He Who Hesitates…

by Sidney S. Stark

“You have to be willing to risk everything, protect nothing, and then you’ll lose nothing in the end.”

Is this advice from a professional gambler or perhaps a world-class downhill ski racer? It’s not hard to find many other possible authors of the seemingly outrageous counsel but a lot harder to identify those who would actually adopt the attitude. But it wasn’t promoted by a teenage boy on a suicide mission. Far from it. The advice came from a  conservative lady in middle-age who’s worked all her life in financial wealth management and been known for her simple, old-fashioned approach to protecting her clients. But her guidance wasn’t offered in relation to her fiduciary responsibilities. It’s her life philosophy and she believes it with the assurance of someone who’s seen the results and been reaffirmed by them often.

So how does one believe in such a philosophy and even if you can get yourself there, how do you follow it? The acceptance is part knowledge and part faith. My own experience has taught me there’s definitely a correlation between risk and reward in life. I may not be entirely comfortable with that but I know it’s true. So that’s a start. Then if you can watch the quiet conviction on the face of someone you trust who’s benefited repeatedly from the maxim you tend to be swayed enough to take the leap of faith yourself. At some point it’s more about the leap than the risk. Most of us don’t want to jump into water where we can’t see the bottom or what’s lurking below the surface. We want assurances and even guarantees before we spend our emotional capital on something or someone we can’t be sure of. But life doesn’t work that way because by the time you’ve stood on the shore long enough to see better what’s going on in the water your chance to swim has passed you by. The winds and currents may have changed and your opportunity is gone.

‘He who hesitates is lost’ is an adage my grandmother was particularly fond of. I never considered her a daredevil or someone to make a decision on insufficient evidence, so it fascinated me that she championed decisiveness over caution. But I thought of that adage recently when my friend presented me with her ‘risk it all’ philosophy and I realized those proverbs were very close cousins, and so I’ve really lived in close proximity to her advice most of my life. Have I ignored it to my own detriment? Possibly. Should I have moved faster when I recognized opportunity knocking at my door? Probably. The hesitation and insecurity my grandmother always warned me of undoubtedly caused me to lose out on a lot of possibilities in life. But both she and my friend would be proud of the way I’ve changed my risk aversion in recent years. I’ve begun to feel as if it’s almost my duty to explore a new lifestyle for women my age who don’t want to throw all of the life they’ve lived up until retirement out with the bathwater but do want to reinvent themselves. Clearly there’s room for another way of retiring (or not), working (part-time or full), and living (so many styles to choose from). These are weighty items and ones that threaten to rock the boat, but all things women of this generation need to explore as a duty to the next generation coming along.

So I say to my friend that I agree with her wholeheartedly and champion the cause to risk it all if winning a full life is the goal. I admit to still testing the water a bit with my toe before jumping in, but that’s more of a reflex action than a consideration. I often feel I was lost too often in the first half of life and don’t intend to let the second half disappear the same way. I thank those who came before me and with me who urged me to be willing to risk it all. I’m already raking in the rewards.

Question@You: Do you agree you have to be willing to lose in order to win? Let us know.

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