Measured Differently

Sheila Ray Montgomery

5.0 (5)
Careers

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

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.

36 min
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."

33 min
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."

34 min
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.

39 min
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.

34 min
Mar 24

Are You Funny? (David Lynam)

In this episode, we get to know David Lynam—successful drummer, multi-business owner, and rising comedian—who brings an honest, energetic look into what it really takes to grow creatively and professionally. David shares why motivated people always set new goals, how self-awareness shapes success, and why he often gets his best work done late at night. He breaks down the raw fairness of comedy—where the only question that matters is "Are you funny?"—and explains how some comedians across the country act as "secret weapons," opening doors, offering guidance, and elevating others behind the scenes. A major theme of the conversation is networking. David dives into the power of relationships, the importance of being around people more established than you, and his ability to become a "chameleon" in any room. As he puts it, one connection can shave ten years off your path, and networking is often the "fast pass for business." From reading people by their actions to understanding how a split second can define success or failure, David offers an insightful, funny, and refreshingly real perspective on ambition, comedy, and building a meaningful career. Disclaimer: Dr. Sheila Ray Montgomery holds a Doctorate in Education. This podcast is not medical advice.

36 min
Feb 23

Chosen Change (Rebecca Mason)

In this episode of Measured Differently, I sit down with Rebecca Mason, owner of Love Them Train Them, for a thoughtful conversation about redefining success, embracing change, and centering relationships. For much of her life, Rebecca experienced success as something heavy—like a hammer. Over time, she reframed it into something simpler and more sustainable: accomplishing what you set out to do. She shares how success truly takes a village, why relationships are at the center of everything she values, and how structure, dedicated time, and intentional schedules support her sense of peace. Rebecca talks openly about change—how the first impression is often panic, why change can be scary, and how learning to try to find the good makes all the difference. She introduces the idea of chosen change—the kind of change she actively seeks and loves—and reflects on her joy in fresh starts, new experiences, and possibilities. Her final definition of success is both grounding and powerful: Are you happy? Do you have a sense of peace about what you're doing, or are you living with regret? This episode is a warm, encouraging reminder to ask questions, push past fear, and reach for what you truly want—because relationships are everything.

35 min
Feb 16

Taking the First Step (Vince Fabra)

In this episode of Measured Differently, Vince Fabra has an honest conversation about purpose, fear, and what it really means to step into your life. Vince reflects on questions that linger long after the laughter fades—What are people going to say when you die? and What does true happiness actually look like? For him, success comes down to fulfilling his purpose, even when fear makes it tempting to stay still. He talks openly about the struggle of believing in yourself enough to take the first step, the fear of making the wrong decision, and how sometimes not choosing feels safer than choosing and failing. Throughout the conversation, Vince shares insights like "They haven't met you yet," and asks how we can take more ownership of what the universe offers us. At the heart of it all is a simple truth: relationships are everything, growth requires risk, and claiming something as yours means accepting responsibility if it doesn't work out. This episode is thoughtful, vulnerable, and deeply human—a reminder that being measured differently often begins with the courage to move forward anyway.

34 min
Feb 4

Feeling Like It's Enough (TuLe)

In this episode of Measured Differently, we sit down with TuLe, a Vietnamese immigrant who has spent the last 20 years building a life in Alabama alongside her husband—her best friend—and raising their son while owning two successful nail salons. TuLe shares a definition of success that quietly reshapes everything: feeling like it's enough. Through stories of work, love, resilience, and morning coffee, she reminds us that success doesn't have to be loud or endless—it can be rooted in contentment, possibility, and believing that it should not be impossible to build a life you're proud of. This conversation is a powerful reminder that sometimes success is simply being happy where you are. Also my disclaimer: Dr. Sheila Ray Montgomery holds a Doctorate in Education. She is not a medical doctor, and nothing in this podcast should be considered medical advice.

26 min
Jan 1

Redefining Success: Saying It Out Loud (Introduction)

Measured Differently: Real Life Said Out Loud begins with an honest, grounding conversation that sets the tone for what's to come. In this introductory episode, Dr. Sheila Ray Montgomery sits down with her best friend, Rachel, to ask a question many of us inherit—but few of us stop to challenge: What does success really mean? Together, they unpack how society defines success, who gets left out of that definition, and why it takes real bravery to change course when the old version no longer fits. Rachel reminds us that "our society has deemed success in a way that not all of us fit into," that "it's brave to change," and that we must learn to "value people who do the real work." This conversation isn't about polished achievements or perfect timelines—it's about honesty, courage, and redefining success on human terms. This episode launches a 36-part interview series featuring 12 men, 12 women, and 12 strangers from across the United States—real people with real stories—each answering the same question: How do you define success, and how do you maintain it? This isn't about having it all figured out. It's about saying it out loud.

33 min

10 Episodes

5

out of 5

5 Ratings

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

Creator

Sheila Ray Montgomery
Years Active

2K
Episodes

10
Rating

Explicit
Copyright

© 2025
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Measured Differently