"No regrets though. My mantra is that if you're not striving to automate yourself out of your own job these days, then you're holding something back, and not truly contributing your most valuable work."
Shouldn't you be, though? Shouldn't your most valuable work be reserved for you?
If that works for you, then I'm envious. But I can't operate like that, as an employee or a human. I prefer to give a 100% earnest effort and fail personally, rather than give less and "safely" watch everything fail around me.
It's an attitude that comes with risk, but not without personal reward. If I'd held back in my publishing career, then I'd still be an editor somewhere, just waiting to get laid off anyway. Instead I'm here on HN. I get to be in the vanguard of what comes next. I have direction and forward momentum in my endeavors. IMO ultimately that's a far more rewarding and valuable place to be, and worth the trouble.
It's not dishonest in my situation and industry. Traditional publishers are failing. It's not a secret. These organizations are largely run by veterans who like the "smell of paper" 1990s way of doing business. "Reserving my most valuable work for myself" would've been sucking up to those people without exception, keeping my jobs, climbing that burning ladder, and continuing to make myself a passive accessory to that overall decline. I made different choices.
Shouldn't you be, though? Shouldn't your most valuable work be reserved for you?