At any crossroads, would you just ask yourself “How bad could it get?” and then just jump in? I did, many times, and never lived to regret anything.

As I write this, the year is 2024, and I just turned 73 years of age. I am reasonably healthy, kinda fat as I always have been, and generally doing okay and happy with my life. Now, from my “high” vantage point, I can look back over the years and and experiences, many events and times stand out and for a variety of reasons. But most notably, those things that I did where it is now clear that I did them for the wrong reasons. In most cases, I had convinced myself that I was doing the right thing, but with the benefit of 20/20 hindsight, it is very easy to see how I had been fooling myself, sometimes fooling those around me, and even sometimes, not fooling anyone except myself.

This is a generalization, and sounds a bit moralistic, but nevertheless, it is true that so often I was doing what I was doing for the money, for the resume, for the attention, for the approval, for the applause, for the material gain, for the achievements, for the hoped for acclaim that the achievements would bring, and for the need to prove to myself that I was worthwhile.

That is not to say that I always did wrong things for right reasons or right things for wrong reasons. Everyone can, if they take an honest look at themselves, identify lots of illustrations of such actions in their lives.

I set my personal golden rule to be that I would try never to do anything that I would be likely to regret later. I think that unconsciously the corollary was also in play, that I never wanted to regret not taking the risk, not sticking my neck out, and only ever being brave enough to always stay on the safe ground. To act out a life with such restrictions is to live as a slave to fear and I just could not rationalize such action to myself. Part of this motivation came as a legacy from my father and all his generation where being any kind of a coward, even within your own mind, was unacceptable and you forfeit your right to call yourself a man.

I had developed a method of evaluating risk by a combination of two processes. First, I would run the idea or venture being considered past as many people that I could find who I thought might have an opinion that was worth hearing. Of course, there were as many different opinions as there were people whom I had invited to give me their thoughts. People’s opinions are invariably tainted in some way by that person’s own personal experiences and often their bias is easy to spot making their advice easy to evaluate. The collection of thoughts could then be distilled down to a reasonable expectation of the likely outcome for me. The second process was to work out just what was the worst possible scenario if all my ideas and plans were wrong, and everything totally failed. How bad could it get? What would I have to do to recover? What would be my fallback position? Would I get another chance? Would I really be so terribly worried if I didn’t?

By this process, I could get a clear picture of what was most likely to happen if I proceeded down that path, and also how bad things could get if everything went to hell for whatever reason that I had failed to take into consideration. Thus, I now have clarity and confidence in my decisions.

I have never regretted any decision - ever. Not that every decision was always right or always turned out right. If every move was right I would be a in a very different position today than where I find myself. Some bad decisions turned out later to work out for the best anyway. Amazing how sometimes the seemingly worst possible outcome turns out to be the start of an entirely new direction that works out infinitely better in the long run in a totally unpredictable way.

So, that is just how life works out, well, my life anyway. I never regret anything, and I surely don't have to die wondering how things could have been. At the worst, I can proudly say that I gave it a go and I gave it my all. How other people judge the outcome is none of my business. I have posted this on my own website just for the record, and certainly not in the manner of offering advice to anyone on how they should conduct their lives or make decisions.

Perhaps the background questions operating here are:
1. How bad could it get if I have a go and it doesn't work out?
2. How will if feel if I am not willing to give it a go and find out later that it would have worked out wonderfully well?

So, back to the start... How bad could it get"