Right There With You

Cass Cooper | The Chaos Whisperer

Right There With You is a podcast for those of us navigating the intersections of work, life, and pressure in real time. Cass Cooper, The Chaos Whisperer™, breaks down what’s actually happening beneath burnout, misalignment, and leadership fatigue. Giving name, language, and permission to move differently. Each episode focuses on real tensions through expert conversations and real-world insight. We don’t just tell stories—we diagnose what’s not working and reframe how to lead through it. Here we know that: Soft skills are not soft. They are infrastructure.Burnout is a design flaw, not a character one.Clarity is how we stop surviving chaos and start leading through it. Join the Community:✨ Patreon: patreon.com/RightThereWithYou ✨ And Follow Cass: www.TikTok.com/just_cass2.0

  1. 4d ago

    We Don’t Need More Content. We Need More Connection.

    We have never been more connected to our devices, yet so many of us are struggling to feel connected to each other. We scroll, post, comment, network, and build personal brands, all in the name of community. But visibility is not belonging, engagement is not intimacy, and an audience is not the same thing as a community. Community has become another thing to build, brand, measure, and monetize. But genuine community is not a marketing strategy. It is a human practice rooted in care, reciprocity, vulnerability, and the willingness to show up for one another beyond the curated version of our lives. In this episode of Right There With You, I sit down with Mai Nguyen, founder of Held Here, to unpack what we lose when we confuse content with connection. We explore community as both memory and movement, the wisdom of Indigenous community traditions, and the ways online spaces can inspire belonging without replacing the relationships that sustain us in real life. Because the goal isn't to be seen by more people. It's to build spaces where people can be known, understood, and held. In this episode, we explore: Community building beyond content and engagement: Why follower counts, comments, and polished personal brands cannot measure the depth of human connection, and how emotional resonance offers a more meaningful way to understand community.Belonging, vulnerability, and emotional safety: How genuine community grows through curiosity, reciprocity, consistency, and the willingness to show up for people in ordinary moments, not just when it is convenient.Online connection, Indigenous wisdom, and the future of community: What traditional community practices can teach us about belonging, why technology should be a gateway rather than a substitute for human connection, and how to create spaces that put people before performance.Meet Mai NguyenMai Nguyen is a community strategist, consultant, experiential designer, and founder of Held Here, a human-centered community strategy consultancy rooted in the belief that community is both memory and movement. Drawing on her background in data analysis, Mai works at the intersection of online and in-person connection, emotional clarity, storytelling, and cultural sensitivity. Her work challenges organizations, founders, and brands to move beyond transactional engagement and create experiences that foster genuine human connection. After nearly a decade in corporate, Mai is building a business grounded in a purpose bigger than any job, role, or title. The takeawayCommunity is not something we manufacture through content. It is something we practice through care. We need spaces where we can stop performing, share our lived experiences, challenge one another with honesty, and feel less alone in our humanity. Technology can help us find our people, but meaningful connection requires us to do something with that discovery. We don't need more content. We need more connection. Hosted by Cass Cooper, The Chaos Whisperer™ Making Sense of Work, Life, and Pressure in Real Time. Connect with CassWebsite: iamcasscooper.com Instagram: @just_cass2.0 TikTok: @just_cass2.0 LinkedIn: Cass R. Cooper Work with CassFor leadership strategy, organizational clarity, and consulting support: knowbetterdobetter.co Right There With YouStop reacting. Start interpreting.

