Email Drafts the Hard Way

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I start about half of my emails in some sort of note system. Some start as scribbles on paper but most start as plain text in nvALT or Drafts for iOS. This isn’t so much about the tool as the motivation and process.

I learned a hard lesson early in my adventures of writing words on a computer screen: The last thing you write is the recipient address.

The recipient should only be added to an email when it’s time to push the Send button because buttons are easy and words are hard. A few modern email services make it easier to recall a sent message, but far too many do not and it’s just not worth the risk to me.1

My habit of drafting email has its origins in fear but I’ve grown to appreciate the side benefits.


Because I write in an application other than my email client, my draft is available anytime I want to work on it and generally doesn’t require syncing. Now, many mail apps will keep a draft in sync through IMAP but having my drafts in the same note archive I keep all of my other text, means that I know for sure where it is.

Better Tools

I use Editorial, Drafts and Write on iOS and several top-notch text editors on the Mac.2 They all support tools like TextExpander and also bring their own bag of tricks to the party.

Email is a really wonderful system. It’s self documenting and automatically establishes relationships and timelines. There are some rough spots though and search in most email clients isn’t terrific. Storing my draft emails in Dropbox means I can direct much better search tools at the files than I can get from a Mail app.

Replies, Notes and Bad Habits

Separating my email replies from my email clients had an unexpected influence on how I reply to messages. I loathe inline replies because sacrifices readability in favor of author laziness. Not having access to inline text means I really have to read the message I’m replying to and understand it. That’s the only way to paraphrase. So instead of inline replies, I generally address questions in full but succinct sentences and I provide written context.

Regarding the girl with the lefty scissors, I believe she was attacked by Scout Redford on a motorcycle and was merely defending herself. Mr. Shukusky was not involved directly.

The second bad habit plain text resolves, is exuberance for adding attachments. Not inserting images until after the text is written means that the text mostly needs to stand on its own. Attachments should supplement the message, not hold it up. The challenge is not forgetting to add the attachment before pressing send. Most emails don’t need attachments.

It takes a conscious effort in most note apps to create an email.3 I usually use copy and paste. This means I can add my own notes to the draft while I work or add them alongside in a separate reference file. I love this. It allows me to take my time and really think the message through rather than shooting it off only to realize I missed something and need to send another follow up.


There are so many alternative ways to work outside of an email client that I’ve lost interest in listing them. But there are a few that stand out for their convenience and flexibility.

First, drafting an email in a task manager is an excellent way to remember what I’m doing and why it matters. OmniFocus has a notes section, so does Asana or any other proprietary task manager. Any plain text task manager like TaskPaper is built for writing text. Keeping my drafts in a task manager means contexts are easily assigned and reminders make sure I get the work done. I rarely do this, but it does work well.

FastMail has a built-in note service. These aren’t IMAP drafts. They are separate and really only accessible through a web client. But if you work on the web, it’s a great way to separate drafting a message from the email client, but still keep it close at hand.

If all else fails, start a new draft email. It’ll work. Start the draft and don’t add a recipient. Just write.


The most valuable suggestion I can provide is to pay attention to your email draft. Know who you’re sending the message to and know what the intent is. This doesn’t make my email harder and it’s not a religion for me. I try my best but only liars and failures deny their weaknesses. I still use the reply button in email. The convenience and speed is undeniable and sometimes the appropriate message is just a simple yes or no. But I also try to remember that sometimes a CC list isn’t the best way to have a meeting.

Everything I’ve suggested can be done in an email client. The best email clients make it easy. It just took something a bit more extreme to change my habits for the better.

  1. Then there’s Outlook on Exchange which fools the sender into thinking they’ve recalled a message but really it just draws more attention to the mistake. You might as well call the person and ask them to delete the message before you use the “recall” function with Exchange. You don’t run over someone with your car and then back up to tell them it was a mistake. ↩︎

  2. My number one most used app is probably nvALT just because it’s convenient, reliable and I know what it does well. Number two is probably Sublime Text and number three is probably Write for Mac↩︎

  3. Drafts or Write for iOS are notable exceptions. ↩︎