According to dreamdictionary.org, this is what my recurring dream means:
Scared of Flying:
Flying in a dream can either be exhilarating or a nightmare depending the dream. Not being able to control your flight in your dream is rare but it does happen from time to time. Scared of flying has everything to do with lack of control in your life. Dreams of this nature suggest you have trouble controlling the path in your life. No matter what you do there is some interference. You have to ask yourself what is causing me to be afraid to take control of my life, and how to get back on track. Another possibility is with being afraid to fly is that you might be having trouble keeping up with the high goals you set. You may feel that you can crash at anytime.
I’m no Freud or Jung, but that is a completely spot-on analysis of my dream. I’ve been dreaming of flying for a few nights now, and no it’s not as liberating as you think it’d feel. While takeoff was easy, I had a million worries while I was soaring through the sky.
Basically, in the dream it is night, and the city is twinkling below me. It’s cold and I worry about not having enough to wear. It’s high and I worry about falling – that fear plagues me consistently throughout the dream. It’s not quite the witching hour yet so there are people on the streets, and I worry about being seen. My toes are freezing up, and I want to go higher but I don’t quite dare to.
Always, there is something holding me back. But the wind rushes past me, and my cheeks are cold. I want to feel freer than I am.