Learning a language with Anki is effective and frustrating for precisely the same reason: they test vocabulary at just the right time, when you're just about to forget the word.
Review sessions become one long beating-yourself-up. "I know I know this!"
Conversation
This is a significant (and underappreciated) design challenge!
For me a key insight is that we haven’t found good representations of progress. You need to see/feel your overall progress; emphasizing individual items produces the problem you describe.
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Do you think it's possible to represent progress for language learning within the system, when the ultimate measure of progress is defined by interactions outside of the system (convos with native speakers, understanding foregin language media etc.)?
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Yes, I think some decent interim measures of progress are possible. For instance, if we know that conversation becomes much more rewarding and fluid when the first 200 vocabulary words and grammar rules are fluent, that would be a meaningful measure.