No, not the board game. I’m talking about taking risks in life. In order to accomplish anything out of the ordinary, you have to take risks. The key thing to remember is to do everything you can to bound your risks. I’ve been thinking about how to do this a lot lately.

I want to pursue other career options but I am over 50 and I have to think about the risk of age discrimination. Not in the careers that I have in mind, which are all variations on the theme of self-employment, but rather as relates to my fall-back position. What if I don’t make a go of being self employed and have to go back to work as a (gasp) employee? How do I mitigate the risk that I might not find anyone that wants to hire me because I’m over 50?

So I’ve been thinking about how to ease into this change. How to dip my toes in and test the water before I quit the day job. The problem is, I don’t know if I have the stamina to hold both a day job and work on a start-up at night anymore. And the other consideration that looms large in my mind is the cost of insurance. I have good insurance where I work. How do I ensure that I have uninterrupted insurance when I take the leap to self-employment.

It certainly is a lot to think about. Right now I’m not real worried about these issues because I’m a long way from taking the plunge. But if I plan on ever doing anything of this sort, I need to start making progress in that direction.