Ep. 90 - Letting Yourself Be Happier

"I wish I had let myself be happier."

In this episode, I share insights from a conversation with ChatGPT on one of the most profound regrets from Bronnie Ware’s memoir, The Top Five Regrets of the Dying, based on her experiences caring for patients in the final stages of life.

The conversation dives into the active word in that statement—"let."  

What does it mean to let ourselves be happier? Why do so many of us resist it? And how can we shift from waiting for happiness to engaging with life in a way that leads to true fulfillment?

This discussion expands into what it actually means to flourish—not as an achievement, but as a state of engagement with life.

In this conversation, we unpack why flourishing isn’t the absence of struggle, but the presence of growth, momentum, and vitality.

Key Themes Discussed:

• Why the regret "I wish I had let myself be happier" is so powerful
• The role of permission—how we unknowingly block ourselves from happiness
• What it truly means to flourish (and why it’s different from just feeling good)
• How flourishing can exist even within struggle
• The distinction between reflection for insight vs. reflection for transformation
• How happiness is better understood as progress toward something meaningful
• Dan Pink’s Autonomy, Mastery, and Purpose framework for motivation
• Practical ways to move from passive thinking to active engagement

Key Takeaways:

• Happiness isn’t a goal—it’s a byproduct of meaningful progress and flourishing.
• True fulfillment comes from engaging in growth, not achieving a static state.
• Struggle doesn’t mean failure—it often signals growth, expansion, and momentum.
• Flourishing is about engagement, not external success.
• Autonomy, Mastery, and Purpose are key drivers of lasting fulfillment.
• Asking “What makes me feel alive?” is powerful—but acting on it is what leads to transformation.

Reflection Questions:

Take a moment to journal or think deeply about these:

• Where in my life am I already flourishing, even if I haven’t noticed it?
• What’s keeping me from giving myself permission to flourish and engage more fully with life?
• How can I move from thinking about change to taking action?
• Which of the three (Autonomy, Mastery, Purpose) do I need to focus on more?
• What’s one small action I can take today that aligns with what makes me feel alive?

Resources Mentioned:

• The Top Five Regrets of the Dying by Bronnie Ware
• The Modern Maverick: Why Writing Your Own Rules is Better For You, Your Work, and The World by Ed Haddon
• The Happiness Advantage by Shawn Achor
• Drive: The Surprising Truth About What Motivates Us by Daniel Pink
• Howard Thurman’s quote: “Don't ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.”