On Writing

The only post I hope to have to write about writing.


A lot of people only see me from the perspective of this website, and so to the readers of this site, I am a writer. Naturally then, a lot of the email from this site whittles down to: how do you write so much? ((For the record I do not think I write very much.))

So much?

That’s relative, because I think I write about 50% as much as I would like to write. And far less than many others, but then again when I did put up my status page and saw that over one million words had been published — well then yes, that seemed like quite a lot.

I also don’t really believe in writing much about writing itself — just as I try hard not to get roped into blogging about blogging. At the end of the day though, this question gets asked enough that I felt it would be easiest for me if I went ahead and wrote one post about all of this — so that I can just share this link when I am asked.

Also, as a side benefit, I get to talk a lot about me, and that’s always nice.

Why I Am a ‘Writer’

I’m not one to run around and tell anyone that I am a writer, but I also don’t attempt to categorize myself any one way — by my profession or otherwise. Likewise I won’t be caught saying I am a thinker because that shows a lack of thought.

With over a million published words, over the course of almost five years, well at that point it felt fair to say I am a writer — in at least one way.

More than any of that, this site or my readers, I am driven to write. Writing has become a passion and obsession for me. I can’t go long stretches of time without writing, and writing feels worth while to me — even if to just to clear my mind.

Often writing has become my mental vacation.

Writing can reset me.

But I also can’t stop writing. I feel bottled up, and unable to take a break. I have to get something down, even if it is some trite bullshit. I need to write.

Maybe that doesn’t make me a writer in your eyes, but if it doesn’t then I frankly wonder what does make someone a writer in your eyes? Wearing a scarf, or a publisher to nag me? I collect real money from my writing, and have a sustained and real audience, while also having a passion for writing.

Maybe I should call myself a writer.

I’m not sure how I get away with not calling myself a writer now that I think about it.

Where I Write

A lot of people wonder where I write. Maybe I am a coffee shop writer, or I have a cabin, a special area or place. Maybe a nice keyboard, or typewriter, or notebook. Nope, none of that, because that’s not an integral part of writing. What I’ve found is that the only part of writing that matters is the actual act of writing.

Nice tools are only that: tools. They exist to make your life easier or happier, and not to make your words better.

So I write at my office on my Mac. Or wherever I am on my iPad. Or standing somewhere random on my iPhone. Or in bed. Or sitting at the dinner table. Or in a coffee shop.

I don’t use some asinine old computer with a DOS based word processor, because I don’t believe in actively making my life harder. But I do need focus — I need to be able to see just my words and not be distracted by the other minutia that one deals with. You can’t drown it all out, but good tools and locations can help.

So I try to write somewhere quiet, or evenly loud — what many call ‘white noise’. I try to write in Ulysses because I am familiar with it, and comfortable using it. I don’t have to learn it, and it works well. I write as much as I can on my iPad because it forces more focus — I have to remove my hands from the keyboard to distract myself with other apps.

Place Dream

I have this recurring fantasy about crafting the ultimate writing space. It starts with a large desk, something like 4 feet by 10 feet, and it is in the middle of a room. Except the room is a warehouse, and the warehouse is a vastness of dark.

One light, shining down on the desk.

The desk only has a large monitor with light text set on a dark background.

The cursor blinks.

There’s a keyboard, but no mouse — writing requires only a keyboard.

My chair sits slightly spun, waiting for me to slink into it. It’s quiet, but there’s the sound of rain on the metal roof. I can think, and the air above the desk seems limitless. I can see my desk perfectly, but there is nothing but that blinking cursor to think on.

It’s ludicrous to ever think such a place would be good for writing. Some of my best work has come amidst the most chaos. The screaming kids in the other room. A cramped desk. A bad chair. A shitty tool. But the idea was there, and in that moment I had the drive to push past the idea, and to the true idea.

Most of my writing may be done on a MacBook Pro with a CODE Keyboard in Ulysses, a MacBook, or on a similar setup on my iPad. But that’s in no way an endorsement of that being the best or only way — it’s just the way I am approaching it this month — the distractions which I have told myself are worth it in the end because somehow they make me a better writer.

In truth they only make me happier, perhaps that makes me a better writer, perhaps not.

