Inspired by The Top Five Regrets of the Dying by Bronnie Ware

By Valerie Hall, Estate Planning Attorney

I often meet people at a turning point in their lives: they've lost a loved one, or they’re beginning to confront their own mortality. In those moments, it’s not just about documents—it’s about what really matters. That’s why I was so moved by Bronnie Ware’s book, The Top Five Regrets of the Dying. Ware was a hospice nurse who spent years listening to people reflect on their lives in their final days.  If you have not yet read this book, I highly recommend doing so!

Their reflections weren’t about bank accounts or bucket list trips. They were about relationships, authenticity, courage, and love.

Here are the five regrets Bronnie Ware heard most often—along with a few thoughts on what each of us might do now to live (and leave) with fewer regrets.

1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

How many of us spend years—or decades—trying to meet others' expectations, only to realize we've lost track of our own dreams? This regret is a wake-up call: our time is limited. If there’s a passion you’ve put on hold, a truth you haven’t spoken, or a version of yourself you’ve buried, maybe now is the moment to honor it.

Estate planning angle: Your legacy should reflect who you are—not just what you own. That might mean writing a legacy letter, preserving family stories, or making choices in your plan that reflect your deepest values.

2. “I wish I hadn’t worked so hard.”

This regret came up especially among men in Ware’s experience, many of whom missed their children’s youth or their partners’ companionship. It wasn’t just about long hours—it was about lost presence.

Takeaway: Time is the one asset we never get back. What if we protected it as fiercely as we protect our retirement accounts?

Estate planning angle: A clear, thoughtful plan saves your family countless hours of stress, decision-making, and court involvement—giving them more time to grieve, remember, and heal.

3. “I wish I’d had the courage to express my feelings.”

Stuffing down feelings often leads to fractured relationships and deep regret. Ware’s patients wished they’d told people they loved them—or spoken up when they felt hurt.

Takeaway: It's never too late to have a healing conversation.

Estate planning angle: Don't let unresolved conflict shape your legacy. Use this time to clarify your intentions, reconcile when possible, and leave instructions that speak not just to logistics but to love.

4. “I wish I had stayed in touch with my friends.”

We get busy. Life happens. And suddenly, years have passed. But in the end, it’s relationships—not resumes—that matter most.

Takeaway: Reach out to someone you’ve lost touch with. Tell a friend what they’ve meant to you.

Estate planning angle: Some of my clients have chosen to include small gifts or personal letters for old friends in their wills—ways of saying, You mattered to me. It's a beautiful thing.

5. “I wish I had let myself be happier.”

This one surprised me. But Ware explains that many people didn’t realize until the end that happiness is a choice—that we don’t have to stay stuck in old patterns or let fear run the show.

Takeaway: Let yourself laugh. Forgive more easily. Choose joy where you can.

Estate planning angle: Planning ahead gives you freedom and peace of mind. You’re no longer carrying the weight of what ifs. That freedom can open the door to more joy—now.

Final Thoughts

Legacy isn't just about passing down money. It's about passing down courage, clarity, love, and presence. The regrets of the dying can become guideposts for the living—if we’re willing to listen.

If you’ve been putting off creating or updating your estate plan, consider this your invitation. Not because you're dying—but because you're living. And because those you love deserve the gift of peace, not chaos.

Let your plan reflect not just your assets, but your heart.

Want to talk about your plan?
Call Lang Hall Law Offices at 888-973-5043 or schedule a consultation here (it's free!) We’re here to help you live—and leave—with intention.