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7 Potent Ways To Live And Die Without Regret

I must change my life so that I can live it. Not wait for it.

Add up all the stories told from deathbeds; the regrets, confessions, sorrows, secrets, petitions for forgiveness, and desperate calls to turn back the clock, and we have an infinite library of tragedy.

I must change my life so that I can live it. Not wait for it.
—  Susan Sontag

Death’s Day is coming — today, tomorrow, or it could be decades away.

Good health and youth do not protect anyone from death’s decision.

When death calls your name, you must go.

In my late teens, I almost died in a car accident, but death let me off the hook.

Not long after, death called my best friend, then my father.

I pushed their deaths into the shadow and ran into the light but soon discovered that chasing light created too many fears and even bigger shadows.

Then I found a wise teacher and teachings that led me back to the darkness to befriend death. Since that time I have allowed myself to remain with the awareness of death and this has driven me to interact with life more purposefully and joyfully.

In this essay, I reveal the 7 things I have learned about regret and death:

  1. Take a leaf from the Top 5 Regrets
  2. Explore other cultures
  3. Break the silence around death in daily life
  4. Learn the skill of change and letting go
  5. Meditate on death
  6. Interact with myths, art, and symbols of death
  7. Express your experience of death

1. Take A Leaf From The Top 5 Regrets

What we can learn from those near death, is that regret is the greatest pain.

Nurse Bronnie Ware spent 12 years working in palliative care, caring for patients in the last 12 weeks of their lives. She collected stories and published a book, The Top Five Regrets Of Dying.

My friend Ann Marie is a nurse who worked in palliative care for twenty years. She carries her patient’s stories so deeply that being with her is sometimes heartbreaking.

Together these nurses have thousands of stories, and yet their top 5 regrets are identical.

Regret #1. I wish I had the courage to live a life true to myself, not the life others expected of me.

Bronnie: “This was the most common regret of all. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realize until they no longer have it.”

Ann Marie: “Unlived dreams are usually blamed on circumstances — not enough time, money, or the needs of family taking precedent. When my patients are near death it’s clear that these are excuses for fears and a lack of self-belief. The result is deep sadness or deep bitterness.”

Regret #2. I wish I hadn’t worked so hard.

Bronnie: “This came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship. Women also spoke of this regret, but most were from older generations. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.”

Ann Marie: “Most men feel that their lives flew by as they climbed the ladder of success. Some of them are fortunate enough to get to know their children post-career, but for many, estrangement had set in. It was too late.”

Regret #3. I wish I had the courage to express my feelings.

Bronnie: “Many people suppressed their feelings in order to keep peace with others. As a result, they settled for a mediocre existence and never became who they were truly capable of becoming. Many developed illnesses relating to the bitterness and resentment they carried.”

Ann Marie: “I’ve only ever had two types of patients, the emotionally expressive and the emotionally repressed. The emotionally expressive can be a real handful, but they’re easy to get to know and to help. The emotionally repressed lose the ability to know what they want (even for dinner ). It’s tough to help them.”

Regret #4. I wish I had stayed in touch with my friends.

Bronnie: “Often they would not truly realize the full benefits of old friends until their dying weeks and it was not always possible to track them down. Many had become so caught up in their own lives that they had let golden friendships slip by over the years. There were many deep regrets about not giving friendships the time and effort that they deserved. Everyone misses their friends when they are dying.”

Ann Marie: “Petty disagreements often end decade-long relationships with family and friends. Only when facing death do they realize just how petty those disagreements were.”

Regret #5. I wish that I had let myself be happier.

Bronnie: “This is a surprisingly common one. Many did not realize until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to themselves, that they were content, when deep within, they longed to laugh properly and have silliness in their life again.”

Ann Marie: “Many of my patients suffer deep emotional wounds that began in childhood and become life-long agonies that keep them isolated from others. In the final weeks of life, there are many tears, and many of those tears are from childhood. These are the lucky ones, as some, mostly men, can’t cry”.

1. Don’t wait.

2. Welcome everything, push away nothing.

3. Bring your whole self to the experience.

4. Find a place of rest in the middle of things.

5. Cultivate don’t know mind.

— Frank Ostaseski — The Five Invitations: What Death Can Teach Us About Living Fully

2. Explore Other Cultures

We rarely imagine that our ever-busy lives could end without a moment’s notice. We may not imagine it, yet people of many cultures do.

