I've worked out some nice routes for myself over time. I most enjoy running when I feel like I'm alone, which is why I like to go on long jogs through the forest and along empty country roads. If all else fails, I can always run my laps on the university gym track at night when no one else is around.
Have a look at this video showing my favorite route:
Video: Running through the Cleveland City Park
Running is all about motivation! When you feel like you're about to reach your limit, do you give up or carry on? If your answer is to carry on, then you were born to run; if you'd rather give up, then running will help you overcome your weaknesses in the long run.
It's important to set realistic goals when you go running. Set the bar a little bit higher every time and you'll soon find that you're capable of things you didn't think were possible. This attitude carries over into many areas of life, by the way: whether it's at the workplace or in their personal life, runners tend to have a can-do approach that people will respect.