How to Overcome the Fear of Failure and Develop the Will to Win

7054186821_5d273048fb_bHave you ever felt like you cared more about “not failing” than you cared about winning?

That you cared more about “appearing to be badass” than you cared about doing the things required to become a badass?


Then you’ve experienced loss aversion.

In fact, those are some of the most common symptoms of loss aversion. Loss aversion is something that all of us experience from time to time: it’s a cognitive bias that’s wired into us.

But it can be dealt with. It can be fought. All the world’s top performers in fields such as poker, finance, sports, and business have found ways to overcome their loss aversion.


Guess what happens if you don’t do anything about it–if you completely neglect the fact that you have a bias towards being more afraid to lose the things you already have, than going after new things?

An extreme example of this would be hoarders.

You know, the people who cannot bear the thought of losing even a single one of their useless items. It seems strange to “normal people”. But to the hoarders, who suffer from a heightened form of loss aversion, this is no joke. Those people will literally cry and despair for fear of throwing away that old cage they used to keep their pet in, ten years ago.

You see, when the hoarder thinks about losing an item, even though it’s useless and ugly, his brain will distort reality for him and make it seem like it’s the most valuable item on earth. His brain will come up with a thousand rationalizations as to why he has to keep this specific item!

Pretty pathetic, huh?

If you saw it happen in real life you’d probably laugh at it.

–But you shouldn’t, because you’re under the very same delusion yourself. Just to a milder degree. You have a bit more control over your brain.

I remember reading in Seth Godin’s book, The Dip, that the best time to look for a new job is when you don’t need it, and the best time to switch jobs is just before you get too comfortable. Before you get too attached to your job and your colleagues. That way you avoid getting your reality distorted by loss aversion.

Let me tell you about a guy I know.

I know this guy because we have mutual friends. He is a relatively smart guy in his mid-twenties. He graduated with top grades from a decent college. He then felt entitled to getting a great first job. But to his surprise he never got it.

Then he spent nearly two years searching for more jobs like that. He still didn’t get it. So he started coming up with a ton of excuses about the job market and how unfair Sweden is.

After a while I told him to shut up and deal with it. I told him that perhaps it’s time he changed his strategy and stop expecting that the big companies he was applying to would do the heavy lifting for him. Big companies are notorious for treating applicants like crap–because they get thousands of them.

I also told him that his approach isn’t working: His good grades obviously weren’t enough to impress. I then told him that grades are for losers. Relationships, favors, and personal initiative are for winners. Losers wait to be picked. Winners assume they are picked, step up, and provide value in any way they can. And if they don’t know how, they humbly offer to do free work, and make sure that it’s good work.

The guy was quick to object,

But I don’t have any connections… I don’t know them?

–That’s exactly why you need to take the initiative. Pick up the phone. Ask to speak with the person who’s in charge. Ask that person what they’re working on right now. Then you use the magic words: “How can I help?”

I then specifically instructed him on how he could do this.

…By leveraging his main hobby–a hobby that happens to be very useful for just about any business. It also happens to be the case that this guy is a senior member with an official position in a club where he practices his hobby.  He could therefore align his hobby with his job search and kill two birds with one stone.

All he had to do was to make a list of 10-20 interesting companies, call them up and offer a free consultation related to his useful hobby. He’d probably get at least 3-5 positive answers. Then he’d go there and teach those guys how to become better at this activity. This would normally cost them money, but because he’s such a nice guy he’d do it for free.

By doing this he’d get to know employees from this company. He’d form a relationship with them while at the same time providing a ton of value and putting his best foot forward. This would make the job application process a ton easier, because now they will like him.

Pretty smart strategy, right?

Beats competing from a stack of resumes, doesn’t it?

But he never even picked up the phone.

Instead he went back to school–for no other reason than fear.  He got too comfortable being without a job and paradoxically didn’t want to lose what he already had–which in this case was…Nothing.

The fear of failure outweighed the will to win.

Loss aversion got the better of him.

Why You Must Overcome Loss Aversion

Indeed, why?

Because you need to overcome it if you want to become someone who thinks accurately. Someone who makes intelligent decisions. This is mandatory.

You will also need to overcome loss aversion in order to successfully promote yourself and your work.


