Cary Siegel’s “Why Didn’t They Teach Me This in School?”—An Open Letter Response

Cary Siegel went to an excellent high school and college, then graduated from a top business school with a finance concentration. Next, he learned what he ACTUALLY needed to know to manage his personal finances. Why Didn’t They Teach Me This in School? is the book he wrote to share his lessons learned, first with his five children, then with others.

Subtitled “99 Personal Money Management Principles to Live By,” Siegel’s book has become a best-selling graduation gift for good reason. It covers topics such as budgeting, spending, credit cards, investing, mortgages, insurance, and much more in plain English. It’s full of practical, real-world wisdom and tips that, unfortunately, you probably didn’t learn in school either!

After my son received a thoughtful pre-graduation gift of Cary Siegel’s book as a college student, I read the book and jotted down some additional thoughts, which are made public here. After helping people in all 50 states with their personal finances for the last 30+ years using Prosperity Economics philosophy, these distinctions may provide a different perspective.

Siegel says in the “Caveat to All” at the start of the book, “This is one man’s perspective that he is giving to his children… Hopefully, it will help others think about their own personal money management.” And with that, I’ll contribute my own perspective, shared with my son and now beyond, in the hopes that my distinctions added to Siegel’s will provide extra value to an already worthwhile personal finance primer.

First off, Principle 8: “Spend Just One Hour Each Week Learning about Personal Finance,” is very astute guidance.  Even if you are of the camp that thinks “money does not matter,” in order to live on this earth, we do use money and so we might as well learn a bit about it.  Furthermore, you’ll want to be a lifelong learner and this is a great subject to start with.

However, I disagree with Principle 36, “It’s OK to Overpay the IRS Over the Course of a Year.”  This is giving the United States government an interest-free loan for 18 months! You overpay in January of 2018, you don’t see that refund until after April 2019. It is SO much more efficient to work with the human resource department of your employer to get your withholdings as close as possible to what you actually owe. Or if you are an entrepreneur and paying taxes quarterly, work with your bookkeeper or CPA to estimate your taxes.

Siegel calls it “forced savings,” but overpaying the IRS is a poor substitute for actually saving. Personally, I’d rather keep my money working for me and building my savings, knowing I’ll have to pay some taxes once I file my return!

I also philosophically disagree with Principle 41, “Negotiate Everything.” I’ve learned there are two perspectives one can have in life: Scarcity and Abundance. If you “leave some money on the table” with an abundant attitude in your dealings with businesses, there tends to be more good that comes from that type of relationship than forcing every last penny out of every relationship in a scarcity-minded approach.

Siegel suggests it’s worth it to “look cheap” or “feel rude” if it saves you a lot of money over a lifetime, but I suggest that when you behave cheaply or rudely, it causes losses in other areas that you can’t measure. (Although it’s one thing to negotiate a used car and quite another to negotiate “everything.”)

Principle 43, “Debt Is Bad” forgets the financial fact that your own money has a cost. This principle which is closely related to Principle 50, “Understand the Time Value of Money,” is often forgotten in personal finance discussions. Siegel wisely included Principle 50, and while I agree debt (especially unsecured debt like credit cards) can be bad, it is important to understand and measure your opportunity cost! Should you rent forever to avoid a mortgage or walk three hours a day to avoid a car loan? No.

We must analyze each financial decision such as the decision to take on debt by looking at the alternative. Test the assumption that “Debt is bad” with the question, “Compared to what?” For example, if you have a safe investment that pays you 7% and you can get a car loan that costs you 3% and you have $25,000 to work with, you are much better putting the money into the investment and taking out the car loan. Workbook question: What is the spread and what is the profit on the above scenario? (Hint, you’ll need a financial calculator to figure it out.)

I commend Siegel for stating in Principle 49 that if you do have a debt to pay off, you focus on the one with the highest interest rate as it is the most costly.  And I’d like to add that you can check your FICO score for free at, estimate how to raise your score at, or get credit help at

Now for Principle 58, “Invest in your 401k—at Least to the Company Match,” we have a split opinion.  I’m thrilled to see Siegel state to fund your 401(k) only up to the MATCH level, not the MAX level, as so many personal financial experts recommend. Yet I’d like to add that you only start your 401(k) once your emergency/opportunity fund is well on its way. (Principle 18, “Always Have an Emergency Fund,” I’ve added the “opportunity” word as it helps motivate us to keep saving.)

