Study. Look into symbology (or semiotics) to understand proper meaning behind symbols. Look up mythology (especially Greek mythology) to have a better understanding of the significance of common symbols and text.
Consider your talents. Are you a pianist? Give your pony a piano. Are you a writer? Give them a quill and ink.
Take your interests into consideration. Depending on whether or not your OC is a representation of you, you can use symbols from any reach of pop culture. If you like Star Wars, use a lightsaber or Stormtrooper helmet.
Take a look at your occupation. A cutie mark determines what your pony is destined to be good at. Do you have a job that you excel at? Granted, a burger grill or office cubicle probably won't tickle your fancy for a cutie mark, but think outside the box.
Think about your pony's hobbies, skills, or profession. Is your pony a crime-fighter vigilante? Give them a mask as a cutie mark.
Look at your pony. Is your OC based on or heavily influenced by a particular theme? Electronics, holidays, or even other fandoms. If your pony is say, Christmas-themed, give them a candy cane or holly wreath.
Consider your own virtues. You may or may not consider yourself an outstandingly virtuous person, but everyone has a significant virtue. Try referring back to the symbol studies. Come up with something that visually and accurately represents your virtue. A magnifying glass could represent curiosity, an hourglass could represent patience, a shield could represent perseverance, and so on.
Be creative when deciding on your cutie mark. Think outside the box. The My Little Pony fandom is large and ever-growing, and only a fraction of those fans have OC's, but that's still a lot.
Sketch out a sample once you have an idea. If you like it, test how it looks on your pony.
Make the decision. Once you have an eligible candidate for your pony, choose it and add it to your pony.
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