Real-life examples of self-sabotage. At its best.

19 minutes reading time

Many people who barely know me assume that life is and always was easy for me – that I always had beautiful girls around me, operated with large sums of money and spent time with rich and powerful people in fancy restaurants.

That’s the most wrong assumption ever. I was extremely poor, even more extremely fat, life broke me again and again, I had to deal with so much shit it would take thousands of pages to describe. Every time I got knocked down, I stood up again; from when I was little onward.

But not always. There were many times when the problem wasn’t that I wouldn’t stand up after being knocked down, but that instead I made sure I knocked myself down in the most brutal way possible. It’s called self‑sabotage and is one of the worst kind of behaviors that can happen to a person.

Don’t confuse self-sabotage with failure. When you fail you act, and because of a weak strategy, unpredictable outside forces, wrong assumptions or any other reason, things don’t turn out as planned. Failing definitely sucks, but self-sabotage is completely different and a much more brutal beast.

I will share with you the most prominent stories of how I performed perfect self-sabotage. Some of the stories are funny, some are sad, but all of them are more or less humiliating.

I’m sharing them with you for one reason only – for you to become aware of how self-sabotage looks like and stop doing it. You just have to promise that you won’t laugh.

There are three main situations when self-sabotage happens:

  • Something good is going on for you and you make sure you kill it
  • It’s time to stand up for yourself, but you instead bow down and do nothing
  • You fight for something you really want and when you get there, you destroy it somehow

Reasons for self-sabotage are always deep psychological issues of inadequacy and a feeling that you don’t deserve it.

It’s part of the personality that comes from misguided upbringing or past traumatic experiences and that leads to becoming an emotional midget that blocks himself when something good starts appearing on the horizon.

It was the same in my life. I have the most complex personality possible regarding relationships, money, body and many other areas of life. It’s so complex I should invent a new word for extreme complexity.

The good side of a complex personality is that it enables me to write eye-opening and life-changing articles like this, understand many different aspects of life and identify hidden patterns. The downside is that I have to deal with all this variety of ups and downs which is many times not easy, trust me.

In this article, you will learn at least:

  • How self-sabotage looks like (through funny and not-so-funny stories from my life)
  • Why self-sabotage happens
  • Typical examples and situations of how people self-sabotage themselves
  • What you can do to overcome self-sabotage
  • Other practical examples that will help you overcome this monster

Now let’s go to the stories and at the end of the article, to a few suggestions of how to deal with self‑sabotage.


Taking the test

I was the best pupil in primary school. I had straight As and math was my favorite subject. I was the fat and nerdy kid you see in the movies. In the last year of primary school, it was time to take a test for potentially getting a scholarship in high school. If you scored well on the test, there was a great chance the scholarship was yours.

I miserably failed the test. After the test, everyone had a counseling session with the school psychologist and she was so confused at my session. I was the best pupil in the whole primary school, but I scored so low on a quite simple test of general intelligence. And remember, math was by far my favorite subject.

I was also surprised back then. I had no idea what was happening. I know now. Deep down, I felt I didn’t deserve the scholarship. Remember when I mentioned that I have a very complex relationship with money? Consequently, I of course self-sabotaged myself. I intentionally failed the test all the way.

In the end, I of course didn’t get the scholarship, simply because I felt deep down I don’t deserve it. Self-sabotage at a very young age at its worst.

  • Area of self-sabotage: Money
  • Type of self-sabotage: Not performing at your best

On the school trip

Every few years in primary school, a whole generation (several classes with 100+ pupils altogether) went on a few days’ trip, be it to practice sport activities, explore nature or to get more familiar with any other different subject. Besides learning activities, such trips were always a lot of fun.

It was the last such trip in the last grade of primary school and I was really excited about it. I’m not sure what the purpose of the trip was, but I knew we would play tarock cards with my friends, learn a lot and see the “world” (a village a few hundred miles away, but back then that was a real adventure for me). It would all be perfect, except…

There was this bully from the other class. And somehow I became his target on this trip. It was the same as you see it in the movies, he was threatening me and all that shit, and it made my trip miserable. Afterwards, when we got back from the trip, he simply stopped, it was just those few days.

