How Smart People Make Dumb Financial Mistakes (so that it doesn’t happen to you!)

The Problem Is Far More Insidious Than You Realize

Key Ideas

  1. Reveals Todd’s stupidest, most expensive financial mistake.
  2. Discover what causes most financial mistakes so you don’t fall into the same trap.
  3. The two simple formulas that can save you from the most expensive mistakes.

It seemed like a smart idea at the time…

I sold the hedge fund business and became financially independent at age 35. What could be wrong with that?

After all, it bought me the freedom to embark on a 6 month trip and live the dream I had put off since college – long-term travel through the Middle East and Europe, with nothing more than a backpack, credit card, and no worries in the world. My whole life lay before me as one grand adventure.

Seriously, I had no right to complain.

Yet, it was one of the worst financial mistakes of my life. It cost me millions – many millions of dollars. I was so caught up in living my dream that I lost all financial perspective.

I had no idea at the time that I had just followed the classic recipe for a foolish expensive financial mistake.

I was about to find out the hard way, and hopefully these lessons will help you avoid doing the same.

financial mistakes image

What Causes Financial Mistakes

In a perfect world there would only be two causes of financial mistakes:

  1. Bad information
  2. Flawed reasoning.

If humans were perfectly rational then we could take the all information available, process it to an accurate conclusion, and consistently make smart financial decisions.

Unfortunately, we don’t work that way.

We don’t live in a perfect world, and our brains don’t work like perfectly programmed computers.

My personal experience is the bad information problem, while appearing significant on the surface, is a relatively small factor in the financial decisions that I’ve blundered.

Rarely have my financial mistakes been driven by bad information. I’d consider the information issue a relatively minor problem easily solved by due diligence.

More insidious is the bad reasoning problem.

We humans aren’t rational computers. We make decisions emotionally, and support these decisions through rationalization.

The ability to rationalize a bad decision knows no boundaries and is remarkably insidious.

I say this with deep humility, having observed my own decision process for decades, and I’ve coached hundreds of clients through the same. Nobody is perfect. We all make these mistakes, including you and me.

For example, my own decision to sell the business was driven by my emotional attachment to living my dream of traveling the world, free as a bird, with nothing more than a backpack and a credit card.

I was so attached to that dream that I rationalized selling the business for less than it was worth under the delusional premise that this action was necessary.

It wasn’t, and that was the critical error.

The truth? I slaughtered a valuable cash cow business for a few pounds of hamburger when I should have savored the sweet milk it produced for decades into the future. This mistake cost me millions of dollars – literally.

I was blindsided to alternative ways of viewing the situation by the narrow focus that my dream caused. My reasoning became one dimensional. My analysis was polar: the classic prescription for a bad decision.

Somehow, I got it in my head that if I wanted to travel the world, I couldn’t do it while running a business. Therefore, I had to sell it. Wrong.

It never occurred to me to hire and train staff to run the business in my absence so I could retain the income, and still enjoy my freedom. Oops.

Or I could have hired another money management company to take over day-to-day operations, giving me the freedom I desired while still retaining ownership. Double oops.

There were many possibilities, I just couldn’t see them. I was blind. That is how bad financial mistakes are made – blindness.

The point is, I got distracted by other competing goals (my dream of world travel), and failed to focus adequately on managing the financial implications of the decision properly.

My flawed reasoning allowed the sale of the business to become an “either/or” decision when it was nothing of the sort. Either I sell the business or I don’t live my dream of world travel. Nonsense!

There were many ways I could have lived my dream and kept the business. I just didn’t look for them because… well, I wasn’t looking.

More Examples of Expensive Mistakes

As it turns out, my financial mistake is not an isolated example of this problem. In fact, it’s quite common. It’s the most common way we make foolish blunders, so please pay close attention, and don’t follow in my footsteps.

While there’s no definitive research providing hard data, anecdotal evidence from my work with hundreds of financial coaching clients tells me the number one cause of the truly expensive, large scale financial mistakes is conflicting goals causing you to not properly weigh the financial implications of your decision.

For example, every day someone chooses to sell his home far below value because he isn’t getting any better offers, and has conflicting needs to either move, or get out from under an oppressive mortgage payment.

The desire to get on with his life is rationalized as the reason to sell below value – sometimes at absurd prices.

“Experience is simply the name we give our mistakes.”-Oscar Wilde

Many times I’ve been told of people who accepted a low-ball offer out of desperation, only to hear someone tell them they would have paid more if they had any idea they were willing to sell that low.

There are always alternatives.

