This is known in the craft as monologophobia. Theodore Bernstein, a NYT journalist, who coined the phrase, described a monologophobe as someone 'who would rather walk naked in front of Saks Fifth Avenue than be caught using the same word more than once in three lines of type'.
The most common example is journalists' aversion to repeating words like 'said' or 'told'. People don't _say_ things any more, they: continue, explain, add, verbalise, enunciate, vocalise, and so on.
I think I suffer that...I've edited a few HN comments recently after realising I'd used the same word twice in a sentence. Even the previous sentence's overuse of the first person pronoun is bothering me...
I think it's drummed into people at school not to overuse the same word. However, this is, as usual for school, an oversimplification.
Repetition is to be avoided when it is that repetition itself that stands out unattractively. In the previous sentence, "repetition" is repeated deliberately in order to emphasise that the referred-to noun remains the same[1].
If your grammatical gymnastics to avoid a repetition become more annoying than the repetition itself, just leave it. (Again, I could have found a circumlocution here for "repetition", but would it make things better? Would it have the same nuances? Would it rather distract from the actual meaning of the whole sentence?)
Off-topic (and I do hope not too personal; I don't mean to be a grammar bore when we're not here for the grammar): overuse of ellipses is far more aggravating, to me, when parsing a comment than an unintentional reuse of a common word like "I". It stands out most because I have a colleague who does it all the time and it drives me up the wall as I can't tell if there's a implicit conclusion that I should be intuiting(...)
If I have to pick something I overuse, it would be parentheticals (like this).
[1]: If short on space, you could distil "... when it is that repetition itself that stands out ..." to just "... when it stands out ...", but what "it" represents is now implicit, the whole is more neutral and the emphasis is lost.
Though I don't think something must be hard to be worthwhile, I think there's something in what you say. 'Trust in what is difficult' is a theme in the works of one of my favourite poets, Rainer Maria Rilke. It is the focus of 'The Man Watching': http://www.michaelppowers.com/wisdom/rilke.html
Exhibit 1 would probably be the inaction of newspaper publishers 20 years ago as Craigslist took the classified ad business away.
Exhibit 2 might be the NYT taking on massive debt 10-15 years ago even as it was pretty clear that their business was changing. Money was cheap and their magic 8 ball said outlook good, so that was all they needed.
Exhibit 3 is probably the lack of care publishers have around the user experience on the web. AMP and IA is Google and Facebook saying "your product is great, your presentation is terrible". A 500 word story should load on a phone in under a second all the time.
Exhibit 4 would be lowering of the editorial bar by lots of outlets. This is probably the big one in my opinion:
* the NYT reporting in the run up to the Iraq war still bothers me, trust is hard to earn and easy to lose
* editors know that there aren't always two equal sides to every story, but that's the format they have
* their interview formats seemed designed so that a question with a yes or no answer can be spun on fly into a statement about something unrelated
* when everything is called breaking news, nothing is breaking news
* the patterns of news outlets are so obvious, that they are easy to manipulate (how many hours of television and lines of print were spent on Obama's birth certificate?)
Exhibit 5 is probably the overly conservative approach to the web. A digital newspaper is the obvious path and it's the only one too many outlets are exploring. Buzzfeed is a nice exception. I don't even think they expect readers to go to their website. Buzzfeed packages everything for sharing and the content flows just about everywhere. I don't think the conservative behavior of most outlets is due to lack of ideas. Some very smart people (like Dave Winer and Jonathan Abrams) have expressed a lot of interesting ideas that nobody seems to be willing to experiment with.
A decent amount of shrinkage in the news business was overdue. If you travel and read local papers, they are all almost exactly the same. If you watch local evening news, every program has the same format and basically the same set. There's a ridiculous amount of duplication and redundancy and getting rid of that frees up a lot of resources to work on other stuff. Fortunately, I think the shrinkage is mostly complete.
To clarify, I want to shine a light on results wrongly removed: cases where freedom of expression, and the public interest in remembering, outweighs the right to be forgotten.
https://www.libraryofmistakes.com/