Me, I don't try to push the state of the art. I just try to protect against known attacks, and I trust we won't come up with new attacks too quickly, the same way I trust we won't break existing crypto too quickly.
From there, I just have to make sure a number of mathematical properties are followed, and voilà I have a secure system according to current standards. It will be guaranteed to hold out as long as no one comes up with some new unforeseen attack. And even then, I suspect everything has been pretty much worked out. The primitives themselves, with few exceptions, are still not proven secure, but the constructions have sound security models.
Which is why now, we don't need to do stuff like the cryptopal challenges to build secure systems. We just need to avoid the relevant pitfalls, which have already been figured out by smarter people.
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Then there are side channels, but those are whole 'nother can of worm (except maybe timings, which are pretty well understood by now).