Dear Jinae,

It sounds like you are stuck in some weird twilight zone between feeling ambitious and playing it safe. Fear of failure should not modify the standards you set for your work. Aim as high as you can and THEN fail; don't compromise and choose more familiar tasks so you can avoid bigger failures.

I have plenty of my own failures, but it's the colossally weird stuff that often ends up succeeding; ideas that sound unjustifiably stupid in writing can become really amazing paintings. Allow yourself to explore those weird ideas more, because you never know what great things they may become!

Having said that, while I think that your concerns about balancing specialization and versatility are valid, you are too quick to make value judgments of your work based on how familiar your subject matter is to you. It's ok to use what you're good at as an anchor for exploring new territories.

As for your worries about audience, you shouldn't overly concern yourself with what they want. We can't get into every person's head and analyze what they want to see, and they themselves don't usually know the answer until they're staring it in the face. If all you can make is an educated guess, you're likely to stifle your own creativity and end up with something cliched. And neither you nor they want that! If you make something you really love, it will attract people who will love it as well. This discomfort you feel about having to make something you don't believe in, just because you think it may appeal to someone else, isn't helping you stay motivated and it sounds like it's affecting your art for the worse. Emotional distress is common enough among artists without the additional frustration of forcing oneself to make boring work. You say that you'll happily slave all day and night on art so long as it's a personal project. So let your "work" be personal as well! Choose to do projects that you'll love to do, and stop compromising.

Sincerely,
Dana