When I first launched this podcast, I talked about Bronnie Ware’s Five Regrets of the Dying, and how reflecting on them can help us live more intentionally now, so we don’t get to the end with regret.

Lately, those regrets have been top of mind for me again, especially after the recent loss of someone close to me.

I believe the five regrets of the dying can serve as gentle check-in points to help us live more fulfilling lives today.

Here are some reflection questions inspired by those regrets:

1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
→ Check-in question:
What would I do differently if I trusted my own inner voice and intuition more?
What does “a life true to me” look like for right now, in this season of my life?

2. “I wish I hadn’t worked so hard.”
→ Check-in question:
What am I working so hard for, and is it worth it to me?
What do I wish I had more time or energy for?

3. “I wish I’d had the courage to express my feelings.”
→ Check-in question:
What emotions have I been pushing down that want acknowledgment?
What would emotional honesty look like in one small interaction today?

4. “I wish I had stayed in touch with my friends.”
→ Check-in question:
Who do I feel most myself around and when did we last connect?
What relationships need tending, even in a small way?

5. “I wish I had let myself be happier.”
→ Check-in question:
What brings me joy that I haven’t made space for lately?
How could I make that a priority today?

I encourage you to take a few moments and really reflect on these questions. They’re not just nice questions — they’re a roadmap for how to live.

Ready to start creating a life you love? If you’re feeling stuck but ready to take action, let’s talk.

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Original music by David Delaney of The Whiskey Boys: Linktr.ee/whiskeyboys