I have a lot of goals for individual people to contact them in some way at a certain frequency, but the more unusual goal is my general keep-in-touch goal. For this goal, I made a list of people who are long-term friends/acquaintances that I really like, but might drift away from. To get a point for this goal, I have to randomly select one name from that list, and reach out to them. (I use an app called Laza Lists in my phone because it was the first thing I found that easily picked at random from a pre-set saved list, but there are probably lots of options for this part.) No points for hanging out with friends not due to the list – the goal is specifically to do the list-based process of finding someone I haven’t naturally connected with.
When I first get, say, Brittany on the list, I might think to myself, “aaagh, I do really like Brittany, but it feels awkward, it’s been so long since we talked!” (If I ever decide, “no, I don’t really like this person, I don’t want to stay in touch” I can delete them from the list, but so far my resistance is always feeling awkward.) But it’s not worth $5 to not talk to a person I like, so I go check her Facebook to see what she’s been up to, and send her a message commiserating about something annoying that happened at her work, and she replies with another anecdote, and then an hour later we’ve had a really good conversation and made plans for me to visit her in South Carolina. (Or more often it pleasantly fizzles out after a facebook message or two, but that’s fine too, I still get the point.)
What I like about beeminding it is that usually “not talking to Brittany” is essentially a passive decision, but an eep day turns it into paying money to ignore Brittany, something I obviously want to make the active choice to avoid. (I’ve been thinking about starting up a second one for “networking” contacts, who I similarly want to be reminded to check in with.)
For me this is about keeping friends from fading away into acquaintances – in your case, it might work to pick some acquaintances that you think you might enjoy being friends with, and prompt yourself to initiate conversations or shared activities with them. As you do other kinds of social experiments, you’ll probably find new names to add to your list, which can be a metric of success. In my experience a good and rewarding social life is not just going out a bunch of places and always meeting new people – it’s also investing in and maintaining ties with your very favourite people that you found while you were out. So the experiment with extroversion can only need to be a temporary one