Facing Life’s Hardest Truths: My Conversation with Dr. Jill Greenbaum on Resilience, Appreciative Inquiry, and End-of-Life Wisdom

Hurratul Maleka Taj
Jun 3
5 min read

Updated: Jul 25

Throughout my journey as an entrepreneur and leader, I’ve encountered countless challenges that tested my resilience. But in my recent conversation with Dr. Jill Greenbaum on The Unstoppables, I was reminded that the ultimate test of courage is not just in overcoming obstacles but in embracing life’s deepest truths - especially the one we often avoid: death.

Dr. Jill Greenbaum is a force of nature. She is an educator, a visual trainer, a Buddhist chaplain, and an end-of-life guide. Her work is an intricate blend of deep wisdom, spiritual grounding, and practical tools for transformation. Our discussion left me with profound insights - not just about leadership or entrepreneurship, but about what it truly means to live fully, fearlessly, and with intention.

Confronting Life’s Impermanence

I’ll be honest - talking about death is uncomfortable. It’s something most of us push aside, thinking we’ll deal with it “someday.” But Jill’s perspective challenged me. She doesn’t see death as something to fear; instead, she sees it as an invitation to live differently. Her work as an end-of-life guide is about helping people confront mortality, not with despair, but with awareness and purpose.

Listening to Jill, I found myself reflecting on my own journey. As a founder, I have faced moments of uncertainty, but I realized that the greatest uncertainty of all - our own impermanence - can actually be our greatest source of strength. If we accept that life is fleeting, what would we change about the way we live today? What risks would we take? What fears would we let go of?

Jill’s approach to working with individuals at the end of their lives is deeply compassionate and profound. She encourages people to engage in open discussions about their mortality, helping them find peace and meaning in their final days. This reminded me of the importance of legacy - not just in business but in life. What do we leave behind? How do we impact the people around us? These are questions we should all be asking ourselves, not just when faced with mortality, but every single day.

The Power of Appreciative Inquiry

One of the most striking aspects of our conversation was Jill’s use of Appreciative Inquiry. In a world where we’re constantly asked to solve problems and fix what’s broken, this approach offers a refreshing shift: instead of focusing on what’s wrong, we focus on what’s strong.

Jill shared a powerful concept which is : looking at "everything", both the positives and negatives and then focusing on the positives to solve for the challenges (the negatives).

It made me think about how we, as entrepreneurs and leaders, often operate from a place of scarcity - worrying about what’s missing instead of leveraging what we already have. What if we applied this mindset in our own work? What if we focused more on our strengths, our team’s strengths, and the resources we already possess?

Appreciative Inquiry isn’t just a leadership tool; it’s a life philosophy. Imagine approaching every challenge - whether personal or professional - not with the question, “What’s wrong?” but instead, “What’s working?” That small shift can change everything.

Finding Strength in Buddhism

Jill’s Buddhist practice is woven into every aspect of her work. Her ability to stay present, to approach life with curiosity rather than fear, resonated deeply with me. She spoke about how Buddhism teaches resilience - not through brute force, but through acceptance. It’s about embracing the now, understanding that everything is impermanent, and finding peace within that truth.

As an entrepreneur, I’ve often felt the pressure to control every aspect of my journey. But what if true strength lies in surrender? Not in giving up, but in trusting the process. Jill’s perspective reminded me that we don’t have to have all the answers - we just need to be open to growth, to learning, and to change.

She also spoke about mindfulness and how it’s not just about meditation but about how we engage with the world. In business, in leadership, and in life, being mindful means making conscious choices rather than reactive ones. It’s about pausing, reflecting, and acting with intention.

Lessons for Entrepreneurs and Leaders

This conversation wasn’t just inspirational - it was deeply practical. Jill’s work offers so many takeaways for leaders and entrepreneurs like myself:

Embrace impermanence. The only constant in business and life is change. The more we resist it, the harder it becomes.
Use Appreciative Inquiry. Shift your focus from fixing problems to amplifying strengths. It’s a game-changer in leadership and decision-making.
Be present. Mindfulness isn’t just a buzzword; it’s a tool that helps us navigate uncertainty with clarity and confidence.
Lean into difficult conversations. Whether it’s in business or personal life, avoiding tough topics only leads to regret. Address them with courage and compassion.

Jill’s lessons extend beyond work - they apply to every aspect of life. In the face of challenges, we have a choice: resist and suffer, or embrace and transform. The latter is where true power lies.

A Personal Shift

I left my conversation with Jill feeling different - lighter, yet more intentional. I realized that being unstoppable isn’t about avoiding hard truths; it’s about facing them head-on. It’s about understanding that life is fleeting and using that knowledge to fuel bold action.

As I move forward in my own journey, I carry these questions with me: If I truly embraced the reality of my own mortality, how would I live differently today? What decisions would I make? What fears would I release?

Jill’s wisdom has given me a new perspective - one that I hope to integrate into every aspect of my work and life. And I want to challenge you to do the same. Ask yourself: What would change if you knew your time was limited? What legacy do you want to leave behind?

Continuing the Conversation

I invite you to listen to this conversation with Jill Greenbaum. It’s not just about death - it’s about life. About living fully, leading fearlessly, and embracing every moment with purpose.

Let’s continue this conversation. Share your thoughts with me - what resonated with you the most? How do you confront life’s hardest truths? What practices help you stay present and intentional?

Join me for this powerful episode of The Unstoppables. Let’s redefine what it means to be unstoppable—together.

💬 I’d love to hear your thoughts - let’s continue the conversation in the comments!

📖 Watch the full episode here: https://lnkd.in/g6nFtyMB

🎧 Listen to the episode here: https://lnkd.in/g6vm3rQX

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