“I think I’m resigning.” This stark declaration, uttered not in a moment of quiet contemplation but amidst a professional meeting, marked a pivotal moment for Jennifer Outlaw, a seasoned leader whose journey of career reinvention has become a compelling narrative for a modern workforce grappling with evolving definitions of professional fulfillment. Her candid admission, shared during an episode of the HRchat Podcast, unveiled a deeply personal yet universally resonant struggle: the disconnect between a role that appears perfect on paper and one that feels fundamentally misaligned with an individual’s core values and well-being. What followed was not merely a career shift but a profound redefinition of success, leadership, and personal alignment, offering invaluable insights for HR professionals, executives, and individuals navigating their own professional paths.
The Genesis of Discontent: When Success Doesn’t Feel Like Success
Jennifer Outlaw’s story, as recounted in the HRchat episode, resonates with a growing number of professionals, particularly those in senior leadership roles. After decades dedicated to non-profit leadership, building a career marked by significant achievements and external validation, Outlaw reached a critical juncture. Despite holding positions of prestige and influence, an insidious internal disconnect began to manifest. She described it as a visceral feeling, something "you feel in your body," an undeniable signal that the traditional markers of success—titles, status, and the accolades of others—no longer brought genuine fulfillment. This internal dissonance became impossible to ignore, culminating in her public declaration of resignation.
This phenomenon is not isolated to Outlaw. Recent data highlights a pervasive sense of disengagement among employees globally. A 2023 Gallup report indicated that only 23% of employees worldwide are engaged at work, with a significant portion actively disengaged. For leaders, the pressure is often amplified, leading to burnout even in seemingly desirable roles. The "Great Resignation" movement, which saw millions of workers voluntarily leaving their jobs, particularly in 2021 and 2022, underscored a widespread re-evaluation of work’s role in life. Professionals, post-pandemic, are increasingly prioritizing flexibility, purpose, and well-being over traditional career ladders. Outlaw’s experience serves as a microcosm of this broader societal shift, illustrating how even those at the pinnacle of their careers can find themselves questioning the very foundations of their professional identity. Her decision to step away was not impulsive but the culmination of a growing awareness that her values had diverged from the demands and expectations of her role. This led her to a pivotal question: What if success isn’t about climbing higher, but about aligning deeper?
From Formal Leadership to "Builder and Connector": A Redefined Impact
One of the most compelling aspects of Outlaw’s transformation is her conscious decision to move away from formal leadership titles. Instead, she now identifies herself as a "builder and connector"—a role focused on creating, strategizing, and fostering collaboration among people. This shift represents a significant departure from hierarchical structures and a embrace of a more fluid, impact-driven approach to work.
This redefinition aligns with emergent trends in the future of work, where agility, collaboration, and a focus on intrinsic motivation are gaining precedence over rigid organizational charts. Modern professionals, particularly those with extensive experience, are increasingly prioritizing:
- Autonomy and Flexibility: The ability to shape their work around their lives, rather than the inverse.
- Purpose-Driven Work: Engaging in activities that align with their personal values and contribute meaningfully.
- Skill Development and Application: Focusing on leveraging their unique strengths and continually learning.
- Impact Over Measuring success by the tangible contributions they make rather than the prestige of their position.
For human resources professionals, this evolution in leadership identity poses critical questions regarding talent management, leadership development, and organizational design. How do organizations define and recognize impact beyond traditional managerial roles? How can pathways for influence and contribution be created for individuals who excel as "builders and connectors" without necessarily aspiring to C-suite positions? The emphasis shifts from managing people to enabling ecosystems of collaboration and innovation, where value is created through networks rather than strict reporting lines.
The Power of Genuine Enjoyment: Why Play is Serious Business
A core tenet of Jennifer Outlaw’s reinvented career philosophy is deceptively simple yet profoundly impactful: choosing work based on what genuinely brings joy and energy. For her, this meant leaning into activities she naturally found fulfilling, such as strategizing, fostering connections, writing, and creating. Too often, career trajectories are shaped by external expectations, societal pressures, or a predefined notion of what one "should" do next. Outlaw challenges this mindset, advocating for radical honesty about what truly energizes an individual.
