It depends on what are the consequences for failure. In war, lack of preparation means death of your men at minimum, and the collapse of your nation at worst. In training, failure makes you stronger. It's a good argument for managers to create a working environment where employees are not afraid to fail. I absolutely agree that starting early is the best and fastest way to learn. Too many people avoid it because of the negative consequences for making mistakes.

> In war, lack of preparation means death of your men at minimum, and the collapse of your nation at worst.

This is the fallacy that keeps people locked in over preparing. The way past it is to identify less risky goals that are still aligned with that particular objective. So in war your objective is to learn the enemy's weaknesses. So you could try trading with them, to survey their defenses. Imagine the Vikings at Lindisfarne, they are not going to go in blind. They first build a trading relationship, selling fish, and as friends they can see how strong the Abbey is, how many monasterial guards there are, or when the collection trays are the most full etc. Very little risk right? Similarly with sales, where your risk is your reputation. Say, you can't afford to jeopardize it with your one big connection because you spent a decade building the relationship. Well then you go in asking for advice on your idea, something low risk, instead of trying to make a yes-no sale.

I would say that all these alternative goals you mentioned can be classified as preparing.

(Over) Preparing in the context of war or business is where you keep working without engaging the enemy or the customer. The classic problem in startups, which i’ve been through myself, is where you keep working on making your product without developing your market. If you are doing sales interviews in a startup without a product yet, then you are engaging with the customer, and by coordinating with your product team, you will reduce the problem of over building the product. You need to partition the problem space (the goal space, the overall objective space) in terms of the separate essential pieces that need to be accomplished, once you have this partition of endeavors, then you start making progress in each channel. Over-Preparing is not defined (IMO) as a problem of inadequate rate of progress, rather it is that you can never succeed with your activities because you are not making any progress in a critical channel, and this weirdly magnifies the perceived difficulty of the missing piece, leading to more and more effort in the other channels. A bit like France overbuilding their defenses with the Maginot line when instead aggressive military action in some theater of war before WWII would have exposed the extreme inadequacy of their tank and soldier communication methods.

I feel like this would be a lot easier to explain by phone. My email is riazrizvi at gmail, if you want to set that up. I’m on Pacific Standard. Open invite to anyone.

Its almost as if reality is really complex and pithy slogans are useless for anything other than grandstanding because each situation needs to be appraised on its own terms

Not totally useless, they help the less experienced understand what dimensions they should be thinking about:

- fast vs slow - big investment vs little - strong customer service vs Google-like "for the masses" customer service - focus on customers vs focus on employees

There are no silver bullets and no advice is always right.

But just talking it over can be useful, as opposed to diving in without even thinking.

True