Michael Schechter's Writer Workflow

Editor's Note: Michael Schechter first caught may attention over at BetterMess.com with some clever ideas about OmniFocus. He writes smart things about productivity, writing and blogging, which are unlikely topics for me to follow. But Michael writes regularly and he writes well. He writes honestly about things he cares about or is trying to figure out. His articles are generally long reads that say something meaningful without preaching or selling something. I read his stuff everyday. I also follow him on Twitter because he continues to say funny, clever and nice things there too.

If you like, please provide a brief bio

I'm Michael Schechter, the sole blogger over at A Better Mess and one of the two "Mikes" on the 70Decibels Podcast, Mikes on Mics. I also work in our family's 65-year-old jewelry company and focus on the digital aspects of our business. I live in an insanely overpriced and cramped apartment in Brooklyn, NY along with my tolerant wife, two young girls and our dog.

Why did you start BetterMess.com

The truth here is that I'm a mess and I really, really want to get better. I benefit from thinking things through in writing and began publishing with the hope that both myself and others would benefit from a healthy mix of tips, tactics and self-deprecating honesty. The site started out as a personal blog on my personal domain MichaelSchechter.me. It went through several iterations, including being the 4,201,376th blog on social media and a highly unread life-streaming site (all of these god awful posts still live on the site for posterity). Over time, I found I really enjoyed the writing, but that I wasn't going to keep at it unless I honed in on a subject that really mattered to me. I shifted my focus to creativity and productivity, two areas that I'm interested in yet constantly struggle with.

How do you capture your ideas and research an article for your sites?

I have the memory of a goldfish, so quick capture is essential for me. Because of ADHD, I can lose track of things at an alarming rate, so developing a system around capturing ideas was essential. I started by trying to keep all of my ideas in a task manager (at the time I was using Things, but I've switched to OmniFocus nowadays), but this was clunky. After a marathon day of listening to the Mac Power Users podcast, I discovered the first of Merlin Mann's two workflow episodes and became a devout Simplenote and nvALT user for anything related to my writing. I useTextExpander snippets to name my files and capture a few lines to remind me of what I want to say when I have the time to write. The apps are synced with one another, so regardless of where I am, I can capture or expand on any of the ideas floating around in my brain.

As for the research side of things, my site tends to be well lived rather than well researched (read: my site is not very well researched). However, I do spend a good amount of my energy responding to the things I've read. This almost always comes from articles in Instapaper (which now lets me send text to Simplenote) or a podcast in Instacast (where I will open up a note in Simplenote and do my best to capture whatever thought I'm looking to respond to. I also appreciate well-turned phrases and capture these for future use or inspiration on a Tumblr blog.

How do you find inspiration and how do you keep track of your ideas?

The ideas I'm most excited by tend to hit me when I'm reading or listening to the work of others. Where many do their best thinking in solitude, I prefer to allow the words coming in to collide with whatever ideas have rolling in my head. In the past, this inspiration would leave just as quickly as it came, but thankfully my capture process in Simplenote on the iPhone or nvALT on either of my Macs has proven to be an effective bottle for storing my lightening. I don't use any folders here, but carefully name my text files for easy recall. I also use a very lightweight tagging system to remind me what is posted, ready for editing, working, abandoned or just waiting for expansion. That arsenal of ideas has proven to be an invaluable asset on the days when I go looking for inspiration only to find it's gone missing.

Can you provide an overview of your writing process?

I have two distinct processes, one for my blog posts and another for longer form projects like my monthly articles for a trade magazine in the jewelry industry.

Most of my blog posts are almost always written free form. The title or core idea will hit me and I will jump into Simplenote or nvALT to capture it. Sometimes momentum takes over and I write the piece on the spot (I find this happening more and more often on the subway); other times, I will go back to what I was doing and return to expand or eliminate the idea at a later date. The actual writing itself happens in Simplenote on the iPhone or in Byword on my Mac (with the files being stored in nvALT). Once I really dig into a post, I'll tag it as "Working", when I feel I've gotten it to the right point, I switch the tag over to "Edit". I struggle from what's known as "Chimp Grammar." As in, I possess the grammar skills of a chimp, so my exceedingly patient wife is kind enough to read things over. She's also more than generous when it comes to telling me when something I've written makes no sense. Even when I'm writing a geeky post, I try to keep it so a non-techie can understand, so she's proven to be an ideal test audience for me. If needed, I reset the tag to "Working" and try to find a better balance of geekiness and clarity.

