LISTEN: Making the Switch from tech Writing to Fiction

Let’s take a slight diversion for the holiday season and do a mashup of career and hobby! I’m joined by Thomas Henson (@henson_tm), and we’re talking about making the jump from being a tech writer to a fiction writer. And, if you’re looking at becoming a tech writer, there’s some useful bonus advice there, too!

Writing Workshop Conclusion: Review Your Piece

Time for part 5, our final installment! If you’re not familiar with this workshop, read the overview first. In this part, you’re going to review what you’ve written before you unleash it on the world.

I always wait a day or two before I re-read a piece; it lets me get into a different frame of mind so I can do a “fresh” read. I’ll sometimes catch some typos (although I’m admittedly terrible at doing so, usually), but more often I’ll run across an awkward phrase, or a sentence that doesn’t scan like I wanted it to, or something substantive like that.

I start by taking my original bullet list (from Part 2) and making sure I’ve hit all those points. If I didn’t, I revise.

I don’t do this as much now, since I’ve got 19-odd years of experience, but especially for short pieces I used to read them aloud. If something sounded stilted, or “off” somehow, I’d rewrite it. I don’t want my writing to sound formal or cold or standoffish; I want it to sound like me. Reading it aloud is the best way to see if it does that.

If there’s to be a formal edit of my piece, this is where I’d turn it into the editor. If not… it’s off to publishing.


Take a look at what you wrote in the last piece, with the above advice in mind. Do a revision pass or two, but leave it there: don’t get into an endless cycle of modifications. A published piece is useful; one in and endless loop of rewrites isn’t.


Hopefully, this little workshop has illustrated the process I use myself, and offered you a tip or two that you’ll find useful.

I’m super-biased toward the written word. While I acknowledge that it’s not a perfect form of communication, it’s one that’s served humanity better, and for longer, than anything else. I don’t know if we’ll be able to watch today’s digital videos a hundred years from now, but I’m betting we’ll still be able to read.

With that in mind, I hope you can find something to write about, and that you do it. Eventually (trust me), if you do it enough, you will be amazing at it (assuming you’re not already), and it’ll start to be a habit that you don’t want to break.

Writing Workshop Part 4: the Writing

Time for part 4! If you’re not familiar with this workshop, read the overview first. In this part, it’s time to write your piece.

Largely due to my detailed and aggressive outlines, writing has always been a little easy for me. I mean, if you’ve got an outline with 3rd- and 4th-level headings, you’re only writing a few paragraphs for each heading, in most cases. So “writer’s block” tends to not be a thing for me.

I try to write in a casual voice. College “technical writing” classes, I swear, ruin people. The best compliments I get are the ones where people say, “I’ve seen you speak, and when I read your book or an article, I can hear your voice in my head.” That’s amazing to hear, and it’s absolutely my goal.

Avoid passive voice:

The computer is now powered up.

It’s passive because we don’t actually know who did the action to what. Go with active voice instead:

You turned on the computer.

There’s a person here: you. It’s fine to use I and you in your writing; only use we if you’re referring to both yourself and the reader.

We see here that the car is in drive mode.


You can see that the car is in drive mode.

Much better.

For each outline heading, try to write one paragraph that makes the main point for that heading – and there should generally only be one point. An additional 2-3 paragraphs can go into more detail, explain supporting concepts, outline variations, and so on. But you should be able to see how each subsequent paragraph supports the first one. Someone who only reads the first paragraph of each heading should still get the basic gist, even if they don’t get the full story.

For God’s sake, stop press <spacebar> twice after periods. Your high school typing teacher is probably dead by now. We have proportional fonts now, not IBM Selectrics.

It’s also fine to not use your outline headings in your piece. I’m not doing so in this piece. This is short enough that a run-on narrative works. But I still used the outline to decide what order to use when I covered things.


It’s go-time! Take your outline and write a piece!

Writing Workshop Part 3: the Outline

Time for part 3! If you’re not familiar with this workshop, read the overview first. In this part, we’re going to turn your bullet list from Part 2 into a proper outline.

Once I have my list of “things I have to cover” in bullet-list form, I’m ready to create an outline.

