Best and Worst

Sometimes, it feels like each day is roughly equal in it’s impact on the entirety of life. Like a game of basketball, sometimes you are up or down. Sometimes by a little or a lot. However, the pace is relatively stable. The score only changes by 1-4 points per play. Even giving up the maximum four point play can be erased in two possessions.

However, is this an accurate reflections of life? Is the impact of each moment roughly equivalent? Perhaps, life is more like soccer. Occasionally you score a goal. Occasionally someone scores on you. A 90+ minute game hinges on a few moments. In a low scoring game, a single play could determine a win or a loss.

Which is a better metaphor for life? Looking at bibliographies of strangers, most people’s lives are reduced to the best and worst thing that the person did. “Well he was a great senator and brought us jobs, but he also got caught up in that scandal.” or “Sure Woody Allen made great movies, but there was that whole pseudo-stepdaughter relationship.” Rarely is the day to day mentioned. Did he order the lobster when someone else ordered a burger at lunch knowing they would split the bill? Did he remember people’s names? Did he have road rage? i.e. the things that fill most of our days and judgements of other people.

Of course, how people typically judge a stranger’s life is not necessarily correct or important. Nor is it the point. It is simply an example of an activity where the average doesn’t matter. The only thing that matters is the minimum and maximum. Summer interns are usually remembered similarly. Did they do something awesome and did they screw up anything badly?

Venture capitalists are usually judged (financially) by their best investment. Their batting average doesn’t matter (at least for early stage VC’s). A private equity investor is trying to avoid an investment that’s a total loss because they will never shake that black eye. They are focused on avoiding a worst case scenario.

There seem to be quite a few activities that have these properties of irrelevant averages. The tails are the story.

Most of life feels like a game of averages. It seems to be the way that our brains are wired. However, a single youtube video can now garner 100 million views and launch a career (The Chainsmokers). We like to believe that consistent effort and hard work lead to a fair reward. In many ways, reducing a lifetime of events into two moments, seems unfair. Worse, if we follow the soccer analogy, goals can happen at any moment. Constant vigilance is required to not miss a setup for a maximum life moment.

Perhaps, it’s worth deciding if an activity will be best-worst. If it is, logic dictates that we ignore the middle, avoid catastrophes and try to exploit the smallest chances of a breakout win. Of course, life can be a lot more pleasant by shifting some best-worst activities to a steady, more controllable focus. For example, defining life happiness by your reputation to strangers is extremely fragile. Any moment can ruin you. Defining your happiness internally is not subject the variation of a best-worst process.

On the other hand, sometimes a best-worst view can be freeing. Most of life’s decisions will not dramatically affect the rest of life. Overpaying for dinner, getting stuck in a broken subway car will not matter. Meeting someone you marry will be a huge deal for many people. Getting a small increase in salary won’t really matter. Breaking into an industry you love will matter. So would being convicted of a serious crime.

To use a poker analogy, if the ante and pot size for most of life is really small, ignore it. Just make sure you win the big hands if they are 10,000x more important than the typical hand. In fact, use the small hands as a way to position yourself to win. Accept a lot of small hand losses to get information about how other people play. Perhaps lay a trap by establishing yourself as a person who recklessly bluffs by losing some of the small stakes hands. Then when you have a huge hand, people might think you are bluffing and you can win enough to just leave the game thereby remove the chance of losing the huge winnings.

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