Because you must believe in your own sense of value, and that whatever you do (product/content/idea/talent) is good enough to put out to the public and offer to other people.

If you don’t believe in whatever you’re doing, your ego’s defensive mechanism will overpower your desire for greatness. Your will to win will be overshadowed by your fear of failure. If that happens, you will not dare to put yourself out there and get the feedback required to improve over the long-term and win.

You must not let this happen to you, ever.

For if this is the case, you will not dare to make serious moves, and you will essentially be “playing the game not to lose”. You will care more about staying safe and maintaining your current appearance.

–That means you placed your sense of self-esteem in the hands of an external force, outside of your control.

I’d call that a losing strategy.

Would you agree?

How Overcome Loss Aversion and Develop the Will to Win

Here’s what you’re going to do — you’re going to create a list (four actually):

1) Why do you want to do this?

Figure out as many reasons as possible before moving on. Find your WHY.

2) What will happen if you don’t do it?

List as many things as you can here too. Further strengthen your reasons for taking action.

3) What are the risks? Why are you afraid? Why are you hesitating?

This is where it gets interesting. You might struggle with this, because your ego doesn’t want to face its fear. It prefers being afraid to seeing things logically — because then it might be forced to change.

Give step 3) some serious thought — and be honest. Describe each reason/excuse as well as you can.

4) Logically obliterate each one of those reasons/excuses

Take all the things you came up with in point 3), pick them apart, and analyze it as far as you can.

After having done this a while you will realize something cool: That your fear is irrational. That is lacks a solid foundation. That it exists as a result of inaccurate thinking which in turn made you jump to the wrong conclusions.

If you’ve read Marcus Aurelius’s Meditations, this is what he’s doing for most of that book, dissolving limiting beliefs and the like while carrying on a conversation with himself.

5) Rinse, wash, repeat

Do it some more, and if you come up with the same answers — be sure to remind yourself of them often.

Why do this?

Because negative emotions are stronger than positive emotions by default.

According to studies by Daniel Kahneman loss aversion is about 1.5-2.5 times stronger than your will to win, at least when it comes to money. The only way to beat that is by “practicing” the positive thought more than you practice the corresponding negative one. Eventually the neural pathway associated with the positive thought gets stronger than the negative one, and it becomes you baseline belief.

It sounds easy — and it is. But it requires a lot of concentration and courage.

If you feel that you’re lacking in either of these qualities, let me remind you that…

You must overcome loss aversion if you want the following things:

  • To feel less scared, and stop giving a shit about losing things that don’t really matter
  • To dare to promote yourself, your brand, your product, your business, or your ideas
  • To take control of the development of your self-esteem and to increase your ability to think accurately

Most people unconsciously flinch and give into fear. Even when their future depends on it. Like that guy I told you about who’s now wasting his time in university reading some bullshit course he doesn’t need. He’s doing it out of fear.

Do not let this be you.

When you are faced with the situation of being forced to make an important decision, but find yourself feeling irrationally afraid, remind yourself:

What is the upside?

What is the downside?

What’s the worst thing that can happen if you try out something new? Probably nothing that you can’t handle.

What’s the best thing that can happen if you try out something new? Probably something you want very badly.

When in doubt, think about that.

Put it on your whiteboard or computer screen.

And assume control.

Photo credit: Flickr


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  1. My loss aversion comes from having lost everything I’ve ever wanted to achieve. Set goal, achieve, lose it. Goethe wrote something like “whatever you dream you can do, begin it. Boldness has genius, magic and power in it.” That’s how it worked for me. Time and again. But maybe I don’t feel safe with what I’ve achieved. Houses, money, people, I either feel compelled to get rid of them or it ‘happens’ to me. So I’m stuck right in the middle of wanting and achieving because I can conceive it in my head and feel enthusiastic, but when I start writing down a plan of action, something in me snaps shut. I can only guess what it is. I’ve asked myself the questions many times and I’ve even had trauma therapy. My fear of working towards something that doesn’t seem to want to stay with me is perhaps bigger than my enthusiasm to want it? I am trapped in fear. But what of, isn’t clear to me, ha ha! I hate being stagnant, because I was always a bit of a challenge junkie, but am now too scared, it seems. I have a manuscript for a book, 9/10th completed. I’m not finishing it, are you kidding? Self love, God’s love (as an anti-dote to the wrath of god, as preached by my father), self-compassion, mindfulness, practised for months in a row, these have calmed my mind, but not dealt with my fear. Do I need to be patient? Anyway, I’m now trying to get rid of my inner mean girl, or girls, oh shucks. Reactions, anyone? Female, 57.

