Exploring the Human Side of Technology: Lessons from Community, Memory, and Art with Jonathan Massimi

In this episode of the To Be and Do podcast, Phil Amerson reconnects with Jonathan Massimi, a multifaceted thinker, author, and community pastor based in Kitchener, Ontario. Their insightful conversation dives deep into the evolving intersections of technology, memory, and community, using the lens of art, faith, and personal artifacts to ask what it really means “to be and do” in an age dominated by screens and algorithms.

The episode is a reflective journey, centered on the subtle yet profound ways technology shapes not just what we do, but who we are, how we remember, and how we connect.

Key Takeaway #1: Technology Shapes Community — and Ourselves

A major focus of the conversation is the impact of tools — especially AI and digital devices — on human relationships and community. Jonathan Massimi shares a striking classroom experiment: students first interact and connect deeply while finger painting together, generating art in real-time through conversation and mutual inspiration. However, as soon as they transition to using AI art tools, a “buzzing” creative environment gives way to silence and frustration. Students, now isolated behind screens, grapple with the limitation of having their creativity mediated and sometimes even overridden by the technology at hand 05:33. The result is lost agency and a shift from collaboration to solitary, transactional engagement.

This example makes it clear: tools don’t just assist us — they transform our experience, sometimes narrowing the potential for organic, communal creativity and personal agency.

Key Takeaway #2: Memory and Meaning Are Becoming Outsourced

As Jonathan Massimi thoughtfully points out, technology is also changing the ways in which communities remember and tell their stories. Faith communities have traditionally acted as “holders of memory,” curating and transmitting shared experiences and values through physical artifacts, rituals, and collective storytelling 07:08. Today, much of this memory is being “uploaded” to social media feeds and digital archives, with algorithms deciding what is seen, shared, or forgotten. The conversation raises profound questions: Who owns these memories? What gets preserved, and what is lost? Are we relinquishing our authority over what matters most in our collective histories 08:10?

Through tangible examples — from family photo albums to cherished heirlooms like wristwatches — the episode champions the irreplaceable power of analog artifacts in grounding memory and honoring legacy.

Key Takeaway #3: Intentional Rituals Foster Reflective Human Experience

Both Phil Amerson and Jonathan Massimi discuss methods for reclaiming presence and reflection amidst technological distraction. Whether it’s enforcing “no screen” time at retreats for spiritual leaders to foster sacred silence 09:13, or adopting the ritual of wearing and winding a mechanical watch as a meditative practice, these intentional acts reconnect us with ourselves, our past, and our purpose 15:25. Removing distractions encourages not just deeper connection to others, but a richer inner life and spiritual awareness.

This commitment to reflection over reaction, and meaning over immediacy, stands as a countercultural act in our hyper-digital moment.

Final Thoughts

This conversation between Speaker A and Jonathan Massimi is a reminder that how we use our tools — and how they use us — is not a neutral matter. By remaining attentive to the spaces between (and sometimes away from) our screens, we sustain the practices, artifacts, and communities that affirm our shared humanity. If you’re seeking ways to reconnect with meaning and memory in a digital age, this episode is not to be missed.

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