Why You Mess Up When You Should Know Better

Whether succumbing to harmful addictions, staying in toxic relationships or making other unhealthy choices, here’s why we continue to mess up when we should know better.

Having navigated the stormy seas of adolescence to reach the sunny lands of adulthood, you shouldered the mantle of maturity and assumed the crown of wisdom. Henceforth you forever ceased to make mistakes in situations where you should have known better.

Sound like you or anyone you know? No need to answer this one. Unless you personally know the Dalai Lama (in which case I’d appreciate an introduction).

It is easy to spot red flags in potentially disastrous situations when it comes to other people. We watch with foreboding as a friend gets further sucked into a toxic relationship or as a colleague starts to drink heavily. However, with respect to our own potential mistakes, we walk right through those red flags. We claim not to see them or insist that they only apply to other people.

Should we chalk up our propensity to act foolishly to the fact we just haven’t evolved all that much from our prehistoric ancestors? Or is there a reason we like to learn things the hard way?

The Reasons We Mess Up

Here are 7 key reasons for why we mess up when we really should know better.

1) Knowledge vs Experience

“By three methods we may learn wisdom: First, by reflection, which is noblest; second, by imitation, which is easiest; and third by experience, which is the bitterest.”


Confucius could have added “and most memorable” to the part about learning from experience. You know how telling a child not to touch the hot stove is never as unforgettable a lesson as actually touching the hot stove?

Knowing something intellectually is not the same as experiencing something in reality – that is emotionally, physically and sometimes viscerally.

That’s why watching a sad movie is not the same as actually having your heart broken (removed and stomped all over). And why seeing your friends make mistakes is not the same as making those same mistakes yourself.

Which is ok. We don’t want to gain all of our wisdom from reading books and watching our friends make fools of themselves. We need to make our own mistakes too. We need at times to touch the hot stove, even knowing better. Experience can be a necessary (if hard) part of learning.

“Sometimes the wrong choices bring us to the right places.”

The problem is when we have already touched the stove a number of times. We have felt it burn us, but still want to touch the next stove thinking the experience will somehow be different:

No really, this stove is different! I’ve learned to touch it better! And it has promised to work on the burning-me issue.”

Yeah. Right.

But let’s face it, we all have our version of the stove we can’t stop touching. So why do we keep repeating the same mistakes believing that this time will be different?

2) When Emotions Hijack Reason

“The brain is the most outstanding organ. It works 24/7, 365 from birth until you fall in love.”

Sophie Monroe

It’s true, your rational self works just great… until your emotions stage a coup and take over.

Falling in love? Watch as Common Sense packs its bags, wish you luck and exits stage left.

Suffer from road rage? Watch the rational part of your brain shut down as you convert into a screaming, horn blowing maniac once stuck in traffic.

Why is it that our emotions have so much impact on our behavior? Firstly, it helps to understand that emotions are generated in a distinct area of our brain that evolved long before the rational thinking part.* Emotions have always been a essential part of our survival and are capable of causing us to react even before we have a chance to think. That’s why you jump back upon seeing a snake before you’ve even consciously registered fear. Or when someone cuts you off in traffic you let loose a dirty word in front of your kids before you have time to self-censor.

Secondly, emotions are accompanied by chemicals and hormones that flood our bodies and induce us to react in certain ways. For example, falling in love produces a cocktail of intoxicating chemicals which make us feel good and crave more time with the source of our infatuation.

Our emotions are ancient and powerful. As such, in order to stop repeating undesirable patterns of behavior, the underlying emotional causes need to be recognized and managed.

Emotions are experienced as sensations in the body (for example, that tightness in your chest just before you unleash a torrent of road-rage cursing). By becoming more aware of these sensations and taking time out to breath and regain presence, you can better manage the related emotions.

Emotions that are not processed often remain trapped in the body, resurging when triggered by certain events. For example your recurring road rage may simply be an excuse to release stored anger that relates to an unpleasant past experience. To break this habit you need to access and manage the underlying emotions that have not yet been processed.

* The emotional part of our brain is referred to as the limbic system (which includes the amygdala, a key part of our emotional hardware) and the rational part is referred to as the prefrontal cortex.

3) Short-Term vs Long-Term tradeoffs

To anyone who has not had the experience of waking up with a pounding head, dry mouth, heaving stomach and the thought “WHY did I not stop at a couple beers last night….. instead of 9..and those two shots of tequila?”, I congratulate you on your self-control.

In life we are constantly deciding between short-term and long-term trade-offs. That delicious chocolate cake today is extra kilos for Future “Can’t Fit In My Pants” You. That passionate kiss with your colleague at tonight’s office party is the beginning of painful and expensive legal proceedings for Future “Getting Divorced” You. Deciding to forgo your monthly shopping spree is more financial security for Future “Happily Retired” You.

