Being Too Cool Can Ruin Your Life

Do you remember those kids in high school who sat in the way back of class, goofed off, or didn’t come to class at all? Or what about those kids who grunged out, tatted up, and gang banged their hairs? I used to be one of those kids until I realized I didn’t want to short circuit my life. When grades carry over from freshman year all the way to senior year, I couldn’t afford to mess around.

Because of my immaturity, I ended up getting a mediocre 3.3 GPA out of 4.0 my freshman year. My friends and I were into everything, and I mean everything. Smoking, drinking, hacking, and looking like punks. Nothing we were into was conducive to us going to class. When you have a shiny new motorbike at the age of 14 waiting to be ridden, and it’s parked in the woods where your parents or teachers can’t find it, all you want to do is escape!

Being “cool” has its perks no doubt. Your classmates are nice to you and girls want to be with you. But, being too cool can ruin your life if you become overly rebellious and constantly get into trouble. One time a big fella pushed me over while I was tying my shoe during class, so I punched him right where his glasses shattered into his eyeball. That was a nice two day suspension. If you get mixed up with the law, you’ll also end up wondering everyday whether someone will ever give you a chance again.

When I talk to grade school kids nowadays, I tell them quite sternly to stop messing around. Listen to your parents, stop using, and start abusing the books. Trying survive adolescence is such a harrowing experience for many. The worst is when a kid purposefully does poorly in class so others will stop picking on him.


It’s pretty sad when you come across adults who are obviously trying too hard to relive their high school days of coolness. You know, the woman in braids and a mini-skirt, or the man with the pierced eyebrows and skater hair. If you are 40 years old and no longer in shape, nobody wants to see your jelly rolls. If you need a job, your chances of getting hired are going to go down the tubes if you aren’t willing to wear formal clothing during the interview. You don’t need all that attention after decades of working on your insecurity. Grow up already.

Some kids never grow up and feel they now have to make a statement to be somebody. Marketers know this, which is why commercials try and push the dream to get you to buy things you cannot afford. How many times have you come across someone who is making ridiculous car payments for a car they cannot even pay in cash? How many examples do you see of people buying all the expensive shoes, clothing, and bags while still living at home with their parents?

I’ve got one friend who refuses to wear a blazer or a suite to an interview. Guess what? He’s bee unemployed for 18 months because he can never get past the first round. “Suites are for monkeys!” he says. Who’s the caged animal now living off the government with four roommates as a grown adult with no savings?

Being too cool as an adult is not cool. They can tell us that most people have no imagination and are all conformist zombies following the status quo. It’s their way of justifying being stuck in a perpetual state of high school insecurity where they didn’t do well and are now paying the price. It’s too difficult admitting failure, so they continue to fail over and over again without growing up.

When you’r still bragging to your friends about your high school quarterback or prom queen days, you know you’ve got a problem.


Visit cities like Amsterdam, San Francisco, and New York and you’ll find a tremendous amount of diversity. In fact, I’m pretty sure in a hundred years, most all America’s cities will be as diverse as these three. Everything works well until one person starts imposing their beliefs on others. When the nudists in San Francisco started intentionally trying to flash their bare, disgusting asses in public transportation with children everywhere, that’s when the City finally dropped the hammer to cut that crap out.

You’ll come across “too cool” people all the time who try and make you feel bad for being you. They’ll tell you how they don’t care about money, travel the world, lead exciting lifestyles and are so unique. Don’t worry about them because they are insecure. They find it necessary to impose their ideas on you to justify their own poor decisions. More often than not, these are the kids in high school who slacked off and are now deadbeat losers.

The next time someone tries and makes you feel bad for leading a conventional lifestyle, lend them a helping hand. It’s hard to be a 28 year old with no safety net, no career, and no significant other. Quitting your job at age 25 just because you didn’t like it with no back up plan is stupid. Believing you can do great things while just putting in four hours a week is a genius marketing idea that will get the creator rich, but not you.

And if you’re one of the cool kids described in this article, grow up already. Nobody is going to bail you out but you.

To Recap

* Go ahead and be a nonconformist. This is what the site is all about. Just don’t expect anybody to conform to you.

* Being “too cool” is subjective. The term can be used to describe chasing a trend to overstaying your welcome.

* There’s a balance to everything. At some point, it goes beyond just you.

Examples Of Being Too Cool

* Purposefully doing poorly in school so you can avoid being picked on, or fit in with the in crowd.

* Quitting your job after only a couple years with no backup plan and minimal savings just because you feel life owes you more.

* Not willing to wear appropriate interview attire because “suits are for monkeys.”

* Unwilling to buy insurance because insurance companies are evil.

* Starting another start-up in a completely saturated space because everybody else is doing it and you think you’re special.

* Going against the Federal Reserve and Warren Buffett in investing because it’s always good to be a contrarian investor.

* Blowing all your money on cars, clothing, travel like an idiot because you think you can always make money or get bailed out by the Bank of Mom and Dad, the government, or a spouse.

Untemplaters, why do people impose their ways on others? Do you think there are adults still stuck in high school glory days ala Al Bundy from Married With Children? Why can’t people move on? What are some other too cool examples you can think of?



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Sam is the founder of Financial Samurai, America's fastest growing personal finance site. We believe in reaching financial independence sooner, rather than later. Slice through money's mysteries!


