Back in law school, I was asked a great provocative question. In, of all places, a classroom! This: Would you spend $50 for a 1/1000th chance at $90,000?!
The asking professor knew me pretty well at the time. I even remember feeling already committed as his research assistant the next semester. He thought of me as supremely 'rational', and expected I would automatically say 'yes'. However...
I first fired a question back at him: "How many times can I do it?" He replied instantly, "Once." And I shot right back, "Then, no."
In a one-shot trial, I reasoned, EV (expected value) matters very little. EV is a useful long-term property of repeated events.
Further, a 999/1000th chance of complete failure -- of a cloud with no silver lining -- is hardly ever worth walking into. It is smarter to choose payoffs with more forgiving slopes -- if only because emotional impact & feedback quality do matter. (see prospect theory)
However, I was wrong. Because I hadn't yet appreciated much of what modern life offers the cooly risk-tolerant people -- the people who persevere through predictable failures. Life is full of chances just like my professor's: uncomfortable start-up investment yielding a huge chance of nothing & some small chance of spectacular result. It's not hypothetical -- and it's never a one-shot trial. It's everyday. (Examples: looking for a mate, finding new jobs, making business contacts, buying nice clothes, reading trade journals, calling clients for referrals.) Courage & resilience pay huge jackpots over the long haul. And I know now that I can still use much more of those psychic assets.
Some years ago, John O'Connor was feeling bold whie on a date with a woman named Sandra. Rather than simply ask her out for a second date, he went gung-ho and asked her for more than a dozen dates. What are they doing these days? Still happily married. (She is now U.S. Supreme Court Justice Sandra Day O'Connor.)("Go out on a limb: that's where the fruit is," in Mean Genes)
We [know of] situations in which people risk too much. In many cases, however, we have exactly the opposite problems: we are too timid. The social arena is one important area in which we ought to take more risks.
For ancestral humans, social failures were presumably much more costly than they are for us. Remember that, until recently, people lived with the same group from early adulthood until death. In such an environment, people were doomed to hear about their social mistakes for years as the same group gathered around the campfire to joke about Johnny the Overeager.