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The Top 5 Regrets of the Dying – and What Lessons They Teach Us

By Jennifer Thompson March 15, 2022 Lifestyle

I will never forget my call to Sheila. Sheila and her husband, David, were clients in their late 50s. They were the salt of the earth’ folk.

It was a Monday afternoon. I figured Sheila would probably still be at work, so I would leave a message for her to call me to set up an appointment. One of her bonds had come to maturity. We should meet to do an annual review and discuss investing the cash sitting in her account.

Life Is Unpredictable

To my surprise, she answered her phone. I told her it surprised me to have caught her at home. Then she dropped the bombshell. “Jennifer, my doctor has given me about a week to live. Cancer has returned.”

Sheila had been free of cancer for just over five years. And now, it has returned and ravaged her body. What do you say to someone when they tell you they only have a week left to live? I did not even know you could be so exact about when you’re going to die!

I said, “I am so sorry,” and offered, “Is there anything I can do for you?” The minute I heard my words, I realized they sounded ridiculous, considering what she was experiencing. I mean, what could I do for her?

As she faced her mortality, her investments were of little importance. And she would never make it for her annual review, where we’d discuss her retirement plan and the financial goals for the rest of her life. Because there would not be any “rest of her life.” Sheila died within that week.

That call affected my life; 58 is too young to die. But we don’t get to negotiate with death.

All we can do is make the best of life.

The Top Five Regrets of the Dying

An inspiring bestseller written by Hospice nurse Bronne Ware called “The Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing” tells us how to live fully. Bronne Ware compiled a list of the greatest regrets her patients uttered as they were dying. And these are:

Regret #1: I Wish I’d Had the Courage to Live a Life True to Myself, Not the Life Others Expected of Me

This regret struck me more than the others. How many of us have lived our lives to meet the expectations of our families and communities? Sometimes to our detriment.

Regret #2: I Wish I Hadn’t Worked So Hard

Men primarily articulated this regret. Society appears to value hard work and drive as the blueprint for a life of success. But so many of us are burnt out.

Regret #3: I Wish I’d had the Courage to Express My Feelings

Our fear of the consequences of speaking our truth may be what silences us from speaking our truth. Our fear of disapproval and rejection stops us from showing up fully and authentically.

Regret #4: I Wish I Had Stayed in Touch with My Friends

Friends come and go – maybe a little too easily. With access to social media, it appears more possible than ever to stay in touch in this day and age. But are we connecting? Are you committed to working through disagreements and misunderstandings?

Regret #5: I Wish I Had Let Myself Be Happier

This regret initially surprised me till I thought about it a little deeper. We appear to chase happiness – it’s even in the U.S. Declaration of Independence. With the explosion of positive psychology, you’d think we’d have nailed it. But are we truly happy?

According to Mental Health America, “In 2019, just prior to the COVID-19 pandemic, 19.86% of adults experienced a mental illness, equivalent to nearly 50 million Americans.”

They also inform us that “suicidal ideation continues to increase among adults in the U.S., and a growing percentage of youth in the U.S. live with major depression.”

Living Without Regrets

I will never know if Sheila had any regrets as she was dying. We don’t have to face death to regret some choices we’ve made. As you reflect on your life up to this point, what would your greatest regret be?

What can these five regrets teach you about what is most meaningful in our lives? Choose now to live fully, authentically, and without regret.

Author’s note: I have changed the names of the people in this story for reasons of confidentiality.

What do you regret the most in your life? Is your regret in tune with the ones shared in Bronne Ware’s book? How is your regret different?

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well i’m 76 now and from the age of 8 i was prepped to take care of – help out – do this do that! so here i am still taking care of my 74 year old brother – i have been depended on forever!! if i don’t do things i have guilt feelings, i regret having those feelings too. i am told i’m appreciated by family but many times i am in the middle of things bc i do speak up – this has made me upset to the point i feel sick. so i have made somewhat of a decision. 2023 i promise myself i have to let go of other’s problems, health issues, etc and do more for me, after all i’m told that 76 isn’t old but who knows if one will make it to 77 or 87.

The Author

Jennifer Thompson worked as a financial advisor for over 20 years before starting her own consulting business. She can be reached at

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