  2. This is a quote from one of the men who just won the noble prize in physics for blue LEDs.

    “Initially, people said this research wouldn’t be completed within the 20th century, so colleagues left, one after another,” Mr. Akasaki said, speaking at Meijo University where he remains a professor at age 85. “It never occurred to me to abandon it. I just continued doing what I wanted to do. It didn’t matter to me whether I would succeed or fail.”

  3. This is a powerful statement: “Your will to win will be overshadowed by your fear of failure.” Success or winning always starts on the inside, we have to convince our self that we are able and worthy of our dreams and desire. To feed our self-talk and thoughts with the good and positive. Great post!

  4. Ludvig,

    The quality of your post is indescribable. Keep up the good work because this is THE BEST blog that there is.

  5. Man…I hope that friend of yours will overcome his fears. It looks as if he had the potential to be big rather than “reading some bullshit course he doesn’t need.

    “What’s the worst thing that can happen if you try out something new? Probably nothing that you can’t handle.

    What’s the best thing that can happen if you try out something new? Probably something you want very badly.”

    Loved how you said that!

  6. Hey Ludvig. Great post. What I did to overcome myself in general is to listening to the “me”. (My thoughts, the voice inside my head and so on.)

    The bottom line is, I don’t have a say in what I do. I love the idea of helping others and sharing my knowledge with them. It has nothing to do with me, and everything to do with you.

    It’s unfortunate, but sometimes we are the ones that hold ourselves back from helping others, and even ourselves.

    • Hey Dragos,

      ” It has nothing to do with me, and everything to do with you. ”

      — I think that’s the right mindset to have, at least in business.

      “It’s unfortunate, but sometimes we are the ones that hold ourselves back from helping others, and even ourselves.”

      — That’s true. Very true.

  7. Ludvig,

    Thanks for the thoughtful article and for getting back to my email correspondence with a great answer.

    Perhaps the most interesting (and differentiating) factor in the lives of the successful is their 1) conscious realization, at some point, that their current path would lead to mediocrity and 2) their willingness to set up systems to accomplish work on a consistent basis, regardless of emotional vacillation or enthusiasm. For them, their realization of what it truly means to lead a mediocre life was so appalling (and likely insulting, esp. in the case of prideful men) that they committed themselves to a system to ensure that they not only stood out, but also benefit from this (financially, romantically, and in myriad other ways :)

  8. I have read this blog for around 6 months since I saw your post in b&d , I had never posted before but I read your posts with interests. I used to be a normal student, now I am the best student and that has brought me many enemies and haters, sometimes I feel to the point of just punch them or challenge them for a fight outside but I know if I do that I would get in trouble and maybe have problems in the university, I challenged one and he chickened out and threatened me to tell the directors of my master.

    Anyway, I am working even harder and harder, since I read your post, I have my common place, two blogs and started my website about educational activities. You have been so inspiring and I want to use this opportunity to appreciate your work here, soon I will show you my educational site so you can give me some comments, I could have never believed to build something like that before because I do not have much computer skills.

    • Way to go, Ninja!

      Where are you from btw?

      “now I am the best student and that has brought me many enemies and haters,”

      — Because this doesn’t sound like a typical university in the western world.

      Feel free to email me about your site.

      • well, for your surprise I am studying in Finland, but 60% of the students are from other countries. I will mail you my website soon, just starting but hell it is a start :)
        thanks again for the blog and the free e-books.

      • What is your mail btw?

  9. I really enjoyed this article!

    Several times as I was reading I was reminded of “trading moments”. I like to spread bet on the stock market and I constantly have to overcome this fear of loss.

    It’s funny. Even when I KNOW I’m going to win because I’ve seen this 1000 times before and I recognize the pattern (which is what got my attention in the first place), there’s always that reluctance. What if this time is different? What if I’m wrong? 1000 bucks is a lot of money to lose.