Remember, I was smart. I knew that physical dominance was outlawed. I knew that there was nothing he could really do, because consequences would be bad: if I just stood up for myself and spoke up. But I guess I liked the torture more. I probably felt like I deserved it.

  • Area of self-sabotage: Physical & Self-confidence
  • Type of self-sabotage: Being a victim instead of standing up for yourself

On the stage

It’s the last story from primary school. There was a big stage school play organized to show parents how awesome we are. Almost all of us pupils had to play a part and I was no exception. Well, all I had to do was to recite a few strophes of a poem.

I practiced, and I practiced a lot. It was an easy poem to remember and anyway, I had a really good memory. Then the day of the play came and it was my turn to shine on the stage. I appeared on the stage, it was time to open my mouth, and my mind was empty. Completely empty.

I just stood there on the stage and things got extremely awkward. Luckily, one of the organizers noticed I was in a bad spot and brought me the book with the poem. I read those few strophes and went down from the stage feeling nothing but shame. I promised to myself that I will never carry myself on a stage again.

  • Area of self-sabotage: Public appearance
  • Type of self-sabotage: Complete self-castration

In the club

With my first business partner, and also one of my best friends, we went to Germany to import some goods we were selling on the domestic market. It was a long and exciting trip, and it felt good to be barely 20 years old and doing international business.

From the business perspective, everything went great and that’s why we needed to celebrate. We decided to go to a night club for a few drinks. And there we were, barely adults doing business in a foreign county, thinking to ourselves that the whole world was right at our feet.

The club was still half-empty and the night was young. Two gorgeous ladies entered the club and checked out the scene. They came to us and asked if they can sit at our table (how many times does that happen?). We said yes and now on top of everything, we also had great company.

We could see in the ladies’ eyes that they were eager to see what our conversation will be all about. They waited for our first opening line…

Except that the opening line never came from either of us. We sat there for around an hour, and we were both so afraid to say anything that we were only talking to each other. We self-sabotaged ourselves, when all we had to do is utter a few sentences to start the conversation.

Why? It’s simple. Deep down, we didn’t feel interesting enough (probably being from a country with a lower GDP than Germany. I know how stupid it sounds.).

Then the ladies left and we left. When driving back to the hotel, we were listening to bad shit rap, throwing rhymes along with the rapper about how awesome and superior we are. But we weren’t.

  • Area of self-sabotage: Relationships & Dating
  • Type of self-sabotage: Avoiding talking to people

In the boardroom

The business was thriving and it was time for expansion. Besides doing business, I was simultaneously also going to university and once, we had a lecture from this really successful high-tech entrepreneur who was doing business all the way to Japan and was a real business mastermind.

With my business partner, we decided that we will pitch our expansion ideas to him and try to convince him for a partnership and an investment. After several meetings and presentations, I remember one day late in the evening he called me and said yes. We were super happy.

The only thing left was to agree on all the formalities. We met in their boardroom and we started talking about details. And then suddenly me and my business partner started to fight in the boardroom right in front of the investor. The investor and his partners got quite confused.

After listening to our nonsense for a while, they asked us to leave and come back when we straighten things out. We never managed to do that, because we self-sabotaged our success rather than go after the expansion.

It seemed like something unreachable to us. Afterwards, we both went our separate business paths. Who knows what kind of a company we could have built.

  • Area of self-sabotage: Business
  • Type of self-sabotage: Igniting illogical conflict

At the job

Now I got a new cool job that I really enjoyed and my career was taking off. There was only one thing that bothered me a lot. I felt I wasn’t paid enough compared to how much value I contributed. I was becoming really good at what I was doing, but the payment didn’t go up.

For months and months, it bothered me and I did nothing. I was only doing self-torture, asking myself what if I hear no as a response to my pay raise request. After a few months, I got a new better offer at a different job.

Because I was valuable to the firm, the manager immediately offered to pay me more if I stayed. I complained that I was unsatisfied with the payment anyway and that I was determined to leave. Afterwards, on my last day, we had a very honest talk and what he said to me shocked me quite a lot.

He said I could have easily gotten paid twice as much or even more, if I would’ve just asked. He was waiting for me to ask and negotiate a little bit, and it was a big surprise that I never did, especially considering how ambitious I was in general.

