facebook and Instagram feeds were flooded with arguments, fear-inducing mom groups, and just a general sense of stress. As a new mom, I was overwhelmed to bring my child into what seemed like such an angry and chaotic world.

So, I made a simple but transformative decision: I created a separate art account, followed only artists I admired, and committed to posting every single one of my 1,000 paintings. It’s like I had to cut the cord from one social media universe so that I could enter another. At first it felt a little lonely and sparse, but soon enough, I started building the art community I couldn’t live without now! I’ve made so many friends and feel like I have a good sense of who’s who in the art world. I’m also regularly exposed to the incredible range of styles and subjects that could be painted, and this inspires me to keep learning.

I can’t say I did anything particularly strategic to grow my audience—just posted consistently, used hashtags, commented and liked others’ posts, and made sure my images and content were solid and somewhat thought-provoking. More than anything, I’ve tried to create a space where I can show up, put my work out there authentically, and hope there are people out there who are drawn to it.

I think it’s working. The more I put myself out there, the more I gain in return. Every so often, I’ll post a painting that unexpectedly takes off—“viral” for me—bringing in a wave of new followers. It’s always fascinating to see what resonates, though if I knew exactly why it happened, I’d be doing it every day.

Contact Info:

• Website: https://www.sarahcalandro.com
• Instagram: https://www.instagram.com/sarahcalandroart/
• Facebook: https://www.facebook.com/sarahcalandroart
• Linkedin: https://www.linkedin.com/in/sarahcalandro/
• Youtube: https://www.youtube.com/@sarahcalandroart

Image Credits

Sarah Calandro
Sarah Lourenco
Debbie Calandro
Nanci Charpentier