I am serious about outlines. I do not regard them as a waste of time; indeed, one of the reasons I can be such a prolific writer is mainly because I outline so aggressively.

Take this “Writing Workshop” series. My original bullet list looked something like this:

  • Define your reader – start and end
  • Decide what you’re going to need to cover
  • Put things in order
  • Write to each outline heading
  • Double-check the checklist and revise
  • Reader is the “hero”
  • SLEEP ON THE OUTLINE before you write
  • Read aloud: does it sound like you?
  • One major point per ‘graf

Something like that. That’s not sequenced very well. The first five are in more or less the right order, but the idea of the “reader is the hero” is something I want to cover up front, because it plays into defining your starting and ending points for a piece.

The outline is where I can start to sequence this bullet list. I have some semi-firm rules I use for sequencing:

  • Do not cover a concept until you’re ready to put it into action. I abhor writing that expects me to memorize a bunch of arbitrary stuff before I even know why I care about it.
  • Similarly, do not go into a history lesson on something unless everything you’re covering is directly relevant to understanding whatever it is you’re writing about. If I want to write about gun control in the US, then at some point I need to explain why we have the 2nd amendment in the first place, but I don’t necessarily need to do that up front. I need to do it in a place where it will have maximum relevancy to the topic.
  • Do not foreshadow. I hate pieces that allude to something, and then say, “we’ll cover that later.” Now, this is a rule with a lot of variables. For example, if you sit me down in a car and start explaining how the brake works (which makes more sense than covering how the gas works s your first step), I might well inquire about the other pedal. It’s fine to say, “keep off that for now, we’ll get to it.” What’s not fine is to introduce the emergency brake, and then say, “oh, and there’s this cool thing called drifting – I’ll show you that later.” You’ve just distracted me and now I’m anxious.

If you look at Learn Windows PowerShell in a Month of Lunches, possibly the bestselling book I’ve ever written, you’ll see that each chapter delicately builds on what came before. Chapters don’t foreshadow things that are yet to come. In reading a chapter, you need only what was in the chapters before that in order to “keep up.” That sequencing, for a ~300 page book, took years to get right, but it’s why the book has been so successful.

So I might wind up with an outline like this:

  1. Define your reader – start and end
    1. Reader is the “hero”
    2. Who is your reader?
    3. Who will they be?
  2. Decide what you’re going to need to cover
    1. Simplest path between who your reader is, and who you want them to be
    2. Don’t worry a lot about sequence, but sequence if it’s obvious
  3. Put things in order
    1. Importance of sequence
    2. Outline sub-heads should be coverable in 2-4 paragraphs; if not, break it down to a further set of sub-heads
    3. SLEEP ON THE OUTLINE before you write
  4. Write to each outline heading
    1. One major point per ‘graf
    2. Write in a natural voice
  5. Double-check the checklist and revise
    1. Does the sequence feel smooth?
    2. Did you create any tangents?
    3. Read aloud: does it sound like you?

As you look at your outline, you should be able to think, “yeah, each of these sub-headings could be covered in 2-4 paragraphs.” If you can’t, then you need to break it down even further, with an additional (level 3) layer of sub-heads. I’ll go as far as 4 levels in an outline for a large piece. Because look: this is where all the work is. If you’ve got a detailed outline, writing 2-4 paragraphs for each heading is pretty easy. The piece starts to write itself, once you’ve got a clean, detailed outline.

Once you feel pretty comfortable with the outline, figure out which bit your’e going to write the next day. For a short piece, maybe that’s the whole thing. Before you go to bed, review the outline for what you plan to write the next day, and then go to sleep. Let your brain work on it overnight, and you’ll find that you’re more prepared to wake up and write about it, with less pain, in the morning.


As you might expect, you need to turn your bullet list from the previous assignment into an outline, using the tips I’ve shared here. Again, I’m happy to review and offer feedback until the end of 2019, if you’d like to post your outline’s URL here.

Why my newest book is such a big deal for me personally

On January 1st, 2020, I’ll be launching Be the Master, 4th Edition. Some outlets already have the book available for sale, but for me the 1st is the “official” launch date. This book is a big deal for me, and I’ll share why:

I started Be the Master in 2017, and have produced a new edition every year.