    How I combat it is “state” alteration. I sit back, I close my eyes and I imagine what it would be like to be George Soros, or another great trader. I imagine how they risk billions on big trades, and that’s why they’re who they are and at the top of the food chain.

    I’ll be thinking more on this concept. Thanks for this Ludvig.

    Ps: any more thoughts on Asia? Email me if you want any more specific info or I can help you come to a decision.


    • G-Freedom,

      “How I combat it is “state” alteration. I sit back, I close my eyes and I imagine what it would be like to be George Soros, or another great trader. I imagine how they risk billions on big trades, and that’s why they’re who they are and at the top of the food chain.”


      I’ll email you in a couple of minutes.

  10. Hi Ludvig,

    Really like what you said here…

    “Losers wait to be picked. Winners assume they are picked, step up, and provide value in any way they can”.

    I regards to your friend, I’ve experienced similar situations too and the person just doesn’t go through with it. Do you want to know my solution?

    I let them know it’s their life and their decision. But to NEVER complain to me about the situation again because if it was that bad they would do (or have done) something about it.

    Some may view this as harsh but it’s resulted in a lot less people bothering me with their bullshit.


    • Hey Naomi!

      “Some may view this as harsh but it’s resulted in a lot less people bothering me with their bullshit.”

      — That sounds like the smart and intelligent thing to do, in my opinion.

  11. Dan Erickson says

    What it I said there is no such thing as failure? It’s only a human-made ideal. I only fail if I don’t try in the first place, otherwise failure does not exist in my world.

  12. I can really identify with this, I am so Damn afraid to take risks. I lost a ton of money on the stock market for this reason…
    1. I didnt sell when I should.

    2. I should’ve bought early, but instead was afraid to take a risk and waited until everyone else was on board..

    Fortunately, Ive made a lot more than Ive lost. But i think that loss aversion is the main reason why people suck at investing.

  13. Hey Ludvig I got a weird question for u: whats your IQ?

  14. Don’t you think fear is something that some people find it hard to deal with? Yes maybe for most of us it’s easy to tell people to get over it, but for others it could be some sort of a ‘disorder’ so to speak.

    I come from a country where grades are highly valued, so much so that I hated the culture that made me never want to ever raise my (future) kids there. I know someone who has awesome connections but still did not get hired because he just didn’t excel in his studies, and he did not have the physical skills most company requires.

    It may come as a surprise but some people are ‘wired’ that way from young that they have no choice but to settle for mediocrity because they’re just terribly afraid of failure. And for them, telling them to simply get over it and gain control of their life, might not work, no?

    • Hey Aqilah,

      “but for others it could be some sort of a ‘disorder’”

      — I think the same could be said about just about anything. It could be true, and indeed it might be sometimes. But in my experience that 90% excuses and 10 % truth. So while people CAN have disorders, I don’t think it’s likely.

      “It may come as a surprise but some people are ‘wired’ that way from young that they have no choice but to settle for mediocrity because they’re just terribly afraid of failure. ”

      –This is an interesting take on it, but I, personally, don’t believe this at all. I don’t believe we’re wired to automatically fear failure. For example, kids are rarely afraid of failure, they just go for what they want unapologetically: “Candy? That’s mine!” The thought about getting caught or failing to steal the candy doesn’t even enter their mind. Dogs are the same way.

      I think “fear of failure” is purely a social construct. And I think it can be broken down by applying a ton of logic — by reflecting the pointlessness of fear — and by certain practical methods (like those I mentioned above to Abgrund). But to dare to even use any of those methods you need to push yourself above a certain threshold of decisiveness. That’s where your prefrontal cortex comes in, the part of your brain that is used to make decisions. And if your PFC is weak, which is the case for most people, then you’ll either have to convince yourself that the upside outweighs the downside, or you’ll need to be put in a situation where it’s do or die.

  15. He, he in my not yet published book I wrote this:
    “When in doubt, use your cool head. When moving forward, use your enthusiasm.” Sound similar, doesn’t it?

    What helps me is the focus on target. I’m like a torpedo. My fears can get me off track for a while. But sooner or later I realize I’m getting away of my target instead of getting closer to it and I correct my course.

