Trials and Triumphs: Crafting a New Course for "The Outstanding Artist"


The island of Spetses, Greece

Trials build commitment.

I'm on the back of a moped again, this time with Anna, the island's "witch." She's driving me around the city to meet her contacts and look for alternative places with shade to film. I'm hanging onto the back of the seat, doing my best to stay perfectly level and still as we go up and down steep hills and take sharp pin turns. Meanwhile, Anna holds the handlebars with only one hand because she needs the other hand to wave at the people she knows in the street, which is nearly everyone! Anna yells into the wind, "Elli, are you afraid?"

"I would be less scared if you held onto the bars with two hands!"

Anna laughs and says, "You are just like my mother; she doesn't want to ride on the back either."

The Essence of an Outstanding Artist

Contestants from Season 3 of The Outstanding Artist cries after being eliminated from the art competition

It felt good to have the first challenge filmed and behind us. We didn't account for the sorrow that came with being eliminated and dreaded another elimination round.

When I think back on all the heartbreak, disappointment, and rejection I've experienced in my art career, I realize that no matter what we tell these artists, nothing can fully prepare them. I've faced debilitating self-doubt, utter scorn from other artists in the industry, complete rejection, and ridicule from art dealers and gallerists. I've endured setback after setback, shows where I sold nothing, extreme loss, betrayal, and sabotage, but I've also experienced extreme success, fortune, and abundant blessings. This is the life of an Outstanding Artist.

The Second Challenge

To go far and be able to lead others, we must build our mettle, be tested, overcome challenges, and see trials as sport. The second challenge embodies this theme. The artists will have to paint in a tiny room, work all night, and paint a self-portrait on a little canvas. They had to face themselves in this difficult trial.

Many times in my career, I've had to paint in terrible conditions: cramped spaces, poor-quality art supplies, when I'm tired, hungry, or alone. I've had to paint when I didn't feel like it, wasn't inspired, and was under extreme pressure to perform. This is the life of a professional artist, not a hobbyist who paints only when inspired and in the best circumstances.

Finding New Film Locations

Behind-the-scenes of filming Season 3 of The Outstanding Artist

Because the second challenge is in a small room at night, I have just two days to find another location to film the third challenge. Luckily, it looked like the weather was changing, offering a short reprieve from the heat.

Anna suggests, "Let's meet the owner of the Poseidonion Hotel first. He's my friend. We don't need an appointment."

This hotel is the most luxurious on the island, famously built in the heart of the harbor to mirror the Cannes hotel, where they hold the Cannes Film Festival. Many famous movies have been filmed at this hotel, utilizing its epic spaces and grandeur.

True to her word, Anna walks straight into the owner's office, introduces me, and explains we're filming a reality show in Spetses and could use his help. It was a brief 15-minute meeting, but he enthusiastically agreed to allow us to film there, use his shade, and even offered to help us rent a large boat to visit the caves. He was the epitome of Greek hospitality, and I was overwhelmed with incredible encouragement.

Team Effort in Location Scouting

Next, we zipped through the windy streets to a church near the water, meeting a very sweet and warm priest who was friends with Anna. He had a gorgeous spot for painting, completely covered in shade, overlooking a beautiful view of the sea below. It was picturesque and nestled in the church's garden, surrounded by arches and trees. Anna tells me, "You can paint and film here, but there's one condition. You must allow the priest to share the gospel with your group. His message will take about 20 minutes."

"No problem, it's a deal!"

We spent the entire morning and early afternoon riding around the island on mopeds, connecting with all of Anna's contacts. I met with a diversity of people, including ship captains, restaurant and boutique owners, equestrians, cultural and heritage experts, bus drivers, and chefs. Anna found at least 12 different places where we could film, and these were just her top-tier choices. Everyone I met was enthusiastic, helpful, and willing to let us paint and film without any cost. It was the complete embodiment of Greek hospitality.

The Heart of Adaptability

Elli Milan, Dimitra Milan and John Milan - Judges of The Outstanding Artist sit in discussion about scene setting

I met with Jake, Dimitra, and John during the afternoon break and shared my adventure. Jake was preparing for a long night of filming in the tiny room. "Guys, I found tons of cool places with Anna. We can film at the Poseidonion Hotel! Amazing churches, restaurants, and museums all opened their doors to us. We can literally paint anywhere on this island, it seems!"

Jake responded, "That's awesome, but we'll have to reconstruct all the episodes and redo everything we've planned!

"Yeah, true. The director isn't going to be happy," I remarked.

"Yeah, he'll have to redo all the blocking, lighting, and set up scenes on the fly without knowing in advance what he's in for. It's going to be really challenging," Jake noted.

"But what else can we do? They have to paint in the shade. The hotel setting doesn't really work," I pointed out.