What Time of Day

Any time. Sure, I prefer the early mornings, but I can’t remember the last time I was able to write in the early mornings. Perhaps 2012? Something like that I am sure. It’s still my preference, but writing knows no time.

I write when I can write, just as I write where I can write. Writing in the morning won’t do anything but cause you to write in the morning — instead of whenever else you were going to write anyways.

So just write.

Writing at a particular time of day doesn’t do or change anything for anyone. The only thing that matters is the act of writing itself. Find the time, set it aside, and just write.

The hardest part of writing for me is never trying to start, or finding the time to write — it’s the act of stopping.

Where Do I Get Ideas

At first coming up with what to write about was as much of a chore as the writing itself. As the writing started to flow so did the ideas. As you can see on my status page there is no shortage of ideas.

I’m usually hit with most ideas when I am left to let my mind wander. Whether I am showering, or using the toilet, my mind can wander. One of my favorite ways for working out an idea is to talk it out while I drive alone. Do I look a bit mad doing that? Maybe, but it also works.

My best ideas rarely come in direct response to one thing, but it’s also important to remember that every idea is in response to something. The idea for this post was in response to the email I get, and my wanting to easily help people who email with with questions about my writing.

The best thing I’ve ever done for my brain when I feel like I am out of ideas or inspiration, is to do something completely different. That can be the cliched walk, a hike, being in nature, playing with your kids, or mowing the lawn. It really doesn’t matter, but that mental break from anything which resembles writing usually hits a reset button on my brain. It opens me back up to input, and from there the output of ideas seems to be unrestricted once again.

I feel like it’s a wave. I start to get a rush of ideas and once I crash through those my mind is calm and done. I give it a rest and the cycle starts over again. That seems to about a three month cycle for me of ideas flooding in, writing, resting, and starting over again.

Worst Places to Find Inspiration and Ideas

People never ask this question, but they really should: where have my worst ideas for writing topics come from? Usually they are from my RSS feeds, or from other people in general.

Writing responses to other posts, or in aggregate from what I see in RSS feeds usually leads to trendy topics and not deeper thinking. They are usually written and thought of out of anger or frustration. They are never the posts that I look back on fondly, even if they drive loads of traffic.

Likewise, writing things that are suggested to me from other people usually leads to dull posts. My heart is not in it because I simply don’t care to talk about things I don’t want to talk about. Readers can see that, they can sense it, and they don’t like it.

Controlling that Urge to Write

As I mentioned above sometimes I feel as though I just have to write, or there is such a wave of ideas hitting me that all I want to do is write those posts. But I am busy, I am working, or playing with kids, or sleeping — usually it’s not a good time for me to write.

Instead I toss the idea down in OmniOutliner and add a few lines to it which encapsulates the idea that was in my head. The initial thought, or the clever line that I came up with.

I do anything and everything to get it out of me, and somewhere I trust that it won’t get lost. I used to feel the only way to vanquish these urges were to hit publish, but now I take just as much satisfaction in getting the idea down and committed to a system, as I once did with publishing.

It’s part of the reason my in progress drafts are over a dozen, whereas a couple years ago my in progress drafts were usually one.

Writing Process

This is the top question I get asked, and I took my damn sweet time getting to it in this post, because I really think it is the least helpful answer in these pages. However, since my goal is to reduce email, here’s the skinny on how my writing process works these days.

The Idea

Everything starts with an idea, a thought, I never sit down to write without one — I can’t. If I sit down to write and I simply don’t have a new idea, or an idea of what to write I usually try to pick up on another work in progress.

Since everything starts with an idea, capturing that idea is of utmost importance. I used to track all of my ideas with OmniFocus, using the task name as the post title (or a working version of it) and the notes field for a quick thought about the topic. I quickly fell off of doing this for a myriad of reasons — the top reason of which is that writing doesn’t feel like work to me.

Instead, I track my writing ideas in Ulysses and OmniOutliner. If I am on my Mac I have a Keyboard Maestro macro that I run to fill out details and automatically generate files in both OmniOutliner and Keyboard Maestro. If I’m not on my Mac I typically capture the idea in whichever app is most handy. On my iPhone and iPad that is OmniOutliner.

