Can You Ever Really Beat the System?

Boy, there’s a real question for the ages, isn‘t it? It seems that a lot of us find ourselves scratching our heads frequently trying to figure out “how to beat the system” and no matter how hard we try, we just can’t ever seem to do it. As we sometimes say, the emphasis is on “we” because when you really think about it, some people actually do seem to beat the system and usually that doesn’t seem to include us. Is that time well spent?

Some of us ask if we can ever really beat the system and get ahead, but I've found a different approach to be successful. Here are my recommendations.

It certainly ruins most of your day when you sit and moan about how you “just can’t win” or you don’t have any luck. When you do that, you are probably dooming yourself to even more failures and future frustrations. Wouldn’t your time be better spent on trying to learn and educate yourself more every day so you have a better chance to succeed in your job or hell, everything in life! Trying to learn more and improve yourself will always improve your chances to beat the system.

Me, Myself and I Will Get the Rewards…or the Blame

I’ve done pretty well for myself in life, I guess. I can’t honestly complain about my lot in life since on the list of the 4 billion of us on planet earth, I am probably in the top 25%. I’m not a millionaire, but then again I am pretty sure that I never thought that was really my big and important goal in life. Besides, it may not really be worth all the sacrifices one makes to achieve such a thing. Many really wealthy people appear to live an idyllic life, but many of them aren’t very happy either. The kind of obsessions often related to the ultimate pursuit of money interferes with family and friends and limits a person’s enjoyable free time. I don’t have to tell you that…just pick up the newspaper or watch TV and you can see it every day.

Goals – Do You Have Any?

Besides the oft quoted and pursued “I want to be really, really rich”, what goals do you actually have?

What were or are my goals? Well, having enough money not to worry and being able to provide for my family has always been a big goal. Of course, another one is to feel like I actually am contributing something positive to my job and my friends and family, or even to the world, and in the process try to cause as little harm as possible along the way. I can get that in many ways without being totally obsessed about only money, getting rich and “beating the system”.

I am pretty sure that I wasn’t always thinking in this way, but I have morphed over time into the person I am today and somehow 20/20 hindsight is really clear. It’s definitely a lesson I have learned and you can, too, if you want to.

What are the Secrets to Learning Any or All of This?

I’ll let you in on a few of my own secret “loopholes” and what I’ve found that has helped set me apart from my peers and thus helped in making me more successful in the traditional sense of the word. There are some really common-sense things which are very obvious to me now, but for some reason so many of us never quite see them until the years roll on by. Here’s what I have learned are some keys to my “beating the system”:

1. Be on time, in the right place, and when required, wear the right clothes.

It’s the simplest thing in the world, but unreliable people mess it up all the time. If you can’t be punctual, find the spot where you are expected to be, and present yourself in a positive way, it poses a question about you and your reliability. The system requires reliability…don’t ever be unreliable.

2. Be honest about what you do, including the times you screw up. When you do screw up, it won’t be held against you if it’s an honest mistake, you learn from it, and never ever repeat it.

Unreliable people make repeated mistakes and often lie about them. Eventually they lose when it’s clear that they’re a liability. Don’t ever be a liability.

3. Pay your bills on time, every month.

Why anyone doesn’t make this a priority is beyond me. On-time payment records help build your “financial reputation” and your credit history. You need to manage your credit history and credit score in your 20s, because you need your credit score to get things like a mortgage in your 30s. But, it’s more than that. It’s the right and responsible way to live and if you don’t try doing it, then you won’t and don’t deserve to beat this system, or any other one.

4. Do your taxes on time and do them right.

I’ll be honest, I hate paying taxes. I try in every legit way possible to defer or avoid them and that’s perfectly acceptable to try and do. But cheating on them? No way is that right. The taxes are used to make all of our lives better in so many ways and not just the obvious ones like protecting us and servicing our local towns and cities. So if you enjoy any of that stuff, taxes must be paid and used responsibly.

If you can’t do them yourself, pay someone else to do them for you. A smaller tax refund filed correctly and on time is much nicer than suffering through a tax audit and helps one sleep more soundly at night. Screwing up your taxes is like going to bat with two strikes already on you and no bat in your hands when you try to hit the ball! You’re not going to beat any system that way.

5. Don’t save what’s left after spending; spend what’s left after saving.

Most of us have that completely backwards. We party hardy and then we think about the damages. There really will be a rainy day one day when you need a tire replaced or your TV breaks. That’s why you save in the first place. It’s a fact that if you don’t, that leftover money you thought you’d have somehow is never there. The guideline I learned is to keep at least three months of paychecks in savings. Credit cards charge you interest, your savings pays you interest.

