Navigating The Meaningful Middle With Kelly Nash
Careers don’t always move in a clean, upward line, and hitting a mid-career plateau or transition point can feel deeply destabilizing. This week, we’re joined by Chicago-based Career Alignment Coach and Workforce Development Consultant, Kelly Nash, to talk about how to navigate these shifts and find clarity in what she calls "the meaningful middle."
Kelly shares her own path from advertising to tech - including an 11-year tenure at Salesforce building employee experience programming - and how a layoff led her to considering her future. It's an honest look at identity loss during career transitions, why relying solely on your manager for validation can hold you back, and how to take intentional authorship of your professional narrative.
Actionable Tips & Takeaways
Redefine the "messy middle" as the meaningful middle
When your career path flattens or you feel stuck between where you started and where you want to go, it's easy to view that space as a failure. Instead of trying to rush through it, treat it as a critical inflection point for self-reflection:
Shift your relationship with time: Real career alignment doesn’t move at the speed of corporate timelines. The middle of your career is exactly where you have enough experience to know what you don't want, and enough runway to change direction with intention.
Navigate transition and identity loss honestly: Experiencing a major transition like a layoff often triggers a profound sense of grief. Bypassing those intense emotions to immediately hunt for the next job blocks long-term growth. Give yourself space to process where you are before mapping out what’s next.
Practice true career authorship
Career authorship is the conscious shift from living out a professional narrative written by other people’s expectations to writing one that is authentically yours:
Prioritize clarity before strategy: Tactical adjustments - like an updated resume or a LinkedIn overhaul - only work if they are driven by deep self-knowledge. You have to get clear on your core values and strengths before you decide what execution strategy makes sense.
Commit to visibility and self-promotion: Articulating your unique value clearly and consistently isn't optional if you want to grow. In modern work environments where human connection can easily get lost, building a visible personal brand ensures your contributions are recognized.
Decouple your worth from external validation
Relying entirely on a manager, a corporate title, or an organization to validate your professional identity is a fragile strategy that limits long-term satisfaction:
Own your evaluation process: Shift from a reactive position where you wait for feedback to a proactive stance. Measure your performance against your own goals and values first, treating external reviews as a single data point rather than the final verdict on your worth.
Look for transformational alignment: Success inside corporate structures is often tied to levels and titles. Look deeper at how your day-to-day work impacts your actual energy and fulfillment, and anchor yourself in the real-world impact you have on your team or business.
Explore the structure of a portfolio career
You don't have to compress all of your skills, interests, or ambitions into a single traditional job description. A portfolio career allows you to combine multiple professional tracks to build a more resilient path:
Leverage side projects for corporate clarity: Building a business, a blog, or a consulting track on the side does more than generate extra income - it clarifies what you actually want out of your primary career. Use that side execution to figure out what gives you energy.
Balance strategic planning with openness: Create a flexible roadmap that gives you clear direction, but remain open to non-linear, unexpected opportunities. Often, the roles that offer the most profound alignment are the ones you couldn't have predicted from a standard corporate blueprint.
Links & Resources
Kelly’s Website
Courtney's Substack: Read more of our weekly insights at substack.com/@courtneyattheglassadvisory.
For step-by-step guidance or to explore working with our team to navigate your own professional transitions, you can reach out to explore working with The Glass Advisory directly.
