Masks, Mirrors, and Identity: What Halloween Reveals About Us

Jennifer Sertl #a3r
6 min readOct 31, 2024

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Halloween brings not just costumes and creativity but a unique chance to explore and question the identities we present every day. It’s a playful, even profound moment to consider how the “masks” we wear reveal and conceal who we truly are. As an existential philosopher, I find this season an ideal reflection on identity — a topic that’s never been more relevant as digital authentication now demands we prove we are who we say we are. Yet, beyond technology’s efforts to verify us, Halloween reminds us of a deeper truth: our identity isn’t just about what’s seen but about what we’re becoming, a journey that requires intention and honesty as much as any costume we choose to wear.

In exploring identity, I’ve found several articles insightful, especially in understanding how algorithms shape and reflect our digital personas. These pieces dive into what our data reveals about our values, habits, and aspirations, making the digital realm a mirror of sorts — one that offers a sometimes unsettling, sometimes enlightening look at who we are online.

  • Allison Pugh’s The Last Human Job delves into a future where artificial intelligence and automation increasingly dominate the workforce, reshaping what it means to work and, ultimately, to be human. As machines take over technical, repetitive, and even creative tasks, the roles left for humans hinge on qualities that are uniquely ours: empathy, ethics, creativity, and nuanced decision-making. This shift challenges us to rethink our purpose in work and society, suggesting that our “last job” is to embrace and enhance these human-centric traits. In an era where technology can replicate so much, the article prompts us to consider that our ultimate role is one of connection, care, and understanding — elements that AI cannot authentically replicate. This evolving landscape reminds us that the enduring essence of humanity may lie not in what we do, but in how we approach life and others with intention and compassion.
  • In Fast Company’s How To Be Irreplaceable In The Age of AI , the focus is on how each online interaction contributes to a lasting digital footprint. This article encourages readers to consider the public narrative they’re creating and how deliberate online engagement can build a meaningful legacy, making identity a conscious, ongoing project rather than a byproduct of habit.
  • The New York Times’s Our Digital Selves, Revealed discusses how constant connectivity affects personal identity and community values. The article highlights the tension between public personas and private lives, reminding us that online spaces offer rich opportunities for self-expression while also influencing how we see ourselves and define our values.
  • Fast Company’s Four Principles for Leading with Integrity in a Complex World outlines how these four pillars — intention, integrity, innovation, and impact — can help professionals make grounded decisions in an increasingly complex environment. Each principle serves as a guide for staying authentic and aligned with core values, which is essential in navigating both professional and personal challenges.
  • Are We Better People in the Digital Age? The New York Times examines human nature questioning how digital connections shape our moral compasses and sense of community. The piece suggests that while our online lives can bring out both the best and worst in us, being mindful of our digital influences helps us stay true to our values.
  • Leading with Empathy in a Digital Age Fast Company’s Why Empathy is the Most Important Leadership Skill Today dives into the role of empathy in creating authentic, meaningful connections. As Simon Sinek advocates, this article emphasizes that leading with empathy builds trust, reminding us that authenticity in leadership starts with understanding and valuing others.
  • Authenticity is the New Currency Most of us know what it’s like to be around a truly authentic person and someone trying to be someone or something they just aren’t. Authentic people instill a sense of trust. You trust that what they say and do is based on how they really think and feel. In contrast, someone acting from a disingenuous place might appear unnatural, insecure, or dishonest. But it isn’t always this clear-cut. Given the multitude of pressures to conform in certain situations, many of us find that we aren’t always as authentic as we could be in every situation, opting instead to assume many of the attitudes, beliefs, and even paths of our peers without consideration for what we really want or feel. After a while, it can be difficult for us to tell the difference between our ‘real’ selves and what society, our friends, or our work culture is influencing us to embrace and become. This can prevent us from genuinely connecting with others and erodes our confidence and self-trust.
  • In her latest book, Rewire: Break the Cycle, Alter Your Thoughts, and Create Lasting Change, neuroscientist and brain performance coach Nicole Vignola explores the anatomy of the brain, the nuances of identity and self-awareness, and how something as simple as stating your small wins every day can change your entire life.
  • 8 Strategies for Leading with Authenticity, Empathy, and Resilience — Fast Company Highlighting the importance of authentic and empathetic leadership, this article provides strategies for leaders to build resilience and foster genuine connections with their teams. It suggests that self-knowledge and empathy are essential for navigating complex work environments. Read more.
  • Prioritizing People: Empathy in the Age of Algorithms — Fast Company \ This piece reflects on the role of empathy as algorithms increasingly influence decision-making, emphasizing that human-centered approaches are critical for maintaining trust. The article discusses how balancing empathy with technology can lead to more ethical and effective solutions in the workplace.
  • Harvard Business Review’s New Approach to Building Your Personal Brand shares how to build an authentic brand from the inside-out encourages individuals to align their brand with their personal values, underscoring that authenticity is the foundation of trust. Through self-reflection, individuals can create identities that resonate with who they are, not just what they sell.
  • In an era where connection feels both essential and elusive, TED Radio Hour’s Series A Better You invites us to pause and explore what it truly means to be human. From journeys of heroism and resilience to the impact of design and the profound questions surrounding tolerance and mental health, each episode unpacks an aspect of the human experience that is both universal and deeply personal. Through powerful stories and expert insights, listeners are guided to reflect on the forces that shape our lives — from our relationship with the planet to our understanding of ourselves and each other. These five episodes offer a rich tapestry of insights that prompt us to think, feel, and, perhaps, take action toward a better understanding of our place in the world.

As you step back from Halloween’s reflections, may you move forward with a bit more curiosity and honesty about who you are and how you participate in our complex, adaptive digital world. Whether it’s through the costumes we wear or the algorithms that capture our habits, each glimpse into identity is a reminder that authenticity is a choice — a daily practice in both the real and virtual realms.

In the rigor,

Jennifer Sertl

[ Jennifer Sertl is a thought leader in adaptive leadership, specializing in helping organizations and individuals navigate complexity with resilience and purpose. She co-authored the influential book Strategy, Leadership and the Soul, which explores the intersection of strategic foresight and personal authenticity. Jennifer’s work is centered on leveraging human capital to drive innovation and create value in today’s rapidly evolving landscape. ]

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Jennifer Sertl #a3r
Jennifer Sertl #a3r

Written by Jennifer Sertl #a3r

Biz strategist fostering better decisions,systems thinking, scenario planning. Mind of chess player ♜ Heart of a poet ♫ Inviting depth ... @agility3r

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