It's been a matter of integrity: I like offering my content without any sense that I'm only doing it for the money. It's been a matter of consideration: my readers and viewers are bombarded by advertising everywhere else on the Internet; how refreshing it must be for them to have a break from that. It's been a matter of control: you can't always hand-pick what gets promoted on your site, and the last thing I need is for practically naked fantasy women to spoil the family-friendly appeal of my content, or for gross diagrams of some dude hacking up a lung discouraging even me from looking at my sidebar. It's been a matter of money: I haven't needed that extra income, at least not enough to compromise any of the aforementioned principles.
Suddenly I'm planning for a trip overseas, and the thought of having enough money to eat there sounds appealing. I've toyed with the idea of enabling ads on my creative works before, but this is the first time I've ever given it any serious consideration. This is such a simple and obvious source of cash. How many hundreds—if not bajillions—of dollars have I willfully turned down in the past 5+ years?
But then there are the ramifications of getting paid. Sure, Google. You've already got my personal e-mail, all of my YouTube videos, four years of blog posts, and probably my credit card details all under one roof. Let me give you my bank account, too. Then there's the paranoia that partnering with YouTube to put ads on my videos will draw more attention from the copyright infringement watchdogs. I suspect "fair use" doesn't hold up so well if I'm profiting from videos that are of fuzzy legality to begin with. Is all this, plus the compromise of the twice-aforementioned principles, worth the $100 that I might get paid by the time I'm ready to go on the trip that's prompted this idea in the first place?
An alternative is Patreon, a site that allows fans to become patrons of their favorite content creators, paying them whenever they release new material. I'd need to look more closely at the logistics, but this sounds much more my style. The only problem? From what I understand, creators also need to generate additional exclusive content for their patrons to make it worth their while. I'm barely able to crank out a new video every 1-2 months, and I'm already giving my Facebook followers little tidbits they won't get elsewhere; now I need to figure out more ways to reward and entertain my supporters?
Maybe I'm better off playing the lottery.