My heart on the other hand, frequently says to me, WTF are you doing here, you have more enjoyment writing posts on OcUK, Discord, writing about sports, gaming, tech, whatever. [...]
So where this leaves me is a crossroads; do I throw away a 15 year career and go for a reset? Take some naff job where I have an opportunity to write prose. Maybe take a huge punt and try to create a youtube channel or something. Either way I'm going to take probably an 80% pay cut.
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Shouldn't I just go all-in, try and force my way into doing something else with all the opportunities the internet opens up, try and get to a position where I can earn 20% money but actually enjoy what I'm doing? And if it doesn't work out, nobody is interested, just fall back on the career experience and go back with my tail between my legs?
No, you shouldn't just go all in especially with no experience. That would be like a would-be x-factor contestant quitting their job purely because Simon Cowell is in town.
Mark Zuckerberg and Bill Gates both famously quit Harvard but they had already established their ventures by the time they quit. On the other end of the scale, a friend of mine who runs a small business employing <10 people started out by requesting to reduce his hours at work to part-time after already putting in some initial work on weekends and taking holiday.
You don't even need to quit your work to launch a YouTube channel though, how much content do you think you're going to put out initially anyway?
Likewise re: writing - how many articles are you expecting to write? Is that something that really needs you to quit your job for? A friend of mine writes a regular column for a well-known newspaper, she isn't a journalist or writer however she is a specialist in her field and has previously appeared on the news etc... Are you known in your field? Would a journalist contact you for comment? She hasn't quit her job, she's still working in a senior role and the column is written in her spare time.
Alternatively, if you're going to start writing medium or substack articles/blog posts - are you really expecting to earn a living from that? Where is your funnel? Do you have tens of thousands or better still hundreds of thousands of Twitter followers you can direct to your substack/newsletter?
If you're bored at work then change employers and try to find some new challenge, you shouldn't need to cut your earnings to 20% of your current income just to do something interesting.
If you're pinning your hopes on being a YouTuber or earning a living from writing about games, tech etc.. then you might want to test the waters a bit first! Write a couple of articles or make a couple of YouTube videos, see how well that goes and how many views you get etc..