How Not to Pursue a Second Career

Baby boomers are bombarded with articles and books about how to reinvent themselves, pursue a second career, and “finding their passion” after leaving a traditional workforce position. I support all of these concepts. However, implementing a “second career” plan requires a lot more care than some people realize. Curt Schilling, a highly successful professional baseball player, is now a prominent example of being careless in his “second career” planning.

Schilling last pitched in 2007 and formally retired in 2009. Six years ago he started a video game company with financial assistance from outside investors and from the state of Rhode Island. Two weeks ago, that company went bankrupt without apparently selling a single product.

The failure of a start-up business is not unusual – it happens frequently. This failure is particularly damaging to Schilling because he invested his entire personal fortune in it – $50 million. He may be on the hook for more losses.

Bottom line: Schilling was recently forced to tell his family that “The money I saved and earned playing baseball was probably all gone…Life is going to be different.”

I hope this isn’t true but if it is, it’s a real head-scratcher. If you have a personal net worth of $50 million at age 40, why wouldn’t you hold back at least a few million to take care of your family and your retirement? This is irresponsible behavior to say the least.

Another aspect of Schilling’s second career plan that I don’t get is shoving all of this time and money into a video game company. Schilling’s first career is baseball, i.e., entertainment. The second career is also entertainment, of the video game variety. Does our culture really need another video game company?  I don’t think so.

At age 46, Schilling can probably find meaningful work based purely on his reputation as a ballplayer. Most of us don’t have that luxury. if I had $50 million dollars, I would hope that I would find something to do with it that would benefit people, not keep them glued to a game console.

Second careers for boomers are great but not if they are designed around high-risk ventures that provide only monetary rewards. That sounds like a transition from “working for the money” to “gambling with the money.”

Here is a link to the Boston Globe article about Schilling.

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