If you're referring to sharing work online, I've been doing that since high school. Back then, there weren't such developed social media platforms, and you had to find separate web space to host images, which was more troublesome. Looking back now, those pictures really make me want to dig a hole and crawl into it.
Many years later, after Facebook, Twitter, and DeviantArt appeared, I started sharing my work extensively.
What left the deepest impression on me was that for several years I drew a ton of fanart for The Little Trashmaid. I also collaborated with its creator s0s2 on a short story, which was my first work to exceed 1 million views.
Additionally, a puzzle game that s0s2 released on STEAM included several pieces of my fan works. Thanks to her, my Instagram has over a thousand followers. I'm really grateful to her.
As for family and friends in real life, most of the time I don't actively share with them.
I've also drawn some NSFW illustrations. Although I don't actively share these, I don't deliberately hide them either. I think quite a few of them probably know about it anyway XD.