Measured Differently

Sheila Ray Montgomery
  • 5.0 (5)
  • Careers

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

  1. 4d ago

    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)

  2. 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)

  3. 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)

  4. 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)

  5. 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)

  6. 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)

  7. Apr 28

    Do The Weird (Michael Greene)

    In this episode, we sit down with Michael Greene, one of the founders of Faraway Theater and improv space in Birmingham, Alabama. Michael has always been performing and picking up new skills along the way, learning how to connect them into something meaningful. He doesn't claim strict daily habits—aside from occasionally forgetting his blood pressure meds—but instead lives by a philosophy: there are no right or wrong choices, only better ones. That mindset carries into how he leads and collaborates, emphasizing clear expectations while allowing room for growth and change. For Michael, love is about giving people space to evolve—letting them be who they are without judgment. That same principle shows up in his view of improv: being fully present, open, and responsive in the moment. We talk about relationships as an extension of passion—surrounding yourself with people who are excited about what you're building, who support you, encourage you, and believe in you. Because sometimes, moving mountains starts with simply having someone else who believes you can. Michael shares why doing the "weird thing" matters, why you shouldn't be afraid to go it alone, and how the right people tend to show up along the way. He reflects on the idea that success isn't about perfection—it's about continuing, even after you pause or step away. He also offers a powerful reframe of success: Professional success is being able to pursue what you're curious about while still paying your bills. Personal success is loving people and letting them love you back. And maybe most unexpectedly, he shares that the smartest he's ever felt… was when he chose not to say anything at all. This conversation is a reminder to stay curious, stay present, and keep going—without judgment, and with a little more trust in yourself and others.

    Do The Weird (Michael Greene)

  8. Mar 30

    The Second Act (Polly Brothers)

    In this episode of Measured Differently, I sit down with Polly Brothers, a 65-year-old competitive bodybuilder, longtime fitness professional, wife, mom, and grandmother who is boldly living her "second act." For decades, Polly lived by a long list of "supposed to's"—until a moment three years ago changed everything. Bodybuilding opened a door she didn't know was available, proving what's possible at any age and giving her the freedom to say, "I get to define success now." Polly shares how she asked her family for support before stepping on stage, why mindset matters more than age, and how her motto—"consistency over time equals results"—guides everything she does. She talks openly about finding balance, unplugging through her work with plants, and the grounding power of relationships and honest sounding boards. We discuss enjoying the process, following the plan, and recognizing that we often want results without the work. Polly's approach to goal setting is simple and profound: Am I still enjoying this? Do I still feel the spark? What is realistic? Her definition of success? Inspiring people to be their best—proving that it's never too late to start, shift, or rise. This episode is bold, energizing, and full of wisdom from someone who refuses to "go quietly into the night" and knows she still has more to give.

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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
    13
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Measured Differently