As I write this, the Boston Celtics basketball team is celebrating last night’s victory. Not because it put them into first place… in fact, quite the opposite. Last night’s win mercifully broke a team record, 18 game losing streak.

Things were very different around here twenty years ago. Back then, the Celtics were a great team, and – unlike today, where not only can you get seats, you could probably suit up and play for a few minutes if you asked nicely – tickets were impossible to find. So when my boss handed me two “luxury box” tickets to a Celtics-Lakers game, I was thrilled.

I’d been to the old Boston Garden a couple of times before, but when my friend Fred and I arrived for the game, we weren’t quite sure where to go for the luxury boxes. After wandering around a bit, we found the entrance: A dilapidated-looking elevator, hidden in a corner and manned by an equally dilapidated-looking security guard.

Being the street smart, world travelers that we were, Fred and I took one look at the uninviting entrance and quickly deduced that there probably wouldn’t be any food stands or roaming snack vendors on the other side of that elevator ride. So we stopped to wolf down a couple of hot dogs each, and five minutes later, when we boarded the elevator, we were happy at having “planned ahead.”

You’ve probably already guessed the punch line.

As we discovered, one of the things that makes the luxury boxes so luxurious is the fact that they are stocked to the gills with (free) soda, beer, snacks and a rich assortment of hot food. They even have a man in a white coat and chef hat who arrives pushing a dessert cart at halftime (another happy surprise that prompted Fred to ask, “What’s next, massages?”).

We consumed all we could that night, all the while wishing we hadn’t “wasted space” on hot dogs. Clearly, thinking too far ahead does not always work to your advantage.

Similarly, in working with a new client on an E-Newsletter, one topic which invariably comes up is the “editorial calendar.” Successful businesspeople tend to like planning and structure, and my clients are no exception.

I do my best, however, to convince them that this element of organization is a bad idea.

You see, to me, the best E-Newsletter content is spontaneous – less like successive chapters in a book, and more like a series of great lunchtime conversations. A little of this, a little of that. A little business, a little personal. A little humor, a little serious. You mix it all together, you have a nice time, and when you leave – although you may not remember exactly what was discussed – you make a mental note to get together again soon.

An E-Newsletter, after all, is just a glorified e-mail. On the communications continuum between writing a PhD thesis on the one hand and chatting with your boss in the men’s room on the other (assuming you’re both men), it’s much more down at the men’s room end of the equation.

Consequently, the best E-Newsletters are not so much about publishing, as they are about connecting. In my experience, planning topics in advance dampens this connection, and leads to dry, overly thought out, difficult to give birth do, missives.

Bottom Line: Let yourself and your colleagues off the hook, and just write about what’s on your mind today. I guarantee it will be more interesting for your readers, less effort for you, and a better reflection of your authentic point of view. Not a bad way to make the phone ring.

P.S. Not creating an editorial calendar ahead of time does not preclude having a file of “possible future ideas,” something which in fact, I recommend. The idea, however, is to select the topic of the month based on your current state of mind, rather than a preplanned schedule.