I know of bloggers who have sold their successful websites for 1-3 times passive revenue (advertising, etc.), when the financial aspects of this decision made no sense. The reasoning will be familiar by now.

They were either tired of writing and wanted to move on, or they were tired of dealing with the technology, marketing, and other backend issues related to running the business, and just wanted to focus on writing.

Seldom is the discussion about financial considerations. Finance is pushed to the background because the focus is dominated by personal motivations, and therein lies the problem.

Another example is the coaching client who comes to me in need of an investment plan, after making a series of horrendous investment mistakes causing massive losses. What has surprised me is how many of these investors have succumbed to the life insurance salesman’s pitch.

“At least you won’t lose on this one: it will always be there for you and your family.” True, but at what cost? It’s a distracting half-truth appeal that blindsides the investor from seeing more effective and efficient solutions to the problem.

They’re perfect prey for that pitch because their painful loss blinds them to alternatives.

I could continue on with many examples, but you get the point. When you have conflicting motivations behind a decision, it’s very easy to overlook important financial considerations. The result is an expensive mistake.

However, when you focus on financial considerations, the decisions are usually sound… at least from a financial viewpoint.

How To Minimize Financial Mistakes

There are two ways to minimize financial mistakes:

  1. Educate Yourself – That’s what this site is all about. As you improve your financial intelligence, your reasoning skills will improve. You will develop a good nose for sniffing out financial nonsense. Due diligence skills will help you overcome information problems. The rational part of your brain will be driven by software that applies proven principles. All of this will result in better decisions.
  2. Focus On Financial – Develop self-awareness that notices when conflicting goals are narrowing your field of vision. The goal is to always catch yourself getting sidetracked before making an important financial decision – not after. You must give each major decision a financial voice so that you aren’t blindsided by the financial implications.

Over the years, I’ve improved on both fronts. My motivation is strong because I know how much these mistakes have cost me. Given my financial background, I’ve reached a point where distraction is my most dangerous enemy, causing multiple bad financial decisions in my life.

It has literally cost me millions not just once – but several times. In other words, this idea may sound simple, but I can’t overstate its importance. Seriously!

Yes, even financial experts make horrendous financial mistakes. I’m living proof that it’s remarkably easy to do when you allow your mind to get distracted by competing goals.

It’s one advantage to having a financial coach as a collaboration partner. Your coach is not distracted by your emotional needs like you are.

Learn from my mistakes. Train your mind to properly weigh financial considerations, and look for alternative possibilities when your field of vision is getting narrowed by conflicting objectives.

When you balance the decision, you’ll nearly always discover alternative solutions so that you can have your cake and eat it, too. It doesn’t have to be “either/or”. You can have both when you open your mind to seeing the alternatives.

Now, it’s your turn. Come clean with your favorite financial blunder in the comments below. Owning it helps you grow beyond it, and helps everyone else learn from each other’s mistakes. Share your experience below and let’s all benefit.

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Craig Kingston
Craig Kingston

My wife and I also have a goal of traveling the world.  Our kids are in college now and we have developed our business so that we can do our work anywhere so long as we have internet and/or a phone.  We are looking forward to maintaining our income level while living for short periods of time in other cultures.  We are hoping to get this going later this year.  Hip Hip Hooray!


Indeed, it is true. Many people do not realize quickly enough that things are not going well any more. Education is the key and you should always keep your eyes on income, expenditure and debt.


Your article touched a sore nerve.   I did a similar thing.  I spent 10 years building up a profitable cash-flowing business, then sold it with the idea of traveling the world, when I could've kept it and still traveled the world.  


The big mistake I have made several times: I would get so excited about my business idea that I negated a lot of my "downside risk". This caused me to make business deals with partners (I really "needed" their money!) which disproportionately favored my investors. If something went wrong, then I took most of the haircut. This has happened a few times and it cost me other opportunities to make a killing while I was busy getting myself out of "the hole"! Thanks for the great article!


My big issue is taking things in short spurts. I have chronic fatigue, so being tired can overwhelm my rational thought centers. I just want to get the item and get out -- even if I know a little comparison shopping could save a bit of money. And, hey, sometimes it's worth the trade-off. But other times we have overpaid significantly. Of course, it's not just fatigue. Like you said, rationalization is a dangerously strong force. (The force is strong with this one!) I usually have to put off purchases just so I can make sure the logic makes sense outside the initial frenzy from the simple desire for the item or a "great" sale or whatever.

