How do you improve your listening skills to get to listening to native content with ease, assuming vocabulary and grammar are not the issue?
Here's what I've found does not work:
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Slow/easy language podcasts. Yes, it's important to get started with stuff like that, but it's extremely boring and limited, and it does not get me over the listening hump. The listening hump is all the phonetic and semantic and grammatical changes made to language when it is spoken at speed. By definition, I am NOT exposed to that in slow language podcasts and so listening to an infinite amount of slow podcasts will not teach me.
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Re-listening to work I know. I've found working from transcribed shows that I can understand them all, but it's from a freaky ability to recall the dialogue, not from a newfound ability to DECODE the dialogue. The flip side of that is if there is something I don't understand the first time through, it doesn´t become more intelligible on multiple passthroughs. So I read the transcript and then it becomes yet another thing I remember.
So I'm wondering if there's an entirely different approach. Like, maybe if I tried reading aloud more often, I'd naturally fall into these elisions and ways of speaking, and having produced them naturally myself, I would hear them better? Because right now, my language production is zero. In fact, my language consumption is entirely passive.
Tell me what you did to get over the hump.
reading aloud is a great idea, and great practice! you might find even authors who write the language very much as it's spoken regionally, dropping out silent letters, etc.
if you can find any conversation groups in person or on discord etc, you'll have the benefit of practicing listening and working on your active skills / language production.
for me, listening to a soap opera that includes people with multiple accents & dialects is really useful. the earlier seasons don't have any subtitles in that language, so i was forced to figure out what they were saying either by listening, or sometimes going back with english subtitles & translating it back to that language.
soap operas will follow multiple storylines, you'll get the gist and learn related vocab about particular topics from context, but you'll also be hearing native speakers speaking naturally & in various situations or while they're laughing / shouting / crying / etc, which you'd never get from a monotone slow news podcast etc.
soap operas might be a bit overacted / overdramatic too, so even if you're not understanding every word or phrase, you'll be able to tell someone's angry at another person, etc. i started out with several characters i couldn't understand at all, and now on season 8, i very rarely need to rewatch a scene to understand it & i'm picking up a lot of conversational phrases.
another oft-repeated piece of advice is listening to a daily news & special interest radio programme/podcast, maybe in the dialect you're focusing on. it'll all be native speakers speaking at their usual pace, you might hear athletes being interviewed while out of breath right after a match, or someone angry about a political situation, or someone doing a weekly comedic feature last thing on a friday, etc.
tl;dr: nothing helped my overall understanding as much as working on my reading & listening & speaking skills, rather than only one or two of them. although i'm still guilty of neglecting my writing skills and it shows!