If you wanna talk about the genderbent aspect of my life, I welcome it; I like talking about it, and I pretty much treat it like any other subject. Among other things, although it's seldom been an explicit topic in my work, it's often been a strong undercurrent in ways readers probably don't realize.
Any particular information you'd like to know about me before we start? I'm from Gig Harbor, Washington, and still live in the Seattle area, with my husband and my cat. I drew my first comic strip when I was 5. When I was 11 I drew a comic strip called "Skippy" for my middle school's xeroxed monthly newspaper. In college (I went to the Evergreen State College, which is also Matt Groening and Lynda Barry's alma mater) I started Ozy and Millie, which was a web comic before that was really much of a "thing." (My intention at the time was to get it syndicated, which I guess was the start of my journey to the current moment.) I also started doing political cartoons, which grew rapidly from an attempt to needle certain campus activists into something I took much more seriously.
In 1999 I was a top-3 finalist for the Scripps-Howard Charles M. Schulz College Cartoonist Award. The best thing about that, since only the winner actually gets any money, was having the local newspaper do a story about me.
After I graduated, I got a job as a reporter at the weekly Puyallup Herald, which also let me do its editorial cartoons. I was still doing Ozy and Millie. I barely slept, and ultimately couldn't last at that job. After that I went to grad school, which is what you do when you're not sure what you're doing with your life, and discovered that the Washington State University Daily Evergreen was eager to run my political cartoons. On a whim I named those comics "I Drew This," and that stuck; I drew IDT for five years, which is four years longer than I lasted in grad school, because after a year there it was just absolutely clear that drawing comics was all I wanted to do. So my then-boyfriend (and now-husband) offered to support me while I tried to make a career out of comics. I moved in with him and we've lived together ever since.
That period in the mid-2000s when that happened I think was a highwater mark for Ozy and Millie. It had acquired a dedicated cult following (I still meet enthusiastic fans of it), and after doing it for a few years I'd started to get really good at the whole thing I think, in that way you do when you do something every day for years. I still describe O&M as my Ph.D. in cartooning. (I think I said that to you in San Diego.)
I stopped doing I Drew This in 2008, because I was kind of burned out on political commentary. The liberal blogosphere had grown up a lot in that time and I no longer felt that the internet needed my voice shouting about what a wang George Bush was; I felt my perspective had become more represented. By that time, I had developed other priorities anyway. I began exploring gender transition in 2005, after a moment of clarity led me to admit to myself that I'd always felt like I was supposed to be a girl. This made I Drew This, which featured a self-portrait of me as a major character, awkward to draw. By 2008 I'd had my facial hair lasered off, begun transgender hormone therapy, and legally changed my name (and the gender marker on my driver's license, because that's actually much easier than you'd think, at least in this state).
And transition is a weird time to try to be creative. I've always put so much of myself into my work, and then I entered this phase, which stretched out for several years, where it seemed like I didn't know who I was anymore. Becoming Dana Simpson was a creative project all its own. I had to reinvent basic stuff about my identity as a human being. It became hard, for a while, to have any creative energy left over.
I ended Ozy and Millie, and planned to kind of retreat from internet visibility, do something lower-profile for a while, maybe build up a portfolio as a freelance illustrator and get some side work while I figured out what I was going to do.
I won Comic Strip Superstar in the middle of all that. A friend pointed the contest out to me. I'd actually given up on my expectation of ever being in syndication, by that point, but I was like "if ANYONE has a shot at winning this, I do."
So I won.
I won with a 12-strip sample called "Girl," four strips of which were lifted more or less verbatim from Ozy and Millie, because I felt entitled to mine my own back catalogue. I approached it like a job interview; here are my samples, and I think on the strength of these you ought to hire me as a syndicated comic artist. But I came to realize after I'd won that I actually had no plan for the strip beyond those 12 strips.
"Girl" was about a kid hanging out in the woods with talking animals. Universal steered me away from that title early on, on the grounds that it's really hard to google. I was fine with that. But I realized after being under development for more than a year that I had no idea where this was going. John Glynn, who was my editor at the time, told me flatly that the strip wasn't good enough to syndicate. ("It's better than some established strips, but in this tight market we need it to be transcendent.") So I started experimenting with the concept as part of a quest for transcendence.
Eventually, my little-girl protagonist got named Phoebe, after Holden Caulfield's little sister in "The Catcher in the Rye." And she got paired with a unicorn, who was a one-off character who quickly let me know she intended to hang around. She acquired the name Marigold Heavenly Nostrils from an online unicorn name generator.
The rest you know.
Goodness, that went long! But I like to be thorough. So, y'know. Feel free to ask me anything.