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Dear Creatives,

I have been sitting on this news for a while, and today, I finally get to share it with you—I am hosting a 5-day art retreat in Portugal this November!

The Art to Income Retreat will take place November 13-17, 2025, and it’s designed to be more than just a getaway—it’s a space for artists to truly transform their creative businesses. Whether you’re looking to refine your pricing strategy, develop a stronger brand, or gain clarity on your long-term goals, this retreat will give you the tools, confidence, and mindset to build a thriving, sustainable art business.

Tune into today’s podcast or listen at the top of this email for all of my thoughts!

Why This Retreat? Why Now?

If you’ve been following my journey, you know I believe deeply in the power of goal-setting and taking intentional action. Ironically, I didn’t set out with a clear plan to host an artist retreat—at least, not at first. But I had been toying with two ideas:

* Bringing women together for a transformative coaching experience.

* Creating an opportunity to do something abroad.

At the same time, I was building my 2025 vision board, and—what do you know?—a picture of a women picking lavender and a chateau in Europe (that looked a lot like Portugal) made its way onto it.

Here’s where things get even crazier: I created that vision board on a Monday. By that Friday, I received an email from Sofia inviting me to lead a retreat in Monsaraz. Tell me that wasn’t meant to be.

But I didn’t just stumble into this opportunity. It came from years of preparation—through The Founders Society, The Club, and my own strategic planning—proving yet again that luck favors the prepared. (Listen to the podcast for the full story!)

This was a pinch-me moment, but more importantly, it felt like the perfect opportunity to create something that would truly impact you—the creative who is ready to build a thriving, sustainable business.

What to Expect at the Art to Income Retreat

This retreat is designed to help you:✔️ Refine your pricing strategies and ensure you’re charging what you’re worth✔️ Build a sustainable business model that aligns with your unique goals✔️ Gain clarity on branding, marketing, and financial planning✔️ Overcome imposter syndrome and step into your confidence as an artist✔️ Experience hands-on workshops, group discussions, and cultural exploration in Portugal

This will be an immersive experience filled with business-building strategies, creative exercises, and unforgettable moments. We’ll balance work with inspiration—exploring the local landscapes, enjoying incredible food, and having deep conversations about what it means to create a thriving art career on your terms.

How You Can Join

Spots will be extremely limited to ensure this is an intimate and valuable experience for everyone attending.

If you are ready to sign up or learn more, click here.

I cannot wait to connect with you in Portugal and help you build the creative business you’ve always dreamed of. This retreat is going to be a game-changer.

Let me know—does this sound like something you need? Drop a comment or reply to this email, and let’s chat!

See you in Portugal,Hayley

P.S. Spouses are welcome to join! If you’d like to bring them along for the experience, they can stay at the hotel, enjoy all meals, and participate in add-on activities for an additional $417. The only part they won’t have access to is the daily courses with me. If you’re thinking about exploring Portugal before or after the weekend, this is a seamless way to include them in the adventure!

*All photos pulled from Sofia in Monsaraz website

I️ recently was listening to Anna Wintour’s Masterclass and had a “aha” moment. I️ realized that almost every creative entrepreneur I️ work with falls into one of two categories - The CEO or The Editor. Maybe “falls into” isn’t the best phrase, let’s say strongly leans into one of the two categories.

This realization made me want to write about what I️ keep seeing from a birds eye perspective. Looking from the gallery and coaching positions, I️ have seen a lot of artists grow and that moment when it clicks is the same moment when they learn they have to wear more than just the hat they are comfortable with - they have to wear them all (until you can hire, but we’ll save that for another time). If we call these two “hats” CEO and Editor, let’s break down the difference and what each brings to the table.

