The Regret that Cuts Deep and Lasts Forever

Treat Thompson



This is a republishing of The Steady Fella Newsletter. Twice a month readers use the timeless insights on passion, productivity, philosophy, and happiness from this newsletter to build towards the life they want.

What we’ll learn (in 3 minutes):

👨‍🏫 Topic: The regrets that linger until the end of our time

🔍 Quote: Earl Nightingale on dreams that take time

📜 Passage: Daniel F. Chambliss on why excellence is boring

The Regret that Cuts Deep and Lasts Forever

Unfortunately, we’ll all most likely end our lives with deep-rooted regrets.

Our Deepest Regrets

We’ve all experienced regret. That feeling of sadness, repentance, or disappointment towards something you’ve done, or haven’t done. It’s a very unpleasant feeling. To make matters worse, it’s a feeling that often lingers. Some regrets will come and go, and for some, we’ll have to bear the weight of them for years, decades, or even a lifetime.

These long-term regrets were the subject of a study performed by psychologists Shai Dividai and Tom Gilovich. They came to the surprising conclusion that the regrets that trouble us the most in life aren’t the errors we made, but rather the actions we failed to take.

More specifically, the actions we failed to take related to what psychologists call our “ideal self”.

Your ideal self is who you could be or who you dream of being. It’s developed through our hopes, dreams, and desires of what we want our lives to look like.

This means the regrets that bring the deepest sorrow and linger the longest come from not taking action on your aspirations.

Why Do These Regrets Cut Deep

There are a few reasons why regrets related to our unfulfilled ideal selves cut so deep:

1. Little can be done about them

If you miss your sister's graduation, you can always apologize and make a plan to make up for it. These types of regrets come and go very fast.

In contrast, regrets related to our hopes and dreams oftentimes can't be fixed. The one who got away might be married now, some skills and talents can only be fully developed if you start young, and a once-in-a-lifetime job opportunity only comes once.

2. Self-discrepancy theory

The self-discrepancy theory proposes that a gap between who we are and who we want to be, causes emotional and psychological turmoil.

When we realize that we're not who we want to be, or could be, it causes self-dislike, guilt, sadness, and disappointment.

3. Cool emotions

Failing to take action on things that could've brought us closer to our ideal self leads to "cool" emotions.

Cool emotions are feelings of sadness or disappointment that at the moment seem insignificant enough to shrug off and deal with later.

For example, you tell yourself you're going to start a business while you're still in school, but you end up graduating without ever getting around to it. You'll most likely feel a little bit upset with yourself, but also think that it's not the end of the world.

However, that's the trick these regrets play. It feels like no big deal in the beginning, but the issue gradually unravels with the passage of time.

These regrets reach a boiling point where 10 years down the line you'll find yourself distressed, wondering how you ended up in an unfulfilling place in life.

4. Goals are abstract and unattainable

The final reason that ideal-self regrets won't die or fade away gracefully is that our goals are too lofty and abstract.

Setting these types of goals either guarantees well never reach our ideal self or guarantees we'll never know when we've arrived there.

With so many people reaching their dying days bearing the regrets of never reaching their ideal self, it would seem like the best thing to do is to go on a “seize the day” frenzy. Write that screenplay, start that business, and travel the world.

But the authors of this study warn against that. They say it’s a simplistic strategy that can lead to misfortune. You might regret destroying your financial security more than never starting a business.

The solution Davidai provided was, unfortunately, not a silver bullet. The solution lies in the grey area.

Davidai says, like most decisions in life, it’s about choosing the imperfect solution you can live with.

It’s not about making the right or wrong choice. It’s about which failures you have the capacity to bear in life.

Featured Quote

Never give up on a dream just because of the time it will take to accomplish it. The time will pass anyway. - Earl Nightingale

The timer of life keeps ticking whether you like it or not. No matter what you do this year, a year will pass.

So you might as well spend it pursuing something meaningful

Featured Passage

Excellence is mundane. Superlative performance is really a confluence of dozens of small skills or activities, each one learned or stumbled upon, which have been carefully drilled into habit and then are fitted together in a synthesized whole. There is nothing extraordinary or superhuman in any one of those actions; only the fact that they are done consistently and correctly, and all together, produce excellence.