10 Reasons Why You Fail

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Think of something in your life that you’ve wanted to accomplish but haven’t. Something deep down. Maybe you haven’t gotten around to it, are too timid to go for it, or took a shot and failed spectacularly. Conjure up in your mind that big failure of your life. Perhaps you’re in the middle of it now.

It goes without saying, we all fuck up big time. That’s obvious. Of course, some of us are better at not fucking up than others, but that’s kind of obvious too. And then there are those who string along coulda-shoulda moments throughout their life like the toilet paper I used to string up along my neighbor’s house as a kid—a failure so consistent, it borders on art.

In the years I’ve spent helping other people overcome their personal issues, I’ve often been asked what the biggest cause of failure was that I’ve come across.

Some people have relationship problems, some have money problems, others have anxiety issues, etc. But the biggest problems I’ve seen in many of these people were not specific to relationships, money, confidence or whatever.

It’s easy to figure out how to ask someone out, or how to start a business, or how to just do something even when you’re afraid. Dealing with your fear of abandonment, or your toxic money habits, or your screwed up beliefs about what others think about you? That’s a tad more involved.

Chances are, a profound struggle in one area of your life will bleed over into other aspects of it. The principles of failure are rarely prejudiced. The behaviors and thoughts that sabotage you in one area of your life will stalk you in other areas.

That reticence to ever ask someone out on a date probably plays out in your failure to move to a new city, to take that new job, the timidity around your domineering co-workers, your passive-aggressive relationships with your family members.

When confronted with life’s biggest opportunities, most of us shit the bed. And then we enact a number of strategies to avoid the pain and pressure inherent in reaching for our dreams.

Below are 10 of the most common strategies for reluctance I can think of. We’ll start at the shallow end and work our way to the deep end. Read it and weep.

1. You Fail Because You’re Afraid to Stand Out Among the Crowd

Emerson wrote, “Society everywhere is in conspiracy against the self-reliance of every one of its members.”

People don’t like it when other people change or do something that makes them feel awkward or insecure. Pushing ourselves to reach our own greatness threatens the complacency of those around us, shining a light on their own squashed dreams and failed potential.

In many cases, these people lash out. It makes them question themselves, which is difficult for most to handle.

Why you fail: you're afraid to make a bold move

I talked to a fellow internet entrepreneur last night. He’s started multiple online ventures. Some have failed. Some have made money. All of it was struggle. He spent time traveling around the world and returned home for the holidays, where his father promptly told him that he needed to “be realistic” and get a “normal job.”

Simple fact of life:

People will think you’re weird, crazy, selfish, arrogant, irresponsible, obnoxious, stupid, disrespectful, fat, insecure, ugly, shallow, etc. Those closest to you will often become the harshest. If you have weak boundaries or are not confident with your own ideas and desires, then you’re not going to make it very far.

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    2. You’re Not Persistent Enough

    In 2009, debut author Karl Marlantes finally published Matterhorn, a novel based on his experiences in the Vietnam War. The book was a hit. The New York Times called it “one of the most profound and devastating novels to ever come out of any war.” Mark Bowden, bestselling author of Black Hawk Down declared it the greatest book ever written about the Vietnam War.

    It took over 35 years for Marlantes to get his book published—more than half of his lifetime. He re-wrote the manuscript six separate times. For the first two decades, publishers hardly read it, much less rejected it.

    Most of us give up on something we’re passionate about too soon. And anyone who’s been successful has a tale of struggle and perseverance to share.

    As the cliche goes, nothing worth having comes easy.

    3. You Fail Because You Lack Humility

    There are many people out there who accomplish a little bit and decide that they are an expert. Humility is knowing what you don’t know.

    In the world of online marketing and internet business, I began to notice a trend a couple of years ago in the business owners I met.

    The people who had a big mouth, who regularly went on and on about what they accomplished, exaggerated their successes and sapped the attention from the ether around them—they were moderately successful at best. Sometimes they were not successful at all; i.e., they still had day jobs or even lived with their parents. Yet they were more than willing to dole out their sage wisdom to anyone and everyone who would listen.

    But the people who were legitimate, self-made millionaires, the ones who actually did scale to the peaks of their industries, they often admitted they did not know an answer, they downplayed their successes (or usually never even mentioned them). Instead, they regularly pointed out their weaknesses and how they needed to learn more.

    This did not strike me as a coincidence.

