I Feel Like I Should | Official Trailer

Peay: What the American Dream Leaves Out

Peay is a professor of Black Studies and a native of Southeast Texas with seven years of experience working in secondary education across the Houston area. His work and life are shaped by music, food, Brazilian jiu-jitsu, and a deep interest in how people learn, navigate culture, and make sense of the world around them. Peay starts with the music he never connected with, from boy bands to country, despite growing up in a place where many styles were always within reach. He reflects on Southeast Texas as less of a single musical lane and more of a place where MTV, BET, grunge, R&B, hip-hop, soul, and regional sounds coexisted. From there, the episode turns to the American Dream, Southern ideas about adulthood, race, class, generational wealth, and the promises many people were told would await them if they did everything right. Peay brings humor, clarity, and frustration to a wide-ranging reflection on inherited rules, broken promises, and the world people are actually trying to live in. Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com [http://ifeellikeishould.com/]

Shep: Questioning the Shoulds We Hold

Shep is a queer relationship and sexuality coach and therapist in training whose work focuses on non-conventional relationship structures and kink. After nearly a decade working in sustainability, they returned to school to help people better understand themselves, their relationships, and the expectations they've inherited. Shep reflects on growing up with a deep need to fit in, navigating gender identity, attending fashion school in London, and eventually leaving the industry to pursue work that aligned with their values. What begins with music becomes a conversation about authenticity, belonging, and the pressure to become the person others expect you to be. As Shep navigates another career transition into therapy, we talk about identity, relationships, and the lifelong work of asking where our "shoulds" come from before deciding whether they belong in our lives. Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com [http://ifeellikeishould.com/]

Chris Schumacher: Learning to Want What You Want

Chris Schumacher is a visual artist, photographer, and occasional musician living on a small mountainside farm in Appalachia. Raised in the Deep South, he spent years trying to live up to expectations that never quite felt like his own. Chris reflects on growing up with religious and cultural pressure, trying to fit in, marrying young, and questioning ideas about success, masculinity, and career. Along the way, he began replacing the question of what he should do with something far more difficult: What do I actually want? As Chris navigates a major career crossroads, we talk about creativity, identity, and learning to build a life that feels true instead of simply expected. Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com [http://ifeellikeishould.com/]

Daniel Whitaker: The Pressure to Catch Up

Daniel Whitaker is a graduate student in mental health counseling, a bonsai instructor, an event host, and a self-described professional goofball living in New York City. We begin with a conversation about music, belonging, and the challenge of fitting in before you know who you are. Daniel reflects on growing up in the Midwest, coming out later in life, and finding community while building a life in New York City. Along the way, we talk about identity, queerness, comparison, authenticity, mental health, self-acceptance, and the pressure to feel like you're somehow behind everyone else. We also explore what it means to stop measuring yourself against other people's timelines and start making room for your own. Follow the show for updates and new episodes: Instagram: @ifeellikeishouldpod ifeellikeishould.com Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com [http://ifeellikeishould.com/]

Shane Alcock: Curiosity, and the Paths We Don't Take

Shane Alcock is a filmmaker, father, and self-described interested human being who hopes the caring and compassionate side of humanity can continue to blossom and flourish. We begin with music and the sounds that shaped his childhood in South Africa, then move into family expectations, fatherhood, creativity, and the challenge of finding your own path. Shane reflects on growing up in a fishing family, choosing a life different from the one imagined for him, and an eco-lodge dream that remains meaningful even though it never became a reality. Along the way, we talk about curiosity, regret, deep listening, and the ways music can nurture, connect, and help us better understand ourselves. Follow the show for updates and new episodes: Instagram: @ifeellikeishouldpod ifeellikeishould.com Follow the show for updates and new episodes. Instagram: @ifeellikeishouldpod ifeellikeishould.com [http://ifeellikeishould.com/]