The next step with ideas is to codify and remember the idea itself. I do this with writing witty sounding lines of text about the idea. So maybe a product review will go something like: “It works, but man is it cumbersome.” That gives me a sense on what and where I am going. I may follow it up with a few 1-2 word points. I try to write just enough that my memory will be jogged, but not enough to make it feel like I should have just written the post, or worse, to feel like I am pigeoned holed into writing, or thinking, one thing. I want to allow myself the freedom to shift my thinking, or content if I so decide that is warranted.

The next part of my process is tracking where I am with everything. I need ways of seeing a high level overview of all my writing and where things are at, what my goals are, etc. I do this three ways (because I’m insane apparently).

  1. I track all of this on my status page, that was mostly created for me. But I don’t hide it. The word count, status, and due date are all there for me to see.
  2. I track hard publish deadlines in OmniFocus. If I need to post about something because it is going to launch on X date, I do that in OmniFocus. There is no other thing I trust for that.
  3. I also track status within Ulysses by using tags. The tags I use are: Outline, Idea, In Progress, Editing, Published, PAUSED. These are ways for me to sort the items in there to see what is where.

All of that exists so that I can more readily pick the type of article I want to work on. Perhaps I want to get something pushed out so I will look for something in editing, or something with a high word count that is maybe “close”.

The Outline

Ah, the outline. Most of my life I’ve hated outlining writing. It just seemed like a waste of time compared to, well, actually doing the writing. Long time readers know that this is reflective in my articles — they jump, and sometimes should be re-ordered a bit. In an attempt to fix that issue I started outlining about a year and a half ago. I now attempt to outline everything, and I think I end up with much stronger writing because of it.


I do hate it though. I mean it feels less spontaneous and more contrived. But I feel it makes my writing and points stronger, even if it whacks away at my nostalgia for just writing and publishing.

I tend to not let my outlines get too rigid. I use it at a very high level of 4-5 word lines with headings, trying to find the flow of the article, and what and when to say things.

For me it is all about main points and structure. I then take that outline, made in OmniOutliner, and dump the text directly into my working Ulysses document. I write above the outline and delete the lines I’ve addressed moving through the document.

This way I can always glance down the screen and see where I need to be headed to next, and never get lost in tangents, or head to a point I want to wait and address later.

The Writing

You would think is would be the meat of the post, but I really can’t offer advice here. I think the tried and true advice is the best: just keep writing, and write a lot. And read, read a lot too. That said, here’s the approach I take to writing.

As I mentioned above, I take the outline I have made for the post and drop it directly into Ulysses. From there I write on top of it, deleting lines as I “finish” writing about them.

Before that though, I try to set a deadline for myself. This can come in many forms:

  • Actual date I want to finish by
  • Amount of time I want to work for (Due app works great for this)
  • Where I want to be in the document
  • Word count

The options are limitless, but typically revolve around writing for a set amount of time — usually with a hard stop at some point. I wish that weren’t the case, but such is life. By setting a deadline I have a clear goal for that day, and I get the natural high associated with hitting that deadline — even if the deadline is to just toil away for an hour.

Ok so I get all of that down, and my goal set, now comes what I think is the hardest part. Knowing where you are starting and where you are going with each post. On a typical product review I like to start with why I selected a particular item and guide the reader to my final thoughts of good or bad on the product.

At the very least you can’t start writing without knowing where you are heading. Otherwise you will get lost and your words will stumble and stutter and contradict each other — you need that clear direction to have clear thought.

The Break

Try not to write everything all at once. If you can break up the post, but always re-read what you have written already before starting again — otherwise you may end up being too repetitive. I like to take posts and write them slowly these days.

They don’t accurately reflect thought. If you stop, read, and start again you will often start to revise your post in ways that make everything stronger. You will see the confusion because you will be confused about your old words.

Give your writing time to be forgotten, look at it again, and then fix it.

The Edit

Nothing is sacred in the edit. You cut anything and everything that even has a faint smell of being redundant, or not fitting. If it feels awkward, cut it out. If you later think you need it back, well rewrite it — you’ll probably come up with something better.

Ignore all word counts — it’s not about quantity here, it’s about clarity.

And by all means, change your mind. I often just decide to delete the entire article and start over. I’ve change my mind, or I’ve found a better narrative, and there’s nothing worth saving.

Find the best one or two lines in the post and ask yourself if you just put those in there because they are clever, or because they move the idea forward. Only one of those options should stand as acceptable to you.

