Specifically, the day job shouldn't be too enjoyable if you're making money from it. Once it is, you should start doing it for free and find a job you find less enjoyable.

That just follows in a straightforward way. Now, this may not seem absurd to you, but I dare say it will to most people.

I think the original meaning was "if you love what you're doing, you would not mind doing it even if you're not being paid for it", not "if you love what you're doing, you would refuse to do it for pay, but only do it for free".

Signed, Captain Obvious

I think that is reading into the quote too much, but I can see where you are coming from. I agree with you that such reasoning is a bit absurd.

That only follows from what he said if you completely ignore the context. I honestly can't tell if you actually don't understand that, or if you are being deliberately clueless.

I think if you add in the context it becomes false.

How so?

>Specifically, the day job shouldn't be too enjoyable if you're making money from it. Once it is, you should start doing it for free and find a job you find less enjoyable.

More specifically, market forces dictate that if a job is all sparkles and lollipops, you don't need to pay people to do it, because they'll do it for free in their spare time. Thus, every job has downsides.