DRMacIver's Notebook

A Guide to Starting a Daily Writing Practice

Published: 2020-06-08

Apparently I’m now that guy who gets people to start daily writing practices, so here’s a daily writing about daily writing practices.

The short version

The daily writing practice I’d advocate for is to write at least one sentence, as close to every day as you can manage, in a location that gives you the opportunity to easily write something closer to a short essay should you choose to do so. Ideally this would be in public, under a pseudonym if you prefer, but if you can’t bring yourself to do that it’s also find to write as if it were intended for other people to read but to do it somewhere in private.

The rest of this post will be some guidance on how to make this work for you.

What is the purpose of the practice?

The purpose of the practice is to write every day and enjoy doing so. That’s it.

There are some additional benefits of the practice, but the practice is in and of itself supposed to be an enjoyable thing which puts something out into the world that would otherwise not be there.

Additional benefits include:

It will improve your writing skills, and your communication skills in general, by giving you a place to practice writing.
It will help resolve writing anxiety. You are probably much better at writing than you think you are, but writing feels hard not because writing is hard but because you have a lot of associated anxiety with it (school does that to you). By getting to regularly experience writing as relatively easy, you’ll start to drain some of that anxiety.
You will likely find you have a lot of thoughts that were not getting expressed, and a daily writing practice gives you somewhere to express them.
Daily writing is a good place to think. It doesn’t force you to think deeply, but it gives you a place where you can develop your skills for deep thought should you choose to do so. You will almost certainly become a better thinker through a daily writing practice.
By writing daily you’ll start to notice themes across your writing, and you can begin to draw them out, connecting up your knowledge and thouhts better.
If you share it, people will find your writing useful. They probably won’t find all your writing useful - the point of a daily practice is that you get to write stuff that’s not very good, and that’s fine - but I’m sorry to inform you that if you write every day over a sustained period of time (months, certainly, but probably even within your first week) you’re doomed to write something that people actually like.
- This is good for them, obviously.
- It’s also good for you. People will say nice things about you. You will like that.
- It may also spark interesting conversations.

Success criteria

Success is writing one sentence, almost every day, and feeling neutral to positive about having done so.

Most days you will probably find yourself writing more than one sentence. If you only ever write one sentence you should probably try to write more some days, but I find writing more tends to come naturally for people and writing only a sentence every day is probably a sign that you’re not enjoying the practice rather than a problem in and of itself, so I wouldn’t worry about length too much. Success on any given day is just the one sentence.

It doesn’t even have to be a good sentence. Success in your daily writing practice does not require any quality. If you’re putting it in public somewhere you can explicitly signal that it is practice - a lot of us are using blogs like this one labelled “notebook” to indicate that the writing is just some thoughts that we’re writing down. You can write high quality stuff if you want to from time to time, but it’s not required for success.

You probably won’t write literally every day. Missing a day is fine. If you’re missing a lot of days (more than about one a week on any sort of recurring basis, say) then something is up and you should figure out what that is and what to do about it. Don’t beat yourself up about it - it means something about the practice isn’t working for you, and you should treat figuring that out as a practical problem to solve. Chances are you’re setting too high a bar for yourself.

You shouldn’t hate your practice. If you hate your practice, you’re probably either setting your standards too high, or you’re uncovering some uncomfortable feelings around writing that it might be worth examining (may I recommend some useful emotion management principles?). If it’s the latter, remind yourself that this practice is successful if and only if you hit this incredibly low bar, and that it’s a good practice to do, and that you can set aside your normal standards for writing while doing it.

Failure criteria

I want to be very clear on this: It is OK to try a writing practice and give it up. Beginning a daily writing practice does not oblige you to continue a daily writing practice.

My recommendation would be that if after a month you have not been able to make it work for you in the sense above - i.e. writing almost every day and enjoying it - then you should quit. Additionally, throughout that month you should be actively looking at any problems you run into and trying to solve them. If you get properly stuck feel free to ask me for advice.

The month is just an arbitrary deadline. If prior to that point you decide that the writing practice is making you miserable, and you cannot figure out how to solve that, quit earlier obviously. I’d recommend perseverance if it’s at worstnot quite working for you, but I’d also recommend trying to figure out why it’s not working for you and seeing if you can fix that.

Prompts

One of the most important things to maintaining a daily writing practice is that there should never be any uncertainty if you can do the writing today, and the key to that is to have a good set of prompts for writing.

My favourite prompt is to find some interesting passage of writing, copy it out, and add commentary. The commentary can be any sort of thought prompted by it, or if you’re stuck for what to say you can just explain what the passage is about, provide context, etc.

This passage can come from anywhere - something you’ve read recently, a tweet you’ve seen, a conversation you’ve had, but my personal favourite procedure is to use random pages from books. This goes like this:

Pick a book, ideally one that you’ve read. I prefer using physical books for this, but it’s doable with ebooks. I randomize the book selection but it might be helpful to set aside a favourite novel for this as the default if you don’t have anything you want to use on a given day.
Pick a random page within that book, either by flicking through it or using a random number generator such as random.org.
Find an interesting passage on that page and use that (possibly continuing on to the next page, or scanning back to the previous one for the start of a passage). If nothing catches your eye, pick another page. If still nothing catches your eye, pick another book.

I find this is a very reliable prompt for being able to write something even when I’m not feeling it.

Another prompt that I’ve been enjoying reading but haven’t tried myself is that Lisa has been doing drabbles - picking a topic in philosophy (you can pick your own area, Lisa is a philosopher) and writing 100 word explanations of that topic.

Another useful thing is to keep a file of things that you could write about at some point and if you’re stuck on any given day, scroll through that file and see if any of them catch your eye. I’ve not been using this much recently since I started using the book prompt as my default, but it’s been very helpful in the past and if the book idea doesn’t work for you then try this.

How long should it take

You should tailor your writing to how long you have. If you don’t have long, the prompts are important.

For me I rarely spend less than 15 minutes on it, and even more rarely spend more than an hour on it (this post is unusually long to write because I’m trying to explain something specific rather than just rambling on a prompt, so it might take almost an hour to write).

Key to this is the low quality aspect. Daily writing involves almost minimal editing. If you want an editing practice, that’s separate.

Things to watch out for

The notebook blog is supposed to be an enjoyable thing that you can keep up indefinitely. It can stop being this long before it “fails” and in order to avoid it, it’s worth watching out for some things:

taking too long over posts.
starting to put off writing posts, or not wanting to write them.
doing a lot of editing.

The easiest way to have this is by writing too many good posts! It’s very easy to let your standards creep too high, and you won’t be able to sustain that indefinitely. It’s good to write good posts from time to time, but you’re not going to be able to do it every day.

My recommendation is that to counteract this you should deliberately half-arse your posts at least a couple days per week. Pick a prompt and do the bare minimum amount of work needed to fulfill it.

Getting Started

You should avoid any nontrivial activation energy for getting started and just start. Pick wherever to write is the lowest effort for you to do so, don’t try to do anything complicated to get set up.

Social media is not generally a good choice for this. Twitter, or Facebook, are not very good for the essay format, and I do think it is important to write somewhere where you could write longer posts if you wanted to.

My ideal recommendation is to start a blog or a newsletter somewhere. I’ve been enjoying Substack for my newsletter. If you’re at all programmery doing a static site on GitHub pages is also a good way to go, otherwise wordpress.com is a good option. reading.supply seems nice but I haven’t used it (and it’s currently difficult to subscribe to if you’ve not got an account there, but that may be a feature depending on how shy you’re feeling).

Also, you should get started now. Step away from this post, set up a place to write, and then write something.