I was encouraged to do commissions by my family before I thought I was good enough. Through some connections I got some work drawing characters for some Paizo Pathfinder campaign books. I got paid for those. Done a few odd jobs since then. When I went to digital I started doing free commissions for my friends and the communities I hung with. They're still free for now because I'm still learning things, but when I feel my work has hit a certain quality and I have a portfolio of commissions I'll start asking for money more often. I'm doing one for my extended family which will hopefully get me more work with them, and I'm doing a few logos for people I know which will lead me into more freelance work for people in their industry.
I still have this problem of not thinking I'm good enough to get paid for my work. Even though i know I'm good enough now I always want to get better and not regret doing work that I can do better now. I think after I have better digital practice and get feedback from these few odd jobs I'll have a better attitude about selling my art. Almost all of the paid work I've gotten so far are through the connections I have.
If you're ready to start doing commissions I'd get a gallery together. Be sure to include a wide variety of drawings. Get a list of pricings. You can price by piece or by hourly work (I usually go by piece because it's easier for me). Don't undercut yourself. Don't feel like you should ask for less. You can sell just linework for $25 if you really wanted to. It's sort of like bartering. You will need a bank account and an online bank account. A lot of people use Paypal, which will add a few bucks to your commissions for transaction fees. You can also use Dwolla, which is free. I like to send WiP pics of commissions so I can edit any mistakes. Then I'll send a watermarked version, they approve it and transfer the money, and I send them an unmarked version. No matter how you go about your transactions or commissions, be sure to DOCUMENT EVERYTHING~ and save any emails, messages, or other history between you and your client.
As for getting work, advertise like crazy. Post on facebook, tumblr, imgur, dA, whatever and however often. I've started looking for local jobs for freelance work. A REALLY good way to make connections is to find local events for artists or to simply go drawing somewhere. I got a job doing some concept art for some college game makers because I randomly decided to draw at the subway they work at and they saw me : |