How You Can Stop Letting Your Regret(s) Eat Away at You

A review and reflection on The Power of Regret by Daniel H. Pink

You can skim as follows:

1. What made me read this book?
2. Why you shouldn’t aim to minimize your regrets
3. What are the 4 core regrets?
4. How can you make peace with your regret(s)?
5. How the book changed me

1/5 What Made Me Read This Book?

How often do you look back on your life and wish you had done things differently?

After reading The Top 5 Regrets of the Dying, I wondered:

When can I stop regretting?

It’s one thing to avoid regrets.

But what about all the ones I already have?

How do I know if this is really worth regretting?

How can I move on?

2/5 Why You Shouldn’t Aim to Minimize Your Regrets

Antipicating your regrets can help you make better decisions.

For example, ask:

In the future, will I regret this decision if I don’t do [action]?

Answer the question.

Apply that answer to your current situation.

You have a good start.

But is the less regrettable choice always the smarter choice?

No.

For example:

You should stick to your first instinct on tests.

Don’t change your answer.

But this conventional advice is wrong.

You’re actually more likely to change from a wrong answer to a right answer.

Not the other way around.

But we follow this advice because it leads to minimizing potential regret.

We’re also pretty bad at predicting:

• how intense our future regret will be
• how long our regret will last
• how well we’ll cope with our regret
• if we’ll have regret about our decision at all

So how do you use your regret to make better decisions?

You need to know:

1. When to maximize (pursue the ideal) and
2. When to satisifice (accept ‘good enough’)

Why shouldn’t you maximize everything?

(i.e. Try to minimize every single regret?)

You end up feeling regret all the time.

Before you make your choice.

While you make your choice.

After you make your choice.

Trying to maximize happiness (minimize regret) on everything means destroying happiness on most things.

So optimize your regret instead.

If you’re not dealing with 1 of the 4 core regrets…

Just satisifice.

3/5 What Are The 4 Core Regrets?

The most painful regrets fall under 4 core categories:

1. Foundation — you wish you had done the work.
2. Boldness — you wish you had taken the risk.
3. Moral — you wish you had done the right thing.
4. Connections — you wish you had reached out.

Foundation Regrets

You wish you had done the work.

You want stability.

Foundation regrets sound like:

1. ‘Too much’ when it comes to activities that reward now, not later
2. ‘Too little’ when it comes to activities that reward later, not now

For example:

• I wasted too much money on alcohol.
• I spent too little on studying for my exams.
• I cared too little about my health.

Boldness Regrets

You played it safe and wished you took your chance.

You want growth.

For example:

• I should have asked them out.
• I should have gone on that trip.
• I should have tried to start my business.

Moral Regrets

You wish you had done the right thing.

You want goodness.

Moral regrets are related to 5 pillars:

• care/harm — ex. Did you harm someone? Fail to defend someone?
• fairness/cheating — ex. Did you breach someone’s trust?
• loyalty/disloyalty — ex. Were you true to your team? Sect? Nation?
• authority/subversion — ex. Did you fall short of your obligations?
• purity/desecration — ex. Did you disrespect someone or something you consider sacred?

Connection Regrets

You wish you had reached out to care for a broken or neglected relationship.

You want love.

They take 2 forms:

1. ‘closed door’ — a relationship where your opportunity to restore your connection is gone (ex. someone passing away before you could reconnect)
2. ‘open door’ — a relationship where you could reconnect with some effort, but you risk awkwardness, rejection and emotional turmoil

4/5 How Can You Make Peace with Your Regrets?

Undo it

Maybe you’ve harmed someone (be it a moral or connection regret).

Can you apologize?

Can you give some kind of emotional or material restitution?

Or maybe you’ve harmed yourself (like a foundation or connection regret).

Can you correct course?

For example:

Start paying down your debt.

Reach out to someone you cut off or drifted away from.

‘At Least’ it

Perhaps you can’t repair your past actions (like an action regret).

You can reframe how you think about them.

Ask:

How could your regretted decision have turned out worse?

What’s one silver lining to your regret?

Complete the sentence: “At least…”

Disclose it

You can release yourself from your regret by writing or talking about it.

For example:

Write about your regret for 15 minutes for 3 days.

Talk about your regret into a recorder for 15 minutes for 3 days.

Tell someone else about the regret (but keep it within a time limit — say 30 minutes) to prevent repetition and brooding.

Have compassion for yourself

Don’t criticize yourself for your regret.

That only leads to rumination and hopelessness.

Not productive action to help you move on.

If you normalize your negative experience…

…you neutralize it.

Don’t suppress it.

But don’t exaggerate it or over-identify with it either.

Your regret is normal, universal, and makes you human.

If one of your loved ones told you about the same regret…

…wouldn’t you treat them kindly?

Show yourself that same kindness.

Is your regret something that other people might have endured?

Or are you the only person ever to have experienced it?

Remember that your stumble is part of our common humanity.

Does this regret represent an unpleasant moment in your life?

Or does it define your life?

If you believe it’s worth being aware of the regret but not overidentifying with it — good.

If you believe this regret fully constitutes who you are?

Ask someone else what they think.

Distance yourself from it

You can distance yourself from your regret in 3 ways:

1. Space
2. Time
3. Language

Give yourself space

You can use the ‘fly-on-the-wall’ technique.

Look at your regret as a neutral observer.

Instead of:

I messed up by letting my friendship fray and then doing nothing to fix it.

Say:

I watched someone let an important friendship drift.

But we all make mistakes.

They can save this one by reaching out to meaningful connections more frequently.

You transform your regret into a tool for your improvement.

Give yourself time

Right now, your regret feels heavy.

What about in 10 years from now?

You make the problem seem smaller, more temporary, and easier to surmount.

You replace self-justification with self-improvement.

Use different words to describe your regret

Write about your challenges using 2nd & 3rd-person pronouns:

• ‘you’
• ‘she’
• ‘him’
• ‘they’

You transform your regrets into challenges when you let go of the first person.

You replace distress with meaning when you talk to yourself objectively.

You deepen your commitment to improving future behaviour.

Consider:

Imagine your best friend is confronting the same regret that you’re dealing with.

What is the lesson that the regret teaches them?

What would you tell them to do next?

Be as specific as you can.

Now follow your own advice.

Does your regret involves your business or career?

You can ask yourself:

If I were replaced tomorrow, what would my successor do?

Imagine it is 10 years from now and you’re looking back with pride on how you responded to this regret.

What did you do?

Then do it.

5/5 How Did This Book Change Me?

This book helped me:

• break free of regretting everything I ever did or said (I am a self-admitted recovering maximizer)
• limit what I chose to feel and think more deeply on
• start making peace with my regrets
• focus on anticpiating the regrets that were actually worth mulling over (i.e. those related to my foundation, boldness, morals, and/or connections)

I hope this helped you free yourself from your regrets too.