The 1 Question to Cut Regret From Your Life
Posted on November 19th, 2015 by admin

R E G R E T.

The dreaded six letter word. I do not know how this word isn’t higher on the list of thing we are most afraid of. I am still trying to wrap my head around the idea that we, as a people, are more scared of public speaking than regret.

Are we more scared of insects and bugs over regret?! Sure bugs are nasty but, come on, regret? Let that sink in…

Regret = feel sad, repentant, or disappointed over (something that has happened or been done, especially a loss or missed opportunity).

Regret is is this silent driver within us that tunes us in a particular direction.

The Conflict

I often hear folks saying things along the line of, “I will regret it if I do not do this.”

I also hear the same folks saying things along the line of, “mm, I really want to but that’s a huge risk” or “mm, I want to but I am worried about what [insert family member(s), peers] will think of that decision.”

I am hear to ask you to, ‘hold up & pause.’

Understand Yourself

There is this pull and tug battle we find ourselves fighting often. On one hand, we know the action we want to take and understand that we may regret that may come with not taking action. On the other, these internal scripts that get in our own way. These internal scripts run through us and sometimes, they are so deeply embedded, that we do not even realize they are playing. We allow these internal scripts to run us and odds are often good they we will later regret the stance we took.

Do you understand yourself enough to know what you will regret and do you understand what your internal scripts are that will get in your way?

This is a tough question and no one answer for it.

I would challenge you to consider what your internal scripts are.
If they are related to family members or peers –

How have they responded in their lives when faced with a decision point where regret was involved?
Did they take the risk or not?
What does their life look like now?
Are they happy?
Do they ever talk about a situation they regretted?

Pay attention to your internal scripts and pay attention to why they drive you to allow a situation you mayregret to happen. Pay attention to the drivers of your internal script and consider if they are worth challenging.

My family and peers mean the world to me. I would do anything I could if they needed something. However, I want to minimize the regret I carry in my life and know that I need to let go of any thoughts I have about being worried from their responses to decisions I make.

Through these times of letting go of worries of what they would think, I realized that after my decisions, they were still there. In some cases, there were situations where the people I cared about most did notapprove of the decision I was making but I learned that that was okay too. It was okay because they had to come around. I learned that it was not a ‘me’ issue – it was something my loved one had to reconcile with themselves. Over time, they would come around, too.


Well, because my decision was made and it was hop on, support and care for me or let me go. The people who really care for you will be there for you – maybe it will take some time – but they will be there. At the end of the day, your loved ones would want your support with a decision whether or not you agree, too. If they did not care about your support, then why does theirs matter?

The Ultimate Question To Ask Yourself

When you are wondering whether or not to take action on something and you know regret may be involved you have to ask yourself this one question:

In 5, 10, 20, 30 years, will I regret not doing this?

If we are talking about investing in yourself with a course, more knowledge, this applies.
If we are talking about adopting a healthier lifestyle with food, hikes, walks, swimming, etc., this applies.
If we are talking about taking that International trip to make up for never studying abroad, this applies.
If we are talking about moving across the country for college, to further your career or to start a new business, this applies.

What if I Fail?

This is valid. I ask you to consider what if you do nothing and never know? Failure is great – in these moments, we learn and grow the most. We bounce back with more knowledge than we had before. We have the ability to try again. We have the ability to say, “You know, I tried it, I learned x, y, z and it was a great experience.”

Fail fast, fail often and learn.

Minimize Your Regret

Use the regret minimization framework by asking yourself, “Will I regret not doing this in 5, 10, 20, 30 years?” Let that question guide your personal compass and minimize your future regret.


EVOLUTIONARI' noun, often attributive : ([evolve = to develop slowly into a more advanced state in english] + [ri' = brave spirit in Taino]) a brave person who is known to tap into their inner warrior in order to become the best version of themselves possible.