Numerous cultures live with the constant awareness of death. They treat death with respect, artistry, and verve by celebrating the lives of their dead with elaborate rituals for a smooth departure.

In Japan, dead bodies are not figures of dread. They are seen as the natural end of a mortal life.

Families, including young children, pray over their loved one’s decorated body in fragrant rooms, filled with the favorite foods, and personal effects of the deceased.

Conversations with the dead continue, reflecting on their life, and laughter can erupt as readily as tears.

Sadly, modern Western culture hides death from us. Anti-aging industries and modern medical science are testaments to this. The pervasive message, to believe in the eternal existence of the body, creates inflated egos and delusion.

For all but our most recent history, death was a common, ever-present possibility. It didn’t matter whether you were five or fifty. Every day was a roll of the dice.”
– Atul Gawande (Being Mortal — Illness, Medicine and What Matters in End)

Death is quickly ushered away from our eyes into the shadow of our psyche, making it a miserable affair that leaves open wounds and indelible scars on the living.

It doesn’t have to be like this.

Only yesterday a friend attended a Buddhist ceremony in the city of Sydney to pray for her recently deceased father, and to invite the assistance of ancestors for his safe passage.

My friend is not a Buddhist, but she has intelligently engaged in their rituals for her own healing, for her father, and for all those who gathered on the day.

Become aware of your culture’s attitudes and beliefs about death.

Investigate other cultures and identify the practices and beliefs that make sense to you and touch your heart.

In most Western cities you can find thriving pockets of alternative cultures, far removed from the mainstream, performing rites and rituals that can challenge and even realign your beliefs.

Seek them out.

Eternity isn’t some later time. Eternity isn’t a long time.Eternity has nothing to do with time. Eternity is that dimension of here and now which thinking and time cuts out. This is it. And if you don’t get it here, you won’t get it anywhere. And the experience of eternity right here and now is the function of life.
— Joseph Campbell

3. Break the Silence Around Death in Daily Life

Break the silence around death by acknowledging everyday endings, losses, and transitions; relocations, jobs losses, project completions (successful or not), changing schools, relationship endings, and animal deaths.

Help family and friends acknowledge the little deaths they’re going through as natural and meaningful.

Make death okay for them, and don’t forget to ask that for yourself.

Celebrate or commemorate the endings that are going on all around you.

Recently I admitted my mother into aged care, a significant ending for both of us since we are very close and I have been managing her daily needs for three years.

I had been preparing for this inevitable change, as much as anyone can, practically, psychologically and spiritually, for well over a year. I believe the preparation helped everything go well and yet the transition is still an immense loss. Age is wearing her life-force and memory away rapidly. I feel it deeply.

Friends have helped enormously simply by being present to my exhaustion and grief, and by relaying stories about recent transitions of their own.

Over one memorable dinner, we celebrated my mother’s active life, her necessary and painful transition, and my new found freedom in no longer having to manage her daily needs. We discussed conflicting feelings — loss, grief, change, and freedom.

I showed photos of her; we lit a candle, said a prayer, and ate cake.

Then I called my mother and she was unusually chirpy and chatty.

Something had shifted.


Possibly, but never underestimate the ripple-effect of creating and sharing simple rituals around your deepest feelings.

Everyday rituals

Rituals help us to assimilate all endings (and beginnings) into our psyches.

All of us can rekindle the old art of ritual (and rites-of-passage) within our families and communities. We simply invent them.

No need to make it elaborate. The important thing is to bring yourself to the situation and acknowledge the transition.

Help your children embrace change consciously and joyfully.

For example, you could celebrate your child’s last day of grade school or university. Light a candle as you commence dinner and tell your son how well he did. At the end of the dinner, extinguish the candle and announce, “let the new phase begin!” Open a window, and allow the fresh wind rush in.

How about a symbolic gift for your daughter’s first menstruation to celebrate her rite-of-passage from girlhood to womanhood?

How would these simple little rituals make your children feel?

They may well feel that you’re acting weird, but they’ll get used to it, and soon your rituals will become more meaningful than weird.

