Measured Differently

Sheila Ray Montgomery
  • 5.0 (5)
  • Careers

Measured Differently, a podcast about redefining success through real-life stories.

  1. 3h ago

    Intro # 2: The Journey

    In this episode of Measured Differently, Rachel and Sheila sit down to reflect on the podcast journey so far. Together, they revisit the episodes that have been shared, talk about the conversations and experiences that have shaped the podcast, and explore the many lessons they've learned along the way. From unexpected insights to meaningful takeaways, Rachel and Sheila look back at what has stood out most and how their perspectives have evolved throughout the journey. It's an honest and thoughtful conversation about growth, learning, and what it means to see things a little differently. Join Rachel and Sheila as they reflect on where Measured Differently has been, what they've learned, and where the conversation may go next.

    Intro # 2: The Journey

  2. 3h ago ·  Bonus

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  3. Aug 15

    Love It (Eddie Brill)

    In his conversation with Sheila Ray Montgomery on Measured Differently, Eddie Brill reflects on what he describes as his "crazy life" and the experiences that shaped his remarkable career in comedy. Eddie Brill is a comedian, writer, actor, and comedy teacher best known for his 17 years with Late Show with David Letterman as the audience warm-up comic and stand-up talent coordinator. A champion of authentic storytelling, Brill has spent decades mentoring comedians and helping shape the careers of countless performers. In this episode of Measured Differently, Eddie reflects on his unconventional journey from sketch and improv to running New York's Paper Moon comedy club and booking comedians. He shares lessons on creativity, vulnerability, resilience, and why love and laughter have carried him through life's greatest joys and losses. His message is simple: true success comes from working hard at something you genuinely love.

    Love It (Eddie Brill)

  4. Jul 28

    Creative Chaos (Aura-Leigh Sanders)

    In this episode of Measured Differently, we reflect on the inspiring conversation between Sheila Ray Montgomery and Aura-Leigh Sanders, exploring what it means to build a life fueled by creativity, authenticity, and purpose rather than convention. Sheila sits down with the creative entrepreneur, nonprofit leader, designer, and internationally recognized pin-up model to explore a life driven by passion instead of expectation. Although Aura-Leigh's career has spanned design, marketing, human resources, community development, local government, and the arts, she reveals that every chapter has been connected by one constant: creativity. She shares why she thrives "coloring outside the lines," how late-night inspiration fuels her biggest ideas, and why traditional corporate life never fit her entrepreneurial spirit. Aura-Leigh also discusses her unexpected journey into the vintage pin-up community, the sisterhood it has created, and how embracing her authentic self became an act of resilience after surviving sexual assault. From balancing creative chaos with the guidance of trusted mentors to redefining success as living fully and loving the people who share life's journey, Aura-Leigh offers a refreshing perspective on living boldly, embracing your voice, and creating a life that is unapologetically your own.

    Creative Chaos (Aura-Leigh Sanders)

  5. Jul 12

    Showing Up (Karen Osburn)

    In this episode, we reflect on key insights from the Measured Differently podcast featuring Sheila Ray Montgomery's interview with Karen Osburn. Karen Osburn is an operational strategist and entrepreneur working at the intersection of business operations, technology, and the skilled trades. She serves as Vice President of Product & Operations at Peakzi, an AI platform supporting home service contractors, and is the founder of OsburnAssist, a consulting firm focused on helping businesses streamline operations, strengthen systems, and scale sustainably. With a Master's degree in Construction Engineering Management and experience spanning construction, facility management, and business development, Karen brings a unique blend of technical expertise and strategic insight to the organizations she supports. In this conversation, she shares how her personal and professional experiences have shaped her understanding of success, leadership, and resilience. Karen discusses the importance of how we show up, being present in our lives, and creating space to reset and reflect—especially through time spent outdoors and in nature. She shares how personal loss changed her perspective on what matters most and reinforced the value of compassion, meaningful conversations, and intentional leadership. This episode explores why success cannot be sustained on adrenaline alone, the importance of boundaries and energy management, and how resilience can create deeper compassion for ourselves and others. Karen reminds us that change is inevitable, life is a work in progress, and focusing on what we can control allows us to build stronger, more purposeful lives and careers.

    Showing Up (Karen Osburn)

  6. Jun 16

    Beyond Safe (Victoria Flynn)

    Victoria Flynn is a comedian, speaker, consultant, producer, and improviser who helps people think differently about communication, leadership, creativity, and human behavior. In this episode, Victoria shares her journey from a decade in corporate America to building a life centered on freedom, purpose, and creativity. She discusses why many women leave the tech industry after 35, being labeled "too direct" in the workplace, and how losing her corporate job became the catalyst for change. We talk about overcoming the pain of staying safe, defining success on your own terms, and the daily habits that keep her grounded—including gratitude, saying yes to opportunities, and connecting with people outside her usual circle. A candid conversation about comedy, relationships, resilience, and having the courage to choose the life you want.

    Beyond Safe (Victoria Flynn)

  7. Jun 8

    Know Yourself (Diane Reyna)

    Diane Reyna, a retired speech therapist with more than 40 years of experience, shares her wisdom on what it means to live a successful and meaningful life. She believes that knowing yourself—your strengths, passions, and talents—is the foundation of success. Diane discusses the importance of listening to your body, prioritizing your health, embracing change, and choosing gratitude every day. Grounded by her faith and guided by strong relationships, she explains why friendships are golden, why social media can sometimes weaken human connection, and how a simple shift from "I have to" to "I get to" can transform your outlook on life. Her powerful message is simple: know yourself, put yourself out there, and love. Her final definition of success is both simple and profound: "Know yourself, put yourself out there, and love."

    Know Yourself (Diane Reyna)

  8. May 16

    Always Stay Moving (Ray Reiss)

    On this episode of Measured Differently, host Sheila Ray Montgomery sits down with Ray Reiss — owner of Ray's Bucktown Bed and Breakfast, acclaimed commercial photographer, entrepreneur, and lifelong art collector. Ray shares his deeply personal definition of success: "I can retire and not worry about going out to eat and travel when I want." But for him, success goes beyond finances. It's also found in his close circle of friends, restoring a beloved farm property, and staying endlessly curious about what comes next. The conversation explores Ray's remarkable ability to reinvent himself across decades of change. From launching a five-bedroom bed and breakfast during the early days of the "worldwide web," to surviving the Y2K-era disruption of commercial photography, Ray embraced uncertainty instead of fearing it. Ray also reflects on a widely discussed series of candid college photographs he took in the 1970s — images that beautifully captured childhood and youth in that era. Years later, he met some of the children from those photographs as adults, bringing the work full circle. Throughout the episode, Ray shares the habits and mindset that keep him moving forward: never letting projects slip, staying physically active, eating well, and refusing to stand still — literally and creatively. His newest venture? An interactive online art project built around one belief: "Everybody wants to be an art director." This episode is a powerful conversation about reinvention, creative courage, aging with energy, and defining success on your own terms. "Success is not being afraid to try anything you want to do — then putting 100% into it until you succeed."

    Always Stay Moving (Ray Reiss)
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Ratings & Reviews

5
out of 5
5 Ratings

About

Measured Differently, a podcast about redefining success through real-life stories.

Information

  • Creator
    Sheila Ray Montgomery
  • Years Active
    2026
  • Episodes
    15
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Measured Differently