Unfortunately, when we calculate long-term trade offs we often don’t do the maths well. One reason is because the “here and now” is much easier to imagine, as opposed to the distant and less predictable future. It can be difficult to delay gratification in the moment (that sweet sweet rush of sugar) only for the potential future downside, which may not even happen. This is especially the case if we engage in some “innocent” self deceit. “I’ll definitely go to the gym six times this week to work off this chocolate cake.’

The attraction of “here and now” is even stronger when it is based on emotions or substances that affect the chemicals in our brains (mmm….. sugar and beer). These tend to override our longer-term, more rational self.

At times it makes sense to enjoy what you have now without worrying about the future trade offs. For example, it is better to seek work-life balance now, instead of slaving away in the office during your youth only to reach retirement when you’re too old and worn-out to enjoy it.

Similarly, making not so sensible short-term decisions is ok if done in moderation. The times we drank too much, went out too late and ate too much are often the moments which make our lives interesting and memorable.

“No-one looks back on their life and remembers the nights they got plenty of sleep.”

However, if you are in the habit of making your decisions based on short-term gratification, you are likely sabotaging your longer-term well being. A good decision is one that takes into account both short term and long consequences.

4) Because You “Want” To

Although most people don’t deliberately want to mess up, at times making bad decisions or acting badly has a positive intention (although this positive intention may not be conscious).

Unhealthy behaviour often serves to distract us from something else that we are afraid of facing. For example, drinking or eating to excess distracts us from problems in other areas of our lives – perhaps a fear of intimacy or a deep sense of unworthiness.

Alternatively, making harmful decisions can be a manner to call attention to something (or yourself) and / or punish someone (or yourself).

If you find yourself repeating harmful behavior, finding the true underlying reason for this behavior will help in breaking the pattern. You can ask yourself “What would happen if I stopped this behavior?” – that is, what else would you have to face up to if it weren’t for this behavior?

5) Old Habits Die Hard

Human beings are creatures of habit. We tend to favor the familiar and often operate on “auto-pilot” as we execute our daily routines. Where “mistakes” are embedded into habits, it is much more difficult to change them. For example, if you have a habit of leaving things to the last minute, you’ll likely keep repeating the mistake of arriving late to appointments.

Although habits are hard to change, they are also the key to how we can stop repeating mistakes. Instead of focussing on the error we want to avoid, we focus on creating new habits or making old habits harder to repeat. For example, not buying potato chips makes it harder to continue the habit of snacking every night before bedtime.

The good news is that once you have established a new habit or broken an old habit, you can then revert to “auto-pilot” and no longer need to worry about re-committing old mistakes.

6) There’s Still A Lesson To Learn

“Those who do not learn from history will continue to repeat it.”

Until you learn from your mistakes, you’re likely to keep repeating them. Even when we think we have learned the lesson, if we continue to repeat the same mistake it is because we still have something left to learn.

Often our repeated mistakes are due to deep underlying beliefs that we may not be consciously aware of. For example, if deep down we do not believe our own worth, we will often make the mistake of choosing people that do not value us.

One of the biggest lessons we need to learn is that the compulsion to repeat mistakes generally originates in emotional wounds that we have not yet healed. Something in our past wounded us and we compulsively seek out similar situations in an unconscious attempt to find a cure in the situation, rather than seeking the cure within ourselves.

This type of pattern is illustrated where someone continues to have toxic relationships. Each relationship wounds the person more, yet they continue to seek similar relationships with the belief that this next relationship will be the one that works out and cures all.

The reality is that no-one can heal our wounds but ourselves. Further, until we recognize our own wounds we cannot start the healing process. Instead we will continue to repeat old patterns and make the same mistakes.

7) You’re in Denial

“By not admitting your mistakes, you are admitting you will repeat them in the future.”

Ah yes. Denial is not just a river in Africa. It’s the refusal to recognize that a mistake has been made or refusing to accept responsibility for the mistake.

Denial will pave the way for you to keep making the same mistakes over and over, because you’re not admitting that you made a mistake in the first place.

It’s not easy to take responsibility for a mistake. Admitting errors requires vulnerability and therefore courage. However, by recognizing an error it converts into a lesson and gives us the opportunity to learn instead of repeating the same error.

Mistakes – The Good, The Innocent, The Bad & The Ugly

Not all mistakes are created equal. The good ones allow us to learn and grow. The innocent ones are those that do not cause material harm and instead illustrate that moderation rather than perfection is the key to enjoying life. “Another slice of chocolate cake? Well I’ve just finished my 5th…. so yes please!”

The bad mistakes are the ones we continue to repeat unnecessarily and the ugly mistakes are the ones that we not only repeat but that harm ourselves and the people around us.

Recognizing and learning from mistakes is important. Equally important is differentiating between the innocuous mistakes that we should simply move on from and the unhealthy ones that we need to address and stop making.

Facing up to our mistakes can be uncomfortable and challenging. However those who have the courage and perseverance to do so will find themselves greatly rewarded.

“The successful man will profit from his mistakes and try again in a different way.”

Dale Carnegie

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