Well, remember my complex relationship with my money. It was a big internal conflict. I felt I deserved a higher payment and not at the same time. Rather than doing something, I was focusing on my internal conflict and self-torture. Complete self-sabotage.

  • Area of self-sabotage: Money
  • Type of self-sabotage: Self-pity and internal conflict

In the gym

I was in a serious relationship for 11 years and the relationship came to an end. Even though the agreement to end the relationship was mutual, it wasn’t an easy thing to go through. I was very angry, sad and completely disappointed in life.

I tried many things to ease the pain (also a lot of stupid things). I started going to the gym as one of the positive ones and I liked it a lot. I was training more and more, the first muscles started to appear and I trained even more.

There was only one big problem. I still saw myself as a fat guy, since I was fat for the most of my life, so it was time to self‑sabotage my success.

I started to exaggerate a lot. Pre-workout drinks, creatine and other supplements, spending hours and hours in the gym until my body was shaking like crazy. When everything in the body broke down, because of me overdoing it, I decided to do a little bit more.

In reality, it was nothing but self-sabotage, and so the day came when I hurt myself. By having no strong foundations, doing exercises wrong and exaggerating with workouts over all common sense, failure was inevitable. Years later, I still have to deal with the injury and pain, and I can’t train normally. It’s a big question if I ever will.

Yes, complete self-sabotage.

  • Area of self-sabotage: Body, health
  • Type of self-sabotage: Injuries, illnesses

Failing at doing

There are many more stories. Opportunities for self-sabotage are everywhere.

These are only a few selected stories of how I sabotaged myself. There are many others and you may not believe, a few of them are quite more shocking than the ones above. Maybe I’ll share them some other time, who knows.

You will always make sure things happen as you feel and believe deep down inside.

There are many opportunities for performing self-sabotage and putting yourself in the victim position. To name only a few:

  • Money
  • Dating and flirting
  • Relationships
  • Sex
  • Accomplishments
  • Bosses
  • Public appearances
  • Happiness
  • Health and body
  • Showing your talents
  • Dealing with family members
  • Dealing with authority figures like doctors and lawyers
  • Facing bureaucracies and clerks
  • Doing a job you hate
  • You name it

No matter how healthy of a person you are, there is definitely at least one area of life where you shine at sabotaging self. Self-sabotage can be done in many ways. Here’s the list of the most popular methods of self-sabotage:

  • Freezing
  • Running away
  • Hiding
  • Not acting
  • Acting to your disadvantage
  • Not asking
  • Performing below your capabilities
  • Procrastinating
  • Picking fights you shouldn’t
  • Injuries (not all of them)
  • “Accidents” (not all of them)
  • Self-harm
  • Not showing up
  • Sleeping in
  • Being late
  • Suffering from internal conflicts
  • Drowning in self-pity
  • Not standing up for yourself
  • Indecisiveness
  • Temper issues
  • Excessive worrying
  • Negative habits
  • Being isolated
  • Emotional eating
  • Impulsive spending
  • Self-sacrifice

Last but not least, below are different feelings, beliefs and convictions behind every self-sabotage. This is where lies the real cause that you have to tackle if you want to stop doing such nonsense.

  • Inadequacy and a feeling of low self-worth
  • Hopelessness
  • Helplessness
  • Overwhelming yourself
  • Jumping to conclusions
  • Self-labelling
  • Undervaluing the reward you deserve
  • Perfectionism
  • Fear of failure and looking stupid/unattractive
  • Fear of success
  • Fear of disapproval and criticism
  • Coercion and resentment
  • Low frustration tolerance
  • Guilt and self-blame
  • Shame
  • Confusing strength with manipulation and evil acts
  • Disaster will befall you if you act
  • Something bad will happen to you (you will lose a job/person)
  • God will punish you

Resistance by definition is self-sabotage.

How to deal with self-sabotage

I still self-sabotage myself from time to time. But I do it a lot less than I did it in my past. And now I know better when and why I am doing it, and how to deal with it. Sometimes you can deal with it alone, other times professional help is the only way.

For example, after trying to overdo it with exercising again, all I needed was a simple sentence from my personal trainer, that was “just fu*king stop”.

