I did up a little pen & ink self portrait a while ago, the first one since art school, and it was an interesting experience.
One of the side effects of getting older that I hadn’t anticipated was difficulty reconciling how I actually look with how I imagine I look. The “me” in my head doesn’t completely match up with the real-life external “me” anymore (if it ever did) which resulted in some struggles when I was thinking about how to draw myself.
In the end I went with a pretty straightforward drawing without a lot of detail (I was creating it as a new social media avatar). It definitely looks like me, but me with my streaks of white hair and developing crow’s feet absent. Maybe when I am feeling a bit more courageous I will make one for myself that is a little more true to life.