Earth - I've struggled with this one since I was a child. Being of an age, astrology was a big thing in my parents' circles when I was young. Based on my birth date, I felt like everyone was trying overly hard to push some stolid, sedentary, weighty materialism of earthiness onto me, and I hated it. People would always point at my stubbornness as exemplary, which would infuriate me. My stubbornness was not slow, solid or weighty; it was something like an ember that would roar into flame at times.
Several years ago I made a concerted effort to grow plants, to become aware of the life and rhythm of growing things, and it's made a difference. I can almost see earthiness by way of the things that grow from it, and while it's a much more tenuous set of meanings, I can make more personal sense out of the set of meanings clumped around "Earth".
Air - Air has always made sense to me. As a child, I was so aware of presence(s) in moving air that it frightened me, because they seemed aware of me as well, and challenged my sense of scale in very threatening ways. Whenever I would get my "migraines", or if I was well and truly sick, I always wanted a open window. Fresh, moving air, full of the scent of outside both near and far, anchored me. To this day I can't stand to be inside with still, stale air for long.
I read somewhere that several cultures consider mind to be an aspect of wind. You partake of mind as you breathe in and out, creating temporary localized instances of something much larger. This makes sense to me in deep ways. Wind is a comfortable presence to me, one in which I take both solace and delight.
Water - It's hard to talk about water without slipping into cliche. Water feels like home to me. Whenever I first see the ocean I start to tear up, as though I can't contain all that is suddenly going on inside of me. The difference in scale between myself and the ocean has never really frightened me; if anything, I took comfort in the deep, caring, vast presence that seemed to welcome me. Rivers and streams (when not clogged with pollution) are happy moments of the unquestionably real for me, and I always take a moment alone to say hello, and touch the water when I can. I feel like my connection with water is strong enough to easily be dominant, save for the almost out of scale connection with Air.
Fire - This is the element that feels most personally distant to me. While it may not be causally connected at all, I had very early accidents in and around fire. I feel off a low stool and into a bonfire once, and accidentally walked barefoot across coals that had been dumped out of a charcoal grill, both before the age of five. I like fires, though I don't love them most of the time, and experience them as something like an object, not a presence. I associate fire with anger, which may be part of my problem. I have been an angry person for most of my life, and I struggle to be productive with it when it does arise, but it's very much a work in progress.
Curiously, I don't particularly associate light, which I sometimes do experience personally, with fire. Nor the sun, for that matter, which seems strange on reflection.