At the start of 2014 I accidentally started writing a monthly newsletter for a handful of close friends, and I've mostly kept it up since then. It was originally supposed to be kind of commitment device for myself, a way of holding myself accountable to my 2014 goals by commiting to sharing my progress with those friends at the end of each month. It continued to serve that function for the next four years, but also became something much more useful than that.

The easiest, very high ROI step is to simply open up a new Evernote document on the first of each month and title it "February 2018 Update" or whatever. Then just try to keep that tab open. You'll find stuff to put in there. What I end up writing generally falls into a small number of categories:

  • Links to things that I think my friend would be interested in, with a bit of discussion of why I think it's interesting. These also serve as future reference material for me.
  • Updates on my progress toward some goal or another, usually written in a style meant to be at least readably entertaining. This lets me look back over the years and see exactly what I was doing and when.
  • Discovery of some new thing that obsesses me briefly that prompts me to write 10,000 words of evangelism about it (e.g. meditation, hypnosis, trigger point therapy, Alexander technique, Ghokale method posture, jiu-jitsu, longevity supplements, some new AI architecture, Mr. Rogers, EverQuest as an exemplar of Fun Theory, the ketogenic diet, at least four different exercise regimens) which serves as very useful reference material, which I tend to frequently refer back to when the topic ends up being something that I make part of my life.
  • At one point I started writing a story for my friends and sending it to them in installements, which gradually turned into a 50,000 word book over the course of a year.

You don't even have to share it with anybody, I suppose, but I suspect you'll find it much more motivating to actually write in it if you do intend to share it. I created a private Blogger blog in which all these monthly newsletters reside. You could probably do the same thing with a public blog.

That might prompt you to remark, "Congratulations, genius, you've rediscovered blogging." Perhaps that's fair. But I think it does help that I know I'm only writing for a small handful of close friends. For one thing, it gives me a specific audience to write for, which helps focus my thinking. For another, I feel less inhibited, because I know that no matter what I write, I won't end up having to defend myself from a troll.

And the final and most important distinction between a monthly newsletter and a blog -- and, I think, the place where all the value of this practice comes in -- is the time-locked nature of it. You have a month to jot down thoughts, then at the end of the month you have to "finish" those thoughts. Process all the garbage you may have dumped into your Evernote document into something that your friends will actually want to read all the way through. This accomplishes a lot of things.

  • It's a cure for the goodism that leads you to have fifteen unfinished drafts of blog posts that never see the light of day. You've got a month. Wrap it up.
  • You're forced to organize your random notes and copy-pastes and unlabeled links into something readable enough for others that it ends up passing as powerful reference material for your future self.
  • Your thinking on a given topic will "advance" in a way that it otherwise wouldn't. You're forced to finish and polish the stubs of thought processes that you may have thrown in. (A lot of this finishing and processing is happening subconsciously throughout the month. If you know you're going to have to share it at the end of the month, your brain will give you something worth sharing. Without that pressure, your thoughts just tend to continue on, going in circles for years without ever resulting in anything useful to even yourself. Or at least, mine do.)

And if all those specific benefits don't convince you, I suppose I'll add that I feel that the last four years would've been quite impoverished if I didn't have this habit. Or meta-habit, because it's become such an important part of my life that the newsletters are how I keep myself honest regarding my other important habits and goals. Plus I have four years of records of my own life and dense notes on a variety of topics that interest me, that I otherwise wouldn't have.

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15 comments, sorted by Click to highlight new comments since: Today at 9:28 PM

Thank you! The idea of writing for a small circle of friends is amazing, I can't believe I never realized the benefit before. My writing style clearly suffers from trying to be accessible and standardized. And even my creativity seems to work better with a guaranteed audience of 5 people than with a public soapbox of 0-1000.

I felt like the OP was getting a little long, but I’d add that it has helped me to end each newsletter with “discussion questions.” This usually guarantees that my friends actually respond to what I write and we’ve had some good discussions.

Thanks for writing this up! I was interested last time you mentioned it somewhere, and this time you've motivated me enough that I'm going to try it for a couple of months.

Update: I've done four of these now and have really enjoyed it. It works brilliantly for motivating me to keep a record of what I'm doing, and I've had some great followup conversations too. Thanks very much for introducing me to the idea!

Awesome! May I ask how you're going about it? Sending to a small group of friends or keeping it to yourself, what software you're using, how long the entries end up being? Just curious.

I'm happy to answer questions, as I always like rambling about boring implementation details! I mentioned that I fancied trying this on Twitter and got a few takers. Right now I'm going for a pretty low tech approach where I just email it out - I write each one in a Google Doc and then paste it into Gmail and hope the formatting doesn't mess up too much. I could definitely improve this!

I have another Google Doc going throughout the month where I make brief notes on what I've been reading or thinking about, any useful links, etc, so that I have something to work with once I start writing. This is actually really valuable on its own.

I'm not trying for any particular length but seem to be writing a fair bit - the last one was about 5000 words split over three or four topics. Generally one section of it is talking about whatever physics topic I'm currently interested in, and the rest is more of a mixed bag based on what I've thought about that month.

This is a great idea! I think it is different from regular blogging in that it's more of a book club/reading group in newsletter form. How much time do you think you spend on it per month? I would also be interested in reading it if you're open to sharing.

I'll think about this. Perhaps set it up as a blog that requires a password, but I'll give anybody the password who asks.

As you can glean from my EverQuest post linked below, I tend to make a lot of very specific references only intelligible to the friends that I'm writing to. Referencing specific conversations or events from our shared history. I would feel weird doing that in a broader blog context, and I really don't want to sacrifice my ability to just count on my readers having a shared understanding.

Yes, that's a good point regarding having to be mindful of the shared history and not wanting to have to change that to open it up to a broader audience. I guess the easiest thing to do would be to write the same and have the para-readers like me accept that they just won't get certain references.

Moved to frontpage.

(I think you wanted the asterisks to become bullets like they do in other markdown editors. I've changed them into bullets, let me know if I should change them back.)

I'd be very interested in reading about EverQuest as an exemplar of Fun Theory, if you're willing to share.

Sure. I've cut out my lengthy and indulgent love letter to EQ and put it here:

edit: If anybody tells me they enjoyed it, I'll probably just post it as a "blog" post here.

I definitely enjoyed it—probably because it so closely (eerily, at times!) echoes many things I’ve said about World of Warcraft (but never bothered to put into a blog post or anything).

You should absolutely post this as a blog post here; there’s a lot to discuss, here, and I have much to say on this and related topics, myself.

Yep, I would also love to see this as a blogpost here. I also have a lot to share on related topics (2.2k games in League of Legends have shaped my life probably more than I like to admit)