Garry Davis
Garry Davis

Great article, as usual Todd. I hope lots of people read it. Your willingness to admit to a blunder gives you tremendous credibility and hope for the rest of us. Plus it gives great insight into the way you, as a highly successful investor, coach and person, think through decisions now in your life after having gone through that experience. Thanks for sharing.


I've also bought private and public stock on "hot tips," to my and my family's detriment. But my biggest mistake was a loan made to a friend of a family member. He was smooth, and had a reputation as a serious and effective real estate investor. He had a published book with a well known investor who I have tremendous respect for. The family member who referred him to us is trustworthy and the guy had a good history and reputation with him. I loaned him a lot of money on a promise that he would pay it back within 90 days, with a substantial interest payment for our trouble.


Notice that not a single basis for my decision to loan him the money had anything to do with facts or due diligence. It was all emotion-driven and highly flawed reasoning. After four years of fighting with him to try to get it back, we were served with bankruptcy papers, which we challenged and lost, and were screwed out of a lot of hard-earned cash. He had ferreted our money and that of lots of other people into trusts and holdings of other family members to establish his insolvency for bankruptcy. It was a tough lesson to learn with a high tuition payment to the school of hard knocks, and all I got out of it was an FD diploma - doctorate of foolishness.



Great article.  When I find myself potentially making emotional decision or I am confused as to what to do, I always try to step back and do a pros/cons list along with a financial analysis.  I find that when I remove the emotions and focus on making a decision based on the numbers, I am forever happy with the decision.  When I do not do the financial analysi, I rarely am happy afterwards.  Probably because making the decision without looking at the numbers was an emotional one.  Also, not doing the financial analysis was an emotional reflex to justify the emotional response.  Lesson I learned: Always do the financials.



Biggest financial mistakes:

1. Buying on a hot tip. Trying to make a quick kill.

2. Not learning about the real stock market earlier.

3. Not using trailing stops all the time no matter what.

4. Buying home in "wrong section of town".

Marc DM
Marc DM

Thanks for sharing. Very good points. 



Financialmentor moderator

 @Occam Hmmm... sounds familiar. It's nice to know I'm not alone. Thanks for sharing.

Financialmentor moderator

 @AbigailP Yes, that is another excellent idea - put off purchases for a minimum of one day until the emotional component of the decision subsides. If you still want it after the wait then fine. This is another excellent habit for reducing the emotional impact on spending decisions. Thanks for sharing!

Financialmentor moderator

 @Garry Davis Wow! Great story, Garry! Yes, there is no substitute for integrity. One of the questions I always ask coaching clients when investing in someone else's real estate deal is what security they have? Are they on the title? Is it just a promissory note. Are they a recorded lien holder? The reasoning behind those questions tie back to the exact situation you discuss here. Thank you for sharing and helping others in our community learn from your experience. It is a very important lesson.

Financialmentor moderator

 @draiss I really like your approach of putting pencil to paper and completing the analysis in writing. Great input. I also want to emphasize the other insight you "dropped" in at the end and could easily be missed by the casual reader - "making the decision without looking at the numbers was an emotional one." What I take from that comment is the avoidance is a way of protecting an emotional decision that you are, well, emotionally attached to. That is a great insight into human behavior.

Financialmentor moderator

 @hedy1234 My first investment was #1 on your list. Lost 100%. 3 is a religion around here. Would love to have you elaborate on #2. What do you mean by that?



 #2 refers to education/knowledge. I really had no idea how the stock market worked. Buying/selling, using a broker (or not), what does it mean to really invest, where to go to find companies that you should actual buy a piece of, how do you actuall buy a bond, how do options really work, etc. etc.


The real challenge now is that there is so much information how do you narrow down your focus, who do trust when it comes to information? It took a long time and some losses to get somewhere of comfort with this.

Financialmentor moderator

 @draiss  @Financialmentor Uh, actually it is just the opposite. I always have an exit point. I never invest without knowing my exit point. That doesn't necessarily equate to having a trailing stop in the market since that can only be applied to certain securities like the stock market. Real estate, as an example, has no such applicability. Risk must be managed in ways other than an exit point.


 @Financialmentor   I wasnt clear on my question.  What are your reasons for never placing trailing stops?  I prefer alerts myself but wanted to hear your position.  EdD

Financialmentor moderator

 @draiss  @Financialmentor  @hedy1234 Thanks for asking. I actually edited above after your comment to more accurately reflect my intended meaning that I follow the principle religiously. It is a guiding principle, if you will. To call it "religion around here" is careless use of language so thanks for bringing it to my attention. Hope the new version makes more sense.