6. Be realistic about what you can afford.

I see things all the time that I wish I had, but I also realize that they are mostly “wants” that I can surely live without and my “needs” have to come first. My best option to fill the wants is to set them up as goals and work towards them with good financial actions. That reduces my financial risks and makes me much more responsible and likely to beat the system.

When you look for a new car, try to remember that it can bleed you dry with high payments and will decline in value from the second you drive it off the dealer’s lot! Be just a little practical and think about your needs against your wants and it goes a long way towards beating the system.

Is There Anything Else That You Can Do When the System Seems to Have You by the Short Hairs?

Try to learn the reasons behind the rules. While you always want to follow the rules and “letter of the law”, try following the “spirit of the law” too. I have learned that and now I can defend my actions with confidence and determine what my best course of action is to achieve my goals. It’s not always just a black or white choice. I try to use solid reasoning.

This actually happened to me at my job several years ago!

I was asked to resolve an issue using a specific procedure, and escalate the problem to someone else if and when that procedure didn’t work. That was the company rule or “letter” of their law. I tried it and found that the procedure did not work in the case I was involved with and I knew why. I knew (or thought I knew) how to fix it, but it went against company policy to stray away from the prescribed procedure. The procedure was put in place to prevent less knowledgeable people from causing potential damage and I was certain that my “fix” would not cause any damage, and would resolve the issue much more quickly. So, I decided to follow the “spirit” of the rule (or law) and chose to try to fix the issue more independently.

So what can happen?

One is I don’t follow procedure, but I do resolve the issue quickly and everyone winds up happy. I use an alternate route “above and beyond” to get the job done, and this reflects favorably on me and at my next performance review.


Two, I try but I don’t resolve the issue, but still no real damage is done. I can still escalate the issue and let my supervisor know that I tried, and why I did what I did. Because my reasoning was sound, I will still be looked at as someone who went “above and beyond” and this will be remembered favorably in the future.


Three, my actions caused further damage and now I am in deep trouble. I have misjudged the situation and my own skills. Even though I try to explain my reasoning, and I thought I had good reason to think my idea would work, I get a slap on the wrist and a reminder that the procedure exists to avoid this very kind of problem. I wind up learning a very valuable lesson, and will make better judgments in the future. I learn that I need to learn more before I start trying to bend any of the rules again.

Which solution you choose ultimately teaches you something that you needed to learn so you can actually “beat the system”

Your best bet is to learn, absorb, and keep on doing it that way so eventually you have accumulated the necessary skills to be successful! Most companies reward and promote risk takers: people who know when to bend the rules. But you have to know what you’re doing first.

Are you frustrated because you can’t seem to beat the system? Do you feel like the system is rigged and no matter what you do you just can’t win? How do you plan to win and what is that you really want out of your life? Is it ever too late to learn more and make the system work for you?


  1. Interesting post. I think it depends on what people consider “beating the system.” Some try to do it by evading taxes or other responsibilities, which in my opinion is a waste of time. For me, I try to beat the system by using my fiscal discipline and knowledge to take advantage of offers that typically get other people into trouble. For instance, utilizing credit card sign-up bonuses and points for reduced travel costs. Or, taking advantage of a 0% introductory rate to spread payments out (but still paying it off before the introductory rate is up to avoid any interest).

    1. When you use your points or bonuses from your credit cards, I look at that as opportunities that are given by the card companies for you to take advantage of. So in a sense, I don’t quite look at that as beating the system because the system is telling you to beat it and almost begging for you to do so. When it comes to trying to skirt your responsibilities like taxes, I definitely agree with you. It’s not only wrong, but a waste of good energy. I’m often quoted as saying if people would spend as much time doing positive things rather than trying to do something like beating the system, the world would be a better place. Thanks for your input, Tawnya.

  2. Awesome, Gary. One of the best posts I’ve read in a while. I love numbers 1 through 6, but I especially love number 5. That one is a game-changer. Flip your financial mind to that setting and you’ll be going places. This post really resonated with me. For most of my adult life I railed against “the system.” But as soon as I stopped railing and started to fix myself, “the system” became a lot less hostile. Bravo, my friend.

    1. Thank you very much, Mr. Groovy. I appreciate what you said. It does take time for all of us to come to the realization that we can control our destiny if we just put our mind to it and stop making excuses about “the system” and why it just has it in for us. The sooner anyone comes to that conclusion, the better off they wind up.

  3. Prudence Debtfree

    I like what Mr. Groovy says: “For most of my adult life I railed against “the system.” But as soon as I stopped railing and started to fix myself, “the system” became a lot less hostile.” That captures the spirit of your post. It’s really hard for many of us to get humble enough to focus on what seems mundane (like showing up on time) – but that is what can change our lives radically for the better. Great post!

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