My process for articles or my geekier posts is a bit more structured. I don't mind going down a rabbit hole on a blog post, but I can't afford a lack of clarity in an article. These posts will start as a mind map in iThoughts HD on my iPad or MindNode Pro on my MacBook Air. In the past I would send my map into Scrivener as an outline to write my piece (I did this by using OPML, it's a bit of workflow that I stole from David Sparks), but a recent change to iThoughts has me changing things up a bit. Everything I write, regardless of the app or the end use is written in Markdown. iThoughts now allows you to export your mind map into an outline in Markdown. I've been experimenting with putting that outline directly into Simplenote or Byword and bypassing Scrivener altogether. I don't think this change would work well for someone writing a book, but I've found it a worthwhile shift for 700-1500 word articles.

I tend to not like to let formatting get in the way of the writing, so regardless of which workflow I'm using, I save this for last. Once my wife gives me the thumbs up, I open her edited text file in Byword and use a combination of their native tools, some TextExpander snippets and some Keyboard Maestro Macros to add links, emphasis and structure to the piece.

While this likely sounds crazy, the process feels invisible to me and provides a framework for not only capturing, but executing on my ideas.

How long have you been doing it this way?

I really only started pulling this process together about a year and a half ago after listening to that Mac Power Users episode with Merlin. The bulk of this process has been in place for just about a year now.

What enhancements have you made?

Using markdown outlines in Byword for longer form writing has been the biggest change. At first I was worried about the inability to shuffle text around, but thankfully Brett Terpstra pointed out some rather useful keyboard shortcuts for manipulating text in Byword.

I'm also always looking for new TextExpander snippets or Keyboard Maestro macros to speed things up, but at this point I'm feeling happily married to my process.

Do you have a specific work environment or setup for researching and composing an article?

I have a full-time job, a patient wife and two young children, so I've had to learn to be nimble with my writing process. In fact, I wrote this on my iPhone on the way to work. We also live in a small apartment in Brooklyn (or at least it feels small once you've shoved two kids' worth of stuff in it) and have no steady workspace. It was these time and space restrictions that led me to seek out tools that could help me create meaningful work in whatever time or space I have. A lot of this has been inspired by Yuvi Zalkow's videos on writing when you're busy.

Does your workflow change based on the type of post?

At first, the type of piece (blog vs. article) drove the particular workflow I chose. As I grow more familiar with my process, I'm starting to find that it's less about how the piece is published and more about my intent. A thought I want to examine goes into the first, more freeform workflow and things I hope to explain clearly get mapped out.

What parts of your workflow are you looking to change or improve?

I'm getting to the point where I'm weary about changing things. I've spent a tremendous amount of time creating and tweaking my process, but I find that I'm starting to get to a point where the time spent making changes is equal to or less than the savings of any improvements. The one thing I'm hoping and actively begging Brett Terpstra to bring to Marked is the ability to identify the words I overuse as well as the frequent grammar mistakes I make. To some extent, I've shifted my focus away from tweaking my workflow and am focusing that attention on being a better writer in general. Sadly, the tools will only take me so far on that front...

What parts of your workflow are you least willing to change?

Once something works, I am stubborn about changing. I know myself and I can easily get lost in trying new tools. While I attempt to leave myself open to new innovation, I also try to stubbornly shut myself off to apps that boast new features. The subtle differences between apps like Byword and iA Writer aren't going to put a single extra word on the screen and an obsession with them is almost certain to guarantee that less words make it there.

Anything else you would like to share about your workflow?

The best advice I can give anyone who struggles to get their ideas out of their head and onto some sort of medium is to create a cohesive process. Take your strengths and weaknesses into account and make sure that your process factors in things like time restrictions or diverse writing environments. Experiment, but always protect the process once you create one that works for you. Knowing how you're going to get your work done allows you to take your focus off the process and enables you to focus on the work. This is especially essential for those of us who lack focus. There's no doubt that obsessing about your workflows is a form of procrastination, but not having a workflow is just as likely to lead you down the road of the undone. And know that no matter how many of these you workflow posts you read, your process will inevitably look different than anyone else's (no matter how much you steal from them).