Ever since I was a kid, I’ve been in the habit of writing my name, William, in its abbreviated form, Wm, and my first ambigrams were stylized versions of that abbreviation, exaggerating its natural symmetry. This one, with the two letters sharing a leg, was the one I used the most.
I soon realized that this same glyph encoded both my own name and that of my native country, making it both a rotational ambigram and an oscillation. (Of course I wasn’t using those terms at the time. Ambigrams and I would be formally introduced much, much later, through the books of Douglas Hofstadter.)
Some time later I decided to try to expand my Wm into a full William. Filling in the four spaces with illi, I found that an A appeared naturally in the negative space around the second i.
(I think this one also qualifies as a very simple example of what Nagfa would call a romanized kufic. I think I’ll call it kufesque — a technical term which I, Humpty Dumpty, hereby hijack and redefine as “script in any language which completely fills an area, often square, with bands of positive and negative space, all of the same fixed width.”)
My first “real” ambigram — the first one that I consciously thought of as an ambigram, and the first one that could be read left-to-right in an ordinary, linear fashion, was also of my name:
It doesn’t look like much now, and I’m sure plenty of other people have come up with the same basic design and pulled it off in a more aesthetically appealing manner — but it’s what got me started on what has so far turned out to be a rather persistent hobby.