How to Send a Letter via E-Mail

Back in the day, it was a struggle. A right-hander, like me, had to wait for a goose to discard a feather from the left wing. Writing with a quill was a hassle and the ink was always messy.

Email is supposed to be quick and easy. It’s supposed to make our lives simpler. Some lawyers, though, seem not to have embraced this simplicity. It’s like we miss waiting for feathers to drop from the sky.

Sending an email should be very straightforward. It’s dramatically simpler than sending a letter on paper, like we did in the old days. An email, today, is the equivalent of yesterday’s printed, stamped, mailed letter. It’s faster, cheaper, and more reliable (there’s a reason we call the old-school version ‘snail mail’). We live in amazing times. Life is good. This doesn’t need to be complicated.

But, of course, we’re lawyers. So we make things complicated. We find ways to turn the seemingly simple into the overwhelmingly complex. After all, we’re the people still using fax machines. We turn molehills into mountains. We insert a section of definitions into the chores list we post on the refrigerator for our children. We can’t help ourselves.

We make work more complicated, expensive and burdensome

Lawyers are creatures of habit. We do things because that’s the way we’ve always done things. And then we rationalize what we’re doing. We’re super good at rationalizing.

Many of us still send letters, printed on paper, via the postal system, even when we could send an email or a text message. We have our reasons, even if they defy reason.

It’s a little weird how we get attached to our traditional way of doing things. Sometimes we let go–wigs and robes–but sometimes we hang on: desktop telephones, leather upholstery, and paper in the office.

We hang onto postal mail like it’s our mission to keep those folks employed. Go stand in a post office line sometime. The only people in that line are little old ladies mailing their holiday gifts six months early (clearly they haven’t tried Amazon yet) and staff members from law offices sent downtown by the boss (clearly they haven’t tried Sure, there are some homeless people trying to escape the heat or the cold, but they’re hard to distinguish from the law firm staff and the little old ladies.

We sit in leather chairs, talking on a desktop phone, reading pieces of paper. Hunh?

I recently received an email from a lawyer with a PDF file of a letter attached. That’s what got me started on this tirade.

Here’s what I mean:

An email arrives. I open the email. The email says something like “See attached letter.” Yep, there’s a PDF file attached to the email.

I open the PDF, and it’s a letter on firm letterhead.

Hunh? It’s like a Russian nesting doll. You open the first box to find another, smaller, box which contains another, smaller, box, and on and on. A PDF of a letter, inside an email? Why not just type the message in the email?

Where’s my powdered, horsehair wig?

Yes, the other lawyer had written a letter, typed it (or had it typed) on firm letterhead, scanned or converted it, and emailed it to me. This is not the first time this has happened.

Sometimes it’s even weirder. A few days after receiving the email, I got a second copy of the letter, from the postal carrier. Yes, I got it attached to an email, and then got it again via a postal carrier. It’s like deja vu but way less interesting (and far more redundant).

Let me be clear: these aren’t special, magical, letters granting me three wishes or anything. They aren’t letters sent via certified mail. They’re just regular old letters saying the things lawyers like to say.

What’s the deal? I have no idea, but I suspect it’s some kind of old approach melded with a new approach that got twisted and turned into a weird approach.

What’s the story you’re telling yourself?

I’ve asked lawyers why they’re sending letters attached to letters. What’s up with us?

Some lawyers said that a letter, typed out on letterhead and converted to an email attachment, seems more formal or official. We convince ourselves that an older lawyer, or an older judge, might find that formality more convincing or comfortable. Some of us believe that the printed letter is better suited for attaching to a court filing if that becomes necessary.

Some of us, older lawyers included, rationalize our attaching behavior because other ‘older’ lawyers (not us, of course) are uncomfortable with ‘technology.’ Oh, please–my 80-year-old mother sends text messages, complete with emojis.

Besides, I can’t help but wonder to whom a 58-year-old lawyer is referring when they refer to older lawyers. Hear me loud and clear (crank up the hearing aid if you need to): if you’re 58 (like me) then YOU ARE THE OLDER LAWYER. The older, older lawyers are in the obituaries and don’t care whether you email, snail mail, smoke signal, or don’t send the message at all.

Printing out a PDF on letterhead looks nice. But printing out an email also looks nice. Maybe there was a time when printing out an email was tricky or complicated. But that time has passed. We can manage it. Printing an email today can be accomplished just by clicking the “print” button.

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Stop the insanity

For those of you sending these letters attached to emails, I have a request. Please stop it.

Here’s how to send a letter via email:

  • Open a new email
  • Enter the email address of the recipient in the “to” field
  • Enter the email address of anyone who needs to receive a copy of the email in the “cc” field
  • Enter the subject of the email in the “subject” field
  • Type the message and add a few emojis

That’s it. No need to create PDFs or attach them or anything else. Just send the letter as an email.

Of course, you should feel free to attach things to your email. If, for instance, you received a letter on paper and want to send us a copy, then feel free to scan it and attach it to the email. That’s fine.

What’s not fine is sending PDFs of letters via email instead of just sending the email.

If you’d like your emails to appear on something that looks like letterhead, you can do that nowadays, right in your email. Spend five minutes with your computer guru and find out how. If you’d like your ‘real’ signature to appear at the bottom of the e-mail, that can be done as well.

There simply isn’t any reason to do the PDF-attached-to-the-email thing anymore.

Are we all together on this now? Can we stop the insanity and save our energy for real challenges?

Sending letters does, occasionally, prove challenging

I travel full time. It’s not without its challenges. Once in a blue moon, I’m required to send a letter via paper. It doesn’t happen often, but it happens. I had to do it a month ago because the recipient simply would not accept an email. They wanted paper.

Were I in a developed country, I could have easily sent the signed document via the postal system. Oftentimes, even in a developing country, I can send the document via a delivery service like DHL or FedEx. But these services are expensive, and they’re not always easy to track down in small towns.

An alternative which has worked for me a number of times is a service like Mailform or  Mail A Letter. I’ve never used the former (which has a more professional looking site), but have had good luck with the latter (even though the site looks a bit sloppy). These services allow you to email them whatever you want printed and mailed, in exchange for a small fee. They can even use overnight services, certified mail, etc., if necessary.

When you really need to send a paper letter, there are technology options making it easier than ever. I can’t really understand why anyone wants paper, but I do what’s required to get what I want.

Don’t make things more difficult than necessary

We live in truly amazing times. There are so many effective ways to communicate from anywhere in the world, to anyone in the world. I’m constantly astounded at the ease of text, voice, and video communication as I move around the world.

The technology makes it quick and easy to achieve our communication objectives. If things are complicated, it’s not because of the technology–it’s us.

Don’t let risk-aversion make your communication more complicated. Being safe, sticking to tradition, adding redundancy, and then rationalizing it all to ourselves doesn’t make us more powerful, or more effective.

Go with whatever gets the mission accomplished with the least hassle, for the sender as well as the receiver. Keep it simple.

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