Are you familiar with the Myers-Briggs Type Indicator? It's a personality assessment instrument that's based on the theories of Karl Jung, and it has pretty much permeated the professional world. This is the instrument that measures you on the parameters of introvert/extravert, intuitive/sensing, feeling/thinking and perceiving/judging.
I personally love the MBTI. It's given me a lot of insight into work, relationships and how to manage myself for optimal living. There's a chapter on it in my book, The Creative Lawyer. (Stay tuned for my "Celebrity MBTI Profiles!" Coming soon.)
One of the Myers-Briggs dichotomies is perceiving/judging. This relates to attitudes about closure. People with a preference for perceiving like to keep on perceiving data. They are seen as spontaneous, don't mind and may even enjoy last-minute changes, and can have lots of things up in the air without feeling stressed. What they don't like is being overscheduled or forced to make decisions too quickly.
People with a preference for judging like to know where they stand. They prefer to make decisions and get things done. Once they have a reasonable amount of data, they are impatient to move on. They are organized and orderly, and show up on time.
I'm a big J. I'm good at working and not so good at playing, unless I schedule it. (Sad!) The one exception is when I'm on an overseas trip. I can easily while away a day or week in Istanbul or Chittagong; having fun at home in New York City is another matter entirely.
Recently, in a J-like effort to improve my fun quotient (J's often create "programs" for self-improvement), I've been doing some shock therapy by hanging with some P-friends for entire days at a time. P's are excellent at having fun.
My first Fun Coaching experience was with famed writer Faith Adiele (MBTI type INFP), my close friend since 1982, when we met in the Freshman Union at Harvard the day the Boston Herald announced "Reds' Brez Dead."
We recently spent an entire day hanging out in NYC. First we went to a Weight Watchers meeting. Then we had lunch with a mutual friend. Then we saw The Jane Austin Book Club, which was lame but it passed the time. Then we sat in the café of the Rubin Museum of Himalayan Art. Then we went to Soho and walked around. Then we went to Pearl River Department Store and I bought tropical gummy candies. Then we had bubble tea. Then we met famed film documentarian Bennett Singer for dinner at a Persian restaurant. (Only the first and last activities were planned, by the way. The rest were spontaneous.) I periodically felt urges to go home or do some lame kind of work, like check email, but Coach Faith kept me on track!
My second Fun Coach experience was with famed criminal defense lawyer, Laila Sharif (MBTI type ESTP). Laila invited me to a day of shopping at the Woodbury Common Outlet Stores. She was going to rent a car and everything. I honestly found the prospect of going to Woodbury Common scary and disturbing, but I love spending time with Laila and thought it might be pretty to drive out to wherever Woodbury Common is. I was sure there would be some trees and stuff, and not just unhealthy people from the suburbs.
Laila was in a shopping vortex that day, so we ended up spending like 7 hours at the Woodbury Common outlets, which turned out to be truly high-end outlets, not just shlocky fake outlets. I accompanied her from store to store, supplying helpful male-point-of-view comments like, "That looks good on you, you should buy it" and "that makes your boobs look weird, which are otherwise fabulous." We had lunch together and inspired a table of 20-somethings with Coach Store nametags with our nutritious choices. Left on my own, I would have high-tailed it outta there after an hour, but under the supportive yet firm leadership of Coach Laila, I stuck it out. And I liked it!
J's of the world, if you feel a fun deficit, ask one of your P friends for help. In fact, if you are in the market for a Fun Coach I would recommend you make said person take the Myers-Briggs assessment, and toss out all the J's (like me). J's are great for getting things done, but when it comes to fun P's are king.