Editing sucks.

Editing is hard.

Editing is essential.

Be sure to edit.

The Publish

Ok, you are editing and ready to publish. Now you need to stop and wait. Now go back and re-read and edit again, because it’s not ready yet.

Just remember, you’ll always miss at least one typo.

Now Drink

I’m dead fucking serious. Get a whiskey, coffee, Pepsi, water — just get something to drink and kick back for a moment. Publishing is scary and hard, but you did it and you can’t take it back now. Now’s not the time to worry.

So drink.

Because the next thing you have to do is start writing again, or fix a typo that someone catches.

Tools of the Trade

Ah yes, we have now reached the point that most of you have scrolled to first. The area where every person (myself included with posts like this from others) hopes to find that one or two tools that will take their writing up a notch.

It’s not here, but saying that is futile, and since my goal is reducing email about this, well let’s talk about the tools themselves.

I’d first like to point you to Matt Gemmell’s excellent post on Small Screen Productivity as it is a very good starting point on tools. Now, on to my tools. Everything here is either Mac or iOS based — I can’t help you with other systems.

Setting up Your Main System

My tools start with a basic organization of the virtual screens, called ‘Spaces’ on Mac OS X. I use these to segment my activities so that one isn’t distracting from the others.

Here’s my five spaces:

  1. Communication: Email, Twitter, Messages, Slack, etc…
  2. Play: games, or any other other things like Sketch
  3. Safari: Open with Spillio and MarsEdit for quick blogging and reading.
  4. Writing: Usually just OmniOutliner and Ulysses can be found here.
  5. Other: I like to keep one blank space as a zone I can use to quickly work on project based tasks. A new Ulysses window open with a Safari window so that I can work between the two quickly for a short-term project. Or things of that nature.

I let Apple arrange these spaces for me, and I don’t pay much attention to them.

Once I get spaces setup I like to set up a consistent look and feel to all of my writing interfaces: be that Mail, or Ulysses and everything in between.

I use only two fonts:

  • Chronicle for reading
  • Nitti Light for writing

I chose Chronicle so that my proof reading matches the display font on my website, and Nitti because I absolutely love it for writing — it feels perfect to me.

Next I focus on color schemes. I prefer to use two color themes when and where possible: Solarized light, and Writer Pro’s dark theme (even though I don’t use that app). Both come and go in usage, but I would say I edit in Solarized light and write in the dark theme.

That’s the gist of my entire base setup. From there it is all about the individual tools.


I will preface this with saying that the most important things about the software you use to write is:

  1. It must delight you.
  2. You must know it inside and out.

If you can find and do both of those things, then you are golden.

For the actual act of writing I use Ulysses. I prefer it on the iPad, but certainly use it mostly on the Mac.

For notes I oscillate between Vesper and OmniOutliner, with the latter also being my only outlining tool that I use. I’ve recently began playing with Apple’s revised Notes app in OS X 10.11 and iOS 9.

To aid with most things I do I use a launcher, in LaunchBar — though Alfred and Spotlight can be made to handle these tasks as well. I also leverage TextExpander for repetitive names, odd capitalizations and general typos. Keyboard Maestro is a huge favorite of mine for automating tasks — within the context of writing that is mostly for creating links and title casing headings.

Outside of those I use some AppleScripts, fullscreen modes, and Automator to round out the “power tools” section.


I’ve mentioned a few times here that I prefer writing on my iPad, or in fullscreen mode on my Mac. The reasoning there is that I much prefer to not be distracted by anything such as the menubar, background, or well anything else. It allows me to get lost in my words and because of that it is how I always write.

It also makes my Mac feel more like iOS — which when it comes to writing is a very good thing. This is all about focus, so if you don’t struggle for focus with a small window, than that is fine too.

I do all my editing in a smaller window mode because I am often grabbing pictures to add, or simply finding links on the web and a smaller window is easier for that.

The Sum of What I Know

Which isn’t much, but you didn’t come here expecting the foremost expert on writing, you came here to find out how I write. The gist of which is by using Ulysses and a lot of honesty.

I write for my own sake and no one else’s. That’s the key to finding motivation for writing: you do it for yourself.

If I had said that up front you would have thought I was hiding a secret tool, but now I hope you see there is no secret tool.

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