I've been writing letters lately. I started, in part, because I was trying to "play" a game of De Profundis. That didn't last for very long, though I prefer to think that I'm taking an extended breather, rather than throwing in the towel completely on that effort. It's a neat idea for a game, and really challenges me to exercise my creativity in ways I don't normally, so I'd like to return to the "game" at some point. The other reason I'm writing letters is because I want my recipients to have something tangible from me. Even if they don't appreciate it now, I want them to some day be able to look back and appreciate the effort of putting pen to paper, and stamps to envelopes, and to have something physical by which to remember me. I worry, though, that I might be making it too hard for the recipients of my correspondence to read my thoughts, due to my atrocious penmanship.
I wrote all through middle school and high school, for both class assignments and personal pleasure. I only rarely typed things on the family computer. Even when I got my own computer and printer in my room, I only typed the longest of assignments. I actually quite like writing. Unfortunately, I'm not very good at it. My penmanship is abominable, and has always been so. I don't specifically recall any guidance in the art of penmanship as a youth, so either my teachers were just happy that I could coarsely produce the correct characters, or there was no formal requirement for neat writing.
I've always admired people with neat writing. Most of my friends write in a tight, well-formed manner that is easily legible and does not consume inordinate amounts of space on the page. I've taken recently to looking at the penmanship of complete strangers, too, and it seems that the norm is for easy-to-read handwriting. Only a small fraction of the people I've observed have handwriting as bad -- or worse -- than my own.
Part of it, no doubt, is laziness. I'm lazy with the pen. I don't want to spend the time forming perfect characters. My brain is much, much faster than my hand, and as I usually write extemporaneously, I want to get my thoughts on paper as quickly as possible. My rush to record my thoughts exacerbates the issue of my lazy handwriting, resulting in outright sloppy handwriting. I could easily pass my writing off as that of a doctor writing a prescription.
An aside: it was recently suggested to me that doctors intentionally write poorly so that they can claim plausible deniability in the event of malpractice suits. "That's not what I prescribed!" might be a valid defense if the handwriting is not particularly legible. Whether this is true or not, it doesn't help me. There's little benefit to plausible deniability in most of my correspondence.
I haven't received any specific complaints from the recipients of my letters yet, but it's something that's been bothering me personally for a little while. I've recently begun looking at tips on improving handwriting, though I haven't enacted any of the specific suggestions yet.
I should probably go back to typing my correspondence, so that the recipients can actually read it!
I have a couple of thoughts on this.
First, as a teacher I see handwriting that is infinitely worse than yours. Your writing isn't nearly as bad as you think it is. I attribute this to both the age of my students and the age in which we live. Young people, even at the age of thirteen or fourteen, are still developing their grapho-motor skills. Computers have made penmanship less important. Even in the pre-computer age, I never developed truly legible handwriting (I mean cursive here) until late in high school and early college, when I was forced to write quickly while taking class notes and yet have it remain legible so that I could make use of my notes later. You have better training tucked away in your brain than you realize.
My suggestion is tried and true. Practice. The reality is, the more you consciously try to write in cursive in a neat, legible way, the quicker and better you will become at it. As an adult, this won't actually be as difficult for you, since your brain is developed enough and you already have grasp of other important things (grammar, spelling, etc.). You will be surprised at how quickly you are able to adapt.
I have fairly decent cursive, and yet when I use it in class, I have many students say they have to think to read it. This is because they aren't used to reading and writing longhand in the same way you and I are. Keep working on it. It'll get better.
My brother is left handed and uncoordinated. He wrote poorly in school and was beaten on the hand by the nuns in the 60's. It helped his writing a little but mostly it made him hate nuns.
I have had similar feelings and frustrations about writing with a pen. Once upon a time, I event spent the time and effort to take a calligraphy course. Now I can print neatly if I really concentrate but as you pointed out, it is much to slow to keep up with my brain. At least for me, the best answer is to use a pretty font on the computer and forget about writing by hand.