#44 – From the Trenches: Trusting Yourself in an AI World (Cass Cooper)

In this reflective From the Trenches episode, Cass Cooper—a multidisciplinary leader working at the intersection of organizational development, technology, AI, and cybersecurity—joins Josh Peterson to examine what it means to trust yourself in an always-on, AI-driven world. Drawing on her experience across enterprises and cultures, Cass contrasts the hyper-productive, underslept norms of American work culture with the more integrated rhythms of life she has seen in parts of Europe and the Caribbean, where rest, belonging, and community are built into the day instead of treated as rewards for surviving it. She unpacks how chronic overwork, a lack of “white space” on our calendars, and the habit of outsourcing every decision slowly erode our ability to hear our own internal signals.

From there, the conversation dives into how social conditioning—especially for women—teaches people to defer to external validation: partners, bosses, social media, and now AI tools, rather than their own judgment. Cass describes this as a kind of “pink tax” on attention and emotional labor, and makes the case that genuine empowerment requires structured space for introspection, not just better tools. She and Josh explore both the benefits and risks of AI, including the rise of people using tools like ChatGPT to script everyday interactions, and introduce Empressa AI, a platform designed by women for women that blends expert guidance with AI in a way that amplifies, rather than replaces, intrinsic knowing. You can explore the foundation of this work at Empressa AI’s Foundations for Women. For leaders and MSP owners trying to build healthier cultures, her perspective dovetails with BMK’s work on intentional client engagement and experience design and the kind of self-aware leadership development needed to sustain growth outlined in BMK’s guidance on MSP sales consulting for revenue and culture. If you’re ready to bring those ideas into one operating system, explore how the BMK Vision platform can help you build space for both performance and rest.

For MSPs navigating small-business growth and innovation, explore these related articles: how to build profitable service agreements, creating a people-first MSP culture, and improving MSP financial operations through better data.

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Episode Highlights

• 00:00:11 – Exploring cultural differences in work-life balance and how Americans often normalize overwork and under-rest.
• 00:01:12 – Cass shares her multidisciplinary role at the intersection of organizational development, AI, cybersecurity, and leadership.
• 00:06:48 – Insights from Europe and the Caribbean on building lives where rest, belonging, and community are part of the daily rhythm.
• 00:09:17 – The importance of scheduling intentional “white space” and outsourcing draining tasks to preserve energy for what matters.
• 00:12:01 – How women are socially conditioned to seek external validation and to distrust their own judgment and identity.
• 00:21:08 – The double-edged impact of AI tools like ChatGPT on everyday decision-making and social communication.
• 00:24:00 – Introducing Empressa AI, a women-designed platform blending expert advice with AI to support, not replace, inner knowing.

About the Guest

Cass Cooper is an interdisciplinary strategist working where organizational development, technology, AI, cybersecurity, and leadership intersect. With a career that spans building systems inside complex organizations and advising leaders on culture and change, Cass is especially focused on how digital tools shape identity, power, and belonging. Her work centers on helping people and teams build the self-awareness and practices needed to navigate modern work without sacrificing their health, humanity, or values.

As a collaborator of Empressa AI—an AI platform designed by women for women—Cass is pioneering approaches that blend expert human advice with AI to offer nuanced, context-aware guidance. Rather than encouraging over-reliance on technology, she advocates using AI in ways that amplify intrinsic knowing, support better boundaries, and create space for rest and reflection. Learn more at Empressa AI: Foundations for Women →. Cass frequently speaks and writes about work-life balance, the “pink tax” of emotional labor, and the importance of trusting yourself in a world that constantly pulls attention outward.

🌐 Connect with Cass on LinkedIn →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through the From the Trenches series, Josh highlights MSP leaders who redefine growth through creativity, resilience, and genuine client connection.

🌐 Connect with Josh on LinkedIn →

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