A quiet reflection guide
The Five Regrets People
Carry
Near the End
Where These Insights Come From
These reflections are not just philosophical ideas.
They’re not guesses. They’re not theories.
They come from the voices of real people—hundreds of them—sharing what mattered most when time was almost gone.
In a large-scale study published in the Journal of Pain and Symptom Management, over 300 terminally ill patients were asked to reflect on their greatest regrets.
Along with providing you a list of the top 5 most frequently mentioned regrets, I took an approach of offering a series of questions to sit with, on how you can possibly minimize any regrets that you may be carrying.
There are no wrong answers.
“What is hidden in the heart often weighs the most.
But naming it, even quietly, can make it lighter.”
—Dr. Edith Eger
“The simple act of acknowledging our pain is the beginning of healing.”
—Dr. Gabor Maté
THE REGRETS
Some regrets arrive only at the very end.
Others… whisper to us quietly, long before that moment comes.
This guide isn’t here to stir up guilt.
It’s here to help you listen to what still wants your attention.
Whether you’re facing the unknown, supporting someone who is, or simply wondering what really matters—this is a space to reflect, release, and begin again.
Regret #5
“I wish I had lived more true to myself”
Not the life others expected.
Not the version that kept things tidy or acceptable.
The one that felt like mine.
So many people at the end wished they had made different choices.
Not louder ones—just more authentic ones.
Ask yourself:
- What part of me has gone quiet to make space for someone else’s approval?
- What do I want more of in the time I have left—big or small?
- If I let go of others’ expectations, what might I reclaim?
Regret #4
Regret #4
“I wish I hadn’t worked so hard.”
It’s not that work is bad. It’s that it can swallow us.
When people reflected on this regret, they weren’t angry—they were tired.
Tired of missing the laughter in the next room.
Tired of delaying joy.
Tired of trading time for what never truly fed them.
Ask yourself:
- What have I been putting off, waiting for the “right” time?
- What would I do with an hour no one else could claim?
- Where can I soften, even just a little?
“Don’t get so busy making a living that you forget to make a life.”
— Dolly Parton
Regret #3
Regret #3
“I wish I had expressed how I felt.”
Love. Anger. Gratitude. Grief.
So much of it stays inside because we’re afraid of what might happen if we let it out.
But the weight of unspoken feelings becomes its own kind of ache.
Not expressing them doesn’t make them go away—it just makes them heavier.
Ask yourself:
- What do I still carry in silence?
- What would I say—if no one interrupted, judged, or walked away?
- How could I offer those words to myself, first?
“Speak your truth, share your story, and live your message. That is where your true power lies.
-Steve Maraboli
Regret #2
Regret #2
“I wish I had stayed close to the people who mattered.”
Life gets busy.
We drift. We retreat. We protect ourselves from vulnerability.
But in the end, connection is what people miss most.
Even imperfect connection. Even messy love.
Ask yourself:
- Who do I still think of, even now?
- What would it feel like to imagine reaching toward them—if only in thought?
- Could I let that closeness exist, even without a response?
“Grief is unfinished love. And some of it will stay unfinished.”
—Dr. Pauline Boss
Regret #1
Regret #1
“I wish I had let myself be happy.”
Not productive. Not impressive.
Just… happy. For no reason at all.
People often say they postponed joy—until the kids were grown, the to-do list was done, the worry eased.
But joy rarely arrives on a schedule.
Ask yourself:
- Where have I made joy conditional?
- What used to make me smile that I no longer give myself?
- What might it feel like to allow small delight—even now?
“We don’t stop playing because we grow old; we grow old because we stop playing.”
— George Bernard Shaw
A Soft Way to Reflect
You don’t need to journal.
You don’t need to speak.
This part is just for you—to pause, breathe, and notice what’s rising. From you to you.
Try:
- Imagining a conversation you never had
- Letting your body move to a piece of music
- Whispering a truth into the air
- Closing your eyes and saying, “I’m still here. And I still get to choose.”
Even one breath of acknowledgment can shift something inside you and bring more peace.