  2. 4d ago

    You Can't Have It All, and That's the Point

    The myth of having it all is keeping women exhausted, overextended, and chasing versions of success they may not even want. Women are expected to excel at work, show up for their families, maintain relationships, and somehow make it all look effortless. That expectation doesn’t create fulfillment. It creates an endless cycle of overcommitment, comparison, and burnout. In this episode of Right There With You, Cass Cooper sits down with Jess Wass, founder and CEO of Rework It, to challenge the cultural obsession with having it all and make the case for a more intentional approach to success. Together, they unpack how the pursuit of status, the pressure to meet everyone else's expectations, and the unequal burden of unpaid labor keep women stuck on the achievement treadmill. They also explore how to define success on your own terms, establish boundaries without guilt, and make decisions that reflect what actually matters. Because a meaningful life isn't built by saying yes to everything. It's built by knowing what deserves your yes. In this episode, we explore: The myth of having it all and women's burnout: How cultural expectations, unpaid labor, and the pressure to do everything contribute to exhaustion and keep women chasing an impossible standard.Career success, the prestige trap, and work-life balance: Why titles, salaries, and status don't guarantee fulfillment, and how redefining success creates room for work and life to complement each other.Intentional living, boundaries, and prioritization: How identifying your core values, choosing your three most important tasks, and making deliberate trade-offs help you build a life that reflects your priorities.The takeaway: Every meaningful yes requires a meaningful no. You cannot pursue every opportunity, meet every expectation, and protect your well-being without making trade-offs. Success starts with clarity about what matters most, followed by decisions that reflect those priorities. You don't need to have it all. You need to build a life that matters to you. About Jess Wass Jess Wass is the founder and CEO of Rework It, a leadership development and coaching company focused on helping professionals manage up, manage down, and take ownership of their career growth. Her work and insights have been featured in The New York Times, The Wall Street Journal, Fast Company, Bloomberg, and Psychology Today. Hosted by Cass Cooper, The Chaos Whisperer™ Making Sense of Work, Life, and Pressure in Real Time. Connect with Cass Website: www.iamcasscooper.com Instagram/TikTok: @just_cass2.0 LinkedIn: Cass R. Cooper Work with Cass For leadership strategy, organizational clarity, and consulting support: knowbetterdobetter.co Right There With You Stop reacting. Start interpreting.

  3. Sep 22

    What’s All the F.U.D. About? AI, Fear, and Leadership Uncertainty

    AI is everywhere. So is the fear surrounding it. From concerns about job loss and layoffs to questions about whether AI can be trusted, leaders and employees are navigating a new kind of workplace uncertainty. But what happens when we stop letting fear, uncertainty, and doubt lead the conversation? In this episode of Right There With You, Cass Cooper sits down with Corey Kirkendoll, President and CEO of 5K Technical Services and Vice Chair of the AI Advisory Council for GTIA, to talk about what responsible AI adoption actually looks like when humans remain at the center. Corey shares how organizations can move beyond AI fear and F.U.D. by building trust, creating practical guardrails, training employees, and treating AI as a partner rather than a replacement. They also explore what it means for leaders to maintain dignity, curiosity, and humanity while navigating rapid technological change. In this episode, we explore:AI fear, uncertainty, and doubt: Why F.U.D. is shaping the conversation around artificial intelligence, job security, layoffs, and the future of work.Responsible AI adoption and AI leadership: How organizations can introduce AI with training, governance, human oversight, employee buy-in, and clear processes instead of simply turning on new tools.AI and the human experience at work: How leaders can use AI to strengthen customer experience, empower employees, improve decision-making, and help people feel capable rather than replaceable.The future of work isn't determined by technology alone. It's shaped by the people deciding how that technology gets used. The question isn't whether AI will change work. It already is. The question is whether we're willing to lead people through that change with curiosity, clarity, trust, and dignity. About Corey KirkendollCorey Kirkendoll is President and CEO of 5K Technical Services and Vice Chair of the AI Advisory Council for GTIA. With more than 30 years in technology, Corey brings a human-centered perspective to AI adoption, cybersecurity, leadership, and organizational change. Hosted by Cass Cooper, The Chaos Whisperer™Making Sense of Work, Life, and Pressure in Real Time. Connect with CassWebsite: iamcasscooper.com Instagram: @just_cass2.0 TikTok: @just_cass2.0 LinkedIn: Cass R. Cooper Work with CassFor leadership strategy, organizational clarity, and consulting support: knowbetterdobetter.co Right There With YouStop reacting. Start interpreting.

