The Best and the Worst of Being Financially Successful

Being highly motivated to take control of one’s personal finances is a good thing. I think we can all agree to that. The idea of making a practice of the right choices and decisions to provide well for yourself and your family—of being financially successful—is really an ingrained idea in our minds once we are old enough to understand the concept. Again I say good for those who do just that.

Being financially successful is an admirable goal, but how you achieve it counts for more than the goal itself. Here's the best and worst of it.


It isn’t easy to put your nose to the grindstone and work so hard that at times you think that you may have given up too much. It may be at that time that the thought of being financially independent or wildly wealthy gets you through your second thoughts about the sacrifices you might be making to become financially successful.

The Worst of Being Financially Successful

What about those who go just a step or three too far in that pursuit? I’m talking about those who pursue financial success at any cost. You know the ones that I’m talking about even if you don’t know them personally or even know their names (Can you say Michael Milken, Bernie Madoff or even Martha Stewart?)

They’re the ones that start out with a good and well-accepted approach to financial success, and then somehow it goes all haywire. They confuse the word “success” with the word “greed” which raises questions about things like a moral compass and playing by the rules and/or even staying within the law.

There are many innovative people, many of them successful in the world of personal finance, which somehow manage to color outside the lines and break new ground on their road to financial success. That’s a surefire way to get there. Nobody says that you must always take the straight line to get to your goal. Although I’m not the biggest football fan, I have watched enough of it to understand that when a runner gets across the goal line he more often than not takes a route that looks more like a zigzag than a straight line. Life is more often than not exactly like that.

So having said that, it’s so disturbing to me when I hear or read about someone or some corporation that has been discovered to have crossed over that invisible line between huge financial success and breaking the law, either moral or judicial, or both. It makes me think, why does that happen?  Is there something wrong with me, or them? There seem to be so many “thems” and so often they get away with bad behavior for really long periods of time and leave a path of debris behind like a tornado does.

I don’t want to sound like a hypocrite. After all I have been writing about overcoming financial problems and achieving financial independence here at Super Saving Tips now for over 2½ years and I promote financial wellness and all of the good that it can bring. But there is a big difference between those who earn their success without “gaming the system” and hurting others and the ones that do that to become successful.

My Personal Experience

I have crossed paths with some individuals along the way that believed in the concept of success at any cost. Back in the 1990’s, I worked for an entrepreneur who had started a business and was fairly successful. When I came on board, I recognized almost immediately that he was driven by success and wanted to be the biggest and best at what his company category had to offer. When I started there he was already a multi-millionaire. For some reason that wasn’t enough and he needed more. My job was apparently to help him get just that.

On the surface, he didn’t appear to most as someone who might cross the line in order to get what he wanted, fairly or not. That wasn’t true however. If I live to be 100, I will never forget something he told me not too long after I began working for him as his COO. This is what he said to me and I quote:

“Thank goodness there are so many stupid people out there because it makes it so much easier for me to be smart!”


I am certain that that moment in time is when I knew that my relationship with him and the company was doomed. I didn’t think that taking advantage of others by cheating and deceiving them made them stupid nor made him or anyone else smart. What it did do was make me see firsthand how someone can veer off so far from being fair and moral in order to pursue wealth.

I lasted about two years in that environment and fought tooth and nail to make the company better than it was and make it a success in every way in addition to its balance sheet.  I failed at the former but not the latter.  After I left, the company was sold to a competitor for multiple millions and most of the corporate employees lost their jobs in the acquisition. The owner, well, he retired with tons of money and he thanked me for making his company so attractive that he couldn’t walk away from the offer he got. He never felt a twinge of guilt or a thought about the people who had made his fortune and success possible and only thought of them as stupid pawns in the game. I’m still disturbed by that even 25 years later.

The Best of Being Financially Successful

The expression that “money is the root of all evil” has been around a long time. It really isn’t true. Money is something that can provide blessings for people, safety in terms of healthcare, housing, and education.  Charity can come from wealth and so much of it does from the wealthy that support large foundations and charitable trusts. Good comes from money, perhaps more often than the bad does. It always comes down to the person, him or herself, in what money causes and its effects.

I have written about the road to financial wealth before and in every case I say that success and wealth come from within and that money isn’t the only measure of one’s wealth. It has more to do with being satisfied and happy in your life and less to do with creature comforts, power, and having a high profile and status. I don’t think I am alone in that feeling. I don’t think you’re in any way stupid or a loser if you think that way too.

On your road to financial wealth are you taking a course that’s outside the box? Do you differentiate between your wealth and your success? Have you ever dealt with a situation that caused you to change your job because there was a violation of your ethics and/or moral consciousness? What would you do if faced with that situation?


  1. I think I’m on a tradition path. (work for someone)Luckily I have never ran into an ethics and/or moral issue that have forced me to change course.

    My children will be better prepared to zig and zag as they enter the workforce. They will have the benefit of understanding that the tradition path is not the only option.

  2. Lars-Christian

    Great topic, Gary!

    I believe that financial security, and abundance in particular, has little value on its own. If you dedicate your life to hoarding as much cash as you can, at the expense of actually discovering yourself, your values, and living your life according to those values, what’s the point?

    Being set financially only has value when you use it to enable you to live your life the way you want. and, unfortunately, you don’t have to look as far as those who step beyond what’s allowed by law to find examples of people who forget that. Too many of us get caught up in mindless consumption, and chase the dollar to fuel a life that we never even contemplate on the hamster wheel. Moral issues aside, to me, that’s as sad as those who lose sight and step beyond the law to enrich themselves.

