I've been bringing up the idea of coaches for developers with a few teammates, in the spirit that it stands a chance of powering up our productivity by several fold.
By coaches I'm not referring to methodology specific people. If someone carries a title of "agile coach" or "TDD coach", he is not what I have in mind.
What I'm looking for though is someone closer to the caddy in The Legend of Bagger Vance. It's appealing in concept but this is not an engineering endeavour.
The chances of this working out is slim. The bet has to be sized accordingly but the tricky part is in sizing it.
How to tell if you're outdated
An easy answer is skillsets. If the world now requires you to make money online and you're hardly computer-competent, then it's pretty safe to say you're outdated.
That's defining "outdate" by what the market wants. The answer isn't so straightforward if I tweak the definition of "outdate" by what you need rather than what society dictates.
What's market wants are relatively easy to suss out: when they are willing to pay money for it.
But what you truly need (not want) hardly reveal themselves until they are too late.
What value systems you hold dear are subjected to what you need. As your character evolve (often slowly), it's not easy to find out if the value systems that got your here will necessarily get you there.
It's a painful thing to do if you ever find out your honor/loyalty/piety (pick your virtue) is no longer serving anyone. But removing code is largely a good thing. It's finding out what's outdated that's never been put in a framework before (that I know of).