Both require a strong voice, a strong vision, and a level of self-confidence. The issue is that strong voice, vision and confidence often are oriented more in the direction of big picture or small details. Let me elaborate…

Editors love the little details. They love to dream, create the vision and act on visuals. These are people that start with Instagram, build the site before they create the work, focus on photography and story telling and building a brand that is true to them. They focus on the exact right logo, the perfect font pairing, they’d never reach out to a gallery before they feel ready. Every detail has to be perfect, but the business plan…well they’d probably say “that can come later” or even “what’s that”?

The issue with this mentality alone is these creatives neglect strategy. They forget that you have to make a certain amount to make it worth your time. They often burnout because they aren’t focusing enough time on growth and instead are just focusing on creation. You need both. If you only create and don’t see success you suddenly feel like what you are creating isn’t worthy, when in reality it might be in need of a little marketing makeover. Ok, so maybe this isn’t you…well you might lean more CEO and it comes with it’s own problems.

CEOs love the big picture. They strategize. They know exactly how many prints to sell to hit their target, how long a painting takes to create, the pricing required to attend a show.

The problem with single minded CEOs is they focus on strategy and often get caught up in the big picture and don’t just start making. Their hyper-fixation on numbers makes them hold money close versus knowing when to reinvest. To be a successful entrepreneur you need to be a dreamer, a creator, forget the strategy for a second and let the business build it self (to an extent) in the early days.

So what do we do? We each have our unique talents and that is beautiful, but we also have our weaknesses. We have to find a way to do both or find the person or resources to fill in the gaps of where we feel less secure.

I️ hope this exercise does more than make you notice weaknesses, I hope it helps you to realize and recognize your strengths. Being a CEO or Editor is a huge title, and you get to be both! Acknowledge your talents and let them shine.

Thank you for being here and supporting this page. I’ll be back next week.

Talk soon,

Hayley

Weekly Recs

Masterclass - I️ have to recommend it because it inspired the entire episode. So many of these ideas come from reading, learning, and listening. Masterclass is a great resource if you want to learn from the best.

Chantecaille - Liquid Blush - I️ am not a makeup person, but I️ do use a few products every day. This liquid blush gives a slight tint and really layers well on top of my Merit products (complexion stick and bronzer) (which I️ also am obsessed with). I️ use the tiniest dab and it’s lasted a long time. Highly recommend!

Your Honor - I️ recently watched this show on Netflix. If you love a fast-paced thriller then this is for you. The story follows a judge whose son is involved in a hit and run with the son of a very prominent figure in the city…I️ won’t give away too much. If you need something new, then this is for you.

Lions and tigers and bears, oh my!

This iconic quote from The Wizard of Oz symbolizes the unknown dangers that lie ahead. Despite the Tinman having no real idea what lies in the dark woods, he scares Dorothy and Scarecrow into fearing their future journey. Sound familiar?

The unknown can be downright terrifying, especially for a creative hoping to fund their lifestyle, share their personal work, or quit their “safe” career.

Today, I️ dive into the very real fears we all face as creatives. Burnout, overwhelm, the fear of the unknown, the fear of quitting, and more. Don’t worry, it’s not scary. It’s natural to face fears, normal to feel these emotions, but also common to overcome them with the right tools.

I️ share my journey with burnout and how I️ have previously worked and am still working to change these emotions.

I️ hope you enjoy today’s conversation!

Talk soon,

Hayley

Weekly Recs

Cardboard Panels - This is a simple rec, so simple it feels dumb sharing, but it has truly saved me endless time. These pre-cut cardboard pieces perfectly fit in my 12x15 envelopes that I️ ship all my paper artwork in. I️ place the artwork between two pieces and slide into the envelope. It protects the artwork, but also looks nicer than the amazon boxes I️ used to cut up.

No Splash Dog Bowl - Again and crazy rec, but my lab makes a huge mess when drinking water. My kitchen floor was a slip hazard at all times. This no slip, no splash, water bowl has left him hydrated and saved me from slipping and falling countless times. A cheap, but effective find!

Interested in other product recommendations, quick tips, or fun facts? Feel free to send me your questions and I️ will include them here!