Like many artists, I often get emails from students asking for advice. As I don't have the time to answer every inquiry, I will post questions/answers here. All of this is from my perspective, who knows if I'm right or wrong - use what rings true to you, discard the rest.
What is a typical day like?
It's hard to have a typical day as a freelancer, as you never really know when/how much work you are going to have. But as I've gotten more successful it has become easier to have a fixed schedule, and having a baby has also made me have to have more routine in my life. Generally I write in the mornings, and work on art in the afternoons. My child goes to daycare from around 8:30 to 4, so I wring as much work out of those hours as I can.
What hours do you normally work?
My recent schedule is above, but before I got married and started a family I would get up early in the morning and get to work, and quit around 1pm to go watch a European soccer game, or meet my friends for coffee or a beer, or read a book. Those were golden days. These are golden days too, but with less sleep.
Is the job/career you have what you expected? Why or why not?
My career is honestly exactly what I want it to be. I'm very happy with it. I achieved financial security working for newspapers/magazines early on, was able to transition over to doing book covers for sci-fi/fantasy because that was where my passion and love was, and was able to transition from there to writing/illustrating my own books. The next stage, that I'm working on now, is writing my own novels. It took time to build up to where it was exactly what I wanted because I had to pay bills, but over time I've been able to shape my career and point it in the direction I want it to go. The main thing is that I have been the one deciding where I want my career to go, instead of trying to second-guess what the market wants or follow trends. My main career goal is to make work that only I can make, to draw like myself, to write like myself, to have a unique personal voice.
What kinds of people experience the greatest success in the field?
Those who don't give up, who keep trying even when it seems like they'll never achieve their dreams. Probably also people who have a good business sense, who know how to market themselves, to treat their work as if it has value.
What is the best thing about your career?
Hard to pick just one thing, but right now I love that I work from home and get to spend a lot of time with my son. Also I get paid to make stuff up, to smear paint around, it's like I have a job being 8-years old right now.
What do you wish you would have known starting out in your field?
Always ask for more money, and if someone says they can't change their contract, and it is a bad contract for the artist, don't work for them. Contracts should always be negotiable.
What do you wish you had done that would prepare you better for this career?
I have no idea what I could have done to be better prepared. I dropped out of art school, but that ended up being really good for me in the long run. I think you just have to throw yourself in, knowing that you can't be fully prepared, and learn as you go. Don't wait until you think you're prepared - you'll never get there. Learn as you go, make money while you learn.
What advice do you have for someone entering an illustration career? Any words of warning/words of encouragement?
Marry someone with good health insurance.
How do you get that texture?
Google "Jeffrey Alan Love" demo. Back in my day we had to google through four feet of snow both ways when we were trying to figure out how Sam Weber got that texture.