Chris gets
daily offers via email for business. Drawings, shout-outs, interviews, etc - all for money, all genuine offers. If Chris is willing to sit down to put in the minimum required to do these things, then people get what they want and Chris will be fine. My goal is to streamline this process so his fans on Twitter and elsewhere are happy and and Chris doesn't have to worry about being homeless.
I've never pushed this idea before, but with this I see an opportunity to do a demo. Like: okay, you want this thing, and here's a plan that involves selling people stuff that they want so you can get it.
If this works, then when the Impending Doom

happens, Chris will realize that this worked in the past and it's a way to move forward in life. There will also be an actual sense of fail conditions where if the work isn't done, bad things will happen. Those fail conditions exist to a lesser extent here with not being able to make the con, not being able to replace the vehicle.
I'm not
babying him. It's like social work. When social workers help people get jobs, they sort out a lot of these unknowns for the person. I'm trying to lay down an understanding that there is a market for what Chris has always wanted to do (be famous, do art) which can be responsibly exploited for a comfortable life. BUT! You have to actually do it. You cannot delegate official Chris-Chan drawings or cameos to underlings.