5 Sentences To Freedom (or How To Start Living Outside Of The Inbox)


I’ve written about sending short, succinct e-mails in the past (Fear of Competition Is Bullshit), but I’ve never delved deeper into the subject.

I’ve been utilizing the 5 Sentences E-mail Rule for a while now. I first heard about it a long time ago in Leo Babauta’s The Power of Less, but I never thought it was possible for the majority of my communication. In October of 2009 Leo published The Art of Brief E-mails and I decided to give it a shot. Although it took me a while before I felt comfortable using it for almost every e-mail.

I don’t follow a lot of what Leo writes in that article. For example, when I get an e-mail without a subject line I get a weird feeling of anxiety in the pit of my stomach. Kind of a “What the hell is this?” That’s probably just social conditioning so I’d like to thank David for always sending brief e-mails without a subject line to help me out with that. :)

The most important part of Leo’s article, to me, is the section on Editing:

Edit. I know, you want to write it and send it and forget it. Well, that’s rude, to the recipient. You’re saying they don’t deserve a good email. I’m not saying you need to spend hours making every email perfect, but if you can take 10 seconds to go back over an email, remove unnecessary sentences and words, you’ll be doing your recipient (and yourself) a favor.

At first it was a struggle for me …

“But there’s so much back story! This person needs to read the back story before I can get to the question/reason for e-mail!”

When you first start utilizing the 5 sentences rule that will probably be your biggest challenge. You’re convinced whoever is reading your e-mail needs every single extraneous bit of information before they are able to respond.

That is simply not true.

What I’ve found when I receive really long e-mails (not everybody respects the 5 sentences rule) is that usually right at the end there’s the golden ticket.

“So what I’m getting at is … [insert question].”

Everything after the “So what I’m getting at is” part is usually all that is necessary for an e-mail.

Example E-mail

“Hey [Person]!

Thanks for rocking. Quick question: [insert question]

Thank you so much,


Mission complete!

Questions or proposals never need a back story. Never.

I Love To Help

No joke. I love reading e-mails, I love getting to know you, and I love answering questions. I love to help. The problem is, the more this blog grows, the more e-mails I receive and the more difficult it becomes to respond in a timely manner. By putting these rules in place now it will be much easier in the future as this movement continues to grow.

I ask you to utilize the 5 sentences rule not just for me, but out of respect for your fellow Freedom Fighters. They have questions and want answers as well. If you send short, succinct e-mails, that means I can more easily help more of you. Woohoo!

Practice and Social Conditioning

The only way to get better at this is to practice. Start sending very short e-mails to everybody.

More words does not mean higher quality. Unfortunately we’ve been conditioned to think the opposite. In school you had to write a “10 page essay” when 5 pages would do. In blogging an article over 1,000 words is “high quality” while an article of 500 words is “thrown together.” We need to change that because it’s simply not true.

Two of my favorite blogs are by Derek Sivers (Sivers.org) and Seth Godin (http://sethgodin.typepad.com). You will very rarely find them writing posts longer than a few hundred words. Interestingly, they both also respect the short succinct e-mail. Coincidence? No.

The One Situation Where You Should Never Break The Rule

Break rules, except when you need to follow them.

The 5 sentences rule can be broken and I do break it myself. I would say 95% of the e-mails I send are 5 sentences or less and the other 5% are of varying length.

Here is where the 5 sentences rule should never be broken: initial contact.

After the initial contact, you might be asked to go into more detail on your question/comment/statement. In that case, fire away!

It boils down to what Leo mentioned: respect. Sending a busy person (in other words, everybody) a 500 word e-mail is disrespectful of their time. Send them a short e-mail and they will love you for it.


  1. The 5 sentences rule seems to have sense in some cases but not all of them. There are thousands of situations where sending a 5 sentence email is rude. For example, when your good friend asks you how was your holiday. Responding with an email like: “it was fine, thanks for asking” is just not cool. ;)

    As a rule of thumb I would say that it’s appropriate to send a long email if the recipient expects it, and in other cases – send the short one.

    • We’ve been conditioned to think exactly what you just stated. It’s simply not true.

      If a good friend asks me how my holiday was they’re probably asking in person or via phone. You know, if they really are a good friend. ;)

        • I see your point, KK, but I think it’s not true. You can reply in five sentences that your holiday was really cool and that you’ll tell your friend all about it next time you see him. You even got one sentence left to tell him you’ve got pictures to show him.

          • A female would say, in less than five sentances:

            Oh my gosh, it was the most awesome time, we simply have *got* to go for coffee and I’ll tell you all about it. Like this moment: Squatting over a hole in a french loo, salopettes around my ankles,whilst trying to pee on a pregnancy test stick requires a certain level of skill and dexterity I simply do not have. More details later, let’s get together soon… can’t wait to tell you if I saw any stripes or not! XXOO

            See? Works fine for me ;o)

  2. I’m not quite sure I’m getting the part about the “No subject line”. Are you suggesting that the subject line should be omitted?

  3. Totally agree. Have been trying to implement this rule at work, where we get and send *tons* of email.

    Exceptions in my case will be where I need to document a procedure for others, and I type the steps in an email. However, I bet it would make more sense to attach the procedure as a document, and keep the email short and sweet!

    Keep rocking!

    • That’s awesome that you’re starting implement this at work Paul!

      As far as your exception: whether you include it as a separate doc or in the e-mail, it’s still a document. Unique situation. :)

  4. “Brevity is the soul of wit” ~ Shakespeare’s Hamlet
    I’d probably go “80/20” with this advice. Just about everything can be improved be editing with a cruel scalpel, but 5 lines doesn’t make for an amusing anecdote, technical explanation, or personal touch.

