When ‘Enough’ Still Feels Empty: A New Perspective On Fulfillment

by | Oct 29, 2024

More than a decade ago, I set out on a journey I didn’t fully understand. All I knew was that the conventional path wasn’t mine. While many were chasing society’s definitions of success, something inside me craved something different—a deeper, more authentic life. Looking back, I realize that the outcomes I was seeking were clarity, freedom, resilience, and a true sense of belonging and purpose.

I discovered that fulfillment is not a destination. It’s a way of being—a day-by-day unfolding of living authentically and making choices that bring real satisfaction, not fleeting accomplishments. The world constantly pushes us toward its version of success, but I’ve found that true peace comes from staying connected to our own questions and priorities, returning to them even as life changes.

Below are the ten questions that continue to shape my understanding of success and fulfillment. They’re the lens through which I view my life, and through these questions, I’ve learned how to live a life free from the expectations of the world.


The 10 Questions I Sat With (and Still Do)

  1. What moments or memories do I avoid thinking about, and why?
    • These are often where the most growth and healing lie. They challenge me to look at my blind spots and see the lessons I may have missed. This question has allowed me to confront fears and pain points I previously avoided, finding strength and resilience in facing them.
  2. If every title, possession, and achievement disappeared, what would still feel meaningful?
    • This question brings me back to what genuinely matters to me, separate from accomplishments or roles. It’s a reminder that real meaning isn’t tied to what I own or what I’ve achieved—it’s about the connections, experiences, and values that bring depth to life.
  3. What belief about success do I hold that may not truly serve me?
    • I was carrying ideas of success that weren’t even mine, ideas handed to me by society, family, or peers. This question pushes me to check in with my beliefs regularly and let go of those that don’t align with who I am becoming.
  4. If I weren’t seeking anyone’s approval, how would I live?
    • There is freedom in imagining a life where no one else’s opinions matter. This question opens me to live more honestly, choosing actions that align with my values instead of trying to meet expectations.
  5. What brings me joy and makes me feel alive?
    • Joy is often quieter than the world’s version of success, but this question helps me focus on small, meaningful moments—like a conversation, a walk, or a creative project. It’s a reminder to fill my days with what actually brings me life.
  6. What part of myself have I hidden or ignored, and what would happen if I allowed it to shine?
    • We often keep certain sides of ourselves in the background to fit in. This question reminds me to honor every part of myself, even the ones I’m tempted to hide, and to bring them forward with pride.
  7. When was the last time I felt completely alive, and how can I create more of that feeling?
    • Whether it’s a moment in nature, an intense conversation, or simply being in the flow of something I love, remembering these experiences helps me design a life that feels alive and rich every day.
  8. What am I holding onto that no longer fits who I am, and what’s stopping me from letting it go?
    • This question challenges me to release roles, relationships, or habits that weigh me down. It encourages a continuous shedding of what no longer serves me, allowing room for growth and new possibilities.
  9. What does fulfillment look like in this season of my life?
    • Life isn’t static, and fulfillment isn’t a one-size-fits-all achievement. Every season brings new insights and values. This question reminds me to stay present with what truly matters now, not what mattered years ago.
  10. How do I want others to feel after being with me?
  • It’s easy to focus on personal goals, but this question expands my view to the impact I have on others. It reminds me that part of my purpose is to create warmth, kindness, and understanding for those around me.

The 10 Outcomes of This Journey

Sitting with these questions daily, weekly, or even occasionally has led to outcomes I hadn’t anticipated but am deeply grateful for:

  1. Clarity on What Matters: I now have a clear sense of what truly brings value to my life, helping me prioritize the things that fulfill me most.
  2. Self-Awareness and Acceptance: Through understanding my hidden sides and insecurities, I’ve come to accept myself more completely, finding peace in my whole self.
  3. Freedom from Outdated Beliefs: I’ve let go of beliefs that were weighing me down, making space for new ideas that resonate with who I am now.
  4. Authentic Relationships: My relationships are richer and more genuine because I show up as my true self, attracting people who value me for who I am, not what I achieve.
  5. Living with Purpose: I now live with an intention that aligns with my values, focusing on daily actions that feel purposeful rather than chasing arbitrary goals.
  6. Joy in Everyday Moments: I find contentment in small moments—conversations, quiet mornings, creative bursts—that bring real joy, uncolored by external achievements.
  7. A Sense of Lightness: I’ve learned to release what doesn’t serve me, creating a life that feels lighter and more intentional.
  8. Courage to Make Real Changes: These questions have given me the bravery to make choices that align with my values, even when they’re tough, such as leaving toxic relationships or switching careers.
  9. Resilience and Adaptability: With a strong sense of self, I’m able to navigate life’s ups and downs more gracefully, adjusting to changes without losing sight of what matters.
  10. A Lasting Sense of Fulfillment: Fulfillment isn’t a destination; it’s an ongoing experience. I feel it more each day, rooted in choices that come from my true self, not society’s expectations.

Living Free from the World’s Expectations

Living each day through these questions has allowed me to experience a kind of freedom I hadn’t imagined. I’m no longer tethered to the world’s version of success or happiness. Instead, I’m guided by a deeper, quieter fulfillment that doesn’t need validation.

My days are no longer about “doing more” or “achieving more.” They’re about honoring what brings me joy, investing in relationships, and living with integrity and ease. When doubts or comparisons creep in, I return to these questions, reminding myself of the life I’m building—a life that is truly mine.

This journey, more than anything, has shown me that true success isn’t something to reach or possess. It’s a way of being, a way of living each day with honesty, kindness, and a heart full of gratitude for every small, beautiful moment.