Are You Funny?

Always Stay Moving

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."

Do The Weird

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.

The Second Act

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.

Are You Funny?

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.

Chosen Change

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.