Why does pricing feel so vulnerable as a creative entrepreneur? In this powerful episode, Colleen Underwood returns to unpack the deeper emotional layers behind pricing your work. We explore how personal stories, cultural messages, and self-worth directly impact the way we value our time, services, and creative offers.
From money mindset blocks to fears of being seen as greedy or inexperienced, we discuss the common narratives that keep creatives stuck in undercharging or second-guessing their prices. Colleen shares practical tools for overcoming scarcity, owning your value, and making confident pricing decisions rooted in truth—not fear.
If you’ve ever struggled with pricing your art, coaching, or creative services, this conversation is for you. Get ready to unearth what’s really holding you back and discover how to price with clarity, confidence, and alignment.
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Have you ever caught yourself hiding in your creative business? Downplaying your work, resisting visibility, or playing it safe even when something bolder is calling your name? In this episode, I share a surprising story about getting my color analysis done and discovering how deeply uncomfortable it felt to be seen in vibrant, high-contrast colors...because deep down, I’ve been shrinking from visibility.
This episode dives into why so many creative entrepreneurs resist taking up space and what’s really at stake when we avoid being seen. You’ll learn how to recognize where you’re holding back, explore impactful ways to begin stepping into visibility, and understand why showing up fully matters not just for your own growth, but for the inspiration and permission it gives others.
Whether you’re an artist, coach, designer, or creative spirit navigating visibility and vulnerability, this episode offers a grounded, self-reflective look at what it means to be seen and how to start showing up with more courage.
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Have you ever wondered if creating is even worth it when life feels heavy, uncertain, or overwhelming? In this episode, stationery designer and author, Janine Kwoh, is diving into the deeper “why” behind making art, especially during hard seasons. If you’ve found yourself asking questions like “What’s the point?” or “How can I keep creating when I’m emotionally drained?”—you’re not alone.
We’ll explore how creativity can be both a refuge and a response to grief, burnout, and big emotions. I’ll also share insights on redefining productivity, how small acts of creativity can still count, and why community matters more than ever when you’re navigating hard things.
Whether you’re in a creative rut, dealing with loss, or just feeling the weight of the world, this episode will remind you that your art matters, your rest matters, and it’s all part of the creative journey.
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What really happens when creatives find a supportive, intentional space to grow? In this special roundtable episode, I’m joined by five amazing members of The Tillage Village—Kim Hallquist, Tina Noren, Lau Jaimes, Bella Boss, and Lauren Engelkemeyer—as they share the mindset shifts, breakthroughs, and personal growth they’ve experienced through our creative community.
We talk about why traditional memberships and courses often fall short, and how The Village offers something different: gentle accountability, honest conversations, and space to reflect and realign. From battling self-doubt and money mindset struggles to navigating motherhood, burnout, and building a business at your own pace, this episode is full of real talk, inspiration, and practical insights for artists and creative entrepreneurs.
If you’ve been craving a creative community that actually sees and supports you, this episode will remind you: you’re not alone and you don’t have to build your dream in isolation.
Tune in and hear how clarity, courage, and connection grow inside The Tillage Village.
🧡The Tillage Village Doors Close TODAY May 27, 2025!
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Have you ever found yourself stuck in your creative work, not because you’re doing too little, but because you haven’t stopped to reflect?
In this episode, I’m talking about the importance of turning inward, listening to your own voice, and building a creative business rooted in self-trust. You’ll hear the real questions I ask myself, the shifts I’ve made, and why reflection is the foundation for sustainable creative growth. If you’ve been craving clarity, this episode will help you find it, not by doing more, but by tuning in to what you already know.
🎉 The Tillage Village Is Open! Doors Close May 27th!
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What makes a creative support space actually work, especially when everything else feels overwhelming? In this episode, I share a bit of the story behind The Tillage Village and the intentional rhythm that helps creative entrepreneurs build clarity, consistency, and momentum.
If you’ve ever joined a membership that left you more stressed than supported, this conversation is for you. You’ll learn how The Tillage Village is designed around a sustainable cadence of planning, reflection, collaboration, and accountability...and why this structure helps creatives grow without burning out.
Whether you’re feeling scattered, stuck, or just tired of doing it all alone, this episode offers a new path forward with The Tillage Village.