So don’t be afraid to get that kind of help. If you can’t find the way, a mentor, specialist, psychologist, new friend, whoever might help you.

My way was far from easy to stop with excessive self-sabotage.

I vomited before going on stage again. I thought the world would end before approaching a girl. My hands were shaking like there was an earthquake when it was time to stand up for myself. I thought I would eat myself alive when it was time to issue a fair amount on an invoice.

You have to push yourself through self-sabotage and in the rest of this blog post, we’ll look at how to do it. But before we look at different techniques of how to deal with self-sabotage, I have to emphasize the important fact that all the techniques have one common denominator.

Understanding it, fixing your feeling of self-worth (it comes out of self, obviously) and becoming a healthy assertive person.

An assertive person (please read the bullet points below a hundred times or even more if necessary):

  • Likes themselves as they are
  • Has a strong sense of self and their autonomy
  • Has no problems with their needs being met
  • Knows how to express feelings
  • Knows where they’re going in life and what they want
  • Is not afraid of conflict and knows how to set boundaries
  • Takes initiative and contributes creative ideas

When you act in an assertive way, you act out of strength, with the right mindset and awareness that you are as valuable as any other person on this planet. But a lack of assertiveness usually leads to one of two extremes: greed and aggression or symbolic self-castration.

Knowing that, here are a few suggestions on what you should do to overcome self-sabotage:

  • Act
  • Identify the cause and transference
  • Accept reality as it is
  • Read
  • Visualize
  • Get professional help

The only way to deal with self-sabotage is to start managing emotions better.

Just do it

By far the best way to overcome self-sabotage is to gather every single drop of courage you possess, gather all the willpower to surpass negative emotions and do what an emotionally healthy person would do. It doesn’t always work, but many times it does.

You may vomit, you may cry, you may feel like the world is going to end or you’ll go crazy, but that is what you have to do to get proof from real life that you can do better, that there is a way to perform more optimally and that there’s nothing wrong with following your own goals; and that the world won’t collapse.

Example of real actions are:

  • Take full responsibility for your life
  • Speak up
  • Surrender when you don’t have control
  • Express how you feel
  • Set limits and boundaries
  • Face your fears
  • Accept compliments without shame
  • Pay attention to your needs and satisfy them
  • Start saying no
  • Improve your posture and take up space
  • Start taking care of your body and style
  • Stop running away from your past
  • Learn to live in the present moment
  • Start responding instead of reacting (be proactive)
  • Decrease tolerance for mistreatment
  • Save money
  • Stop comparing yourself to others

Now when you act, there are three important rules you have to follow:

  • Be courageous, not stupid
  • Start with really, really small steps
  • Reward yourself

The first one is that there is a thin line between being courageous and being stupid. If you’re being bullied, it makes sense to stand up for yourself, but if there are 10 guys threatening you with knives and guns, surrender is definitely the right strategy.

Self-sabotage always means doing something stupid. So when you become aware that you may be self-sabotaging yourself and want to change your behavior, don’t start self-sabotaging yourself again, only in a different way, and now not even aware of it.

Instead ask yourself: what is the optimal thinking in that kind of a situation, what is the best move you can make to get the best possible outcome out of the situation and what would an emotionally healthy person without irrational fears do. Find the best situation and then act.

The second important thing is to start small. Make a small step into the learning zone or you’re going to enter the panic zone, fail miserably and your desire for self-sabotage will only get stronger. Don’t be impatient and don’t bite off more than you can chew.

If you’re dead scared of public speaking, lecture to your dog first, then to your best friend, then in front of two strangers, then in front of a small conference room, and so on.

If you’re scared to the bone of starting a conversation with the opposite gender, start small. First ask an unknown person for the time. Then ask for directions. Then find a few friends of the opposite gender and get comfortable around them. Then ask for a number and be ready for a rejection; or ten of them until you hear a yes.

And the most important thing: reward yourself. For every small step you make, really reward yourself, especially by mentally focusing on the positive. Be proud of yourself, celebrate, see it as an early win, see the progress you are making.

When people finally start to act, they get the tendency to focus on all the times they didn’t act, the rejections they experienced, how they could do it better, and so on. And that’s how you get straight back to self-sabotage and toxic thinking. Don’t do that to yourself. Focus on the positive.