    • Michal,

      “When in doubt, use your cool head. When moving forward, use your enthusiasm.”
      –Nice quotable. It’ll be on Wikiquotes under your section in 15 years. :)

      ” I’m like a torpedo.”

      –That sounds familiar. I like the analogy!

  16. Ludwig: Your article does a good job of explaining the /what/ and the /why/, but not so much the /how/. Awareness is half the battle, but do you have any concrete, actionable suggestions for breaking loose from familiarity/security?

    • Heathenwinds says

      “breaking loose from familiarity/security?”

      That’s pretty much it right there. You take the things that you feel are comfortable and secure, and you do something else instead.

    • Yes Abgrund,

      I remember you read my book. There is a ton of good advice on this topic there, it’s just structured poorly.

      Here are a few random ones:
      –Walk different ways to and back from work/school (wherever you gotta be every day)
      –Talk to a few strangers per day
      –Speak up in public
      –Formulate an interesting idea you’d like to test out, then “get into character” by boosting your state any way you can and do this thing with full conviction.

      The key to doing these things is that you must know that your brain will give you excuses/rationalizations–and anticipate it. Then you do it anyway. As soon as you feel the inspiration to do it you must act immediately, before your brain talks you out it.

      The key is to do enough of these things to cumulatively “break out of homeostasis” and put yourself in a new mode of being (physiologically speaking).

      But even if you do this one or two days, you still gotta force the consistency to get the momentum to make it more self-sustaining — and that takes a ton of energy and willpower, so you must deliberately focus on doing it every day. And if you stop focusing on it it’ll soon go away. At least in my experience.

      I am about to embark on one of these “sprees” of breaking out of homeostasis soon. I have been gathering up way too much information without taking enough action lately. Time to implement.

      • I like the fact that you provide concrete, actionable suggestions and not just motivational sermons. A good preacher keeps his flock coming back to him week after week for inspiration, but very few of them ever change their lives. He can make them want it but can’t tell them how to do it.

  17. The cause of suffering is attachment – in this case, to familiarity.

    I believe this is closely related to the “sunk cost” fallacy.

  18. “Instead he went back to school–for no other reason than fear. He got too comfortable being without a job and paradoxically didn’t want to lose what he already had–which in this case was

    That sucks man. That’s scary.

    Are you ever tempted to get into education? Start an institute? Something? In the FAR future, to teach people these life skills rather than all those “bullshit courses?

    • Sebastian,

      Yes I am. I am really passionate about learning things and teaching it.

      That’s definitely something I’ve been thinking about doing in the future. Either as a business, or as a contribution after I have become rich enough to do it for free.

  19. Ludvig this post reminds me of your ebook about homeostasis the way you explain the rationalizations. What is the difference? Is there one?

    • Hey Drilon,
      Yeah. It does.

      The difference? Mostly a conceptual one. Homeostasis is MUCH wider and more encompassing than the cognitive bias of loss aversion. But you’re definitely right that it’s a similar rationalization-mechanism. I hope that answers your questions. Thanks for commenting.

  20. Oh boy, he went back to school. Nothing wrong with taking your education further, but he has a terrible reason for doing so. Real pity I think.

    Some people fall into this trap where they think excelling in formal education will instantly grant them a hugely successful life. And especially so for a lot of “smarty pants” who consistently achieve outstanding grades. They’re so used to getting them that it starts to define them in some way, and then they feel lost when they realise they these grades are not as useful as they think they are.

    • I can vouch for that. I have good grades. But so do everyone else…It’s only a prerequisite.

    • Jeremy,

      “Oh boy, he went back to school”

      –Hahaha. Yeah. It is a pity, especially since he didn’t even like it in the first place.

    • Good grades in general are worth no more than average grades. Some employers even avoid people with superior grades, because they know from experience that an intelligent over-achiever will quickly become dissatisfied with the work and the rewards that they have to offer.

      In general, education (especially “higher” education) has nothing to do with acquiring skills or knowledge. You can do this more efficiently on your own, if you really want to, and every employer expects to train every new hire from scratch. Getting a college degree proves that you are able to stick to a goal while enduring boredom, hard work, irrational demands, and unfair treatment. It also shows that you can assimilate to whatever politically correct environment will protect an employer from lawsuits.

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