Die With Zero: Getting All You Can from Your Money and Your Life

cases, this sense of aimlessness can even lead to anxiety and depression.

What Cuban is saying is that he was facing a situation of asymmetric risk: when the upside of possible success is much greater than the downside of possible failure. When you face asymmetric risk, it makes total sense to be bold, to grab the opportunity at hand.

As a result, many people enter retirement with only a vague idea of what they’ll do with all that free time. Or they have some specific ideas—typically trips they want to take—but only for the first year or two. So after a while, they tend to find themselves adrift, feeling aimless and maybe even itching to go back to work, the one place they know

But remember that your goal isn’t to maximize wealth but rather to maximize your life experiences. That’s a big turnabout for most people.

If you wait until you’re 65 or even 62 to dip into your nest egg, you will almost certainly end up working longer than necessary for money you will never get to spend. What a sad thought: to slave away at a job and never get the gold.

Increasingly, given rising life expectancies, retirement experts recommend that middle-income retirees wait until they’re 70 to claim Social Security benefits, at which point they can receive more than 100 percent of their full benefits.

And, depending on when you were born, you can start receiving your full Social Security benefits somewhere between 66 and 67.

The most obvious dates are age 62 (the earliest date you can choose to start collecting Social Security benefits) and age 65 (when you become eligible for Medicare).

In sum, from my perspective, the years you spend earning that extra $500,000 do not make up for (let alone surpass) the number of experience points you lost by working for more money instead of enjoying those five years of free time.