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What Five Years in Tuscany Taught Me About Betting on Yourself

There is a version of this story that is about a Tuscany art retreat: the medieval studio, the cliffside village, the long breakfasts and the wine at two in the afternoon. That version is true. But it is not really what happened this year.

What happened is that a woman spilled a full container of paint on an old wall from the medieval times that she could not clean, and instead of cleaning it up, she painted a mural of poppies over it. And by the time she got home, she had finally had the hard conversation with her husband about becoming a full time muralist.

I have hosted this workshop in Citta della Pieve, a medieval village on the Tuscan and Umbrian border, in partnership with Strada Toscana for five years running. And every year, I say the same thing: I know exactly what Italy is going to give me, and every single time it gives me something completely different.

Why This Isn’t a Travel Story

 I’m upfront in this episode that this is not a slideshow of somebody else’s vacation. I open with a quote from philosopher Martin Buber: All journeys have secret destinations of which the traveler is unaware. That idea is the spine of the whole episode. Getting outside your routine, even a little, even without flying to Italy, is what lets you hear and see things about your own work that routine alone will not surface. It is a theme she has come back to before, including in Episode 63: How Artists Can Reignite Their Creativity and Find Their Spark Again.

A Week Inside a Medieval Village

This year, 11 artists joined me in Citta della Pieve. Mornings started with a slow Italian breakfast before walking through the village to a studio that has stood since medieval times, somewhere between 476 A.D. and the start of the Renaissance. Mornings were spent painting and working on voice, composition, and my trademark mother color method. Afternoons brought lunch, a little wine, sometimes a nap, and by day two, a shift I can only describe as palpable: the artists stop bracing and start actually relaxing into the work.

Story One: Technically Perfect, Emotionally Empty

The first artist I worked with closely this year could do everything technically. Perspective, structure, proportion, all of it. And she hated everything she made. Over the week, I helped her practice trusting a brushstroke before she knew what it meant, and letting go of needing to know where a painting was going. Her work changed so much that it looked like a completely different artist had made it. It is the same trap I have unpacked before in Episode 87: How Imposter Syndrome is Holding You Back as an Artist (& What to do About it), and the same permission slip she gives artists in Episode 140: Finish Your Painting With Confidence: 15 Actionable Steps to Push Through The Fuglies.

Story Two: The Wall That Could Not Be Cleaned

The second artist arrived at a real crossroads: a stable job on one side, a dream of becoming a full time muralist on the other. One morning, a full container of magenta paint slipped from her hands and covered the floor, the furniture, and a centuries old plaster wall. Acrylic on plaster does not clean, it smears and soaks in. Instead of continuing to try to erase it, she asked her host, Pamela Hack of Strada Toscana, if she could paint a mural over the stain instead. She spent the rest of the week painting poppies, an ode to a flower farm the group had visited days earlier. That mural is still on the wall today, and she went home and had the conversation with her husband that changed the direction of her whole career.

Why My Own Work Doesn’t Change Much in Italy

My own paintings do not shift dramatically on these trips, and  I’m proud of that. It is because I have already done the harder work of not needing to know where a piece of art, or a decision, is going before I make it. What Italy gives me instead is a reminder: of freedom, of beauty, and of the fact that routine without interruption can quietly become the enemy of creativity, even when routine itself is not the problem.

Three Things Worth Sitting With

Toward the end of the episode, I name three takeaways I want every artist to hold onto, whether or not they ever set foot in Italy: technical skill alone is not enough, your biggest creative breakthrough might be wearing a disguise when it arrives, and getting out of your routine is not a luxury, it is often the thing keeping your creative life alive. I have talked through the routine and creative block piece of this in more depth in Episode 155: Why Your Creative Block Won’t Go Away (And Exactly How to Fix It).

If you have ever felt like the workshop experience itself, not just the technique, is what actually moves the needle, this episode is a companion to Episode 120: The Healing Power of Art Workshops with Returning Guest, Becky Joan Springer.

What’s Next

Italy 2027 is already filling up. The group stays intentionally small, usually 10 to 12 artists, for one week in a village most tourists never find. If anything in this episode stirred something loose in you, head to the resources below for details.

Resources Mentioned

• Italy 2027 Honest Art® Workshop: https://stradatoscana.com/retreats/jodie-king/ 
• The Artist Who Gets Paid, Jodie’s 3-part workshop (August 20, 25, and 27): https://www.jodiekingart.com/artistseries 
• Studio Elite Mastermind: https://www.jodiekingart.com/studioelite 
• Episode 63: How Artists Can Reignite Their Creativity and Find Their Spark Again
• Episode 87: How Imposter Syndrome is Holding You Back as an Artist (& What to do About it)
• Episode 120: The Healing Power of Art Workshops with Returning Guest, Becky Joan Springer
• Episode 140: Finish Your Painting With Confidence: 15 Actionable Steps to Push Through The Fuglies
• Episode 155: Why Your Creative Block Won’t Go Away (And Exactly How to Fix It)
• Have a question for Jodie? Ask it here: https://forms.gle/hxrVu4oL4PVCKwZm6 
• How are you liking the Honest Art® Podcast? Leave us a review on your favorite podcast platform and let us know!    
• Watch this full episode on my YouTube channel: https://www.youtube.com/playlist?list=PLMquJfuMsSg0fr46BRdia1cWd-81GThzF

Playlists:

🎨 New to Honest Art®? Start Here

🎬 Painting Techniques: Best Of

Want More from Jodie?

Learn from Jodie:

🎨The Color Course for Rebels: https://www.jodiekingart.com/ccfr  

🎨Honest Art® Society: https://www.jodiekingart.com/has 

🎨Studio Elite: https://www.jodiekingart.com/studioelite  

See some of Jodie’s favorite resources:

✍🏻Check out my free guide on how to hang and wire a painting: https://www.jodiekingart.com/how-to-hang-a-painting 

✍🏻Get my top 10 studio tools here: https://www.jodiekingart.com/10-studio-tools-opt-in 

✍🏻Learn 5 things they don’t teach you in art school: https://jodieking.com/work-with-me#free-rescources.0  

✍🏻See Jodie’s favorite things: https://www.amazon.com/shop/jodie_king_ 

🧘🏼‍♀️Guided Meditation for Creative Clarity: https://www.jodiekingart.com/guided-meditation

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