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Step one: be a ghoul who can afford to fail a bunch in a capitalist empire at the height of it's power
(hexbear.net)
Scott Adams has probably failed at more things than anyone you've ever met. So how did he go from hapless office worker and serial failure to the creator of Dilbert, one of the world's most famous comic strips, in just a few years?
No career guide can offer advice that works for everyone. Your best bet is to study the ways of others who made it big and try to glean some tricks that make sense for you. So here Scott Adams tells how he turned one failure after another - including a corporate career, inventions, investments, and two restaurants - into something successful. Along the way he discovered some unlikely truths. Goals are for losers; systems are for winners. Forget 'passion'; what you need is personal energy.
Dilbert
Dilbert was completely fine for a long time, I even remember the cartoon being OK? Then he hit a certain level of success/wealth and his brain broke forever.
Was there a drastic change in Dilbert? I only followed it for a few years, where I remember it having some reasonably funny strips and some bafflingly boring ones, partly because the entire series seemed to mostly revolve around re-telling the same ~10 jokes