Writing Processes, Side Projects, and Time Sucks…Oh My!

Writing Processes, Side Projects, and Time Sucks…Oh My!

Update 2 (3/13/24): I’m constantly amazed at how things can both change and yet remain static over time. Since this was posted, with the below update, I’ve been caught up in layoffs, started freelancing, and built up two new web presences (this newsletter and a blog at my freelance site). Yet the basic premise, and importantly the three lessons, remain solid. Only minor tweaks were necessary to adjust timelines, etc.

Go figure.

Update (mid-2023-ish): I started this draft as something to end ’22 with, and it ended up taking on a life of its own. Then my company had what’s euphemistically called a RIF, or Reduction In Force, and my team went from 6 to 2—me and the social media guy are the only ones left standing. So instead of a year-end wrap-up, I turned it into more of a ‘lessons learned’ kind of thing, you can stay tuned for more updates on how my workflow has been altered, but it’s looking like I’ll be shifting from Senior Writer to more of a ‘managing editor’ and relying on a more contributor-based model for content.

It’s been nearly seven years since I jumped from IT into writing professionally, and two years since I landed my last full-time position, so I thought I’d take a minute to jot down some of the things I’ve learned on this journey.

And now that I’m also making headway on the manuscript for what I hope will be my first novel, the differences I’ve noticed between paid writing (in my case, primarily for tech startups) and personal writing have become clear enough, ironically, to write about.

My last day job was as Senior Writer on the Brand Content team. That means I mostly created newsletters, e-guides, blog posts, and so-called “thought leadership” pieces for the C-suite to post on LinkedIn.

I despise that phrase, but that’s a topic for my therapist.

Working with an editor/manager who came to startup land after more than a decade in journalism means we had a slightly different take on what marketing content should look, feel, and read like. There’s more rigor on my current team than I saw in my first 2 years writing for content farms. For my last couple of pieces, I would estimate I did 5:1 research/interviewing SMEs/outlining to writing.

And in the process learned more than I possibly could have in an MFA program.

The freelance work I’m doing now is similarly positioned between marketing writing, blogging, journalism, and thought leadership. It’s a crowded niche…

Contrast that to my novel. When I first started playing with the idea, I set out the same way I would with a long-form work paid piece—research, research, research. After 6 months or so, I had reams of notes, character studies, historical research on Seattle in the ’00s, etc…

What I didn’t have was a single word of the actual story.

Photo by Florian Klauer on Unsplash

And after another 6 months, same. Rinse and repeat for another year before it hit me that maybe this wasn’t the right process for me.

I can be a bit dim at times.

I turned my attention to figuring out if I could be what they call a ‘pantser,’ or someone who writes by the seat of their pants, letting the story grow organically as they write it. I wasn’t sure I could let the narrative guide how the story developed, but after this much time down the tubes, I was game to give it a shot.

In early September of 2022, I saw a post from someone who was getting ready for NaNoWriMo, National Novel Writing Month and something clicked. This was the kick in the ass I needed to get started. I spent September and October consolidating my previous 2 years of notes into what turned out to be less than 2,000 words of mostly broad plot points and character studies. Then I archived the rest. And on November 1, I wrote the first 1,667 words of my novel.

NaNoWriMo sets a word goal for the month at 50,000. That’s either a great start on a novel or a solid novella worth of words. For me, that word count continued for 2 weeks before I had another epiphany, writing for both a day job AND trying to keep up that much production before and/or after work wasn’t working.

It turns out that while I needed the external accountability the project brought, I didn’t need the external, and arbitrary, word count.

That’s enough of that ramble for today, let’s look at (a highly condensed and summarized version of) three main ideas that have coalesced over the last few years.

Writing processes vary by writer. Or by project. Or maybe by genre. Whatever, they vary.

Do I need to preface this with a “your mileage may vary” warning? No, cool.

When I start working on a paid piece, whether it’s going to be a quick blog, newsletter essay, E-Guide, or something in between—I do some research. First, I check to see what if anything our competitors have to say on the subject. The last thing I want to do is turn out an echo piece, right?

Then I compile my initial thoughts in a ‘notes’ document. Then, I sort those notes, adding more as I find it, into a rough outline. This outline only goes 2 steps deep, as it’s intended as something any stakeholders for the piece will receive and the other last thing I want is reams of notes on minutiae before I even start writing.

Once I have the green light, it’s go time, and the first thing to go is that rough outline. I bulk that thing up until it’s nearly the length of the finished piece. Why? Because now when I move each section into my draft, I can just rewrite it for flow and brand voice as it already contains the stats, quotes, and general ideas for each section of the final piece.

This final step may only take me an hour because I’ve already put anywhere from 5-10+ hours into the research and outlining stages.

Compare and contrast that with pantsing this novel.

I had less than 2,000 words of notes left after the great purge, consisting of vague character sketches, some locations I wanted to be sure to include (it’s set in Seattle, naturally), and a plot outline that was so vague a bystander likely wouldn’t be able to identify it as a novel outline at all. The first draft I completed late in 2023 was 65,000+ words!

Watching it develop, grow, and morph right before my eyes and under my fingers has been wild for this former IT guy.

Humans only have so much mental bandwidth to play with at any given time.

Have you ever reached the end of a day of sitting at your desk staring at a medium-sized screen and realized you didn’t have the energy left to get up and make it to your couch to stare at a slightly larger screen for a while?

That’s been pretty much every day since I started writing professionally. Add in the overload I feel when I have to be present in an office environment, and it’s a wonder I get even the simplest errands run.

That’s not to say I regret making the jump. On the contrary, I may be knackered beyond what seems reasonable, but I’m also more professionally fulfilled than I believe I have a right to be (I’m working with my therapist on that, imposter syndrome, and…some other stuff).

Given the above, how in the hell am I supposed to also make progress on a novel?

That’s a topic for, well probably another book I’m pretty sure someone else already wrote. For now, what worked for me was using my early morning for intense writing sessions, taking a tea break, and then signing in for work.

When I tried saving it for the end of the day, let’s just say it didn’t go well.

A smiling lego figure is wearing a chicken costume.
Sometimes, when I run out of mental capacity, I feel like a Lego dude dressed as a chicken. Photo by Nik on Unsplash

Context switching sucks.

I’m a big fan of the writing Cal Newport has been doing in recent years (and am super excited to jump into my just-received pre-order copy of his latest, Slow Productivity). In A World Without Email, he dives into the time-suck that he calls “The hyperactive hive mind.” For those of you who don’t wonk out over slow productivity or how to work when you’re inundated with Slack messages…Cal is a theoretical computer science professor at Georgetown who moonlights as a productivity writer/podcaster.

In short, as I’ll have more to say on much of this at a later time—context-switching sucks.


It sucks time, energy, and mental bandwidth. To the point where it can take as long as 20 minutes to bring your attention fully back to a task when you’re interrupted (if you must have a citation, I can find it…later).

I’ve experienced that, in fact, it’s been my daily grind for most of the time I’ve been writing full-time. Folks often underestimate how much focus it takes to turn out great writing.

Or code.

Or financial documents.

Anything that falls into the category of “the knowledge economy” takes focused attention to do, and even more of it to do well.

And when you’re being pulled away from that focus by Slack or email alerts, well it’s going to take you that much longer to get back into your groove and turn out the kind of work that you know you’re capable of.