The following is a guest post by Colleen Kong Savage, an illustrator and designer transitioning from SAHM for over a decade to trying to make it on her own as a freelancer. 

Why does asking for money make so many of us squirm? I’m not horrible at it—anymore—just not good. Money is the elephant in the room standing next to the cash cow. Some folks have no fear giving that pachyderm a happy slap on the rump, but others like me look the other way until we are forced to acknowledge it.

I started pursuing my freelance graphic arts business in earnest two years ago. However I have only one year experience asking for money because I had to spend my first year just asking for work. My preferred method of waiting for work to come to me had failed, so instead I sent job applications into a black hole—first as a midlevel graphic designer, then an entry level designer, and finally offering free labor as a 40-year-old intern, trying to get my foot in the door—to no avail. I advertised my illustration skills on job sites.