URGENT: Bussiness moneys for you Dear, sir!!: A reformed SPAM writer helps you stay out of the JUNK folder …

Confession: I used to get paid to write SPAM. It was about 10 years ago, before we all knew that an email from “Your friend Sally” is probably not your friend Sally, but some dude in a Nairobi Internet café trying to scam you out of your hard-earned money. Or, as the case may be, a 26-year-old woman in a cubicle at a Boston company that is now out of business.

I know I’m not supposed to admit this, but I loved this job to distraction even though I hated myself at the end of every day. I was just so good at it — the emails I wrote always got huge response rates. I even heard from the sales team that one particular email moved a customer to tears. It was my “true life story” of meeting my granddaughter for the first time. (I was trying to sell a knitting magazine. I knew my demographic.)

In my defense, masquerading as “Your friend Sally” to get you to buy subscriptions to Needlepoint Now, Bird Talk or the other hundreds of magazines we peddled was a step up from my previous job: writing telemarketing scripts for a product called Brain Gum. (I promise I’ll write a blog about this job soon.)

Those days are gone. I now run a respectable company with my respectable business partner and have a stable of respectable clients.

And while I sometimes miss my life on the dark side, I know I got out just in time. If you know anything about email marketing, you know it’s a tough business these days — even when you’re selling a legit product or service. Why? We’re all just so savvy now. And we have really smart SPAM-filtering software that helps us if we’re not.

SPAM filters in most email software programs comb incoming emails for signs of SPAM and assign points when they see these red flags. The points get totaled; if there are enough of them, your email bypasses the recipient’s inbox and goes straight to the Junk folder.

How good is this software? A little too good: According to Mail Chimp, about 10%-20% of all emails you send – even to people who requested them — will get accidentally routed to the Junk/SPAM folder. What about that other 80-90%? It may not be spam, but it definitely broke some of these rules:

1.)   Spellcheck. Just like your high school English teacher, SPAM filters penalize messages for poor spelling and grammar. Poor formatting gets flagged, too.

2.) Use exclamation marks with caution — and never in the subject line! One is okay, but several? Wow, are you in trouble!!!!!!!! SAME GOES FOR ALL CAPS.

3.)    Avoid SPAM trigger words/phrases. According to Spam Assassin — a popular SPAM filter with the most awesome name ever — here are a few to avoid: “CLICK HERE!,” “FREE!,” “BUY NOW,” “WHY PAY MORE?,” “URGENT MATTER,” “MONEY BACK GUARANTEE” and interestingly, anything that looks like a mortgage pitch. You can see more here.

4.)    Don’t use colored or oversized font. “What do you mean, you didn’t get my email, Grammy?”

5.) Avoid salesy or non-specific subject lines. This is going to sound totally radical, but your subject line should — surprise! — actually tell the recipient what the subject of your email is. Try to be too clever, and you’ll get flagged.

6.)    Don’t use anything but words in the subject line. This means no quotation marks, toll-free numbers, dollar signs, percent signs or, as we have already learned, exclamation marks.

Finally, if you don’t want to be flagged as SPAM, then don’t send SPAM. Or at least don’t make it sound like spam. The above tips will help. Oh, wait — the old me is creeping back.