This pursuit of enjoyment extends to her belief in the critical role of "play" in professional life. Far from being a luxury or a distraction, Outlaw argues that incorporating play and creativity is a necessity, especially in high-pressure environments where burnout is a constant threat. Research supports this perspective: studies have shown that elements of play—such as experimentation, curiosity, and imaginative problem-solving—can significantly boost innovation, reduce stress, and enhance team cohesion. A 2018 study published in the Academy of Management Journal found that playful design thinking approaches can lead to more creative solutions and increased engagement in the workplace. For HR leaders navigating rapid change and striving for sustainable performance, this is a powerful reminder that fostering environments for experimentation, creativity, and even lightheartedness is not merely a perk but a strategic imperative. It contributes to psychological safety, resilience, and a more vibrant organizational culture.
Practical Steps for Career Reinvention: Navigating the Transition
For individuals feeling stuck, depleted, or uncertain about their next professional move, Jennifer Outlaw offers practical, actionable advice rooted in her own experience. Her recommendations emphasize introspection, intentionality, and incremental progress:
- Identify Energy Sources: Begin by listing activities that genuinely energize you versus those that drain you. This simple exercise can reveal patterns and preferences often overlooked in the daily grind.
- Acknowledge the Internal Disconnect: Pay attention to the "nagging" feelings or physical sensations that signal misalignment. These early warning signs, if unaddressed, can escalate from minor discomforts to significant "rock-to-boulder" problems, impacting mental and physical health.
- Define Your Non-Negotiables: Clarify what truly matters to you in a professional context—whether it’s autonomy, impact, specific types of collaboration, or work-life balance. These non-negotiables serve as a compass for evaluating opportunities.
- Embrace Incremental Change: Reinvention doesn’t demand drastic, overnight transformations. Small, consistent steps towards clarity and alignment can build momentum and confidence. This might involve dedicating specific time to creative pursuits, networking with individuals in desired fields, or taking on side projects.
- Seek Support and Mentorship: Engaging with coaches, mentors, or peer networks can provide invaluable perspective, accountability, and emotional support during a transition period.
These steps are about building self-awareness and agency, empowering individuals to design careers that are deeply aligned with their authentic selves, rather than passively accepting predefined paths.
Redefining Identity Beyond Job Titles: A Holistic Approach to Life and Work
One of the most profound takeaways from Outlaw’s journey is her perspective on identity. After leaving a senior role at the age of 50, she made a conscious and deliberate decision to decouple who she is from what she does. This philosophical shift is crucial in a society where professional titles often become synonymous with personal worth. By shedding the external identifiers, she created space to design a "next chapter" focused on:
- Meaningful Contribution: Engaging in work that genuinely contributes to causes she cares about.
- Learning and Growth: Continuously developing new skills and exploring intellectual curiosities.
- Community and Connection: Building relationships and fostering collaborative environments.
- Well-being and Joy: Prioritizing her physical and mental health, and integrating activities that bring her joy.
This separation of self from role is particularly relevant in a rapidly changing job market where career linearity is increasingly rare. It underscores the idea that reinvention is not only possible but often necessary at any stage of life, allowing individuals to adapt, evolve, and maintain a sense of purpose beyond specific job functions. For organizations, fostering an environment where employees feel valued for their intrinsic qualities and potential, rather than solely their current title, can significantly enhance retention, loyalty, and overall employee well-being.
A Call to Rethink What Comes Next: Implications for the Modern Workplace
Jennifer Outlaw’s journey challenges deeply ingrained assumptions about work, success, and leadership. Her story offers significant implications for HR leaders and executives who are tasked with shaping the future of their organizations:
- Rethinking Leadership Development: Moving beyond traditional hierarchical models to cultivate leaders who are adaptable, empathetic, and capable of fostering connection and psychological safety.
- Designing Fulfilling Roles: Creating job descriptions and career pathways that prioritize purpose, autonomy, and skill alignment, not just upward mobility.
- Cultivating a Culture of Well-being: Recognizing that employee engagement and retention are intrinsically linked to mental health, work-life balance, and opportunities for creative expression.
- Championing Authenticity: Encouraging employees at all levels, especially senior leaders, to listen to their internal signals and pursue work that truly aligns with their values.
Ultimately, Jennifer Outlaw’s decision to resign from a high-profile position is more than an individual anecdote; it is a potent symbol of a growing movement toward more intentional, human-centered careers. Her experience encourages a collective re-evaluation of what constitutes a "successful" professional life in the 21st century.
So, the question that her story leaves for every professional, every HR leader, and every organization is profound: What would you pursue if you stopped chasing titles and instead focused on deep alignment with what truly energizes and fulfills you? The answer may very well redefine not only individual careers but the very fabric of the modern workplace.
For more conversations on leadership development and the future of work, subscribe to the HRchat Podcast, connect with Jennifer Outlaw on LinkedIn, and visit HRGazette.com.
