Before resigning, spend a lot of time muttering things like "I could go there, but of course he'd get me 10 moves later", etc.
It will seem that you are a genius, able to look far ahead into the game, processing a multitude of scenarios.
Giving up on a game like chess before you've even properly tried is a losing strategy.
Playing with your customers as though the success or failure of what you undertake with them is a game is also a losing strategy.
I really don't see the analogy between playing games and running a business, if you approach your customers as though it is fine to learn on the job when you know in advance that you do not have the required knowledge or skills to perform the job then I really hope you will not be found wanting.
Likely you will end up in court for non-performance and likely you will lose.
You should take your business and your relationships with your customers a lot more serious than you would take a game of chess.
It was just what came to mind immediately when I started reading your post.
I actually started reading thinking that you were going to talk about Jim Camp's "Start with No" negotiation technique, but your point was entirely different.
As I see it, "Getting to no" is achieved one of two ways.
1) you can connect them with the right fit. In this case you are forgoing the immediate sale, but even though you aren't the right fit for that person, at least you are good at something (connecting) and maybe will make a better sale from a referral, or even from them in the future should their business change.
2) you can try to price them out (raise your price). If they don't take it, then you don't risk your reputation by ruining their business with a bad-fitting product. If they do take it, the lost future sale(s) mentioned in #1 is compensated by the higher price.