Easiest plan, 25%  each in S&P index fund, 30 year Treasury bonds, currency, and gold bullion, rebalanced once a year. The Harry Browne approach. Best portfolio is also the worst portfolio. One million in each sector is best plan. One dollar in each plan is worst plan. Income matters more than any other factor. No one knows the future. Best to save $1,000 to $10,000 per month. Average person can not and does not do this. Average people are broke. Seventy per cent of the world have a net worth under $10,000. Ninety per cent have a net worth under $100,000. Only .6% of the world has a net worth over $1,000,000. Worse yet, that $1,000,000 is only worth $50,000 in US silver dollars. Inflation is a fraud. Few people have any money to invest. Very few. The rich know how to invest because they have millions to invest. The average person does not invest and can’t really get ahead. No one cares about the average investor except how to fleece them with high commissions. The markets average 9% a year and the average investor gets 2%. Never invest in stocks if an average person. Just buy rental real estate and collect the rent with full control and no fleecing. Stocks enrich Wall Street and Main Street loses.

Some really great stuff to start with(since I remember starting out and it seemed like just yesterday even though it’s been 20 years)  are not always books actually, but here goes:

Investing and Macro:
John Hussman’s Weekly Market Comment(Free)
Jeremy Grantham’s Quarterly Letters(Free)
Warren Buffett’s Shareholder Letters Single Volume 1965-2016($3 on Kindle)
Meb Faber’s Books (Shareholder Yield and GAA specifically)
F Wall Street by Joe Ponzio(more shareholder yield)
Seth Klarman’s Margin of Safety(you can find it out there in PDF format)
Intelligent Investor by Benjamin Graham( 2003 Zweig edition)

Trading:
C. Van Tharpe’s - Trade your way to Financial Freedom and Beyond the Matrix
C. Van Tharpe’s Book on position sizing if you can find it($250)
Both Stock Market Wizards books by Jack Schwager

Jared: Millionaire Teacher! Andrew Hallam

Finance, Investing, Money Management, Wealth management, Common Sense. Which is which?

For those of any age, but particularly young people in their 20’s and 30’s, the best book I’ve found for teaching the basics of financial literacy is:

“Millionaire Teacher” by Andrew Hallam - the 9 rules of wealth you should have learned in school

Takes a short weekend to read, but lifetime of benefit. Read most of the others including many you mentioned, for a newbie to finance, money, investments - this is the best I’ve found to start with…

Jeff

Jared, As you noted, there are no shortcuts. I am a self-taught investor over a period of 30 years or so. And I must note that the tuition has been extremely high at times. However, I don’t believe that any amount of book learning can make us good investors. And paper trading can be helpful, but unless you really have money on the line, riding on a trading decision you made, you can’t know how you are going to react to either good or bad results.
My dad gave each of my two sons (his grandsons) $5,000 under a uniform gift to minors tax provision back in the early 90s, and I put it all in a science and technology mutual fund. I chickened out along in the middle of 1998 and changed it to money market funds when each account had around $43,000 in it. If I had hung in there another 18 months, it would have been more than double that, but I could easily have held too long and ended even lower than it did. In any case, along with scholarships and summer jobs, they both graduated from college without any debt.
One of the benefits of actually investing and trading is that you notice things that would otherwise pass unnoticed, and these small insights accumulate over time. Eventually you reach a point where you see opportunities. For example, I would suggest that a fairly low-risk trade right now would be to split a trading account into two halves, and put 25% into Google and 25% into Apple. Take the other half and short equal dollar amounts of Amazon, Facebook, and Netflix.
My logic is as follows: These five companies have been bid up greatly by index fund investing, but trade at hugely different P/E ratios. Google and Apple are at reasonable P/E ratios, whereas the other three are astronomical. When the market is again body-slammed, Google and Apple will come out the far side much better off than Amazon, Netflix and Facebook, meaning the investor will have money to invest at a time when stocks are CHEAP.
One lesson I learned in 2008 is that a stock market crash is not nearly as scary when you have cash available to invest. My paranoia kicked in before things got really bad, and I cashed out nearly half my positions. My accounts dropped some in their overall value, but nothing like the market in general, and rather than agonizing every day about how my stocks were being destroyed, I was watching stocks I wanted to own get cheaper and cheaper.
I did not get in at the bottom, and failed to pull the trigger at all on a couple of stocks that I shouldn’t have let get away, but I remember that my level of fear and angst was much different (i.e. less) than most others at the time. Thus, I like to always have a position or two in my portfolio that will rise sharply should the market crash. That’s my starting over money.

Jared -

I would change one verb in your recommendations. Everywhere you have said “BUY books on ...” should be changed to “READ books on ...”

My shelves hold a lot of good intentions. Reading a bad book is probably better than ignoring a good one.

It seems to me that the first question is, what do you mean about the term finance.  You have roughly equated it with investing.  To me, finance is about a lot more than that.  When I first started getting serious about my money, way back in the 70’s, I read a great book by a woman.  Her name was Vanita Van Caspel.  It truly introduced me to the whole spectrum of managing my money.  Investing was one aspect of that.  Perhaps one of the best insights was her discussion of insurance.  That saved me a ton of money which I later invested.

So your article pertains to investing, not finance.  And I am sure you will get some push back from Bogelheads!