5 Major Regrets Many People Have When They’re Older (and How to Prevent Them)

I want to paint a picture for you.

Imagine living to a grand old age. Maybe 80, maybe 85. The thing is…you’re dying. You know it, everyone around you knows it.

As you lay back on the couch, look at the ceiling, and contemplate your existence – you think back over your life. Some great moments flood in, along with some not-so-great ones.

These not-so-great ones leave you with a bitter taste in your mouth.

You wonder what happened to that cutie you met in college.

You wonder what would have happened if you moved overseas when you had the chance.

You wonder what could have been.

You become obsessed with these thoughts.

A bleak sadness washes over you. Mainly because you know that what’s done is done and your time on this Earth is slowly coming to a close, leaving you with some of your biggest regrets in life.

Millions of people have those thoughts and common regrets in life on a daily basis…and they’re not even anywhere close to dying.

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Why We Have Regrets In Life

why we have regrets in life

We all know that hindsight is 20/20.

You will always regret the things you didn’t do more than the things you did.

Why so?

Human beings are inherently designed to look for problems in their environment. This is what has kept our species alive for millennia. We are always looking on the bad side.

The problem is, we are always looking on the bad side…but most of the bad things that we think about never happen. This is built into us as a “just in case” mechanism to make sure we don’t do anything too stupid.

As a result, we realize that we could have done things a bit better or tried a bit harder.

Whatever it is, it’s over and done with. We can’t change them.

Most people move on and accept it. But there’s some people who ruminate constantly over it.

As we go throughout life, we accumulate experiences. With these experiences are opportunities seized and opportunities missed.

Since you can’t be all places at all times, you will miss out on something. That’s inevitable. Everything in life is a sacrifice.

The question is: is this experience you’re missing out on worth it for what you’re experiencing now?

If the missed opportunities are greater than the seized ones and you realize that and ruminate over it, that’s regret and it’s a terrible feeling to have.

There’s nothing like the feeling you get when you know could have “been somebody”…and you blow it.

Many of our biggest regrets in life occur when we’re in our developmental adult years – late teens to early 30s.

Since that’s the case, this article is going to center around 5 of the biggest regrets that you will have if you waste your young adult years.

I’ve already made the case before but I didn’t spell it out in explicit terms.

There's nothing like the feeling you get when you know could have “been somebody”...but you blew it. Click To Tweet

Biggest Regret in Life # 1: Indecision

Biggest Regret in Life # 1: Indecision

In his seminal book Think and Grow Rich, Napoleon Hill stated that one of the seminal causes of failure was indecision and its twin brother, procrastination. Together, these two forces account for a majority of the misery in daily human existence.

I personally believe that indecision is made easier than ever due to our always-on, Instagram-filtered modern world. We’re always comparing and contrasting against what other people have or don’t have, trying to orient ourselves in the world in relation to them.

I also believe that children and young adults are being encouraged to be indecisive, by the higher education system, just for the sake of getting more money.

I went to college with many people who didn’t pick a major until the last minute and they still ended up hating it.

By the way, speaking of money, this is how people accumulate closets and rooms full of JUNK. Many people just buy things to buy it, not because they really need it.

According to the biggest regrets in life study, indecision is responsible for much of your misery in life.

Indecision helps no one. Just get a gun, pull the trigger, and figure it out along the way.

It also helps if you know who you are as well.

Anti-Regret Tip: Know yourself, rely on yourself, figure out what you want, and go after it like your life depends on it. Because it does.

Biggest Regret in Life # 2: Laziness

Biggest Regret in Life # 2 Laziness

We all have dreams we want to see come to fruition. For too many of us, many of them won’t see the light of day. Why?

Distraction. Sensory overload. Too much this. Too much that. Etc. Etc. Etc.

We say we’re “busy”. We don’t have enough “time”. We don’t “feel like it”. In general, these are all excuses.

We have enough time to surf the Internet aimlessly and watch Netflix, but we don’t have time to learn how to make our lives better?

Listen: you will never have more time or more energy than you do right now.

It takes time and energy to learn a skill or learn something that will vastly help you.

If you can’t work on your dreams when you have a massive expanse of free time and energy, no amount of advice will help you.

