Ask HN: How to freelance with niche programming languages?

On the other hand, business people who don't care about their tech stack often have BIG blind spots in their conception of their desired solution, such as IT leaders that will slam the brakes on your solution if it doesn't fit into their vision of the technology world, who come out of the woodwork in the final hour and doom your project after a bunch of incorrect technology choices were made because the business folks neglected to warn you about these folks and their requirements in advance (even if you probe for this sort of thing, because the business folks choose to operate in a fiction where these people don't exist or are easily pacified).

Thats great advice, and very hard for my tech fixated brain to think that way!

I can't speak to COBOL-based businesses, but I work for a large company that uses primarily RPG ILE. Five of our eight programmers have passed retirement age, but are still holding on. Once they decide to leave the company, we'll will be in a tight spot. I can only imagine its the same way at a lot of other RPG shops.

All this is to say, +1 for consulting/freelancing for legacy tech.

This. As you are an expert in your niche now you need some personal marketing too. Cater code and articles about performance and business cases for your tech stack to these niche communities. It may bring you necessary recognition so one day some CTO may ask you to join their ship.

I've only experimented with Upwork (with mixed results), what are some of the better "middlemen" in your experience?

I think you can shorten that to "You need to network with people who run businesses". Valley startups excepted, high level executives don't usually care if you use Rust, Scala, or Befunge, or whatever. They want problems solved.