Keep your friends close but your enemies as far away as possible.

Don't complain if they punch you in the face for standing so close to them.
You have been warned.

One of the first rules of doing illustrations is you charge for what you do. The second rule of doing illustrations is to sometimes ignore the first rule.
I have asked several professionals about pro bono work and every time I was told that you have to charge at least something. Even if its just twenty quid it from your mate who needs a cover for his band's EP but is stuck for cash who says he can recommend you for all kinds of paid work once they get picked up and you will absolutely be brought along for the gravy train ride into roast turkey station. But most likely you will be the peas or sprouts, acknowledged for your contribution to the overall aesthetic of the meal but discreetly brushed aside and hidden under a napkin. Tomorrow is pizza night anyway.

This is a worst dinner scenario, but not an uncommon proposal if your starting point is 'which of your friends or family could pay me for something'. My advice would be not to get overly invested in agreements like this as, in my experience, it rarely plays out successfully. It is of course good practice at the start to do a few of these jobs, if for no other reason than getting some idea for possible avenues of work as well as gauging how fast you need to work on a deadline. Just be prepared for your would-be client to come back with a few suggestions for re-do's and little appreciation  for the hours it's taking out of your other stuff cause screw it your doing it for free and there in no momentary investment in it. Here's an example of what I mean which happens to be hilarious; 27bslash6.com. If you charge someone twenty or thirty quid for it and they come back and say they want it "different but the same", it's much easier to turn around and say "okay, that'll be €15 for me to do alterations". This creates the possibility for some extra cash while simultaneously restricting how much work you'll have to do for them.

The most free work I've done is for my older Brother. He has run a number of really good comedy shows around Dublin and has sold out shows in the Edinburgh Comedy Festival. And the Fringe Festival if that isn't the same thing. if it is, he did twice as good then. Part of my style has become part of the branding for the shows. My love of black and white (with maybe one colour) suited the aesthetic he was going for.

The first show was called 'Eat Cake' after that very famous French lady who didn't understand how the whole cake/bread to rich/poor thing worked.

The first image was a guillotine that had cut  off a slice of cake. There was no research done as an image of a guillotine had been branded onto my brain by a particularly grim episode of Tom and Jerry earlier in my childhood.

I asked the guys in the show, Damon Blake, Padraig Fox and George Fox (no relation) for some photo's they wanted as their image and I did a trace sketch and then a more stylized re-trace.

There were also special posters made for the Halloween show and a night when the topic was Politics.

 Another show is called 'Auntie's Establishment', which I thought was a great name for a fringe comedy show.

My currant work with Damon is a weekly comic strip called 'This Is Bat Country' on the website humourisms.com

This was as simple as the figures for the first Eat Cake poster. I got a still of The Proclaimers, sketched over it and then drew over that, making up the folds and wrinkles in the skin as I went along. I kept a section of the first sketch under the second figures breathing mask. I lowered the opacity a bit for effect and finished by throwing on a simple screen tone for back ground.

Doing these for Dame has been advantageous as people in the comedy circuits associate my style of drawing with his style of comedy which is pretty cool, but now with traffic from Humourisms, it links to this blog which can potentially link to my other project at Apparently Artists...? where I am a contributor. So in my case the free work has been valued and payed off in one way or another. But like I said, this isn't always the case. Unless you can be damn sure your not going to be under appreciated and stressed out with no return, look critically at the potential benefits and the nature of the task at hand. There is no shame or insult in just saying "I can't do that right now/You'd be better off getting someone else to do it/I'd love to do that! Right after I get all this other stuff done!"

Critical thinking. It's where it's at.