  1. says

    I just found your blog but I will definitely be following it. Self improvement, authenticity, and loving yourself are topics I feel very strongly about. Thank you for sharing these! Something I feel really helps personal development is travel. I am going to South East Asia for 6 months alone as a 19 year old girl. Crazy? maybe, but I really think this will be one of the most beneficial experiences of my life.

    I am bad at checking follow up comments, so feel free to contact me on my blog!

  2. Tb at BlueCollarWorkman says

    Lol, well, yeah, you can ruin yoru life by being too cool as a kid, for sure. But is your life every really entirely ruined? No. The gang I was in, dropping out of highschool, felony on my record, got a girl pregnant…all signs point to an F’d up life. But I dusted myself off, got my GED, found a job that didn’t mind the felony, married the girl, and here I am. If kids don’t mess up as bad as I did, they’ll definitely have an easier road ahead, but if they do try and be cool and mess everythign up, their life isn’t entirely ruined! Anyone can always turn things around.

    I agree iwth you, man, about those earlobe things. What are those? What is the point? Whatever I guess, they’re not my ears.

    • says

      Nice job rebounding TB! You’re right. We live in a land of second chances thank goodness. If not, my suspensions, run-ins with the authority and all that jazz would have been a death sentence.

      I really don’t care what anybody does to themselves. This is what San Francisco is all about. The point is, there’s a time and place for everything. If you want to be so cool as to “screw the world,” well then don’t expect the world to accept you with open arm. Find your niche and be happy and don’t complain.

  3. Bucksprout says

    Beimg too cool has its financial consequences. I have to disagree with you on the guy with the pierced ear lobes and crazy hair 1 because having both doesn’t cost too much especially for a 40 year old and 2 though the fashion statement isn’t everyone’s taste I have to support diversity. The root of the problem of “too cool” or “keeping up the Joneses” is that people dont have an appropriate benchmark to rank or see where they stand financially in a group of people. And we are also comparing the wrong things. Imagine if cool equated to how much savings you have. Wonderful post it made me think if I were being too cool.

    • says

      It will cost the guy a lot if he wants to get a job, because the majority of employers will rightly or wrongly judge him as a liability. But, that is why places at Trader Joe’s or Rainbow Market are so great, as they are very accepting. I’m for diversity as much as the next person.

      The point is, unless you are independently wealthy, there needs to be some sort of conformity even if one hates it in order to get ahead. If all one does is go against everything, everything will go against them.

      Right now in the Bay Area, there is a start-up craze. Everybody and their grandmother wants to start a business b/c it is the cool thing to do. The problem with the herd is that it is often wrong due to a mismatch of supply and demand. Let’s shun the uncool traditional corporate gig that pays well to do a startup 1,000 other people have already come up with.

      Being too cool is subjective. It’s up to everyone to figure out how to manage.

  4. says

    I see middle aged and older women trying too hard all the time. Looking nice is one thing, but even if you’re in shape noone wants to see you in a tube top. It makes me sad that some kids think they need to get into trouble so they don’t get picked on for studying and getting good grades. Even one bad grade can make a big hit on GPA. When I’m screening resumes I always notice when people don’t include theirs and it’s always because they didn’t have a high average when I ask. Grades may not matter in every occupation but they still make a big difference in starting a career in most of them.

    • says

      Messing up in school just to be avoid getting picked on is sad. I think everyone can relate or at least see the kids who are not realizing their potential just so they can fit in, or fit out.

      The majority of people who say grades don’t matter have poor grades. The problem is, the majority of people in power did well in school. Hence, unless the power changes, rebelling by doing crap work is not going to help.

  5. says

    I was also very “non-conformist” early in life. I didn’t realize how detrimental it was too me until early college when a new friend gave me push-back on a different look, saying “different doesn’t mean better.”

    Often, everyone does something because it works. Unless you can improve it, don’t fight it just for the sake of fighting.

    • says

      Lucky you’ve for such a friend. It’s so easy to try and push the envelope growing up until we realize being different just to be different is pretty stupid. If we are naturally the way we are, great. If we want to turn into Dennis Rodman, maybe not so much.

  6. says

    I do not live a conventional life and I am okay with it. I never lived a conventional life neither have you. If you did you would still be working for the “man”! Do I adhere to norms and most conventions? Absolutely! Before I joined Yakezie, I thought I was one in 100 million. I think to be different for sake of being different is a wast eof time. I am different and much more effective than most.

    • says

      You really though you were one in 100 million? If so, that is awesome :)

      Yes, being different just for the sake of being different is pretty silly. I can understand when we are still in school. But as an adult, it gets kind of pathetic.

  7. says

    I live in the richest county in America. I see first hand individuals who think they are “too cool” to recognize common folk. If I walk down the street and make eye contact with someone I say hi and wish them a good day. That might not seem like much to you, but believe me in my county people look at me as if I’m some serial killer because I’m acting out of the norm. Becoming a blogger was a very easy transition for me because I like engaging with other people no matter what there background. Not only that but I am willing to help anyone who asks for it. The the cheesy old saying goes “Being too cool is for fools.”

  8. My Financial Independence Journey says

    Let me add a few to your list (all real examples):

    – Refusal to accept the fact that you can’t talk back to your boss the way you can to your parents or teachers.
    – Refusal to accept the fact that jobs require you to show up on time.
    – Lack of understanding that visible tattoos, piercings, and colored hair turn employers off.
    – Lack of understanding that being contrarian, just to be contrarian, is annoying.
    – Just because you can drop the F-bomb as often as you like, doesn’t mean that you should.

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