I have realized that you always need to think before you act. But... the worst thing is to think too much before you act... Whenever you think too much, you never end up doing anything!
It's like doing a cliff jump, the more you wait the less likely you are to do it. Your decision making is like standing on that ledge and looking down at the water super far below. At that point when you are toes over the edge about to leap into the unknown, of course it's going to look really high and scary. You wait and wait and wait, about to start the countdown, then stopping. This kind of last-minute second-guessing yourself doesn't help you at all and will only make you ruin your jump, if you end up doing it at all.
Of course you want to first go check if the water is deep enough and see how tall it is from the bottom to prepare for the jump. When you look from the bottom it doesn't look that bad. When you ask others, they say they've done it before and they know you can do it. This different viewpoint is essential and gives you the confidence to jump for the unknown!
Then, you just jump, and for a second you think, "Oh man what have I gotten myself into..." but you quickly get used to the acceleration and you just yell your heart out with adrenaline and fun. Then it's over and you run up for another jump.
When making decisions, go "cliff jump" style, or "quick ripping of band aid" style, and just make a calculated choice and go with it 100% without second guessing yourself.
Good post. I think the 'not hesitating and just going for it' mentality is the way to go if its a calculated risk. Like you mentioned, the calculated risk in this case is the water depth. Its similar to hucking a cliff on skis...if you don't have your buddy spot check the landing before hand, you may end up having a nasty landing. I think this applies to all aspects of life in terms of risk. You need to weigh the pros and cons of all major decisions you take. Don't invest all of your net worth into a startup you haven't done your research on. Don't invest in people that are bad influences on you and won't make you a better person. The list goes on...
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