Your conscious relationship with everyday transitions will open new doors of perception. As you mark beginnings and endings with little rituals, you imprint positive psychological structures. This alters how you feel about your life in ways that you cannot predict or imagine.

4. Learn the Skill of Change and Letting Go

Within every change is the seed of death.

If you cannot accept change, it is unlikely you will accept death — your death, and the death of loved ones.

Change is not a concept. It cannot be understood through thinking. It needs to be experienced in your nervous system, again and again, until it becomes part of you.

The word Moksha is Sanskrit for liberation. It refers to the final liberation that occurs when we die and when our spirit is liberated from the body.

Moksha also refers to the smaller liberations that occur throughout our lives, that are required to create a healthy balance between acquisitiveness and release.

To experience Moksha practice letting go of your stuff.

Why? Because every time you do, you teach yourself that you are more than anything you own, more than your possessions, attitudes, opinions, tastes, preferences, and identifications.

As you become liberated from your stuff, you connect with your essential, unchanging Self, and can experience the bliss of just being.

In the end, if any part of you is going to reign beyond your death it is your spirit — not your body, and surely not your stuff.

“If the person doesn’t listen to the demands of his own spiritual and heart life and insists on a certain program, you’re going to have a schizophrenic crack-up. The person has put himself off center. He has aligned himself with a programmatic life, and it’s not the one the body’s interested in at all. And the world’s full of people who have stopped listening to themselves.”
— Joseph Campbell

Let go of your stuff and start listening to your Self.

Let Go

Let go of things that are difficult to let go of; habits that diminish your vitality, the need to be right (even when you are right), and the need to be liked and admired.

Once you get good at that, attempt bigger things, such as your need to always be treated with total respect, or to have your status acknowledged in every situation.

Play the opposite role to the one you are so attached to.

Play the fool, the buffoon, the ignoramus or the scaredy cat. Allow someone to dump on you. Accept their anger and don’t fight back. Let others win for no good reason.

This experiment is not about voluntarily becoming a victim of dangerous abuse. And it’s to be done skillfully; with the right mindset and context. If you are a doctor, you would not want to act the fool with your patients. But in another context, say when you are traveling, you may resist introducing yourself as Dr. Joseph and just be plain old Joe for a day.

The game taunts the part of you that is overly invested in your stuff. You are setting yourself up, watching your ego freak outDeath is occurring. A healthy, voluntary, death.

Practice changing your routines and habits such as your daily travel routes, exercise routines, and diet.

Change your pattern of speech. Remove definitives like ‘yes’ and ‘no’ and become more expressive. Assume a different behavior, introduce different thoughts, move differently.

Give support to others — your great ideas, your time, your honest thoughts, possessions, and money.

Go against your grain. Aim to increase your gratitude and decrease your regrets.

Dead people receive more flowers than the living ones because regret is stronger than gratitude.
— Anne Frank

5. Meditate On Death

While we cannot change our culture’s feelings of abhorrence regarding death, we can work on our individual consciousness.

One way to do this is to meditate on the possibility that your death is imminent.

Death is not waiting for us at the end of a long road. Death is always with us, in the marrow of every passing moment. She is the secret teacher hiding in plain sight. She helps us to discover what matters most.
— Frank Ostaseski

Christian Newman — Unsplash

An excellent meditation to begin this process is the initial stages of Inner Silence.

Inner Silence is a mindfulness technique (passive style meditation) where you deepen, and focus on your breath until you become calm.

You observe the sounds in your environment, focus on one, let it go, then skip to the next. Focus, let go, focus, let go, etc. Allow all thoughts to come and go without trying to suppress or hang on to them.

After performing the initial stages of the meditation:

  • Imagine that your death is imminent, e.g., in 3 days, 3 weeks — whatever imminent means to you. Once you feel connected to this reality…
  • Observe how your feelings change. Even a subtle shift is important to experience.
  • What feelings arise? It could be regret, sorrow, loneliness, anger, gratitude, joy, love, or compassion.
  • Ask yourself about the reason for this emotion.

Now ask yourself a few of the following questions. (All would be too much for one session, so just pick 1-3 that push your buttons).

