Broadening someone's sci-fi horizons

CJ Cherryh's Merchanter books are very Traveller, but they are novels rather than Short Stories. They aren't generally very long, but they are novels. Merchanter's Luck is a great free trader story.

Poul Anderson's Polysotechnic League stories are a collection of short stories (several of them). John Falkayn is probably more approachable than Nicholas Van Rijn. :D
 
I love almost all of these.
For the traveller merchant princes out there, might I add the Tales of the Solar Clippers universe by Nathan Lowell. Fantastic slice of life stories. The Captain Wang books are pretty much him going through character gen as adventure and the Run trilogy is basically a Scout and Merchant having adventures.
 
In the film department, I'd pick Outland. Sure, the plot is straight up Western - it's consciously a remake of High Noon. But it is an excellent depiction of space as an uncomfortable, dangerous place to work but hey, a guy's got to make a living.
CJ Cherryh's Merchanter books are very Traveller, but they are novels rather than Short Stories.
I flat out adore Cherryh - meeting her was the intellectual analogue of a street tough meeting Bruce Lee [1] but entirely cordial - but at the end of every one of her novels I feel thoroughly exhausted and not entirely certain of what just happened. Which is appropriate because that's also how her protagonist feels at that point. (In the last act of one of her books one character manages to ride a subway and it's described like an explorer hacking his way through the Darien Gap, and due to his background it's about that astounding a feat.)

She has written some short fiction, but it's not very like the Union/Alliance/Compact stories. (Some of them are explicitly set in that continuum, but in a faraway place and are not in the least bit Travellery. They can also only be comprehended by reading several other stories by several other authors, in parallel.)

[1] I was not Bruce Lee.
 
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