In 2005, Liverpool reached the finals of the Champions League (European Cup) for the first time in 21 years. Liverpool was clearly underdog to the stylish AC Milan. Big underdog. A lot was riding on that one match - Liverpool was 5th in the league that year, which meant they would not qualify for the competition the next season if they didn't win. Their captain, Steven Gerrard, would probably have gone to Chelski if that happened. These were terrible prospects for a Liverpool supporter like myself.
Should I Bet on My Team?
The question was: Should a Liverpool supporter bet on Liverpool or AC Milan? (do answer or make a guess before you read on).
Suppose I was risk-averse and that I placed a bet with AC Milan. If AC Milan won, I would be compensated monetarily instead by winning the bet. If Liverpool won, the amount I placed on the bet would be lost, but it would hardly matter since the joy of seeing my team win would be great. Effectively, placing a bet against my favourite team Liverpool (and on AC Milan) became an insurance policy for me. On the other hand, placing a bet on Liverpool would have exposed me to more risk since I could potentially suffer the double agony of losing both game and bet.
What appears counter-intuitive to the lay person becomes perfectly rational for a trained economist - betting against your favourite team is the route to greater happiness! It sometimes comes as a surprise to me how few people understand this principle. Even when I pose this question to a class of economics undergraduates, 80 per cent would get it wrong despite hours of lectures and classes on insurance.
History would show that I didn't win my bet on AC Milan in 2005, but did it imply that I "lost"?
The Outcome You Do Not Want
The simple example provides an important lesson - always bet on the outcome you do not want for insurance. You buy a car insurance so that you can receive compensation when you get into an accident. If you "win" the bet with the car insurance company, you would have been involved in an accident already - clearly an outcome you do not want! When you "win", you have in fact already lost.
Therefore, my bet on AC Milan was actually one I would rather not win. Likewise, I would rather pay for healthcare insurance and never have to claim it. When it comes to insurance, it is not a good thing in general to "win" against the house (insurance provider)! The notion that we should buy insurance and try to win against the house is simply preposterous.
Purchasing an insurance guards the individual against downsides. For the risk-averse individual, the insurance offers a peace of mind which improves his welfare regardless whether the payout is claimed or not. A car insurance gives me the peace of mind to drive on the roads - knowing that my financial losses are covered. I buy because I am risk-averse. Whether I get a payout or not in the end - surprise surprise - is actually a moot point.
All Can Be Better Off
Let me turn to the longevity insurance proposed by the government (my writeup here). Many bloggers believe that if an individual does not live till 85 to get the payout, he would have "lost" the bet against the house and be worse off as a result of having paid the premium all those years. I hope by now the reader can see that this is an unsound understanding of insurance. Insurance is not a zero-sum game, one does not lose just because he is not getting the payout.
The idea of an insurance policy is that with a small payment, an individual can guard himself against desperate outcomes, thereby offering a peace of mind if he is risk-averse. The longevity insurance allows people to smooth consumption over their natural lives and not worry about money running out at 85. When risk-averse people pool their risks together, it is possible that everyone gains regardless of who gets the payout in the end.
To sum up, don't worry about kicking the bucket at 84. Living till 85 and collecting the payout does not mean you have "won" either. If you are desperate for $250 at age 85, it means your money has already run dry - hardly an outcome you want.