One of the biggest time management challenges in my life is making sure that I have enough fun. Fun is different from not working. I spend plenty of time not working and yet when I look back on the last few months I wish I had spent more time having the kind of fun that involves going out; the kind of fun that when I get back to work I want to tell people about. Without at least a little planning, non-work time may be squandered on TV, chatting online, and reading blogs.
I don't mean that one needs to plan the fun. Nothing could be less fun than a plan like...
8:00 party starts
8:05 lift beer to mouth, drink
8:10 laugh at joke someone tells
8:11 think of funny retort, say it out loud
That would be dreadful.
However big fun stuff requires planning. Concert tickets need to be bought in advance, anything involving seeing friends requires scheduling it with them in advance, etc. I consider it "fun" to speak at Linux/FOSS/etc. User Groups, but that takes months of advance planning to get on their schedules, book travel, and so on. If I don't invest some time in planning those things, they don't happen.
Therefore this weekend my SO and I spent some time talking about things we wanted to do, marked up our calendar to show when we had off from work (a lot of holidays coming up), marked various conferences we're attending, RSVPed to various parties we'd been invited to, and used our calendar to pick dates to see various shows. Of note, we're going to see Emo Philips perform in NYC on Jan 18, we bought broadway show tickets to see The Farnsworth Invention (written by West Wing creator Aaron Sorkin) on Feb 21, and we're planning on attending a mid-winter SF on called Wicked Faire. The Emo Philips show is general admission... if you happen to be in the area and want to join the group of us attending, please let me know.
However, there are ways to reduce the planning required. One way is to set up a regularly scheduled night. For example, I know some couples that always keep Wednesday night open for "date nights". Families often set aside one night a week for "family game night".
Weekends don't need too much planning: For just about any place in the world there is a web site that lists events in your area this weekend and rarely do they require much planning except having something to wear. If you live in NYC there are sites like Nonsense NYC, Gemini and Scorpio, and FlavorPill. Flavorpill has listings for many cities. My little town of Montclair, New Jersey has BaristaNet which lists many events.
I do like to do spur-of-the-moment outings to see movies, get dinner, etc. but it is difficult to find which friends happen to be in the same situation at the very same moment. Phoning them can be embarrassing... "Hi! Are you free to see a movie in an hour?" is kind of rude, and guilt-inducing if people have to say "no" all the time. I'd rather have a system that would notify my local friends by TXT message. They could ignore it if they are busy, or call me if they want to come. "Local" could be defined as everyone I know on Orkut or FaceBook, that happens to be physically near me (either defined by their address, twitter status, or the GPS on their phone). That would be awesome. Someone should invent that.
What's your most effective way to make sure there's enough fun in your life?