The proper aim of the philosopher, I think, has always been to try to awaken others out of dogmatic slumbers. Before the 18th century, most philosophers were also scientists and mathematicians—also suited to explaining the world to others in ways that may surprise them. I take it that this is what was meant by the blogger who cried out for a philosopher of programming languages: someone to defeat the crippling dogmatism of the field and so allow it to move forward. But defeating dogmatism is no simple task, and it must be done carefully so as to avoid merely shifting the masses to follow a new dogma.
David Hume advocated being a man first, and a philosopher second. I think to be properly human involves a philosophical core: to ask why, to seek answers to questions, to pursue curiosity, to appreciate one’s self and one’s world. Philosophy is largely the practice of grasping onto questions tenaciously- to refuse to let go of something when it becomes complicated or confusing. Philosophers are like explorers in that the better ones are those who continue exploring after the point where others would give up in boredom, fear, frustration.
To function in our society requires a measure of ignorance or apathy, even if it is only feigned and a suspension of one’s questions and deep concerns. Philosophers tend to struggle with functioning in society because they are unwilling (or perhaps unable) to suspend their own queries of what really matters in favor of sitting through vacuous classes, business meetings, and other meaningless gloss that we slather heavily on our lives. As a result, it can seem like philosophers are defective in some important way- that they’re all weirdos to be shunned. Perhaps they are defective, but they might respond that society itself is defective in some meaningful way. They might conclude that those who operate effectively within this defective society are actually defective in some way, and it may be that certain ways of being defective in a defective system are signs of a higher, proper functionality.
Because of (or perhaps in spite of) all that, the unwillingness of the philosopher to be complacent with the illogical, unreasonable, or unethical portions of society can be (and maybe has been, through history) a useful force for progress and refinement. (Even if Socrates and Plato were not able to change their Greece, their example was understood by the framers of democratic constitutions in the modern era.)
In the digital age, philosophers have an opportunity to contribute their ideas and questions to issues that arise in the face our daily technology. Most arguments over the validity of Wikipedia as a source come back to issues in epistemology. Questions over where transactions take place when done online (for issues of jurisdiction) can be framed in terms of ontology (the study of being; where is the thing we call a “transaction”?) Although philosophy is often thought of as history—something that happened in Ancient Greece and then again in Modern-era Europe— and no longer relevant, good philosophy is an essential element of progress in any age. I see no reason why the same curiosity about natural sciences and methodological thinking is less useful in the 21st century than it was in the 4th century BC or 18th Century. There is as much need for careful thought about complex issues today as there ever has been in the world.