Identify the cause

Many times, identifying the cause helps a lot to disarm negative emotions that fuel self-sabotage. When you understand why something is happening, it might help you to deal with it more easily. In order to do that, it takes some painful examination of your past.

As a child, you have to see your parents as perfect and many people still do that as adults. But the fact is that no parent is perfect and toxic errors in upbringing are usually the reason for self-sabotage later in life.

Next to that, shocking events from the past that happened outside of home (and we all have them) are also preventing you from being as assertive as you could be.

Examples of toxic upbringing or shocking situations are:

  • All you heard at home were critiques and you rarely received a compliment
  • Whatever you did was never good enough
  • You often heard “you’re just like your father/mother”
  • You got labeled, like “you’re clumsy”, “you speak funny” or whatever
  • You felt ignored in some way (so why would anyone listen to you now)
  • You were never allowed to have a different opinion from your parents
  • Parent of the opposite gender was abusive/ignorant (so others must be the same)
  • You failed at public speaking at a young age, like I did
  • Somebody made fun of you, even maybe only in an “innocent” way

Examine your past and try to find a connection to why you sabotage yourself. It will help you make the first step towards understanding that what happened to you and how you felt was connected to that specific situation only, and that the whole world is not built in the same evil way.

When you’re identifying the cause, also make sure you analyze what kind of an underlying negative emotion is holding you back (anger, fear, etc.).

Behind self-sabotage, there is always severe negative thinking and negative feelings. With the happiness index, you can pay much better attention to your emotions, and emotional accounting is the optimal way of releasing some of the emotional tension.


Here is an additional very useful exercise you can do to analyze your self-sabotaging behavior:

  • Write down your goal
  • Write down all the behaviors that work against you meeting that goal
  • Visualize doing the opposite of self-sabotage (of how you work towards your goals)
  • Identify worries and fears and other negative emotions that come up
  • Identify what (false) beliefs, convictions and assumptions are holding you back


Identify transference and projections

Here’s a big catch to why you sabotage yourself in relationships. You always strive to make relationships into something that’s familiar to you.

Those are the relationships with your parents and other authority figures from your youth. It’s a relationship blueprint.

Next to that, you frequently project behaviors of authority figures from your youth onto relationship partners later in your life. I know it sounds complex, but bear with me.

If you had an abusive or ignorant parent and if your home was full of drama, guess what, you will make sure that your relationships will be full of drama and that your partner will behave in a similar abusive way that’s familiar to you.

You will look for that kind of a partner and you will encourage behavior that’s familiar to you. With transference, you may see your partner even more negatively than they really are.

If you don’t have the experience of a healthy relationship from your youth, it’s quite hard to have a healthy relationship later in life. Professional or personal one.

Because you don’t even know what it means to have a healthy relationship, there is simply no experience. If your relationship blueprint is really damaged, therapy may be the only option.

Nevertheless, the first step you can make is to write down what kind of relationships you want. You can make personas of your ideal personal and professional relationships. You may list all the things you seek in a relationship and how you define a healthy relationship.

Clarifying what a healthy relationship means to you may be the first step in interrupting self-sabotage in this context.

Then observe yourself very carefully, especially when and why you are intentionally causing disruptions and drama in relationships (working towards what you have written down in your ideal-relationship persona). Doing self-reflection isn’t an easy job, but it’s definitely a good start.

Correct an emotionally toxic behavior with a healthy rational thought.

Accept reality as it is

In the same way as identifying the real cause of suboptimal behavior, accepting reality as it is might help you to stop doing self-sabotage.

You can easily compensate your self-sabotage with fantasies and living in a naïve little world that you construct in your head and escape to.

It may be the easy path, but it’s one that will backfire for sure. Frequently, the underlying conviction behind such a fantasy world is that life should do all the hard work instead of you.

You may wait for the day when the love of your life will appear at your front door, when your boss will finally recognize your value and the greater force will see how good of a person you are and therefore reward you with money, power and glory.

Well, if beliefs like that support you staying in your comfort zone, because you simply must be an exception and you’re convinced that things will turn right somehow and somewhere in the future, you are wrong. Dead wrong.

