Retirement Planning
"Retirement planning is like life insurance. It should be viewed as nothing more than a hedge against the absolute worst-case scenario: in this case, becoming physically incapable of working and needing a reservoir of capital to survive." - Ch. 2: Rules That Change the Rules (Challenging the Status Quo vs. Being Stupid)
In this quote, Ferriss outlines his unorthodox belief that retirement shouldn't be anyone's main goal. If you love your job, why would you want to stop? By comparing retirement planning to life insurance, he is emphasizing that it is a necessary step, but one that should only be utilized in absolute emergencies that are physically incapacitating. In the ideal world, neither life insurance nor retirement is ever needed.
A Cross Between Donald Trump and Joan Rivers
"How else can my 30-year-old friends all look like a cross between Donald Trump and Joan Rivers? It’s horrendous—premature aging fueled by triple bypass frappuccinos and impossible workloads." - Ch. 2: Rules That Change the Rules (Challenging the Status Quo vs. Being Stupid)
In this section, Ferriss is contesting the popular view that more hours of work = better results. In this step of his argument against the 40-hour workweek, he cites these examples: people who work exhaustive hours become (and look) thoroughly worn out beyond their years. It's far healthier and wiser to simply work a smaller number of hours on the most productive outlets, allowing oneself time for rest and relaxation.
A Spectator from an Office Window
"Let’s define “laziness” anew—to endure a non-ideal existence, to let circumstance or others decide life for you, or to amass a fortune while passing through life like a spectator from an office window." - Ch. 2: Rules That Change the Rules (Challenging the Status Quo vs. Being Stupid)
Ferriss is redefining the idea of laziness in this chapter. Diverging from the traditional definition, he expands the definition of laziness to include passive existence. He condemns the popular lifestyle that is successful but entirely subject to the desires and commands of other people. The simile of comparing such a person to a spectator from an office window emphasizes the lack of control in one's own life when in such a situation.
A Drowning Monkey
"I tried swimming and looked like a drowning monkey." - Ch. 2: Rules That Change the Rules (Challenging the Status Quo vs. Being Stupid)
This humorous simile emphasizes the fact that Ferriss is not naturally good at swimming. This section is dedicated to proof that it is better to multiply your strengths than to fix your weaknesses - Ferriss says that he abandoned things he's not naturally good at, like swimming and basketball, in favor of things he is, such as fighting, and it landed him a national title in kickboxing.
Sleeping Like a Baby
"He had always been terrified of plane turbulence, as if he might die with the best inside of him, but now he could fly through a violent storm sleeping like a baby. Strange indeed." - Ch. 2: Rules That Change the Rules (Challenging the Status Quo vs. Being Stupid)
This quote is part of a story Ferriss tells about a man named Hans Keeling. Formerly an attorney, Hans quit his job to move to Brazil and start a surfing vacation company. Once he did so, he felt freedom from the drudgery of his old job; instead of fearing death because of an unfulfilling life, he feels so at peace from his new life that even flying on an airplane holds no more terror for him. This is just one more example of a simile Ferriss uses to describe the wonders of life for the New Rich.