You have one fucking life. Why the hell are you spending it playing video games and smoking weed?

Anti-Regret Tip: Push past the pain. Learn how to work effectively and efficiently. Concentrate all of your mental forces onto a single aim.

Biggest Regret in Life # 3: Neglecting Good Habits

Biggest Regret in Life # 3 Neglecting Good Habits

The individual who wants to reach the top in business must appreciate the might of the force of habit and must understand that practices are what create habits. He must be quick to break those habits that can break him and hasten to adopt those practices that will become the habits that help him achieve the success he desires. – J. Paul Getty

We all know that habits make or break us.

But do we know to what extent? About 90-95% of what we do is subconscious. We are on autopilot most of the time.

Bad habits are easy to form but hard to break. Take cigarette smoking, for example. We all know it’s bad. But there’s still tons of smokers. Why?

Because they just. can’t. quit. It’s got them locked in.

Do you honestly think someone deep down wants to buy a pack of something that he knows will kill him in due time?

Interesting story: at my first job out of college, I was walking across the street to buy lunch with two of my coworkers.

One of them pulled out a cigarette from his pocket and gave it to his coworker. He then pulled out one for himself.

“You smoke?”, he asked me?

“Me? Nah.”, I replied.

“Good. Don’t start.”, he pithily stated.

Interestingly enough, good life habits are also synonymous with good with work habits. I haven’t heard of anyone who’s a slouch in life be a slouch in work.

Most of our generation, the millennials can’t focus. We can’t work effectively. We can’t do deep work. Why? Because we haven’t been trained to do it.

We have been encouraged, socialized, to give into digital distraction for most of our lives.

Now, these habits are easy to fix. Someone who’s 20 can pretty much quit cigarettes cold turkey or learn how to focus when they work.

With someone who’s 60? You’d be better off trying to enter a government building without a security clearance.

Anti-Regret Tip: Identify your bad habits. Write them down on a piece of paper. Make a campaign to eliminate them one by one.

Biggest Regret in Life # 4: Not Taking (Calculated) Risks

Biggest Regret in Life # 4: Not Taking (Calculated) Risks

As a young person, you are built to be expansive.

You see, life follows a cycle. At birth, we are learning. We make mistakes. We grow.

As we expand into adolescence, this cycle upticks. During (young) adulthood, we formulate all of those mistakes into a philosophy of achievement.

We are gifted energy by Mother Nature to transmute our plans into achievement. We use this energy to build a strong foundation that we build upon as we advance in the world.

This energy propels us to take risks. This may mean starting a business, moving to another city, starting a social circle, asking out that girl…anything really that advances our station in life.

As we get older, this natural energy diminishes.

As we get older, we get a bit more conservative, a bit more stuck in our ways. Since we have more to lose, we are more risk-averse.

If you don’t take chances now, you will certainly regret it when you age.

Anti-Regret Tip: Push out your comfort zone more and more every day. Eventually, the world will become your comfort zone.

You will never regret pushing yourself but you will regret not pushing yourself. Click To Tweet

Biggest Regret in Life # 5: Living Your Life By Heresay

Biggest Regret in Life # 5: Living Your Life By Heresay

You will regret living your life by the statements and opinions of other people. Most people can’t make up their mind on what’s right and what’s wrong. Why should you follow their lead?

I used to be made fun of for being “different”. That didn’t bother me. It shouldn’t bother you either.

They don’t pay your bills. They don’t give you free money. They don’t get out of bed for you. They don’t determine your livelihood.

There’s only one thing worse than a person who talks shit. It’s a shitter that talks. Don’t listen to a toilet spew garbage incessantly.

Anti-Regret Tip: Ignore the opinions of others. Most of the time they are wrong and ill-informed.


As I stated earlier, we all have something we’ll miss out on. The only question becomes if what you missed out on was worth it.

You may already have some of your biggest regrets in life in the past that prevent you from moving forward. You need to let it go. Regrets only slow you down and keep your mindset diminished.

You need to vow to yourself that you’ll do everything in your power to make sure that you have as little regrets as possible and ones that you can live with.

What are you doing today to make sure you’re living a life you’re proud of tomorrow? Let me know in the comments.

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