Introduction

Recently I was contacted by a young, fresh out of art school "artist" who specializes in illustration. I put "artist" in quotes because he's currently working at a Starbucks in New York City and trying to succeed on the side. A hard-working, very talented person who just can't seem to break into the field, and finding that the information given in art school just wasn't enough.
Although it's been many years since I've had to start out attempting to become a successful artist, and though the tools have changed, the basic principles remain the same. I'm still marketing all these years later, so I'm going to occasionally post edited versions of the questions asked, along with my responses.

"I get overwhelmed by how to go about getting clients and remembering who I contacted and when. Things keep falling through the cracks and I feel like there are opportunities I'm missing because of it. How can I get my act together and start to run like a business not a class I just need to pass?"

You need software or some kind of formal note taking to help you keep track of names, titles, addresses, phone, etc. It's the kind of thing that will tell you what you mailed to someone, and when, so you know when to make a follow-up call to the mailing to see if you can open a door or elicit a response. You MUST keep this updated. You'll be amazed at how quickly people change jobs, titles, cell phone numbers, etc. There is expensive and dedicated software out there to do this, but I have found that just setting up a table in Word or getting a program like Filemaker pro works just as well.
Whatever software you get, you have to use it to make it worthwhile! I would force myself to cold call, say, five or ten contacts a week (minimum) unless I was so overwhelmed with work that I wasn't getting any sleep. This is something that I had to do throughout my career. Cold calling and being more extroverted is not fun or easy at first, especially if you're shy and/or reticent. Believe me, I know, as that describes me to a "T". Often, it's the way of artists. For more information, I'll get into how to recognize and deal with this in depth later on.