How to Live Life With No Regrets

Bronnie Ware’s perspective on life was transformed by an unconventional character: death.

Working in a palliative care environment, Ware spent her days at the bedside of people in their last 3-12 weeks of life.

Life and death are two sides of the same coin. It’s the inevitability of death that makes life so precious!

Most people avoid thinking about death, but Ware and her patients didn’t have that luxury.

And we should be thankful for that. Their unique perspective gives us insight into some profound questions:

• What lessons of life can we learn from the dying?
• When death is on the horizon, what do people have to say about life?

One of the most meaningful themes Ware observed was the universal nature of regret.

When reflecting on their lives, patients would speak of things they wished had gone differently. And despite coming from different backgrounds and walks of life, a common set of regrets surfaced again and again.

In 2009, Ware chronicled these regrets in an article, Regrets of the Dying.

In case the image doesn’t load for you, here are the Top 5 Regrets of the Dying that Ware outlines in her article:

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 that I had let myself be happier.”

It’s striking how relatable these regrets are to anyone who reads them. I see myself in these regrets, and I’m sure you do too.

Reading them can create a sense of urgency, and a desire do something to avoid these regrets at all costs!

But before considering how to avoid regrets, let’s take a minute to understand the nature of regret more clearly.

Where Does Regret Come From?

Regret shows up when you fail to live in alignment with your most authentic self.

Everyone has the potential to live a beautiful and abundant life that’s deeply rooted in their values and priorities.

Unfortunately, this vision of life is an exception to the rule. Countless obstacles like fear, social pressure, and limiting beliefs get in-between you and your best life.

And when these obstacles overpower your desire to live true to your authentic self, regret surfaces.

Regret is the cognitive dissonance you feel when acting against your truest self.

The more that your choices deviate from your values and priorities, the stronger your experience of regret will be.

But, it would be silly to pretend that all regret is the same. At the highest level, it breaks down into two fundamentally different categories.

The Two Flavors of Regret

Regret comes as a direct result of your choices. After all, choices are the driving force the shapes your life.

The life you live today is the direct result of the millions of choices you’ve made since childhood (plus a bit of environmental influence and randomness.)

Choices in life can be organized into four categories.

1. Aligned Inaction: Things you choose not to do that are aligned with your true self.
2. Aligned Action: Things you choose to do that are aligned with your true self.
3. Misaligned Inaction: Things you choose not to do that are not aligned with your true self.
4. Misaligned Action: Things you choose to do that are not aligned with your true self

Of these four categories, #2 and #3 are where you want your choices to land.

#2 = Do the things that align with what you care about.

#3 = Don’t do the things that don’t.

The remaining categories, Aligned Inaction and Misaligned Action, are where regret rears it’s ugly head.

Regret Category 1: Aligned Inaction

“You miss 100% of the shots you don’t take.”
– Wayne Gretzky

What it is: Actions you didn’t take, but would have been an expression of your authentic self.

Why this happens: You let life’s pressures prevent you from taking action. For example:

• Fear: The negative feelings associated with something not going as you hope it will can be paralyzing. Fears of failure, discomfort, and embarrassment show up frequently.
• Limiting Beliefs: How you characterize yourself and the world around you influences the actions you take. You can be your own worst enemy with self-talk like, “I don’t have what it takes”, “I’m not smart, good, strong, _____ enough”, “I don’t have enough time, money, _____”, or “I don’t deserve it”.

Examples of Aligned Inaction

• Professional: Failing to reach out to someone you admire, for any number of excuses (fear of annoying them, or not being smart enough to make it a good conversation, or…)
• Relationships: Not asking someone out on a date for fear of rejection, even though you clearly have chemistry together.
• Health: Not going to see the doctor for a nagging issue because you fear the visit will reveal something uncomfortable, or force you to change your behavior.

Regret Category 2: Misaligned Action

What it is: Actions you did take, but were not aligned with your truest self.

Why this happens: Internal or external pressures cause you to act in a way that doesn’t align with your best self. For example:

• Social pressures: Group and team settings have powerful influence over individual behavior. This can come from feelings of guilt, fear of judgement, or the desire to be polite (among others.)
• Conditioned behaviors: Your values and priorities change over time. But it takes awareness, time, and effort to change existing habits and behaviors to match them.
• Fooling Yourself: It’s surprisingly easy to convince yourself to do something, even when it doesn’t align with your values, ethics, or priorities.

Examples of Misaligned Action:

• Professional: Working a job that makes you miserable, and rationalizing it because it pays well.
• Relationships: Continuing to date someone even though you know you don’t mutually support each other’s wellbeing.
• Health: Giving into your habit of staying up late to surf the internet, causing perpetual sleep deprivation.

These two categories of regret can feel daunting to face. But since regrets are a result of your choices, this means you have the power to overcome them!

Avoid Future Regrets by Cultivating Self-Awareness and Understanding

There’s no way to consciously prepare for every scenario you’ll encounter in life. After all, most of the choices you make in life happen in a split-second.

