Episode 14 : Building with Courage, Focus, and Clarity with Colleen Underwood
In this episode of Creative Diaries, creative business coach Colleen Underwood of Colleen Annalea explores what it really takes to build a meaningful, sustainable creative practice. Her story bridges the gap between artistic freedom and business structure, offering a grounded perspective on how to stay creative while also building a strong foundation. For creatives who feel pulled in too many directions, her message is clear: clarity, courage, and focus are non-negotiable.
Colleen begins by addressing a challenge many creatives face—lack of focus. While being multi-passionate is a strength, she explains that focus doesn't limit creativity—it gives it space to thrive. Choosing one direction helps creatives build momentum and gain clarity over time. Without focus, it's easy to stall, burn out, or lose confidence altogether. With it, ideas begin to take root and grow.
Another key insight is the role of courage in creative work. Many artists wait to feel confident before sharing their ideas, but Colleen reminds listeners that confidence is the result of taking action, not the prerequisite. She encourages creatives to start before they feel ready and to allow imperfect beginnings. The courage to move forward, even with uncertainty, is where real transformation begins.
The episode also delves into the emotional labor behind building something from scratch. Colleen emphasizes that personal growth and business growth are deeply connected. As creatives step into visibility and leadership, they often encounter doubt, fear, and imposter syndrome. She believes that acknowledging these experiences—and doing the inner work—is essential for sustainable creative growth.
Finally, Colleen speaks to the necessity of creative community. Encouragement, she says, is “putting courage into someone.” Having people around who understand the creative path, offer perspective, and reflect back a sense of value is vital. Creativity doesn't have to be solitary. With the right support, it becomes a more joyful and resilient process.
🎧 Want to hear more? Listen to this episode of Creative Diaries to discover how courage, focus, and community can transform your creative business from an idea into a reality.
Key Takeaways from This Episode:
Courage comes before confidence—action creates momentum, not the other way around.
Focus doesn’t stifle creativity—it strengthens it.
A creative business needs structure, not just passion.
Personal growth supports business growth—mindset matters.
Imperfect action is enough to start—progress, not perfection, leads forward.
Community fuels resilience—connection is part of the creative process.
About Colleen Underwood
Colleen Underwood is a creative business coach who helps artists, designers, and multi-passionate makers turn their ideas into intentional, sustainable businesses. With a background in leadership development and a deep commitment to personal growth, she supports creatives as they move past fear, build confidence, and stay focused on what matters most.
Through her work, Colleen teaches that creativity and structure can exist side by side, and that success doesn’t require sacrificing joy. Her coaching blends clarity, mindset support, and actionable strategy—creating a path for creatives who want to do meaningful work on their own terms.
📌 Follow Colleen on Instagram at @colleenannalea
📖 Learn more about her offerings at www.colleenannalea.com