palladias comments on My third-of-life crisis - Less Wrong Discussion
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What kind of freelance writing are you doing/could you do? Whether or not you have a job at a newspaper, do you have any relationships with editors who you can pitch? Most people enter writing by doing a lot of freelancing and (maybe) ending up with a job, but amassing a big portfolio of clips.
I'm not sure, from this post, which kind of journalism you're interested in. Longform profiles? Reviews? Beat reporting? Editorial?
You can't get steady work doing any of those easily, but you can often get sporadic work (and feedback/experience) doing any of them