“Everyone who drives slower than you is a moron;
Everyone who drives faster than you is a maniac.”

— George Carlin

You’ll be happy to know that my five year old son Jonathan has taken an interest in the game of Checkers. Happy, because he’s making me play with him every day instead of you.

Don’t get me wrong, I have nothing against those of you who enjoy this game. That said, I can’t for the life of me figure out why this particular pastime has survived the test of time. Like fruitcake, crocodiles and Larry King, it’s a longevity truth that has me baffled.

Granted, there are some interesting moments, usually related to those instances when Jonathan and I have a conflicting interpretation of the rules. Yesterday, for example, Jonathan attempted to move one of his pieces backward, a violation for any “non-king” piece. Seeing what he had done, I gently pointed out that he was only permitted to move forward.

Jonathan didn’t bat an eye. He simply pointed at himself and said, “I am, I’m moving them forward this way.”

Naturally, my first thought was that he is destined to play an important media relations role in some future White House administration.

My second thought related to an e-mail experience I had last week. As many of you know who have requested one of my complimentary thought pieces (e.g. ” 10 Really Good Reasons to Quit Your Job and Start Your Own Business “), I send these out via e-mail, and typically follow up over the next few weeks with a sequence of additional free stuff and product offerings.

Last week however, one of those e-mails was sent back to me from a reader named Anne, with the following message:

“In my opinion, requesting your newsletter and even accepting whatever freebies you offer does not grant you permission to spam me. No, not the legal definition perhaps, but it’s most certainly unwanted. One sales-only, no-immediate-value e-mail or issue is one more than I will tolerate.”

Needless to say, this got me thinking. Here I was, sending what I believed to be useful, interesting, targeted follow-up information and yet Anne was offended. Sure, one of the messages was sales-related, but we have a relationship, the offer was on target, the product is high value, and I offered an easy way to stop future messages.

Questions raced through my head: Did I cross some invisible line? Do other readers feel the same way? Does she play checkers?

Anne was open to talking about it, and over the next several days, she graciously responded to my barrage of follow-up questions as I attempted to pinpoint her objection:

1. If I followed up with an additional (but unsolicited) free report to you, would that in your view be OK? In other words, is it the unsolicited contact that annoys you or the fact that I’m offering something for sale?

2. If I offer products for sale in the body of my newsletter, do you think a line has been crossed as well?

3. Does my “value clock” reset to zero with each new communication? If I’ve sent you two or three or ten free valuable things and then offer something for sale, am I no different than the guy who simply contacts you cold with something to sell?

4. A few weeks ago I was writing an article for a local paper and e-mailed my subscribers asking if anybody had examples related to the topic. This had nothing to do with E-Newsletters. Did I cross the line by e-mailing people on a topic other than for which they had subscribed?

5. Would you mind playing a few games of checkers with a really cute five year old?

Anne’s subsequent responses to these questions didn’t surprise me, nor did I agree with them in all cases. Hers were simply — as she put it — “the personal opinions of one person.”

This lack of a clear set of rules in the world of e-mail poses both a problem and an opportunity for all of us.

I t’s a problem first of all because there’s not much historical precedent — we’re all making it up as we go along. Second, the intensely personal nature of e-mail causes people to develop points of view about its use that they don’t apply to other marketing tactics (direct mail and B2B telemarketing for example, are given much more leeway).

It’s an opportunity however, because each of gets to decide where the line is. Assuming you’re over the bar on what’s legal (follow this link for a refresher on the CAN SPAM act of 2004), opinions regarding what’s appropriate are all over the map.

With that in mind, I offer some specific recommendations:

• Figure out where your line is. Just because the “experts” say that a particular approach or tactic is fine, if you’re not comfortable with it, don’t use it. When the e-mail comes in that takes you to task for doing something “wrong,” you want to be able to respond knowing that you consciously arrived at an approach that works for you.

• Expect disagreement. I worked for many years at a large consumer services company. One thing I learned in marketing to hundreds of thousands of people at a time is that given a big enough group, there is literally nothing you can do that won’t cause somebody to object. You could stuff five dollar bills in an envelope and send one to each of your newsletter subscribers and somebody would complain (“Hey, I wanted singles”). Don’t lose too much sleep over it.

• Let the filter do its work. Among the many (OK, hundreds) of things I love about E-Newsletters, one of my favorites is this tool’s ability to filter in the people who like the way I think, and filter out the people who don’t.

Anne, for example, would not be a good client for me. If she objects to the way I market my business, she’ll object to the advice I give her about marketing hers. By talking the way I really talk, saying what I really believe and sending e-mails the way I want to send them, she’ll learn enough about me up front to know that she should walk on by, saving us both a lot of future frustration in the process. On the flip side, the people who think my approach is perfect (for them) will call, and not be disappointed with what they bought.

Overall, I think Anne summed it up best with this final observation: “I won’t be surprised at all if some of your readers disagree.”

I couldn’t agree more.

(P.S. I know you’re aching to weigh in — go ahead, how would you answer the 5 questions above? Click here to tell me!)