🎉 The Tillage Village Is Open! Doors Close May 27th!
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What does it look like to build a creative business that truly fits your life? In this episode, we’re joined by Tillage Village member, Lauren Engelmeier of Camp Clever, who shares how she’s redefined success by aligning her work with her rhythms, values, and season of life.
Lauren walks us through her journey from magazine designer to Etsy shop owner to surface pattern artist, and how years of pivots, rebrands, and realignment have shaped a more sustainable creative path. We talk about shifting from hustle culture to slow growth, building systems that support clarity, and why listening to yourself is the most powerful tool you have as a creative entrepreneur.
If you’ve ever felt stuck, overwhelmed by “shoulds,” or unsure of how to move forward in your business, this conversation will bring so much encouragement and practical insight.
Tune in to learn how to:
Embrace slow, sustainable growth
Create systems that support clarity
Align your business with your life’s rhythms
Redefine what success looks like for you
🎉 Mark your calendar The Tillage Village Opens Up May 13th!
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In today’s episode, we’re exploring why hustling harder doesn’t necessarily bring progress, and why slowing down to notice your energy, creativity, and personal rhythms is the real key to sustainable growth.
I’ll share how chasing productivity without true direction left me exhausted, how the power of noticing is changing how I approach my creative practice, and why honoring your natural seasons matters more than forcing a routine.
We’ll also talk about practical ways to notice what’s working, what’s draining you, and how to build rhythms that actually support your goals.
If you’re tired of feeling burnt out, stuck, or scattered in your creative journey, this conversation will help you reclaim your energy, realign with your vision, and move forward with more clarity and peace.
Want more? Listen to Episode 18 with Lissie TeeHee all about planning to the seasons
🎉 Mark your calendar The Tillage Village Opens Up May 13th!
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Feeling stuck can bring up so much shame. It can make you feel like you’re doing something wrong or not working hard enough. But more often than not, it’s not laziness that’s holding you back....it's disconnection.
In this episode, we explore the real reason so many creatives feel paralyzed in their work. When you lose touch with your vision, it’s easy to slip into burnout, confusion, and chasing what everyone else is doing.
I’m sharing how that disconnection shows up, why blindly following advice can steer you off course, and the simple journal prompt that helped me find my way back to clarity.
If your work has been feeling foggy or misaligned, this episode will gently guide you back to connect with yourself. 🧡
🎉 Mark your calendar The Tillage Village Opens Up May 13th!
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Come with me and revisit the fourth solo episode I ever created—first aired in November 2022—while I recover from hernia surgery ❤️🩹.
In this episode I define "nourishment" and what it means to truly care for ourselves so we can create from wholeness, not depletion. In seasons of overwhelm or exhaustion, this gentle episode is a reminder to honor your pace and refill your own cup. We’ll explore alignment, creative rhythms, and rest that restores. Consider it a soft landing if you’ve been running on empty. 🧡
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Creative delays can feel frustrating, isolating, and full of shame—but they’re a normal part of the process.
In this episode, we’re talking about the messy middle, the “stop-go” rhythm of creative work, and why your pace doesn’t determine your worth. I share my own slow journey with the creation of The Tillage Magazine and how I’ve learned to trust the timeline.
We’ll also make a left turn and explore the setbacks Walt Disney faced when building Disneyland and how even big dreams take time. It's your reminder that if your project is taking longer than expected with hiccups: you’re not behind—you’re becoming. Your dream is still valid, and it’s worth finishing.
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🌸 Last week of spring break here, and I hope you enjoy an episode that is sure to bring so much alignment in your life and give you a new perspective on success that first aired November 2022.
It is so easy to fall into comparison and feel the pressure to gain a massive following while running our creative businesses. In today's episode, Leana of May We Fly, shares her story of discovering who she is and what is “enough” for her. She defines what a running a "quiet" business means to her, what her own version of success is, and how working from a quiet space allows her to be more centered in her art practice.
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🌸 It's time for a little spring break here! I hope you enjoy an episode that is near and dear to my heart that first aired in October 2023.