  4. Sep 15

    Visibility Without Clarity Will Exhaust You

    What happens when building a business starts to feel more like performing success than actually building something? Cass sits down with Nomiki Petrolla, product leader, startup founder, and advocate for expanding access to entrepreneurship for women in tech. With more than 15 years of experience in product strategy, design, and startup development, Nomiki brings a candid perspective on what it really means to build publicly, build imperfectly, and figure things out in real time. We talk about the pressure to look polished and established before you've actually figured out what you're building, why women often second-guess expertise that comes naturally to them, and how visibility can build trust when it's rooted in honesty instead of performance. Nomiki also shares why she's committed to the long game, how she defines discipline, and why community matters when you're building something from the ground up. And we get into the bigger question underneath entrepreneurship: What kind of life are you actually building all of this for? In this episode, we explore:Why visibility without clarity can become exhaustingWhat women lose when they mistake confidence for certaintyWhy sharing the messy parts of building can create deeper trust than polished expertiseThe difference between commitment and discipline, and why both matter for the long gameHow building a business can become a pathway to creating the life you actually want At the heart of this conversation is a reminder that you don't have to perform certainty to prove you're capable. You can be an expert and still be learning. You can build in public without making your entire life public. And you can pursue ambitious goals while staying connected to the life you're building them for. Sometimes the work isn't becoming more visible. It's becoming more honest about what you're building before everyone else gets to see it. About Nomiki PetrollaNomiki Petrolla is a product leader, startup founder, and advocate for expanding access to entrepreneurship for women in tech. She is the founder and CEO of Theana, a platform designed to help women tech founders move from idea to launch, with an emphasis on action, validation, community, and building confidence through the process. Hosted by Cass Cooper, The Chaos Whisperer™ Making Sense of Work, Life, and Pressure in Real Time. Connect with CassWebsite: iamcasscooper.com Instagram: @just_cass2.0 TikTok: @just_cass2.0 LinkedIn: Cass R. Cooper Work with CassFor leadership strategy, organizational clarity, and consulting support: knowbetterdobetter.co Right There With YouStop reacting. Start interpreting.

  5. Sep 8

    Success, AI, & the Power of Becoming Yourself

    You’re Allowed to Rewrite Your StoryWhat if the story you’ve been using to define success was never actually yours? In this conversation, Cass sits down with Miri Rodriguez, global executive, author, and thought leader in AI strategy, storytelling leadership, and ethical innovation, to unpack the narratives that shape how we work, lead, and define our lives. Miri shares how she learned to question the stories she inherited about success, ambition, and what it means to be a woman in the workforce. From growing up as the daughter of preachers and discovering the power of storytelling to navigating Microsoft as a woman who refused to stay in one professional lane, Miri makes the case for owning your narrative—and being willing to rewrite it when it no longer serves you. The conversation also turns to AI, gender equity, and the emerging portfolio economy. Rather than treating technology as the end of human value, Miri challenges us to consider how AI can amplify our uniquely human capacity to connect, create, contribute, and build something bigger than a traditional career path. In this episode, we explore:Why the stories we tell ourselves can become a hidden source of burnout—and how to recognize when you’re living inside an identity you’ve outgrownHow to define success for yourself instead of inheriting someone else’s version of what your life is supposed to look likeWhy owning your narrative is a form of power, particularly for women navigating systems that were never designed with them in mindWhat the rise of AI can teach us about the enduring value of human connection, creativity, and communityWhy the emerging “portfolio economy” may give women new ways to build careers, income, and lives around the full range of what they have to offerAt the heart of this conversation is a simple but powerful idea: you are the author of your story. You can question the narrative, challenge the rules you inherited, explore what else is possible, and become more of who you are. And sometimes, the most courageous thing you can do is wake up the part of yourself you've been taught to keep quiet. About Miri RodriguezMiri Rodriguez is a global executive, author, and thought leader focused on AI strategy, storytelling leadership, and ethical innovation. She is the founder and CEO of Empressa AI, a growth and skilling platform designed to help women build AI fluency, expand their opportunities, and participate more fully in the emerging portfolio economy. Her work sits at the intersection of technology and humanity, with a focus on using AI to amplify—not replace—the uniquely human qualities that help people connect, lead, and create change. Connect with CassHosted by Cass Cooper, The Chaos Whisperer™ Making Sense of Work, Life, and Pressure in Real Time. Website: iamcasscooper.com Instagram: @just_cass2.0 TikTok: @just_cass2.0 LinkedIn: Cass R. Cooper Work with CassFor leadership strategy, organizational clarity, and consulting support: knowbetterdobetter.co Right There With YouStop reacting. Start interpreting.

