Lifetime of regrets vs. the regret of a lifetime?

Chatting today with a friend and the topic of regret came up. Now, I’m not going to be one of those types who claim to have “no regrets” you know, the whole “no regrets no remorse” thing is a little too macho and played out for me. Sure, I have things that I regret doing. Times when I lost my cool or situations that, in hindsight, could have been dealt with in a bit more diplomatic of fashions. However what I strive to not have is the regret of NOT doing something. That, that I think is the real killer. The thing that will haunt you till your dying days, that gnawing wonder of “what if”.

Of all the lessons my father taught me, the one that stayed with me the most was this. Around the time he was my age things were going quite well for him. Work was good, his boss liked him and just gave him a pretty hefty raise as well as a larger portion of the company to manage. Thing was, he was unsatisfied working for someone else, deep down he knew he could do it better, be more successful and make more money. Thing was in order to do it he would have to start from zero. Loose the posh office, expense accounts, company car, and relocate to a desk in our living room and try to build a company from scratch and a few dollars he had put aside. This, this was madness. His peers were thinking about buying sports cars and vacation homes, not forming startups. When asked, he told me this. “I don’t want to reach the end of my life and look back at it and wonder what would have happened if I never stepped off the safe path? I never want to regret not taking the chance”

Now this does mean one should go out and do every stupid thing that pops into one’s head in the hopes of not having regrets. Rather, to me at least, it seems that when faced with a tough choice, a choice that could lead to great happiness or possibly to great heart ache, one should never choose to not make the choice. This life is fraught with regret; of things we should have done differently it is the regret of not doing something, of staying on the safe and well lit path that is to be avoided. At the end of your days, who wants to look back and wonder “if only I took the chance?”