The first edition was really all about the core message, “help other people.” The book grew out of this blog post, which posited that wherever you are in life, at least a small number of people helped you get there by offering you knowledge, skills, and experience, often at no cost to you. I suggested that you owe it to them to pay it forward, drop your Imposter Syndrome, and start helping others the way you were helped.

In speaking with people who read the first edition, the biggest push-back I got was, “I’d love to, but I don’t have time, and I need to focus on my own career.” So the 2nd Edition expanded the message to include “Achieve Success.” I wanted to make the point that you can be successful, but that you need to develop a methodology for doing so.

The next push-back was, in hindsight, predictable: “but how do I achieve success? What is success? And what about my personal life – isn’t that important, too?” Yes. And so the 3rd Edition moved on to discuss “Defining Your Success,” with an increased emphasis on the 2nd Edition’s push to “Define Your Self” as well.

Both the 2nd and 3rd Editions were accompanied by a workbook I call “The Grind,” which is a formalization of the journals I’ve kept for myself for the past decade or so. These journals are how I keep myself focused on who I am and what I need to success. They’re how I know when I have succeeded, so I can stop trying, and instead start focusing more effort on other people.

With the 3rd Edition, I started doing online and live workshops, and really sitting down and helping people, hands-on, work through these ideas for themselves. And for dozens of people, it worked. I’ve met people who are delighted they could “exit the rat race,” actually appreciate what success meant to them, and start giving back to the communities that have supported them.

There was still something missing, though, and it took about a year of reflection to figure it out:

I’d gotten the message backwards.

I believe that your life, and the people you’ve chosen to be in it with you, are the most important thing there is. Any success you achieve should solely be to support that life. You work to live, in other words, rather than living to work.

And so that’s where the 4th Edition – about a 30% rewrite, with the remaining 40% reorganized and edited pretty heavily – comes from. I truly believe that, if you read the book and take the time to understand the message, it can make a difference. I truly believe that if you do The Grind, however silly it seems at first, it will work. I know, because I’ve now got hundreds of people who’ve extended their trust to me, gone through with it, and come out better-off.

In many cases, as one reader said, “I think I went in expecting answers, but what I really learned was which questions to be asking, and I realize that’s more important.”

Be the Master is one of the projects I’m proudest of seeing through this far, and I feel the 4th edition is where the book can now sit for several years.

As part of the 4th edition launch on 1-January, everyone who’s signed up for the mailing list on (just scroll to the bottom of the page to sign up) will receive a huge list of special offers, including:

  • A free copy of the book in ebook form
  • A copy of the book in hardcover form, using a just-for-this-event “vintage” cover design
  • Access to a $99 online workshop in February
  • An opportunity to support the development of an audiobook
  • …and more.

I hope you’ll take advantage. If you’ve gotten a past copy of Be the Master and never quite got through it, I hope you’ll consider making a New Year’s resolution to get the 4th edition, dig in, and give it a shot.

Thanks for all your support.

Writing Workshop Part 2: List Your Points

Time for part 2! If you’re not familiar with this workshop, read the overview first. In this part, we’re going to look at making a list of points that you intend to make in your writing.

The toughest thing about writing is deciding what you will actually write about. It’s easy enough to set a starting point and end goal, as I write about in the previous Part of this workshop, but actually figuring out what goes between them can be hard.

I like to do this by brainstorming a list of bullet points that I need to hit on. As much as possible, I’ll try to put these in order.

I want to emphasize here that I personally do not value mind-maps. Maybe those work well for larger pieces; I don’t know. I’ve not run across a lot of successful writers who create productively from mind-maps. If they work for you, go for it, but remember something: while they can be good for endlessly capturing ideas and the relationships between them, mind-maps are horrible at evolving a linear sequence of ideas that build on each other. I see so many people spin and spin, growing ever-larger mind-maps, who come no closer to a cogent, sequential narrative after all that time.