  6. Sep 1

    It Doesn't Make Cents: Measuring Value Beyond Money

    What If Your Value Isn’t Measured in Money?What happens when you spend years building a successful career, hit the markers you thought would make you feel accomplished—and then realize you don't actually want your life to be organized around the next title, promotion, or paycheck? In this episode of Right There With You, I'm joined by Jonathan Sims, a senior software engineer and founder of the Reciproc8 Project, a Brooklyn-based community-powered platform designed to connect people through the exchange of skills, knowledge, resources, and services without requiring money to be the center of every interaction. Jonathan shares what happened when a promotion at Goldman Sachs didn't materialize after months of intense work—and how that disappointment forced him to confront a bigger question: Who gets to determine your worth? What began as a career reckoning eventually became a different vision for community. We talk about what happens when we stop treating every relationship, skill, hobby, and interaction as something that has to be monetized. We explore the value of reciprocity, the hidden power of “soft skills,” and what it might look like to rebuild the village many of us have outsourced. In this episode, we explore:What happens when a career milestone you thought you wanted no longer feels like enoughWhy your worth cannot be reduced to your title, salary, or professional outputHow hobbies and everyday skills can become opportunities for meaningful reciprocityWhy community is infrastructure—not a luxuryWhat we might gain by asking “What can I give?” instead of only “What can I get?”Jonathan also shares how Reciproc8 evolved from an idea into a community-centered platform where people can offer and request everything from coding and cooking lessons to moving help, tax navigation, acupuncture, and other forms of knowledge and care. At the heart of this conversation is a simple but radical question: What remains when money isn't the only currency? Maybe it's connection.... Because your value has never been limited to what you can produce. And sometimes clarity begins when we stop asking, “How can I profit from this?” and start asking, “Who can I support?” About Jonathan SimsJonathan Sims is a software engineer and the founder and executive director of the Reciproc8 Project, a community-powered platform built around mutual exchange, skills, resources, and connection. After nearly seven years at Goldman Sachs, Jonathan began rethinking what success, community, and reciprocity could look like outside of a purely transactional economy. Find Reciproc8: www.recipri8project.com If this episode gave you language for something you've been carrying, share it with someone who needs the reminder that your value is bigger than your output. Hosted by Cass Cooper, The Chaos Whisperer™ Making Sense of Work, Life, and Pressure in Real Time. Connect with Cass Website: iamcasscooper.com Instagram: @just_cass2.0 TikTok: @just_cass2.0 LinkedIn: Cass R. Cooper Work with Cass For leadership strategy, organizational clarity, and consulting support: knowbetterdobetter.co Right There With You Stop reacting. Start interpreting.

  7. Aug 26

    You’re Not Powerless. You Just Need a Better Map.

