For myself the answer to that question is extremely easy. NEVER.
Oh wait, I remember a really cool photograph of me. I may have been two or three years old. I had amazing blonde hair and was rocking a killer looking pimp suit. It was the 70's, what do you expect?
But seriously, I really do not have any good looking pictures of myself. There are a few portraits that I have when i was in grade school, but they all suck.
If you know anything about school photos they are a joke. The photographer that goes to the school to snap the pictures rarely knows anything about photography. Their job is to get every the kid in the school in front of their camera as quick as possible. What exactly does does that mean to you? A fast, one shot, shitty looking, hope you didn't blink, take it or leave it photograph of your child.
Parents purchase the overpriced picture package because that is a current "professional looking" photograph of their child.
Besides, who really has 30-60 minutes of time to invest and get a great looking photograph that you will want to hang on your wall and appreciate every time you walk past it? Unfortunately, most people do not.
Smart phones are great. You can text, surf the internet, post on Facebook, Snapchat, Twitter, play games, use 1000's of apps and take pictures. Oh, I forgot, you can actually use it as a phone and call people. Because of smart phones everyone has a camera on them 24/7. And because of that smartphone most people are now "photographers".
I posted a portrait on my Facebook page with the tag, "Celebrate your SELF, not your selfie". A friend of mine replied, "But I like selfies".
Selfies are like fast food. They are quick, low quality, and available in seconds. The negative side is that selfies are terrible looking photographs and easily forgettable.
When was the last time you were so excited about eating at McDonalds that you took a photo of your food, posted it on social media and bragged to all of your friends that you are enjoying the best tasting hamburger you ever ate and wanted to share your experience with them? Probably never?
When my father passed away five years ago I searched and searched for a great looking photograph of him. The majority of the pictures were old Polaroids of him where he was holding in his hands a cigarette, a beer, or sometimes both. The only respectable photograph that I could find for his obituary was a tiny, low resolution picture that I was not proud to use. Unfortunately, it was the best I had.
How do you want to be remembered? By your family? Your children?