min read
Braden Mosley

The 5 regrets of the dying: How to not regret them

In the famous book 5 Regrets of the Dying, Bronnie Ware recounts her experiences working as a palliative caregiver.

In the book, she identifies the top 5 regrets of those who are dying:

  1. “I wish I'd had the courage to live a life true to myself, not the life others expected of me.”
  2. “I wish I hadn't worked so hard.”
  3. “I wish I'd had the courage to express my feelings.”
  4. “I wish I had stayed in touch with my friends.”
  5. “I wish I had let myself be happier”

After watching the final episode of the Disney+ series “Limitless”, where Chris Hemsworth (aka Thor) wears a suit that makes him feel 50 years older, and joins a fake retirement home.

One of the main lessons Hemsworth learned was that aging is something you can fight, and live miserably, or accept and understand that “it’s not worse, just different”.

As someone who prioritizes my physical and mental fitness, the thought of growing older scares me.

So, today I will dissect each of the 5 regrets of the dying and search for changes I can make now to prevent such regret.

1.  “Live my true life, not what was expected of me”

One of the harshest displays of expectation I see today is wedding planning. Almost a year ago, I married the woman of my dreams. Throughout the year-long process of planning the wedding, she felt incredible amounts of regret, pressure, FOMO, and stress.

The high expectations our society places on weddings combined with the “perfect” weddings constantly displayed on social media is making brides feel like they are not enough.

But, if we take a step back, we can see that pressure to be perfect is self-imposed. We can create systems to help us put less pressure on ourselves.

I believe relieving this pressure starts with small, daily habits.

Famous author, James Clear says, “You don't eliminate a bad habit, you replace it.”

For example, if you have a habit of opening Facebook and scrolling until you feel like a pile of garbage, delete the app. Pick up a book instead.

Sometimes, people don’t want to go to extreme measures because “it shows a lack of self control”…

Well, I say show self-control by putting the right systems in place to stop a bad habit. Then, eventually, you no longer feel the urge to check Facebook at all.

2.  I wish I hadn't worked so hard

Studies show that About 40% of people over the age of 55 still work. If you feel like you are a workaholic, I’m right there with you.

I struggle with this one. I enjoy helping others, but sometimes, this makes me a “workaholic”. My mind constantly conjures up new business ideas and systems. I need to be more present.

A mentor of mine recently told me “I work to live, I don’t live to work”.

This reminds me of Simon Sinek’s famous book *“*Start with Why”

**If you are able to identify why you work so hard (needs to be deeper than money), you will be able to compartmentalize your attention as needed.

For example, if you work to provide for your family, they are your why. This will help you remember to be present when you are with them.

After all, what’s the point in working so hard if you neglect the very thing you are doing it for?

3.  I wish I'd had the courage to express my feelings

You environment is the external controllable that has the highest ability to change your mind.

Environments that cause you to suppress your feelings are toxic.

Older generations often have parents that buried emotions deep down in the name of “being a man” or a “strong mother”.

In reality, emotions are the very thing that connect us to one another. They make us feel empathy, and help us build stronger relationships.

If you feel like you are surrounded by people who don’t want you to express your emotions, you need to change your environment. It is not healthy.

Harvard.edu alludes to a study that shows isolated face a 50% greater risk of premature death than those who have stronger social connections.

I believe an inability to express emotions to someone who listens is incredibly isolating.

Most of the time, we are afraid to express emotions due to a fear of being judged. Throughout the history of mankind, humans have developed a fear of being shunned from the community. Thousands of years ago, in hunter-gatherer tribes, this meant death.

Most cultures have a saying similar to the Australian “Tall Poppy” proverb.

Some social groups have a tendency to “snip” the tallest poppy - the one that stands out. If you are afraid to get “snipped”, you will often suppress your emotions and try to fit in.

Here are a few things that will happen if you can change your environment and start sharing your feelings:

  • Those who want to judge will show themselves (these are people you don’t want to associate with anyway)
  • Those who are on your side will feel a stronger bond with you.

Next time you suppress your emotions, think of what Martin Luther King Jr once said,

People fail to get along because they fear each other; they fear each other because they don’t know each other; they don’t know each other because they have not communicated with each other.”

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

I’ll be the first to say I struggle with this one.

It feels like it’s is not in my nature to stay in touch with people - people I love and genuinely miss.

Usually, we lose a connection with friends over time and space, and the only way to maintain it is to reach out to them.

There are a few “false rationalizations” that prevent us from reaching out:

  1. “It’s a 2 way street”

This is the most common objection I hear to reaching out to old friends. “They don’t make an effort to reach out to me, so why should I reach out to them?”

This stubbornness will not serve you well in any way. Worst case, they don’t respond, or tell you they have moved on, giving you closure. Best case - they say they have missed you so much and can’t wait to see you.

  1. “The grass is greener on the other side”

When you grow apart from friends, you may feel like the relationship is not as good as it once was, like you used to have so much more fun together. “there must be people out there that are like me”.

In reality, the grass is green where you water it. So grab your hose.

  1. “I’m too busy”

This is my objection. I don’t prioritize reaching out to old friends. However, I also don’t judge myself for it. I am currently in a season of building a career and a family. Building friendships is not something I’m “putting off” it’s simply not at the top of my priorities right now.

However, I know that if I don’t prioritize it at some point, it will become a regret later in life.

5.  I wish I had let myself be happier

My wife and I recently went to see Jocko Willink, a former Navy Seal, leader, author, and speaker. The thesis of the talk was about decisions, and ownership.

”You always have a choice to make”, Jocko said, “The situation does not dictate our action, our action dictates the situation”

Happiness is a choice.

I understand this is easy to say. I’m not going to spew philosophical quotes or bible verses how happiness is internal.

Instead, I will point you to the very phrasing of this final regret…

”I wish I had let myself be happier.”

No matter how bad the deck of cards you’ve been dealt, you have a choice to make. You can let it consume you and rip the happiness from your soul, or you can use it to make you a better person.

The 2 parts of regret you may not consider

I like to say there are 2 things required to feel regret:

  1. The action or inaction that future you will want to change
  2. The act of regretting something you did

I try to preemptively cut out the 2nd part, eliminating regret altogether.


I tell myself “you made the best decision you could with the information you had at the time.”

Also, in the case that I did not do the best I could do with the information I had, I forgive myself and plan how to be better in the future. It’s the only non-destructive option.

That’s all I’ve got for today.

Hope it was helpful!

See you next week!

Subscribe to the Newsletter

Join 1,000+ readers of Retirement Reimagined for tips, strategies, and resources to gain financial freedom in your 60s.

100% privacy guarantee. No spam, ever.
Share this article on:

Taking the tired

out of retired

Subscribe to begin

Join 1,000+ readers of Retirement Reimagined for tips, strategies, and resources to gain financial freedom in your 60s.

100% privacy guarantee. No spam, ever.