Need advice on book for my mom, who is relatively anti-investments

[SumZero]

I checked out the reading list sticky in this thread, but I want something that is accurate and smart while focused for my mom's needs (which I think are more basic than most of the recommendations in the list).

My mom is risk adverse (and anti things that involve luck), (relatively) anti-gambling, and sees investment as just a form of gambling (ironic that she gets this part but uses it to make investment bad rather than gambling ok). She basically has background moral issues against investments feeling that it just feeds people's greed vice. I.e., the reason prices go up is because people are greedy. The reason investments return money is people are greedy and lucky. And greed is definitely not a good thing! Combine this with the fact that she isn't interested in detailed education on how markets or specific investment devices work and it is difficult to talk about financial planning with her. When she hears from friends or investment analysts she is very results oriented in her approach (So and so tripled his money with this advisor in the last 2 years; therefore, the advisor must be great).

My description probably overpaints the picture, as most of the moral stuff is background beliefs that color her decisions, and not an outright THOU SHALL NOT INVEST/GAMBLE type belief (in fact she does believe SAVING is a very good thing, just INVESTING is a dubious thing). Fortunately my mom doesn't have a problem with the controlling your spending, or not running up credit card debt, or writing a budget or any of that type of personal finance issues. Just with approaches to investment and also retirement decisions.

My mom is a recently retired teacher (although she still can and does substitute teach for a few years to supplement income) and has investment decisions to make around her pensions (gov't and teachers) as well as a bit of retirement savings. My fear is that due to her background that through some combination of her background, inertia, and/or sketchy investment "advisors" she is going to do very poorly on her investments. Something she doesn't necessarily have the financial cushion to absorb easily.

My mom generally likes reading. My mom has also, from time to time, asked me questions about some of her investment decisions but talking to her about them is difficult because of all this combined with the fact that I don't know all the choices and my mom doesn't have a good framework to talk about the details or risks or tradeoffs of the various decisions or what her goals are.

I'm looking for book recommendations for my mom either on:

- how the market works, how investment works, how economic theories work (like inflation or EV or risk/reward tradeoffs), etc. but from the POV of someone generally not that interested in these type of things (like an outsider's guide).

- how one personally should approach investments again with an eye to her background beliefs and certainly not one that offers the motivation of greed (I.e., not one that is focused on "think of all the money you can make" as an end to itself).

Bonus points for books that offer a perspective or advice that:

- Is concentrated, or includes lots of examples or advice, for people in their late 50s and retirement age (rather than in their 30s and 40s).

- Is Canadian focused. US books are fine, but given my mom is in Canada any talking about 401ks, IRAs, mortgage deduction issues, estate tax planning, etc. isn't relevant.

- Ties any of the investment with analogies to poker and/or gambling. My mom is OK/cautiously interested in my poker hobby and accepts that it isn't bad as long as I'm only gambling with money I can afford to lose and that I'm not losing it or self deluding or addicted to it. She's even expressed occasional interest in learning what the "poker thing" is all about.

And I'm also open to the idea that I may need a combination of books (like one on randomness and EV, another on general approaches to investing, and another on retirement planning in Canada).

I'm also open to any recommendation of books focused to my needs as an interested in economic issues, relatively educated about investments personally being asked to advise my mother from time to time.

Thanks!

[Sniper]

Start Late, Finish Rich by David Bach... Maybe, read his "The Automatic Millionaire" first.

[DesertCat]

"The little book that beats the market" by Joel Greenblatt actually has a good section on what makes a good business, and what makes s a good investment. It's explained in very basic terms, and might counter some of her feelings about it just being greed driven.

[Thremp]

Good luck man. I'd hate to be in your position.

Maybe try and use a Mom and Pop example except that there are millions of Moms and Pops who each own a little bit.

[SlowHabit]

A simple analogy I used was asking my mom about a friend's business that she thinks is great and is making a lot of money. And what she would do if her friend ask her to be part of the business and take part of the profits. All she have to do is pay her friend a certain amount of the business's worth.

Then ask her what large corporations that she think is a great business. Well, she can be an "owner" of that business by buying shares of that business.

[MuckerFish]

Maybe something on the motivational front might help. The Richest Man in Babylon might fit the bill. A lot of why investing is good type of stuff without focusing on the greed aspect. After that maybe you can then introduce her to some of the more quantitative lit.