The Five Whys: Uncovering Your Career Fears

By Heather Coleman-Voss, CPCC, CEC, CPLC

Do you have a mean inner critic? You know the one - that voice that whispers doubts just when you're ready to make a change. "I'm too old to change careers." "I don't deserve that promotion." "It's selfish to focus on my dreams right now." These thoughts aren't random critiques - they have deep roots, and understanding those roots is the first step toward transformation.


The Power of Asking Why

The Five Whys is a transformative tool that helps us dig beneath surface-level fears to uncover what's really holding us back. But this isn't just about asking "why" five times—it's about giving yourself permission to question beliefs you might have carried for decades.

Let's look at a real example that might resonate:

Initial thought: "I'll never be financially stable or secure on my own."

  1. Why? "Because I've always relied on others for financial decisions."

  2. Why? "I don't trust myself with important choices."

  3. Why? "I made some mistakes when I was younger."

  4. Why? "I was never taught how to handle money properly."

  5. Why? "Growing up, I learned that women shouldn't worry about money."

Root Cause: "The inherited beliefs and societal messages about money and capability are still influencing how I view my own financial potential."

This is where our deeper healing work begins. When we uncover a root cause like this, I ask a crucial question: "How old were you when you first learned these messages about money and capability?" The answer often reveals specific memories - perhaps of watching adults handle money or hearing direct messages about who should manage financial decisions. These memories point us directly to the age where healing needs to begin.

Common Patterns in Career Transitions

Through my coaching practice, I've noticed several recurring themes, particularly among professionals in their 40s and 50s. While these patterns affect people across all gender identities, they often intersect with unique societal pressures and expectations. (For a deeper exploration of how these patterns specifically impact women's career journeys, see my article "Breaking Free: Women, Career Transitions, and Societal Expectations.")

To illustrate how these patterns work, let's explore another example:

Initial Fear: "I'm too old to start something new."

  1. Why? "Because all the opportunities seem meant for younger people."

  2. Why? "I feel out of touch with current trends and technology."

  3. Why? "I've spent the last two decades focusing on everyone else's needs."

  4. Why? "I believed being a good parent/partner meant putting myself last."

  5. Why? "I learned early on that putting myself first was selfish."

Root Cause: "The messages I internalized about self-worth and caregiving have convinced me that prioritizing my own growth is wrong."

Again, we look to the past to heal the present. "How old were you when you first learned that your needs should come last?" For some, it might be age six, taking care of younger siblings. For others, it might be age twelve, when they started putting aside their own interests to meet family expectations. Each memory reveals a younger version of you that needs attention and healing now.

Meeting Your Inner Child

This is why the Five Whys technique is so powerful—it doesn't just identify limiting beliefs, it leads us directly to their origins. When we use the Five Whys, we often discover that our adult fears are speaking with much younger voices—and frequently, multiple younger voices. Your inner child might need healing at different ages: perhaps at age six when you first learned to stay small, at twelve when you were told to be less ambitious, and at sixteen when you started putting others' needs before your own. Each of these younger selves might be carrying different pieces of your story, all influencing your present choices and beliefs.

Consider someone contemplating a major career change. They might need to work with their inner child at:

  • Age 8, who was told their creative ideas were impractical

  • Age 13, who learned that others' approval mattered more than their own desires

  • Age 16, who chose a "sensible" career path over their true interests

  • Age 22, who set aside their dreams for immediate financial security

Understanding these connections isn't about dwelling in the past—it's about healing these different parts of ourselves that still influence our present choices. Each age that surfaces brings its own wisdom and needs for healing. And here's something magical: every time you tend to a younger version of yourself, you're not just healing the past—you're transforming your present moment. Even more beautiful? Somewhere in the future, a more confident, empowered version of you is cheering you on, grateful for the healing work you're doing today. You are creating a cycle of healing that spans past, present, and future.

The Freedom of Understanding

As you engage with the Five Whys and tend to your inner child's needs at various ages, transformation happens naturally. The mental energy once spent second-guessing yourself becomes available for creativity and innovation. Decision-making becomes clearer as you learn to trust your intuition. The anxiety about change begins to fade, replaced by a growing comfort with taking up space and pursuing your dreams.

This journey often parallels the experience of adjusting to a healthier workplace environment. The same tools that help you understand your career fears can help you embrace new opportunities with confidence.

Moving Forward with Support

This deep internal work deserves gentle guidance and support. As your trauma-informed career coach, I help you navigate the Five Whys process with care, identifying patterns and creating practical healing strategies that align with your true desires. Together, we celebrate each step of your growth, no matter how small it might seem.

Remember: Your dreams aren't too big, you're not too late, and it's never selfish to invest in your own growth. Your higher self is rooting for you. You're exactly where you need to be to begin.


Ready to transform those limiting beliefs into stepping stones for growth? Your inner critic doesn't have to have the last word. Take the first step toward the career and life you deserve by scheduling a free Discovery Call at www.careersavvycoaching.com. Together, we'll explore your journey, discuss my coaching packages and costs, and create a path forward that honors both who you are and who you're becoming.

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