Take this “Ask Me Anything” article on US Supreme Court Justice appointment. I knew when I set out that I wanted to make sure I made a few specific points:

  • Justices need to be impartial, but no human is apolitical.
  • What we say about our system to schoolchildren doesn’t necessarily reflect the complex reality of it.
  • The Constitution leaves a lot of blank spaces.
  • The Constitution is mainly a list of powers reserved for the Federal government, and everything else devolves to the States.

And so on. Those things aren’t necessarily in order, but they’re necessary to answer the question I was asked. As a second pass, I’ll try to order those in some sensible sequence. So I’ll rearrange the bullets until I feel they’re starting to form a narrative.

This bullet list is critical to me, because it serves as a literal checklist. When I’m done, I want to make sure I’ve covered each point. And yeah, sometimes I’ll go back and decide a bullet didn’t need to be covered, and that maybe I was being overly ambitious. It’s fine to modify as you go – just be wary of “scope creep,” and adding more than you need to cover to accomplish the goal of the piece.

After I get my bullet list done, I really triage it. Take this piece on DACA, for example. One of my goals, at the outset of the article, was to be “unbiased.” But as I started making my bullet list, I found myself with items like this:

  • Point to examples of the grief the DACA uncertainty causes.
  • Explain what Executive Orders are.
  • Explain discretionary enforcement.
  • Kids shouldn’t be punished for what their parents do.

As you can see, a couple of those bullets are contrary to my stated goal – they’re my opinions, and I didn’t set out to write an opinion piece. So during triage, I removed those. I’ll usually do triage a day, or even a few days, after I make the initial list. That gives me a cooling-off period, and lets me come back to the list with a fresh set of eyes.


Taking the topic you’ve decided to write about, and your “start” and “end” points (from the Part 1 assignment), make your bullet list. Again, I’m open to reviewing and offering feedback prior to the end of 2019 if you post a link to your work as a comment here.

Writing Workshop, Part 1: Set the Scene

Time for part 1! If you’re not familiar with this workshop, read the overview first. In this part, we’re going to discuss the first thing I do anytime I start writing: set the scene.

Now, that’s not the same as “setting the scene” in a story, per se, but it’s close. For example, consider this article on impeachment in the USA. Right at the outset, I did two important things:

  • I stated who the article is for. That’s important, because it sets up some instant assumptions. Someone not from the US, for example, might not even be aware that we have two houses within our Federal legislature, and so my writing needs to take that into account.
  • I implicitly stated my goal. I want to explain what impeachment is, in a non-partisan fashion.

Any good bit of writing needs to put your reader in the center seat. The writing needs to be for and about them, not me. A lot of writers will tackle this bluntly and head-on, which is fine:

I’m going to teach you how to reinstall macOS on a computer where the operating system needs to be reset to the factory condition. I assume you know very little about installing macOS, but that you have a copy of the installation software on a USB drive that will attach to your computer.

That’s a pretty straightforward statement, but it can also be a bit “cold” for me. I might start with something like that in my planning process, but my actual prose might be a bit different:

Ever have a Mac that you need to sell or give to someone else? You’ll want to reset everything back to factory defaults, and make sure your own personal information is removed, right? But what if you’ve never done that before? So long as you have a copy of a macOS installer on a USB drive, the process is pretty straightforward. Let’s get started!

I’ve said the same thing, there, I’ve just done it in a bit more of a narrative style. In just one short paragraph, I’ve laid out the WIIFM: What’s In It For Me. I’ve let the reader know what’s expected of them, and what they’re going to get out of it. This isn’t about me – it’s about them.

And another thing: most of the time that I’m writing, I’m not writing about something that’s new to me. That is, I’m not experimenting, figuring stuff out, and writing about it. I’m usually writing about something I know well. There’s a very good reason for that.

Teaching someone something through writing is a linear, sequential process. As the writer, I pick where I start, where I go next, and where I finish. “Where I start” is determined by who my reader is at the outset, and “where I end” is determined by who I want them to be at the conclusion. Everything in between needs to present the shortest, smoothest path between those two points.