Life wants you to fight. Life wants you to go after your goals in a socially acceptable way, without hurting yourself and others.

There is no such thing as a free lunch. You will have to get your hands dirty, there is no other option. So evict any wussiness and false beliefs and start fighting. Stop resisting, and accept reality as it is.

You only have one life and you have to live it right the first time. Much like you have to get it right the first time if you jump out of a plane with a parachute. There is no second chance.

So make sure you aren’t freefalling from the sky, waiting for someone to bring you the parachute. Because there won’t be anybody, you will only crash hard on the floor. With a big sign saying that a self-saboteur landed here.


To simplify, you sabotage yourself because unfortunately, your brain was wired in the wrong way because of toxic past experiences. So what you have to do is to rewrite them (build a new subjective map of reality).

Imagine your body as a piece of hardware and your brain as the organ that runs the software to operate your body and tell you how to experience life – from making everyday decisions to how you feel about certain situations.

It’s a very powerful machine you have in your head, but as I mentioned, a few wires have been misplaced. We can call these misplaced wires bugs. Brain bugs come from many different sources, like suppressed traumatic experiences, cognitive distortions, limiting beliefs, lack of awareness, false knowledge transmitted from others (the Earth is flat?), and so on.

If you want to fix brain bugs, you have to update your software. And you update your software by reading, listening to lectures, talking to people, observing different situations, reflecting and other similar situations.

The formula for updating your brain (learning) is = Download + Process + Apply

Among all the ways of “downloading” knowledge to update the “software” that your brain runs, reading is one of the best and most popular ones. So read and read a lot, and that will help you build a new perspective on life.

Read personal development books, psychology books, biographies, anything that will open a healthier perspective on how to act in life. I read hundreds of books in the past and I can say without any doubt that reading really changed my life.

Besides reading, you can observe healthier assertive people, spend time with them, interview them, watch videos and online lectures, you can talk to a therapist, regularly reflect on your actions, and much more.

There are many ways how you can download and process knowledge to update your brain. Find what works best for you and after reading and processing, don’t forget that the key is to apply it. So act.


To apply newly acquired and processed knowledge, you must answer three simple questions and then stick to them:

  • What will you start doing?
  • What will you stop doing?
  • What will you continue doing?



As you know by now, until you believe deep down inside that you can achieve something, you will not work in that direction or even if you do, self-sabotage will come into play sooner or later.

Luckily or not, your brains have a hard time distinguishing reality from your imagination.

If you really relax, close your eyes and imagine things like …

  • Going to an ATM and having $1,000,000 on your bank account
  • Speaking in front of a thousand people
  • Talking and flirting to a supermodel
  • Getting an A or a raise

… certain feelings will accompany your mental representations and specific thoughts start to pop out.

Maybe something like Never in a million years, that’s not for me, I would rather die, that’s too hard for me or that would be awesome, I can achieve that, yes, yes, yes etc.

Now here’s the trick. What if you visualize something, experience negative feelings and then slowly start to enforce positive feelings?

With this kind of exercise, you will trick your brain into a different mental representation and how you see yourself. This is how visualization can help you overcome self-sabotage. You can read more about it here.

You have to support it by acting, but it might be the first right step. Just test it, if it works for you.

Get professional help

Sometimes the feeling of inadequacy and that you don’t deserve something are so deeply enrooted that professional help is needed (mentors, coaches, psychologists, etc.). There’s nothing wrong with that.

When you have a body injury, you go to a doctor, so if your soul is suffering why wouldn’t you get professional help. It may cost you more and the process may be longer, but definitely more thorough.

It’s really not worth it to live your whole life in fear. Actually it’s better to live one day as a lion than 100 years as a sheep. Now stop self-sabotaging yourself. And I will too.

Failing to achieve a goal in the past does not predict your ability to achieve the same goal in the future.

About the author

Consulting and management coaching

Blaž Kos has managed venture capital investments over the past 12 years and participated in the development of the start-up ecosystem in the region. Today, he advises companies on growth strategies, process optimization, the introduction of lean agile methods and the digitalization of business. In addition to the Slovenian blog, he also writes an English blog, which was selected among the 50 best bloggers in the world in the category of personal and business growth.
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