A mindfulness practice that cultivates self-awareness and self-understanding is an effective way to consistently make choices that align with your truest self.

Self-awareness helps you see your daily decisions more clearly, in the moment.

Without self awareness, you end up going through life on “autopilot”.

But when you’re present to your experience, you have the opportunity to act with intention.

Meditation is the most effective way to build self-awareness, and understand the nature of your mind.

(If you’re looking for assistance building your habit, Mindful Every Day is a month-long online course I created to help you do that! Or click here for more information from the Beginner’s Guide to Mindfulness.)

Self-understanding helps you see yourself more clearly. When you’re clear about who you are and what matters to you, it makes every decision easier. There are fewer options to consider, because you’ve articulated that certain things don’t align with your authentic self.

To develop self-understanding, make time for introspection via journaling/reflection. Write about your life, what’s most important to you, what brings you up, and what you’re challenged by.

If you’d like to kick-start your journaling and reflection process, enter your email in the box below. I’ll send you a download with a variety of prompts to start understanding yourself deeper.

It’s important to note here that mindfulness is called a practice for a reason.

Meditation and journaling aren’t about perfecting your self-awareness or understanding. Life is dynamic, and you are constantly growing and changing. Your values and priorities, and the nature of your mind, will shift with time.

While it’s important to live in a way that avoids regret altogether, it’d be shortsighted not to address dealing with existing regrets, or new ones when they arise.

Letting go of Past Regrets (The Silver Lining)

It might seem like the experience of regret is devoid of positive qualities. But that’s not the case!

There’s a silver lining hidden within regret: Feelings of regret are powerful learning opportunities.

Since regrets arise when you make choices that aren’t aligned with your authentic self, they serve as a guide to understand your values and priorities more clearly. Half of knowing what is aligned with your authentic self is understanding what isn’t aligned.

Despite this silver lining, regret is nothing worth holding on to.

What’s happened in the past has shaped you, but it shouldn’t control how you act in the future.

So, when you become aware of feelings of regret, take time to reflect on it, and let go.

Here’s a structured reflection you can use for that purpose:

1. What do you regret?
2. What action did you take/not take to cause this?
3. What prevented you from acting in a way that’s aligned with your best self?
4. If presented with the same situation in the future, how would you act differently?
5. Can you accept that this event has passed?
6. Do you see how this event has helped you learn about yourself?
7. Are you ready to let go of these feelings of regret so the past doesn’t control your future?

Avoiding the Top 5 Regrets of the Dying

With greater understanding of regret in hand, let’s revisit the Top 5 Regrets of the Dying, and how you might avoid them in your own life.

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

• Type of regret: Unaligned action + aligned inaction
• This regret shows up when: You let the pressures and expectations of other people dictate your behavior. Instead of acting in line with your priorities, you act in accordance with somebody else’s.
• How to avoid this: Understand that other people have different incentives and priorities than you do. In the event that they don’t align with yours, don’t succumb to the pressure of expectations. Know that it’s not inconsiderate to live by your priorities.

2. “I wish I hadn’t worked so hard.”

• Type of regret: Unaligned action
• This regret shows up when: You let your professional ambitions squash your other priorities.
• How to avoid this: Hold your priorities top of mind, and remind yourself of them regularly. Let go of impatience in your work and career that causes you to ignore other priorities.

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

• Type of regret: Aligned inaction
• This regret shows up when: You let fear of discomfort prevent you from being vulnerable with others.
• How to avoid this: When faced with the option to choose comfort or courage, pick courage.

“Integrity is choosing courage over comfort; choosing what is right over what is fun, fast, or easy; and choosing to practice our values rather than simply professing them.”

― Brené Brown, Rising Strong

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

• Type of regret: Aligned inaction
• This regret shows up when: You project discomfort on the act of re-engaging with someone, and it prevents you from reaching out at all.
• How to avoid this: Make a commitment to “going first”¹ in social interactions. Instead of waiting for someone to engage with you, choose to reach out proactively.

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

• Type of regret: Unaligned action + aligned inaction
• This regret shows up when: You don’t give yourself permission to be happy with life as it is. Instead, you seek more, with the hope that getting more will make you happy in the future.
• How to avoid this: Focus on living in the wholeness present moment, instead of deferring happiness to a later point in time. Choose your desires carefully, with awareness that desire is a decision to be unhappy about something until you get it.

Regret-Free Living

Regret is uncomfortable. At times, it can seem to consume your entire being.

But the real tragedy of regret isn’t it’s emotional experience. It’s the fact that regret represents a departure from the path of your best life.

Focus on living a regret-free by showing up as your authentic self on a daily basis. Let go of the fears and obstacles that prevent you from spending your time and energy in ways that aligned with your priorities and values.

Regret-free living is a never-ending journey of exploration, challenges, and self-discovery.

But with greater self-awareness and self-understanding, you’ll be well equipped for the journey.

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1: Hat tip to Gabrielle Reece for the “Going First” philosophy, as discussed on The Tim Ferriss Show. Audio clip here.