    4. You Fail to Network and Build Strong Relationships

    I’m a perennial loner. I’m also a mild control freak with my projects. Whether it’s insecurity or obsessiveness or plain arrogance, I have trouble letting people influence whatever I’m working on or am passionate about.

    It’s counterproductive. It single-handedly submarined my aspirations to be a professional musician once upon a time (an industry based almost entirely on networking) and I’ve surely missed quite a few opportunities over the years with my internet business because of my hesitance to reach out and connect with others who could help me.

    10 Reasons Why You Fail

    It’s said that around half of people hired for a job know someone within the company that’s hiring them.1 But even in the non-professional world, isolation can undo you just as quickly.

    Instead of going broke, you just go depressed. Creating a wealth of social and romantic relationships hinges on the ability to meet people and connect with them in a meaningful manner. Research shows that living without regular social contact is as unhealthy as smoking cigarettes.2

    5. You Fail Because You’d Rather Argue Against Advice Instead of Taking It

    Guaranteed express ticket to sucking: trying to be right instead of good.

    I don’t care what it is, if you’re more invested in arguing your point of view against people who are trying to help you than you are in improving yourself, then you’ve effectively given up. And for all of your brainiac debating, you’re still too stupid to see it.

    To succeed at anything, there’s a feedback loop that must be in place: try something -> get feedback and results -> learn from feedback and results -> try something new.

    People who are dead set on arguing why what they already believed is right (despite it not working) are effectively breaking the chain off and not accepting feedback. Therefore they will never change.

    Not to say that everyone should always take advice from everybody, but you should accept feedback whether you believe it’s relevant or not, not try to argue your way into looking like you were right all along.

    The people who suffer from this problem tend to be highly intelligent and extremely insecure. It’s a bad mix, because the more intelligent someone is, the more they’re able to rationalize their own bullshit excuses to themselves, and the more their intellect is used as a defense mechanism to protect their fragile ego.

    6. You Fail Because You’re Too Distracted

    Facebook newsfeed, Tweets, Reddits, sub-Reddits, Imgur, check email, Facebook again, back to Imgur, oh a funny comic strip, post on Facebook, check email again, message on Facebook, funny cat pictures, tweet funny cat pictures, look on Reddit for more funny cat pictures, rinse and repeat.

    Distracted man with headphones
    Image credit: Sara Cimino

    I apologize if I just described the majority of your waking life.

    But the affliction of attention saturation disorder is not limited to useless social media interactions.

    Earlier this year I experimented with giving up sports and politics for a month. I was blown away with how much information I once considered vital and important soon felt like meaningless fluff—sensationalized info-tainment meant to keep me clicking rather than informing and influencing my life.

    Practice some self-discipline in your life.

    7. You Fail Because You Don’t Take Responsibility for What Happens in Your Life

    Also known as having-an-excuse-for-everything disorder. To fix the problems in your life you must have power over them. You can’t have power over aspects of your life unless you take responsibility for them. Therefore if you don’t take responsibility for what happens to you, you fail.

    There are numerous situations in life which may seem completely unfair and insurmountable, like God decided to piss in your Corn Flakes® unfair, and there’s nothing you can do about it.

    I know it’s tempting to blame your problems on some external factor, to insist that it was impossible, that it wasn’t your fault, that you couldn’t have done anything to help it, you see, it was Abu the taxi driver who accidentally ran over some little boy’s dog, and the guy actually pulled over to see if it was OK causing a more-than-unnecessary 30-minute delay, and the police came and questioned you until they realized you offered little Timmy some beer to make him feel better—i.e., to help him erase the impending decades of trauma and images of blood-splayed sidewalk that will surely haunt the first quarter of his life—and stop the crying, my god, the little brat could fucking cry, you were just trying to help, to clear his poor undeveloped psyche with some alcohol; but hey, then the cops came and the (drunk) little bastard told them about the beer, told them everything, ab-so-lute-ly everything EXCEPT that you were just being a nice guy, which you obviously never get credit for; and dude, it’s not your fault cops are so anal-fucking-retentive about child alcohol laws; it’s a fucking puritan, fascist state anyway; and hey man, I’m sorry I didn’t show up; it’s not my fault, I promise it will never happen again; there’s always the next wedding, right? I won’t be in jail for that one, I promise.

    Yeah, fuck people like that.

    8. You Fail Because You Don’t Believe It’s Possible

    I’m a little hungry, so I’m going to outsource this bullet point to the Dagobah system ($3 an hour, great turnaround time) where Jedi Master Yoda will fill you in:

    This isn’t some sort of manifestation/affirmation crap. There’s no supernatural power at work here (well, with Master Yoda there is, but with us, no).