Presenting the New Plan

Then Jake had a moment of inspiration. "You know, having different locations will actually make the show better, too. Each place can symbolize the theme of each challenge and represent a stop along the artist's journey. It will elevate the show to a higher-end experience. Plus, everyone will get to see more of the island. Let's do it!"

Now, the real work begins. We must tell the director about the changes and convince him it's for the best. I have to figure out the logistics for transporting the equipment and people to each location. I met with one of the two bus drivers on the island and explained that I would hire him for several days. He assured me his schedule was pretty open since the tourist season hadn't fully started yet.

The Artist's Journey

Jake Dunn, the host of The Outstanding Artists gives the contestants instructors about next challenge

It all felt so overwhelming and beyond my capabilities. To depart from the safety of our plans and the sanctuary of the hotel, to venture out into the city, make a big scene, work out all the logistics, and hope for good shots and lighting each time seemed like a feat for Hollywood professionals, not just us, a small art school trying to make a difference.

I knew I was confronting myself again, grappling with my own self-worth. The feelings of not being enough were resurfacing, accompanied by my fears and the pressure and responsibility on my shoulders. This time, my trials were too many possibilities, an abundance of choice, not a lack of opportunity.

Stepping Outside of Comfort Zones

My whole world was expanding, revealing the potential to weave an incredible story of the hero's journey – the artist's journey. It could truly be a beautiful, poetic story that we all live – a story of knowing that we all have greatness within us. We each have an invitation to an adventurous and exceptional life, leaving behind the mundane and safety to enter a world of trials and challenges but also victories, overcoming, and profound transformation.

Tonight, the artists would sit in their tiny room, tasked with creating something extraordinary to move forward. They would face discomfort, exhaustion, and self-doubt. The invitation to an incredible opportunity became real, as they realized it comes with adversity and trials. To understand what you can endure, lean on God to get you through, and witness your strength and power to overcome every obstacle is the joy of finding your greatness.

Share your experience in the comments below! 


  • Blaire H. Christman

    Hi Elli: I have spent most of my life trying to find my purpose. Through all the ups and downs and disappointments, there has been only one constant and that has been art. I’ve dabbled with sketching/drawing and have never painted anything. During some of our big storms & hurricanes, my parents would join us on the floor to color and share stories. My father was a commercial artist and my mother (in her youth) painted, sculpted, and occasionally sketched. So, one would think that art would be easy to get busy with. And I did want to. I took all the art classes offered at our high school and I was ready to go off to college to study fine art and writing. I was also up to receive a scholarship to a Liberal Arts College, but I became engaged and we announced it in the local newspaper. I didn’t get the scholarship. But didn’t know that I was rejected for it due to our engagement for some years later. I just chalked it off as one more thing I wasn’t good enough for. I was a failure and a disappointment to my parents and family. Anything else I attempted over the years, basically ended up the same way. I struggled in school, even in classes that I really wanted to excel in. I did get married, twice, and raised 3 children, but only God knows how I managed to do that. You see, I am on the Autism Spectrum. I found out that I have Asperger’s a few years ago. I am considered High Functioning. All of my attempts and failures could have been avoided long ago, had I been tested. All my struggles to do things like my peers and even my siblings could have been avoided to some degree. I think differently and approach things differently and I missed out on so much, so many things. I still have some struggles now. My husband of 33 years passed away 10 years ago and I have felt lost for most of those 10 years. My children and grandchildren are all grown and living their lives. I think it’s time for me to get back to living mine and do the one thing that I’ve always enjoyed and go from finger painting to creating and painting what I see and share it with others.
    Thank you for being you and creating your school and inspiring so many.

    Elli Milan Art replied:
    Thank you for sharing your story Art is very healing and serves sometimes as a consistent anchor in our lives grounding us to what is true and beautiful.

  • Nicole S Fuentes

    We mentor a group of girls from a local trailer park community. We do an art project with them every other week. We had a space we were hosting them and at the last minute that space fell through. We found herself in a strangers garage. We were all very much out of our element and questioning what we were thinking. We laid out a sheet on the floor of the garage for the girls to spray paint on jean jackets we had gifted them. The garage was filled with fumes and so cold. This was our Christmas get together. Not the best scenario to host a Christmas party. We read the story of how Mary and Joseph traveled and couldn’t find a place to rest and ended up in a stable. It brought tears to my eyes as I realized we were just where we needed to be at that moment. A powerful night. Humble beginnings!

    Elli Milan Art replied:
    Wow! Niki. I bet you feel stretched. That’s when amazing things begin to happen!

  • Christine Moody

    Following this journey has been a real highlight to my days.
    Cannot wait for more episodes to follow!
    Thank you, you inspire.
    Elli Milan Art replied:
    Yea! This Thursday new episode! 🙌🏽

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