Learning and experimentation, however, are often non-sequential. I might try something, research a bit, try some more, and then realize I’ve screwed up and need to start over. I don’t want that to be the “narrative” a reader follows, because it would be confusing. So I need to write about things I already know and have done. That way, I’ve already charted out the smoothest path, and I’ve identified and eliminated the tangents I may have burned time on when I was learning.

Another point: don’t feel you can only write things that would impress other people. Most people who’ve worked with PowerShell for a while, for example, would tell you that Don Jones is a master of the shell. They’d be wrong. Very, very wrong, in fact. They see me that way because in most cases they learned the fundamentals of the shell from me, or my books, or my classes, or something. What they don’t know is that, past that entry-level and intermediate stuff, I’m nigh-useless. I’m really good at explaining what I do know, and there’s a lot of value in that, but there are plenty of people in the PowerShell world who far exceed my knowledge and skill, especially in more esoteric, advanced topics. So it’s fine to write about “basic stuff.” Someone out there will need it, and benefit from it.


This assignment is twofold. Remember, you’re welcome to post your work in a blog post, or in a Markdown doc in a GitHub public repo. If you post that URL as a comment to this article prior to the end of 2019, I’ll do my best to review it and offer feedback. Sorry, but I can’t commit to offering feedback after the end of 2019.

Part 1: Decide what you’re going to write about. Try to pick a topic you can do in about 1,000 words, which is roughly two pages in Word. That means you need to think small. And it doesn’t have to be technical: you might explain something about your government, for example, as I sometimes do.

Part 2: Decide who your reader is and who you want them to be. Writing of this nature is about making change, and in order to do that, you need to define your start and end points, so that your writing can cover the in-between. This might be as easy as, “someone who doesn’t know what a Home Owners’ Association is” and “someone who can explain what an HOA typically can and cannot do.”

Get to it! You’ve got a week!

Self-Paced Writing Workshop: Be a Better Writer, Blogger, Wordcrafter

After several reader requests, a great many discussions, and a good bit of thinking, de-constructing, and planning, I’m ready to launch a “self-paced writing workshop.” This will consist of a series of blog posts, right here, along with exercises you can do on your own. The goal?

To help you become the best writer/blogger/whatever you can be!

Now, some caveats:

I’m not going to assume you want to do technical writing, although this’ll work perfectly well if you do. I’ll try to provide both technical and non-technical examples as I go.

I’m not going to focus on the specifics of the language. That is, I won’t be trying too hard to exhibit perfect grammar, spelling, or punctuation. In professional writing, you tend to have an editor to help with those things, and I also don’t want to assume you’ll be writing in English, which is all I know. What I’ll cover should be applicable in any language.

If you’d like to play along, I suggest logging into your account (or creating one, if you don’t have one), and subscribing to this blog. That way, you can get an email notification each time a new post goes up (which will be roughly weekly, if you’d rather set a reminder to check back manually). You can always un-subscribe once the series is complete.

And a stern warning: like many topics, this will only work if you play along, which means actually doing the exercises. In fact, I’m happy to review as many as I can through the remainder of 2019. So I suggest that you set up a blog, if you don’t have one – ones are free, and you can take it down when we’re done, if you like. As you complete each exercise, post its URL as a comment to the corresponding article here, and I’ll go through them as best I can. Make sure your blog permits comments, because that’s where I’ll leave my feedback.

And now a request! If you’re a good reader, then I ask that you lurk in the comments on my articles. Grab the URLs as they’re posted, and go have a look. Offer your own feedback to the author. Be polite, be professional, and be constructive – meaning your feedback is actionable. This is how we can all help each other not only get better, but gain more confidence in our work. Confident people produce more, which benefits us all.

The initial articles I post won’t have you creating full blog posts. Oh, no. We’re going to go through the process. So your initial posts will be capturing thoughts, producing short outlines, and so on. Again, you’re welcome to take your blog down, or delete the articles, once you’re done, if you don’t want your “process” to be saved for all time.

Alternate way to participate: perform your work in a public GitHub repo, and post that URL instead when you’re soliciting feedback. Commenters (including me) will open an Issue with feedback. Commenters, please open one Issue for all of your feedback; don’t open one for each comment you make.

Sound good? I’ll see ya next week!