As my husband and two kids left in the aerial tram towards their second ziplining adventure last week, I felt a pinch of an unpleasant feeling in my heart.

I had decided to skip the second ziplining. I thought I could redirect this investment to a spa. I opted for pampering rather than adrenaline.

But, as my family leaves without me, I recognise the unpleasant feeling as regret.

I notice a part of me trying to fight the regret. In my mind, I defend my decision to skip the ziplining.

I mentally go through the reasons why my decision was correct.

My body does not like the sadness of regret. My ego does not want to admit I was wrong.

And then I decide to allow myself to feel regret.

I know from my vision work that regret is one of the most powerful tools for clarifying what you value.

As I allow the sadness to surge, I think that I potentially missed a peak experience with my family out of fear. What if we would have had an extraordinary amount of fun together? Flying over the jungle?

Regret is sadness over a choice we made when we compare the might-have-been scenario to the present.

Feeling the regret helped me clarify something I value: unique experiences with my family.

In his book “The Power of Regret”, Daniel Pink shares research about how regret is useful. Ir helps us make better decisions, improves our performance and adds meaning to our lives.

Allowing ourselves to feel regret, learn from it and move on will fast forward our growth and evolution.

The Four Types Of Regret

Pink found that we have four key types of regrets. Let’s go through them.

Foundation regrets

The key theme here is “I wish I had done the work.”

In the fable of the ant and the grasshopper, the grasshopper parties all summer instead of collecting food. When the winter comes, he has a foundation regret.

Foundation regrets include: “I wish I had saved more,” “I wish I had eaten better and exercised more,” and “I wished I had less alcohol or no tobacco.” “I wish I had studied more or worked harder.”

We often discount the future over the present. We do not grasp the power of compounding. Even small actions, positive or negative, have disproportionate results over time.

Boldness regrets

The key theme here is “I wish I had taken that risk.” I often help people avoid this type of regret when we work on their life vision.

Start that business, change careers, speak up more, move countries, ask that person out.  

The data is conclusive that we are much more likely to regret what we did not do than what we did.

Morality regrets

The critical thought here is, “I wish I had done the right thing.”

According to the data, these are not the majority of people’s regrets, but morality regrets are painful.

People regret bullying someone during school years, cheating on their partner, lying, etc.

Connection regrets

There is nothing that predicts happiness more than love. Most of our regrets are in this category. Wishing to have spent more time with someone, regretting falling out, etc.

The theme here is “I wish I had reached out.”

How to deal with regret

I sat with my family this week, and we listed our regrets in each category.

Then, we extracted the lessons from them to make better choices in the future.

Here are some of my regrets:

  • I wish I had educated myself about nutrition sooner.
  • I wish I had treated some conflicts with friends better in my teenage and young adult years.
  • I wish I had my nanny until 17:00 and not until 18:00 last year so I could have spent more time with my kids.
  • I wish I had not wasted years complaining about others in my twenties.

These regrets make it clear what I value: health, family, friendship, and happiness.

By allowing myself to feel regret, I know how to make better choices in the future.

It is important to note here that regret does not equal shame. Shame is feeling that we are less worthy because we made a mistake.

Mistakes are human. We need to approach our regrets with self-compassion and forgiveness.

If we do not acknowledge our regrets, we do not learn and keep making the same mistakes

If we ruminate in regret, we get stuck in misery and the past.

Both courses of action are suboptimal. There is a better way.

Here is my invitation to you.

  • List all your regrets in the four foundational areas.
  • Extract the learnings. What do these regrets tell you about what you value, and how will they influence your future decisions?
  • Forgive yourself and your mistakes with self-compassion. You did the best you could with the level of awareness you had at the time.


Regret is not pleasant, but it is better to feel it and learn rather than avoid it and continue making the wrong choices until the end of your time on earth.

Ripping off the bandaid is less painful than taking it off slowly. Feeling our regrets is less painful than continuing a life out of alignment.

Take care,


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PSS: If you are contemplating a big career change in the new year, my interview with VisionPath Alum Mustafa Bosca might just provide the inspiration and insights you need. Mustafa left a consultancy partner role, launched his own business, and created more wealth in 3 months than he would do in a year in his old job. Watch it here.

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