Second guessing myself (playing the “what if” game), is a waste of my most precious resource, time. All my life I am making choices, and as a Stoic, I now attempt to make those choices based on what I believe will best align with my values, beliefs and objectives.
Sometimes the choices will bring about the desired result, sometimes not. But even when they don’t, I cannot say I made the “wrong” choice (assuming I am the only person impacted), for I cannot say that the alternative would have brought me what I wanted either.
Life is a constant stream of sometimes seemingly random events and as a Stoic I know that the limits of my control end with the actioning of my choice. What happens beyond that is up to fate, and fate can and will find alternatives that I had not even considered. My marriages that brought me my precious children for example.
Like winning the lottery and dying in a car accident to pick up the winnings, was “winning” the best choice? I cannot know what the next moment will bring, so to worry about whether I have “won” or “lost” is equally futile. I will make my decision based on what I know and can do in the moment and then will move on with living. If there is an existence after death then perhaps I will have the opportunity to see my journey through the map of my life and see what the alternatives my choices would have brought me. Until then, I will continue to do the best I can with what I have and know in the moment.