If you are a young artist and enjoy doing work whether anyone is paying you or not, and if you are lucky enough to have like-minded colleagues who are creative and are non-bitter, non-complaining types -- then by all means you should work on projects together. Sometimes great things may come of it. At the very least you will experience the joy of creating something out of nothing.
However, there will inevitably be times when you will be reminded that nobody cares as much as you do about the work you do. That is, you should never expect that your work will be as important to anyone else as it is to you. You will find that even the most creative of your colleagues can let you down if you trust them to care about your work as much as you do.
Designers and art directors are the most problematic because artists depend on them and have to trust them. On one hand, you have to be cordial and professional, even when they are not, because of the power they (temporarily) hold over you. And on the other hand, you have to force yourself to be a pest - even if that's totally against your nature - in order to make certain they aren't ignoring all your notes or (worse) are planning to get "creative" with your work. I've been lucky enough to work with several really great designers, and often the fault has been mine when something went wrong -- I wasn't clear enough or assertive enough. Or -- I trusted them to know what would look best. Remember - your work is just not as important to them as it is to you.
I'm nowhere near a good designer myself. I've designed several of my own books simply because of that inability to trust anyone else - which came about after I was unhappy with some of the decisions the designer made on my 1993 book Black Cat Crossing. But all artists who do illustrations or books must inevitably work with designers and art directors. You cross your fingers and hope you get one who is sympathetic to your work.
I've tried to be a control freak sometimes. Other times I've tried to be all "zen" about it. Trusting your art to someone is hard because you often just have that one chance for it to be published and look good and it can be heartbreaking and discouraging if it comes out looking bad. I've handed off work to friends or colleagues a few times where the results ranged from mind-bogglingly incompetent (putting pages of a comic out of order) to just frustratingly disappointing -- like this board game from 1994, PANIQUE.
(By the way - I apologize here to any non-artists - who have read this far - if this all sound like a lot of belly-aching. Trust me, I count my blessings every day that I am fortunate enough to be able to do the work I do! I'm not complaining at all and in fact I've worked with quite a few really incredible designers.)
So - about PANIQUE: I don't blame the very nice folks who produced the game. They came up with the idea of doing limited edition silk-screened board games by cartoonists (me, Dan Clowes, Lloyd Dangle and others I'm forgetting). Their hearts were in the right place and they put a lot of time and hard work into the project for very little (no?) reward. Still, I wouldn't be honest if I didn't say I was disappointed with the end results. But, again - I didn't stay involved throughout the process, I just handed over the art -- so - really -- I have no one to blame but myself that the finished game didn't live up to whatever my expectations were.
So - the less said about the final printed games, the better. Instead, I just wanted to be able to show off the art I created for the it.
I loved board games as a kid. I even created several hand-drawn board games and card games when I was young that I then tried to get my siblings or friends to play with me. So when this opportunity arose, I happily agreed to do it, even though I realized that the limitations that were stated up front would restrict the games to the most basic level. We could have a spinner and little figures to move on the board, but no cards. And the board would have to be small - only around 9" x 12, " which limited the length of the game. I did end up playing the finished game a few times with friends and it worked just fine -- except that it was all over in about two minutes!
So - I apologize to the couple of dozen folks who bought my game (although some people have told me they enjoyed it) -- rest assured that nobody made a cent on the thing. It was one of those projects you (should) do when you are young(ish) - because you enjoy doing the work.