I'm in a fun course called Wisdom Unlimited, and one of the first projects is to create a visual display of everyone with whom we interact on a regular (weekly to monthly) basis. (This includes people we interact with only via email or on the phone, and also everyone from our close friends to our dry cleaner.)
It's not an illustration project and everyone else used photographs, but I wanted to draw people, and I'm finding I got a lot out of doing so. For one thing, spending the time to draw them, is sort of a metaphor for the fact that having any single person in your life involves some sort of investment in time or mental energy.
What I also became aware of is that there are people I consider close friends that I couldn't include because I don't interact with them on even a regular monthly basis! Some may say that that's just how life goes; however, what it made me realize is that there are only a finite amount of people we will know and interact with in our lifetime, and we really do have a choice in determining what that looks like.
Anyway, as I said, this is a work in progress, so I'm adding people as I go. For example there only about 5 or 6 people depicted with whom I interact only online, and I need to complete that section of it. (The total number of people to be included based on the criteria of the assignment is 50 to 100.)