“I think I’m resigning.”
It’s not something most professionals plan to say out loud in the middle of a meeting—but for Jennifer Outlaw, that moment of honesty became a turning point. What followed wasn’t just a career shift; it was a complete redefinition of success, leadership, and personal alignment.
In this episode of the HRchat Podcast, Jennifer and I explore what happens when a role looks perfect on paper but feels fundamentally wrong—and why more professionals, especially senior leaders, are starting to listen to that internal disconnect.
When Success Doesn’t Feel Like Success
Jennifer’s story will resonate with many HR leaders and executives. After decades of nonprofit leadership, she reached a point where the prestige of her role no longer matched how she felt day to day. That disconnect—what she describes as something you “feel in your body”—became impossible to ignore.
Her decision to step away wasn’t impulsive. It was the result of a growing awareness that traditional markers of success—titles, status, and external validation—were no longer aligned with her values.
That realization sparked a bigger question: What if success isn’t about climbing higher, but about aligning deeper?
From Leader to Builder and Connector
One of the most compelling shifts Jennifer describes is her move away from formal leadership titles. Instead, she now identifies as a “builder and connector”—someone focused on creating, strategizing, and bringing people together.
This shift reflects a broader trend in the future of work. Increasingly, professionals are prioritizing:
- Meaningful contribution over hierarchical authority
- Flexibility over rigid career ladders
- Purpose-driven work over prestige
For HR professionals, this raises important considerations about how organizations define leadership and create pathways for impact beyond traditional roles.
The Power of Doing What You Actually Enjoy
A key theme in our conversation is deceptively simple: choosing work based on what you genuinely enjoy doing.
For Jennifer, that meant leaning into activities like:
- Strategizing
- Teaching
- Creating
Too often, careers are shaped by external expectations—what others think we should do next. But Jennifer challenges that mindset, encouraging leaders to get radically honest about what energizes them.
This kind of clarity doesn’t just improve job satisfaction—it can also enhance performance, creativity, and long-term sustainability.
Why Play Is Serious Business
One of the more surprising insights from our discussion is the role of play in leadership.
Jennifer is a strong advocate for incorporating play and creativity into professional life—not as a luxury, but as a necessity. In high-pressure environments where burnout is a constant risk, play can:
- Spark innovation
- Reduce stress
- Improve problem-solving
- Reconnect leaders with curiosity and joy
For HR leaders navigating rapid change, this is a powerful reminder: sustainable performance requires space for experimentation and creativity.
Practical Steps for Career Reinvention
If you’re feeling stuck, depleted, or unsure about your next move, Jennifer offers practical, actionable advice:
- Start with quiet reflection: Create space to think without external noise
- Name your intention: What do you actually want more (or less) of?
- Test your strengths: Talk to trusted friends or colleagues for honest feedback
- Find aligned communities: Surround yourself with people who share your values
- Consider coaching support: A coach can help unlock new perspectives and options
These steps aren’t about making drastic changes overnight. They’re about building clarity and confidence incrementally.
Listening to the “Nagging” Signals
Jennifer also highlights the importance of paying attention to early warning signs—the “nagging” feelings that something isn’t quite right.
Left unaddressed, those signals can grow from small discomforts into what she calls “rock-to-boulder” problems. For HR professionals, this is particularly relevant when supporting employees through engagement, retention, and wellbeing challenges.
Redefining Identity Beyond Job Titles
One of the most powerful takeaways from this episode is Jennifer’s perspective on identity.
After leaving a senior role at 50, she made a conscious decision to separate who she is from what she does. That shift allowed her to design a next chapter focused on:
- Healing
- Sustainability
- Long-term learning
- Flexible work
It’s a reminder that careers are not linear—and that reinvention is possible at any stage.
A Call to Rethink What Comes Next
Jennifer’s journey challenges us to reconsider some deeply ingrained assumptions about work and success.
For HR leaders and executives, the implications are significant:
- How can organizations support values-based career paths?
- What does leadership look like beyond titles?
- How can we create cultures where alignment and wellbeing matter as much as output?
Ultimately, this conversation isn’t just about one person’s decision to resign. It’s about the growing movement toward more intentional, human-centered careers.
So here’s the question we leave you with:
What would you pursue if you stopped chasing titles?
For more conversations on leadership development and the future of work, subscribe to the HRchat Podcast, connect with me on LinkedIn, and visit HRGazette.com.