To examine the math of the 401(k) and see why I DON’T recommend that you make your 401(k) your main investment and why the “company match” might not make as much difference as you think, get a paperback copy of Busting the Retirement Lies. It crunches the numbers and also gives you a whole new paradigm for what to do instead of pursuing a typical “retirement,” which will likely leave you bored and/or pinching pennies.

Principle 62 warns young people that their landlord will probably try to keep their security deposit for no good reason. While this unfortunately can happen, Siegel’s advice to not pay last month’s rent (forcing the landlord to use their security deposit as last month’s rent) isn’t sound and could set up a young person for a bad credit reference! A security deposit isn’t the same as last month’s rent, and landlords require them for a reason, to have recourse in the event of tenant damage. Always act in good faith and don’t assume that other’s won’t.

Moving onto Principle 63, “Buy Less House than You Can Afford” is a smart strategy, yet Siegel implies that a future goal should be to pay cash for a house. Similar to the issue with #43, he’s forgotten your own cash has a cost. Mortgage interest which is currently deductible and some of the lowest cost money you’ll work with is very efficient debt and you would be better off storing your savings somewhere where you can access it. There is a saying: “you can’t eat equity,” which means that equity that builds in your home is not money you can easily access when you need it!

Additionally, Principle 69, “Get a Fifteen-Year Mortgage” is a recipe for challenge since as in 63, you are building net-worth (an asset minus a liability) in a place you cannot access.  Home equity (the value built by paying cash or using a 15-year mortgage or pre-paying a 30-year mortgage) is not an efficient asset.  I like to use the C.L.U.E. acronym to help me remember to build assets that I have Control over, are Liquid, can be Used for anything I want and act like Equity, meaning they can be borrowed against so that I can make use of the asset and its ability as collateral.

As a financial calculator that compares loans reveals, the money you think you are saving in interest with a 15-year mortgage would be better used invested somewhere else. As it’s not that difficult to earn more on an investment than today’s 4 or 5% interest rates, I recommend that you get a 30-year mortgage and invest the difference. You’ll end up far ahead AND with more control over your assets.

Siegel nicely left open Principle 73, “Term Life Insurance Works Best for Young Adults.” He suggests to start with term life insurance while also noting that there are other types of life insurance that may benefit a person if they learned more about them.

Now I’d like to introduce a non-financial thought that may affect you throughout your life and does affect your finances even if at arms-length. It’s that of your “unique ability,” a term coined by Dan Sullivan of Strategic Coach and stated by others as your passion/purpose/soul work, etc. that Siegel brings up in Principle 98, “Approach Your Job Following the Three P’s: Passion, Politeness, and Persistence.” It is important that you continue to learn about yourself around this area and as you do, things like Principle 75, “Don’t Invest Your Time and Money in Multi-Level Marketing Programs,” may be very inaccurate. I know quite a few people who use those programs as either full or part-time jobs, love them, and earn quite a bit of money for their work, while also loving every minute of it.

This same idea flows into Principle 77, “Read Your Automobile Manual Cover to Cover.” Yes, if you enjoy that kind of thing. Yet I feel it is better to pay for expert help—or trade for it, barter is doing something you love so you can give up something you hate—in many areas of life. This will give you better results while also being happier and less frustrated. You may need to know how often your oil needs changing, but you don’t need to play mechanic unless you want to.

Same with Principle 88, “Learn How to Fix Things.” Yes, if you enjoy tinkering and are good at it.  Otherwise, paying someone else to do it helps them, satisfies you, and keeps money moving and good will flowing and things in working order—your mindset included.

Lastly, I want to commend Siegel for Principle 94, “Set Up Both a Checking and a Savings Account.” You’ll soon learn that savings is both a noun and a verb, and the act of putting money into a savings account in a way that builds up a habit is both freeing and powerful.

Want to Learn A New Perspective about Money?

There are many places to learn about money, as Siegel suggests in Principle 8, from the internet to books to successful family members and mentors. We encourage you to consider alternatives to the “popular” money advice you’ll get from banks, brokerages, and Wall-Street-driven institutions that may be better at making money from you than for you.

If you are new to this blog, a good place to start is our Prosperity Accelerator Pack, which includes a complimentary ebook, Financial Planning Has Failed, along with a video, audio and summary sheet of the 7 Principles of Prosperity™.


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