Working for Friends

Friendship bracelet via Etsy

Today's Question: How do you work for friends?

Working for friends should be fun but it's usually insanely hard. Requesting payment from friends is even more insanely hard (almost embarrassing). I've had a handful of experiences working for friends some good, some fun, some hair ripping, and once may have unfortunately ruined a friendship.

This question is so hard I don't even know what to write. (I've been staring at a blank page for about an hour now... then a little more... and then did everything and anything else to procrastinate from writing this for a few more hours.) There really is no advice on this one. Everything is so relative. How close friends are you? Is your friend a creative too? Do you have the same vision? Do you have the same style and taste? Are they willing to let you have artistic freedom? Is your friend super bossy/easy going? How big of a project is it? How much time and energy will it take? Will the project help your portfolio?

What I've learned from working with friends:

• I'm glad I'm my own boss ;) just joshin'
• Being patient helps.
• Best working for trades (a new dress or a dinner date etc.) Asking your best friend for payment is awkward.
• Sometimes just knowing you're helping a friend is payment enough... plus it's always great to add projects to your portfolio.
• Try to stay to your friends vision. (Awkward if you think your friend's ideas are stupid/bad/uncreative. Maybe just do them anyway to stay friends... or constructive criticism is good stuff.)
• Working for strangers is seriously so much easier. Don't have to worry about things getting awkward around payment or hurting feelings when you don't have the same taste etc.

Have any of you freelancers also had trouble/fun working with friends?