N.N. Taleb writes:
Again, on that account, the detractors of Donald Trump, when he was a candidate, failed to realize that, by advertising his episode of bankruptcy and his personal losses of close to a billion dollars, they removed the resentment (the second type of inequality) one may have towards him. There is something respectable in losing a billion dollars, provided it is your own money.
I think that this is one among many factors that the media missed in their coverage of the 2015-2016 presidential race.
Thomas Sowell once said that, “It is hard to imagine a more stupid or more dangerous way of making decisions than by putting those decisions in the hands of people who pay no price for being wrong.” He was speaking about the school system, but this is a sort of categorically imperative principle for management, leadership, and so-on. And Taleb gives the example of university professors that wait until they have tenure to start saying wildly incorrect things that influence the world negatively and yet they are in no danger of losing their pay-checks.
The nice thing about skin in the game is that it allows you to experience volatility in two directions financially. If you find work or a calling in which you have no skin in the game, then you have less risk as well as less opportunity for growth.
Of course, skin in the game is scary.