    Just my two cents 🙂

      1. Lars-Christian

        Yeah, I in no way meant that as a comment on anything I’ve perceived from you, Gary. It was a general observation, and if I felt that you propagated the mentality I objected to, I wouldn’t be a regular reader. Just wanted to clarify that.

        Keep up the good work! 🙂

  3. I think some of those scammers you referred to start off with good intentions but somewhere go astray. Years ago when it came time to file my taxes the IRS was unable to find a record of that particular employer. I called him for his tax ID, which he gave me, but he never fessed up about what he had done. He had withheld my taxes but ketp the money to keep his business afloat. The IRS said I was due my refund and they went after him for taxes and penalties. He was someone who prided himself on ethics in the way he handled customer service, but on a personal level he couldn’t manage his finances ethically.

    1. Mrs. Groovy, I think you’re right about the majority of people who lose their way when it comes to their ethics. But I also have to say that there are some when they get away with something that’s just not right, develop a taste for that because it’s sometimes the quickest way of getting what they want. Unfortunately, I have seen it happen many times.

  4. Emily @ JohnJaneDoe

    I think I’m going to go philosophical for a minute, if you’ll indulge me.

    Ethical behavior seems such a big problem now, and it’s hard to identify why. Have our standards for ethics changed? Maybe. Certainly over centuries, if not lifetimes. But our idea of appropriate jokes, topics of discussion, etc has certainly changed since I was a young adult.

    Has our tolerance for unethical behavior changed? Probably….investigative journalism, tabloid journalism and tell-alls mean we tend to dwell on bad behavior and outrage is the common response. On the other hand, there’s this countermovement to greater demands for ethics, and hyperpartisanship seems to be poisoning ethics in politics.

    Or have societal pressures changed so much that people are no longer scared of their bad behavior revealed? (Possible) Do we celebrate bad behavior as a culture in the age of Real Housewives?

    Interesting things to think about, as always, Gary.

    1. Emily, you have certainly touched on many of the questions that I often ask myself. I believe that there have been a lot of changes in the ethical behaviors of people and I’m not exactly sure what the reason for that is. As a child, I suffered from what I have called the “I don’t want to be sent to the principal’s office” mentality. Thinking that way kept me from doing things that would be wrong or disappointing to my parents. Today, it seems that doing something wrong is not a stigma, in fact, it might be a great way to gain publicity, fame (notoriety), and money. I think that’s pretty sad. I just wonder if that’s going to keep spiraling downwards. Thanks so much for your comments.

  5. Rich Growth Tips

    “The expression that “money is the root of all evil” has been around a long time. It really isn’t true. Money is something that can provide blessings for people, safety in terms of healthcare, housing, and education.” It is absolutely right! Pursuing financial independence without crossing the red line is the right direction. Otherwise, the person who is pursuing financial freedom only earns and keeps money for other people.

  6. James

    To be financially successful takes time, and I accept this fact. That said, what I do is be at my best in becoming financially responsible. This year, I will save more consistently, try to work on more side hustles to increase savings, and stick to my budget, making sure it is effective.

  7. Ending our #yearofno has caused me to reflect on these questions quite a bit myself. What is success? How do we keep our values while trying to reach financial independence? I can say that I’m so happy the internet has introduced me to good people like you. I know it’s possible to provide for your family without hurting others to do so.

  8. One of the disturbing things I observed in my earlier jobs working for a very successful man in his late 60s, about ten or so years ago, was that he had decided that his financial / professional wealth was a mandate from the universe. He was rich therefore he could not be wrong, and he was above the law. Not unlike our POETUS who declared that he can’t have conflicts of interest by virtue of his position even though the two are not inherently linked, that boss believed that it was totally fine for him to behave unethically and unlawfully, and it was his employees’ responsibility to support him in those unethical endeavors. I did my best to push the office culture away from that during my time there but knew that the best thing for me to do would be to leave as soon as I could.

    Years later I heard from other longtime industry leaders that he was notorious for that and that absolutely no one wanted anything to do with him. They had to do business with him, but many chose alternatives as soon as it was possible. One significant part of his career ended when those leaders were able to sever their ties with him.

    He didn’t learn anything from it, of course, I was just glad to see that other people saw his transgressions as I had.

    I worry, though, that this attitude will become even more prevalent as it has been in recent years. That isn’t a healthy culture to live and work in.

    1. Thank you for sharing that, Revanche. I’d like to believe that inherently people are good and that the experience that you and I both had is not typical of how business and finances are generally conducted. The problem is that when you experience these severe situations, you remember them forever. Hopefully, we have more reminders of honest and hard-working success stories than we do about the exceptionally self-centered and greedy people that we come across. I really appreciate you sharing your story.

  9. Fruclassity (Ruth)

    That IS a disturbing thing your boss said! The expression “Money is the root of all evil” is a misquote of a passage from the Bible that says “For the love of money is a root of all kinds of evil.” It’s the love of money – not money itself that is at the root of things like the disturbing attitude of your old boss. As you say, many wealthy people are very generous. They clearly love how they can help others with their money – more than they love that money itself. Great post, Gary!

  10. Christopher Hay

    As bad as what you boss said, it’s even worst that so many other businessmen and entrepreneurs think they same way, just we don’t know. I believe in morals, although I want to be financially successful, I don’t think I could do it by using “any means possible”.

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