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by motohagiography 1744 days ago
As someone who previously kept a successful side hustle in arts and lifestyle journalism* while working full time in tech in my 20s and early 30s (wrote fashion and lifestyle columns and articles for newspapers and magazines) - do it as a side hustle first.

There are lots of arts talent roles, but here's one view from writing:

It costs you nothing to find editors and pitch articles to them in your off time, and you can see how far you get. Quitting a tech job to pursue it without making money on it first is substituting a commitment ploy on yourself for using your actual skills to succeed. Do you want to be a martyr to your own dream because it represents the reinvention you desire, or do you want to survive to have the choice to do the thing well? Writing is 90% an itinerant sales job, and the marginally better quality of your writing to anyone elses is going to go through the filter of the house voice of editors first anyway. A "career" in journalism now is more of a political career than one in arts. Sure, there's performance involved, but it's mainly a narrative gatekeeping role that is unrelated to artistic talent, insight, or skill, and getting a full time role favors a certain kind of navigator or operator. Being 70th percentile writer talent is just table stakes.

Figure out if you are organizationally savvy enough to land a prestige magazine/media job, and then ask, if you're really that good, why would you waste that skill for an intern level salary in a dying business, when the skills could make you jr. exec level at a real social center of power like a platform company, ibank, political campaign, etc.

If you like the arts, partner up with a gallery owner and invest or raise money for them.

I'd recommend abstracting the roles you're considering from the work itself. e.g. Do you want to write opinions instead of code, manage writers instead of developers, sell and trade in access instead of products, etc.

It's possible you just want to be a professor, which is its own decades long slog through adjunct hell as well, but the beauty of relatively high paying tech jobs is that you can use them as leverage into these other things on the side.