    BTW, I feel ridiculously fortunate to have found your blog and I genuinely appreciate what you do. Thanks.

    • Get crafty and your amusing anecdote or personal touch will shine through. It works on twitter, right? :)

      Technical explanation: understood. Unique situation.

      And thanks so much. Great to know you enjoy my work!

  5. “Living outside of the inbox” Such a clever title!

    This is a great tip, and I can see how it would be efficient and sufficient for the uncommon amount of emails you receive. :) I tend to put too much detail and back story even in more personal emails to people I know. I’m sure they would appreciate me cutting to the chase every once in a while.

    I don’t receive much email outside of that, but when my blog gets bigger and the inbox count gets exponentially bigger, I will remember this post!


  6. I sure like using the five sentence policy and site in getting to the point fast.
    It’s a good process to improve my written dialog to be clear and impact-full.
    And thus, will do the same on the other end.

    • Thanks Todd, you hit it with this: “It’s a good process to improve my written dialog to be clear and impact-full.” I wish I would’ve written that in the article. ;)

  7. Good topic.
    I have been working on implementing this since I read The Power of Less. Although I seem to spend just as much time writing the short email response, because I do go back and make sure I am giving the right information and not being rude.
    What about when commenting on a blog? do you think the same rule should apply? oops 6 sentences :(

    • It doesn’t apply to blog comments although that would be an interesting test as well. :)

      As far as the time it takes: yes, it’s a struggle at first. With practice it will come much quicker. You’re training your brain to think about strictly what’s important instead of all the fluff.

  8. At first, the idea of the backstory being unnecessary seemed to promote abruptness or the absence of context to situate the question or proposal. However, if you have developed a relationship, then the backstory/context is part of the relationship. For example, as a reader of your blog, I’ll do some checking to see if you’ve already discussed something before I ask a question or submit a proposal.

    • Backstory definitely isn’t necessary with friends or acquaintances unless it’s asked for.

      That said, a backstory on initial contact to a busy person will, many times, result in your e-mail being ignored. 5 sentences makes it easy for someone new to you to respond instead of putting it off or ignoring it completely.

    • I know what you mean and I used to feel the same. But if my 5 sentence e-mail answers the question I realized it’s an unfounded feeling. Keep at it Anthony!

      P.S. Everybody reading this: Anthony does awesome shit like http://write.fm – Check it out!

  9. Love this. I do practice sending short emails but then I apologise for it adding an extra sentence. An example of an email from me:

    Great see you Sat.

    All good here.

    Sorry to be brief. Busy.

    x A

    People have written back saying don’t apologise I like it! So here’s to more brief emails flying back and forth between us:)

    DMs on twitter are great too.

    • Thanks Annabel. I agree with the people: no need to apologize. The extra sentence isn’t necessary. ;)

      And twitter is good practice for sending short e-mails. :)

  10. Hmmm. Interesting. When you mentioned Sivers and Godin doing shorter posts, that got me thinking as well. Perhaps mine are TOO long sometimes.

  11. This is something I need to change. I have a tendency to ramble on and on, never thought of it as a disrespect to the recipient’s time to send a long-winded email, but it absolutely is. Nice stuff!

  12. Hmm.. Interesting stuff.. but I totally agree..

    I always try my best to send short emails since I like
    it when I GET short emails that don’t take too much
    of my time..

    Long emails are needed sometimes though..
    Great stuff.

  13. Less is certainly more. But while you omit your backstory, make sure you tell the recipient WHY you’re asking the question. You might be off base in asking it in the first place, and unless you make the objective clear, you’ll waste time talking at cross purposes.

  14. “It is with words as with sunbeams. The more they are condensed, the deeper they burn.” ~Robert Southey.

    The trick is to convey what you mean concisely and succinctly without losing rhyme or meaning. Whilst I agree Your 5 sentence e-mail rule most certainly applies to initial contact, a 500 word email is only disrespectful to the recipient’s time if it is long-winded waffle sans benefits or value.

    Thanks for sharing.

  15. I couldn’t agree more! But I will say that for most people, this takes practice. I work in an area of communications within a large company, and I am constantly trying to convince the powers that be to distribute SHORTER pieces.

    Surveys, focus groups, and anecdotal feedback all indicate that employees want to quickly discern the point of the message, and then get back to doing their job. All that background or “back story” as discussed above — totally not necessary.

    My suggestion: Start with the “what you need to do” or “how this will affect you” or “the question is” and, only if absolutely necessary, you can add a section titled “background” if you think it’s critical. I promise, after some experience, you will realize that in nearly all cases you can eliminate the “background” section and no one will even notice.

    • Thanks for adding your thoughts Barb. It does take practice, and I’m pretty sure I mentioned that in the article. If not, I meant to. haha :)

  16. Ah, but some like to read :) I exchange pages-long emails with a friend from across the pond, for example. We’ve never met in person, but have become good friends through intellectual exchange, albeit in type + through email form! I suppose you could replace it with Skype, & we’ve tried that too, but something about hashing out philosophies + the like through writing just works!

    Definitely think I could condense some of my emails, though! Your overall point is well taken- thank you!

  17. This makes me happy. After reading this I decided to scan through my “sent” emails and discovered that my focus on more effective emails has led to 5 and 6 sentence emails without me even aiming for it. Very interesting (and cool).

  18. I agree that brevity is important. I appreciate a clear, concise email.
    I’d rather do just enough than too much.

    I wonder, though, if the desire for a short email is a symptom for our ever-shortening attention span.

    Where are we trading connection and relationship for efficiency?

  19. I am such a terrible offender of breaking this rule… I work in PR and notice people often writing just for the sake of writing. From now on, concerted effort to edit and re-edit myself. Will link to this from our intranet and see if anyone listens.

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