In this episode, Nicholas Wilton of Art2Life takes you on a rollercoaster journey from doubt to self-belief, sharing his inspiring story of how art saved his life. Join us as he explores the power of intention, finding your creative sweet spot, and the importance of embracing vulnerability in the artistic journey. This episode is full of takeaways that encourage you to follow your creative hunches and create substantial, impactful work.
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Every creative project—big or small—holds valuable lessons that can elevate your work, but only if you’re paying attention. In this episode, we explore how staying curious, embracing mistakes, and reflecting on the creative process can lead to continuous growth.
Through real-life examples, including making better pancakes and Pixar’s evolution in animation, we’ll uncover how each challenge presents an opportunity to refine your skills. You’ll also learn three powerful ways to become more aware of what your work is teaching you—so you can improve faster and with more confidence.
If you’re ready to make every project a stepping stone to growth, this episode is for you! 🧡🌿
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Why is it so hard to boldly declare what we truly want? Fear of judgment, doubt, and the desire be seen as humble often keep us silent. But if we don’t claim our dreams and desires, how can we ever pursue them?
In this episode, we explore why declaring our dreams feels vulnerable, the difference between saying "I want to be" and "I am," and how visualization can help bring our goals to life. You'll learn why speaking your desires out loud isn’t arrogance—it’s self-trust and the first step toward creating the life you want.
If you’re ready to overcome fear, own your ambitions, and take action with confidence, this episode is for you. Can't wait for you to tune in!
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Creative careers come with seasons—times when work feels slow and uncertain, and others when it feels overwhelming. So how do you navigate both?
In this episode, I’m joined by Airin O’Callaghan, a children’s book illustrator, to explore the challenges of building a creative business, from struggling to find work in the early days to learning how to say no when opportunities start flooding in.
We’ll discuss how to make the most of slow seasons, when to take on work (even for free), and how to align projects with your long-term vision. Airin shares her journey of perseverance, taking risks, and ultimately reaching a point where she can be selective about the work she takes on. We’ll also dive into embracing balance in different stages of the creative journey.
Whether you’re just starting out or figuring out how to juggle too many opportunities, this episode will help you make intentional decisions about your creative career.
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Change is inevitable, but that doesn’t make it easy. Whether it’s a shift in your career, relationships, home, or even the world around you, navigating change can feel unsettling.
In this episode, I dive into the discomfort of transitions, why change feels so hard, and how we can move through it with resilience and self-compassion. I share personal stories of major life changes—from career shifts to changes in my business—and explore the emotional weight of change, the power of small anchors, and how even the hardest transitions can bring unexpected goodness.
If you’ve ever felt lost in the in-between or struggled to embrace new seasons, this episode is for you. Tune in for insights, encouragement, and practical takeaways to help you reframe change as an opportunity for growth.
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Are you building your business based on what you truly want—or what you think youshould want? In this episode, we explore what it means to run a creative business in a way that feels aligned, sustainable, and fulfilling.
Artist, Brigida Swanson, shares her journey of stepping away from social media, redefining success, and focusing on what actually works forher business. She opens up about the fears that came with quitting traditional marketing, the unexpected growth that followed, and how trusting herself has led to more clarity and contentment.
If you’ve ever questioned whether the way you're running your business is right for you, this episode will encourage you to step back, evaluate what truly fits your life and energy, and give yourself permission to do things differently.
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Feeling stuck after a creative break? In this episode, I share my journey of stepping away from The Tillage Podcast for over two months—why I took a break, the unexpected guilt and self-doubt that followed, and how I finally found my way back. If you’ve ever struggled with taking time off or felt awkward returning to your creative work, this episode will help you navigate the emotions, embrace rest as a vital part of the creative process, and ease back in with confidence. Tune in for insights on creativity, mindset, and the reality of stepping away and coming back.
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In this episode, I share the highs and lows of a challenging year marked by burnout, personal struggles, and difficult choices. From stepping back from running my business full-time and restructuring it entirely, I’ve learned that true growth often requires embracing discomfort. Through moments that felt like breaking points, I’m discovering how these “growing pains” are actually shaping me into a more resilient and better version of myself. Join me as I reflect on how discomfort can be a powerful guide on the path to transformation, and hopefully, inspire you to see your own struggles as essential steps toward growth.
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