  • How do you relate to those close to you? Are you open, or partially open? Do you share your feelings so that others know you?
  • What are you doing beyond a self-orientated existence? Are you consciously using your life-force to improve the lives of others?
  • Are you running after money and success to the neglect of your relationships?
  • What would those closest to you say about you at your funeral?
    What would you like them to say?
  • Are you actively healing your emotional wounds or allowing them to separate you from loved ones?
  • Recall any unlived dreams. Are they still alive and desired? If so, how you can make this dream happen? If not, do you have a new dream?
  • Do you have a clear purpose for your life?
  • Do you wish to leave a legacy? If so, describe it.
  • Write your insights after this meditation. What do you want to change?
  • Ensure you end with an energizing (active) meditation, such as Ajapa Japa or Prana Meditations take strong breaths to re-energize your body. Massage yourself.
  • Be kind to yourself all day long.

6. Interact with Myths, Art, and Symbols of Death

It has always been the prime function of mythology and rite to supply the symbols that carry the human spirit forward, in counteraction to those that tend to tie it back.
— Joseph Campbell

Death in the Media

Media images of death, whether broadcast through the daily news, television, movies or games, are intended to keep your eyes peeled to the screen.

These gruesome images manufactured for maximum impact wear thin after a while. Attention drifts away from the screen. It’s all so predictable and dull.

Crime stories get more sadistic, bizarre, and autopsy-orientated by the year because of our numbness to manufactured death. “Let’s get another close up of the disembowelment,” calls the director, hoping this shot will disgust his fans into word of mouth advertising.

He doesn’t get that we’re overexposed and numb to violent antics and that upping the gore bores us even more.

In the movie theatre, kids, teenagers, and adults want the same thing — to be emotionally moved. When a well-drawn character expresses subtle displeasure, we’re hooked. We’ll worry about her; we’ll root for her— until she wins.

Now that I’ve vented, I’ll get to my point…

Being numb to the image of death is unhealthy. It means that you’re numb to the most dramatic event of life.

Media’s proliferation of manufactured death does not prepare us to encounter a dead body in the flesh.

It’s important to make a conscious distinction between media death and real death. You create this distinction by getting in touch with more authentic, complex depictions of death through myths, imagery, and symbols.


Myths explore the interplay of opposites: love and war, pride and humility, ignorance and wisdom, creation and destruction. They help cognize the ultimate opposites of the human condition, life, and death.

As you become absorbed in mythic drama, you begin to feel the opposites within yourself.

Reading about the gods of death and the afterlife awakens your sleeping chamber of death.

Each myth you read will teach you more about life and death than a dozen self-help books could ever do because myths penetrate your unconscious mind. As you know, your unconscious creates your reality.

Read the Greek myths of Thanatos or Hermes; escorts of souls to the underworld. Choose Egyptian Anubis, the Dog-Headed protector of the mummification and the underworld. Attempt to understand Kali, the Hindu Goddess of time, and destruction (of illusion and negative ego).

Goddess Kali — Destroyer of Time and Illusion

Dive into the drama, and you’ll soon see how myths and their archetypes play out in your life, and in the life of your friends.


If you are remotely interested in cognizing death, then you will want to re-sensitize your feelings about death.

The way to do this is through contemplating images of death. Not by exposure to popular media, and mainstream movies (as discussed), but through thoughtful and illuminating depictions of death.

Evolved artists, photographers and filmmakers will often provide a fascinating and educational path into death. Art functions in a similar way to myths. Art touches the universal truth in us.

As you experience the creator’s work take notice of the feelings and thoughts that arise in you.

Art can evoke deep memory, both personal and universal. It can awaken intuitive self-knowledge, and expand your emotional and intellectual range which is constantly being dulled by the normality that society demands.

Art can evoke deep memory, both personal and universal. It can awaken intuitive self-knowledge, and expand your emotional and intellectual range which is constantly being dulled by the normality that society demands.

Thinking About Death — Frida Kahlo

Reading the artist’s story is illuminating.

Frida Kahlo’s Thinking About Death features a skull and crossbones on her forehead.

In ancient Mexican culture, the skull and crossbones symbolize rebirth and life. In Eastern spiritual traditions, the center of the forehead is believed to be the portal to the third-eye of psychic vision.

Kahlo painted her self-portrait in 1943 while bedridden through a severe illness. Death was on her mind, yet she portrays herself against vibrant, living nature. She sees abundant life in death.