    We spend a lot of time trying to fix ourselves when things aren't working: work harder, become more visible, communicate better, prove our value, be more strategic. But sometimes the problem isn't our individual performance. It's the system around us. In this episode of Right There With You, I'm joined by Cassie Clayton, a systems thinker and strategic leader whose career spans technology, analytics, research, and AI. We talk about what happens when you stop looking only at your individual experience and start asking better questions about the systems you're operating within. Cassie shares how curiosity helped her navigate complex organizations, build influence, and understand why certain problems keep happening. We also get into the pressure high performers face to keep executing, the relationship between performance and advancement, imposter syndrome, and why being exceptionally good at your current role can sometimes make it harder to move into what's next. In this episode, we explore:Why understanding the system can be more powerful than simply working harderHow curiosity can become a leadership and career superpowerWhy high performers can get stuck being valued for execution instead of strategic thinkingHow to stop internalizing systemic problems as personal failuresThe “ask why five times” approach to getting beneath the problemCassie also shares a practical way to start seeing systems differently: build a flow chart. Start with what you can see, then keep asking why until you understand what's actually driving the outcome. Because once you understand the system, you have more choices. You can work within it. You can change it. You can challenge it. You can leave it. But you don't have to mistake lack of understanding for lack of power. You’re not powerless. You just need a better map. About Cassie ClaytonCassie Clayton is a strategic leader and systems thinker with experience across technology, analytics, research, and AI. Her work focuses on understanding complex systems, asking better questions, and helping people and organizations navigate change with greater clarity.

  8. Aug 18

    Don’t Burn Yourself Out to Prove You’re Ambitious

    Ambition doesn't have to cost you your health, your family, or your humanity. Full Stop. You can have high standards. You can be deeply ambitious. You can want more. And you can still have boundaries. For too many high-performing people, exhaustion becomes evidence that they're doing enough. We say yes to everything, work longer, carry more, and quietly become the infrastructure holding everything together. But sustainable leadership isn't about lowering your ambition. It's about building success that doesn't require your constant depletion to maintain it. In this episode of Right There With You, I'm joined by Jennifer Roy, CEO of Nucleus Networks, an MSP based in Vancouver, Canada. Jennifer is an operations leader, entrepreneur, mother, and advocate for creating workplaces where people can do exceptional work without unnecessary barriers. We talk about what it looks like to lead with high expectations while still putting people first—and what Jennifer had to learn about boundaries, saying no, self-care, motherhood, and the pressure to prove herself in a predominantly male industry. Jennifer also opens up about something many accomplished leaders rarely say out loud: even after 15 years of leadership, she still experiences imposter syndrome. In this episode, we explore:Why sustainable leadership doesn't mean sacrificing ambitionHow Jennifer moved from “I'll outwork everyone” to understanding her limitsWhy saying “yes, but” can be more powerful than simply saying yesThe connection between gender, imposter syndrome, and overworkHow to create boundaries that protect the things you can't afford to sacrificeJennifer's approach to leadership offers an important reminder: being committed and running yourself into depletion are not the same thing. You can have high standards. You can be deeply ambitious. You can want more. And you can still have boundaries. About Jennifer RoyJennifer Roy is the CEO of Nucleus Networks, a managed service provider serving organizations across Canada. With 15 years of experience in the MSP space, Jennifer is an operations-focused leader passionate about solving problems through people, process, and innovation. She is also an advocate for increasing opportunities for women in technology and building workplaces where people can thrive. Keep the conversation going: If this episode gave you language for something you've been carrying, share it with someone who needs the reminder that ambition and sustainability can coexist. And if you're ready to stop reacting and start interpreting, join us inside the Right There With You community on Patreon.

Ratings & Reviews

5
out of 5
4 Ratings

About

Right There With You is a podcast for those of us navigating the intersections of work, life, and pressure in real time. Cass Cooper, The Chaos Whisperer™, breaks down what’s actually happening beneath burnout, misalignment, and leadership fatigue. Giving name, language, and permission to move differently. Each episode focuses on real tensions through expert conversations and real-world insight. We don’t just tell stories—we diagnose what’s not working and reframe how to lead through it. Here we know that: Soft skills are not soft. They are infrastructure.Burnout is a design flaw, not a character one.Clarity is how we stop surviving chaos and start leading through it. Join the Community:✨ Patreon: patreon.com/RightThereWithYou ✨ And Follow Cass: www.TikTok.com/just_cass2.0

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