Knowing the boundaries of your expertise, knowing when to pass a job on to an entity that is more experienced and knowing which customers are a 'good fit' and which are not is a winning strategy.

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.