Head to the art gallery and watch your emotional and intellectual landscape expand.


Just as myths and art bring complexity to the psyche, so do ancient divination systems.

The I Ching (The Book Of Changes), is an ancient Chinese system of divination. It consists of 64 hexagrams that illustrate the laws of nature and cosmos as they pertain to the stages of human development.

Each I Ching hexagram is a piece of actionable wisdom that begins with an image, a metaphor for a particular stage of life.

For example, the I Ching Hexagram 23. Collapse describes a large, mature tree with its fruit ready to fall. The image is used metaphorically for the human experience of collapse. Collapse occurs because of extreme fullness, the load is too much to bear, and the cycle of growth has reached completion.

Collapse is followed by Hexagram 24. Returning, which describes a seed beginning to sprout. In nature, life always follows death.

All your deaths will give birth to something. Nothing will be lost.

The I Ching is famous for the phrase Contemplate the Image.

The ancient seers knew the power of the image to teach and heal.

Holding divination images in mind as you face your small and big deaths connects your individual experience of life with Nature itself. This helps you to break through the isolation of the death experience and to realize that you belong to something far beyond your control. You are never alone. You are part of the great mystery and awe of life.

The Tarot works in the same way. The archetypical journey of humanity is illuminated through imagery.

It is unfortunate that most modern Tarot readers forget to suggest that their clients explore their own relationship to the imagery as the reading takes place. The cards usually face the reader.

You can use Tarot cards to expand your relationship to upheaval, change, and death by contemplating the image.

Don’t worry about the official interpretation initially, use your interpretation — your intuition. Read the book later.

Rider Waite Tarot Death Card

What does the image say to you? What feelings does it evoke?

In almost all Tarot decks the death card includes the image of a small child. Why would that be?

This exercise will teach you a great deal about your cultural and personal beliefs and feelings about change, endings, and death, and importantly, how you feel about life.

Your life!

7. Express Your Experience of Death

Expressing your experience of death is powerfully healing and awakening.

Your photograph, painting, collage, song, dance, sonnet, or poem connects you with the death process.

Nic.Co.Uk — Unsplash

Once your work is complete, you see your relationship to death reflected back to you. Return to it 3 months or a year later, and you will learn even more about this critical relationship.

You don’t have to be great at it. It’s about the expressive process, not the outcome.

Recently, a relative died.

She was difficult to love because of her severe psychological issues that caused her to want to hurt others. She would often fight her impulses to lash out and hurt. Just as often her impulses won. Afternoon tea usually included a generous dose of her venom.

The day before her death, she lucidly expressed her regrets, realizations and her reluctance to die, because of them.

I wrote this poem on the day of her death.

Death’s Day

I’ve spent my days running away
Wishing a miracle would come my way
Appeasing the Moon and Saturn too
Desperate for anything to relieve my gloom

Don’t send me there just yet, I pray
Don’t call in my angels, keep them at bay
Stall great Nature in her dutiful task
Of expiring my life. Oh please, just ask

Give me time to repair these broken threads
To beg forgiveness from family and friends
To dream of what life could have meant
Had I more easily made amends

Then I’ll go peacefully to the unbound world
I’ll leave a little kindness amidst the anger I hurled
I did feel for some, though rarely expressed
Compassion as well, though seldom confessed

It seemed weak to me, so I kept my cruel shell
Unleashing my woes onto all who fell
Into my web of careful deceit
Where I demanded allegiance and flattery

Despite the pains my illness brings
I know none greater than those I’ve inflicted
And this is the real tragedy of my life
That I brought so much sadness and strife

My only excuse is my childhood wound
From the day of my birth a great curse loomed
My father would say, “You’re ugly as sin.
You will never marry or have children.”

My mother, too weak to come to my aid
Allowed the curse to keep me afraid
Of daring to believe I am worthy of love
Of ever having faith in a caring God

Please shed a tear for my sad, sorry soul
Now that you know my dreadful toll
I did care for you in my fractured way
But only now I know love as I greet death’s day

Do stuff. Be clenched, curious. Not waiting for inspiration’s shove or society’s kiss on your forehead. Pay attention. It’s all about paying attention. Attention is vitality. It connects you with others. It makes you eager. Stay eager.
– Susan Sontag

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