    The mind’s unconscious beliefs about possibilities inform the level of effort and expectation of success from the body’s behavior. For instance, one study showed that athletes who held inaccurate positive beliefs about their own abilities outperformed athletes with accurate or negative beliefs about their own abilities.3

    Beyond that, people who overestimate what they’re capable of are far more likely to actually, you know, get off their ass and try. And when you try and learn from your failures, you can eventually lead yourself to success.

    So, a little delusion of grandeur goes a long way. Now if you’ll excuse me, I’m going to pay Yoda $3 to help me with some parallel parking.

    9. You Fail Because You’re Afraid to Care

    Many people catch the indifference bug. They lack a clear, true passion. They’re reluctant to invest themselves top-to-bottom into a venture, project or pursuit. Many of them give up quickly. Others just lose interest. Many lack the wherewithal to even begin.

    Chronic indifference is an insidious defense mechanism. It undermines the drive and motivation required to overcome it.

    Unconsciously, many people are terrified to invest themselves into something because investing themselves into it could potentially lead to failure and failure could potentially lead to a lot of thoughts their psyche is not yet prepared to face: questions about self-worth, competence, being worthy of love, etc.

    Look, I’m no Freud, but in my experience, people crippled by indifference don’t overcome it until some other emotional issue in their life is uprooted, confronted and kicked out.

    10. You Fail Because Deep Down, You Don’t Think You Deserve What You Want

    Many (or most) of the bullet points above are actually top layers for this underlying cause: believing you don’t deserve what you want.

    Many of us, at our core, have buried beliefs and feelings about ourselves that aren’t so savory. Maybe we were teased a lot growing up, or our parents and teachers told us we wouldn’t amount to anything, or we were punished for being smart by our peers.

    Whatever happened, something happened. And something inside us makes us feel uncomfortable with the idea of accomplishing too many great things as a result.

    Entrepreneur and business consultant Sebastian Marshall wrote in his book Ikigai:

    Last night, I was talking with my friend. I said, “If you did this, I’m pretty sure you could get your first client at $400/hr within 90 days.” It would have to be his main thing for the next 90 days, but it would likely work.

    His core goal right now is total financial freedom. And I laid out a plan that would get him there.

    But will he do it? I ask him.

    He cringes and says… “No. I won’t.”

    “So, that’s a million dollar question. Why won’t you?”

    He replies, “I don’t know. I don’t even like thinking about it really, but I’ll try to. I don’t know, fear? I have to confront my potential and the fact that I’m not living up to it? It doesn’t feel right? I don’t feel ready? I don’t think I deserve that much? I think I’d have to study longer first? I don’t know.”

    Why don’t people do it?

    Hell, I offer to make people money for free, draw up a simple, clearly workable business plan, offer to help out. 80+% of them don’t take it.

    It’s another self-esteem conundrum: you always find a way to get rid of what you feel isn’t rightfully yours.

    The heights and burdens of success make some feel like a king and others like a fraud. For many, getting what they want summons that worm-tongued voice in the back of their mind, prodding their insecurities and fears until they find a way to destroy everything they worked for.

    It may be a relationship with the best person you’ve ever loved; it may be a dream job you can’t bring yourself to take; it may be a creative opportunity of a lifetime which you ignore for more “practical” pursuits; it may be merely hanging out with people who you actually admire and feeling like a ghost.

    Whatever it is, the sludge pool of doubts bubbles up and finds a way, always finds a way, to ruin it for you—to make you ruin it for you—and that’s the hardest truth. It’s you. There is no other in this equation.

    And as much as you deny it, that fear will always linger and remain as an invisible barrier, a clear film separating you from happiness, pushed through and never broken. These issues can be overcome. But it’s painful and gut-wrenching.

    And then there’s always just another layer, simmering further below, more fear, ever-present, something we all eventually face over and over and over again.

    But if you don’t believe me, believe Yoda:


    1. Cappelli, P. (2019, May 1). Your Approach to Hiring Is All Wrong. Harvard Business Review.
    2. Holt-Lunstad, J., Smith, T. B., & Layton, J. B. (2010). Social Relationships and Mortality Risk: A Meta-analytic Review. PLOS Medicine, 7(7), e1000316.
    3. Starek, J. E., & Keating, C. F. (1991). Self-Deception and Its Relationship to Success in Competition. Basic and Applied Social Psychology, 12(2), 145–155.