Combining traditional time management with the day job and writing on the side is such an incredibly huge topic. Eight chapters and there’s still more to follow (I’m at 12K so far!).


Depending on who you read these days, some gurus recommend scheduling everything as the solution to managing everything. I think a lot of this is that if you let firefighting in and do busy work tasks, it’s amazingly easy to get a lot done, and yet nothing done.

If you’re in a state of overwhelm, it’s also easy to use busy work tasks as a way to procrastinate.

Probably the best description of this from the writing side is revision. You’re overwhelmed by the big project of a novel, so you circle back to tweak the words in the first chapter one more time. It appears productive, but you’re actually not finishing anything.

Scheduling is supposed to help with this, but it’s, like most time management tips, slapping a bandage on and never solving the problems underlying it. Scheduling is an attempt to corral all the stuff behind fences of electronic blocks.

But schedules have their uses.

Cal Newport advocates filling in all the slots on your calendar with generalized task planning. Like if you have to do administrative tasks, lump them together under a one hour slot named Admin Tasks.

I tried this in the days following the COVID-19 shutdown. It was probably the best time for me to do it because everything was so chaotic, but not in a normal way. I had to change directions rapidly, and it was sometimes easy to lose track of where I was.

Doing it led me to ask other questions. How did I handle it for the side hustle?

So I asked Cal Newport, and he brought up the question on his podcast (sorry, I don’t know which one it is anymore). He said to schedule it like everything else. Then later contradicted himself on another podcast.

But I’d asked because I felt like I need something, though I wasn’t sure what.

The Cal Newport time block self-edited itself. I found myself ignoring the schedule. It’s more natural for me to go with the flow than follow a strict structure.

The sequential structure felt a lot like outlining.

To me, if something is due on a specific date, it doesn’t matter down to the date and time when you do it. Finishing it and not being sloppy with it is the most important thing.

Filling every slot in treats me like I’m too stupid to know when I’m supposed to do stuff.

But I also recognize that I needed a little structure, or I’d miss completing important things.

Here, you also have to factor in that creatives think and work differently. Time management gurus don’t understand us.

They say they do, much like outliners say they can teach pantsers (not!). The gurus assume we need to see how they organize their day and magic will happen. All the problems will go away.

It creates different problems.

Unfortunately, the solution is stating that we’re not following the system correctly. That sounds a lot like when outliners tell us if we’re having trouble with the outline, we’re not doing it correctly.

That’s unhelpful and treats creatives like they’re broken.

The first solution is to ask different questions. Not how do you schedule everything, but how much do you need to schedule?

We’ll take the example of running and reviewing reports. Let’s suppose first that you have a report you have to review and make corrections, then turn it in by Friday. The normal way most people would do it is to run the report on Friday. They get interrupted and run the report later. Now they’re scrambling on their review, miss something, and email it.

And get an email back about the thing they missed that’s now an emergency. On Friday afternoon!

So put your creativity to work. What’s going to help your future self on Friday?

That’s the day winding down into the weekend. What can you do to prevent any chaos on Friday so you’re not taking it into the weekend?

So now you might look at what day early in the week would be the best timing to run the report. You might decide that if you run it on Monday, you’ll miss some issues that would develop during the week because other people are waiting until the last minute.

You add a slot on Wednesday, with the option of shifting days if the timing isn’t right. For me, I put an hour slot in the morning in Outlook, where it’s easy to see on the calendar. If I have to scroll, I’m probably going to miss it.

For titles, I just put exactly what it is: XYZ Report. None of the active verb nonsense. That’s a time management tip that treats me like I’m stupid.

But that report review is still taking a lot of time to do, especially with interruptions coming in. You want to make sure the review is done on Wednesday, not stretching out across the days, where it’s likely to be a victim of more interruptions.

What else can you do?

Back to your putting your brain to work. You realize there are two other reports you can run that identify the issues in different ways. At this point, your critical voice says (because it has to get its foot in), “They’re not required.”

But you put “ABC & DEF Reports” in a morning slot on Monday. Since these don’t have to be submitted to anyone, you can do fast scans for problems. It might be submitting a ticket to another office, asking a supervisor to approve a record or even just a quick fix to the record.

If you haven’t guessed, this is a form of cycling!

Cycling is a technique long-term professional writers use when they write. They write a scene, then cycle back that last five hundred words. They scan through it, add more detail, maybe add a sentence to clarify something. If they realize they need to add a sentence in Chapter 2 to connect with an event in Chapter 11, they move back in the story to do so, in the live first draft. It’s not revision, done after the fact to fix things. It just tidies up as you go along.

It looks like a lot of work and may be in the beginning if you’ve let things go. But this is something that builds on itself. After the first few rough rounds of it, you’ll find that it’s a lot easier to work through.

When I schedule these, I do them as a recurring task, set until the end of the year. That way, I’ll review what I’m doing and make any adjustments. The “hour” is meaningless, as is what time I have to do it. It’s there to make sure I do this task.

What is a must is doing it in the morning.

I used to run an agent pitch session at a writer’s conference. I watched how they did it and knew I could do better. The biggest problem was they went off their own schedule almost immediately. Once they did that, there was no hope of getting caught up.

This happens to everyone who allows other people’s “emergency by delegation” to take over their schedule. If you don’t get to this task until the afternoon, you risk not doing it all.

With the writer’s conference, I cracked the proverbial whip. I made sure they stayed on schedule in the morning. Sometimes delays crept in during the afternoon, but they didn’t impact the entire day.

When one agent arrived and discovered that his associate had quit, we suddenly had a huge problem. He said he would take on appointments for both of them. But I couldn’t allow this problem to cause the entire schedule to shift. So I told him to do what he needed to do, and we’d work around him. Then I ran the sessions as normal and talked to the writers who had to wait for the agent.

This is the core problem of scheduling every slot in a world driven by interruptions. It breaks easily. It’s naïve to expect that by simply filling in the blocks, you’ll be able to do everything.

It doesn’t matter if you start this task fifteen minutes later than scheduled because Joe Smith called with a question. It doesn’t matter if you run ABC report and don’t find any issues because you’ve been cycling. It doesn’t matter if you run ABC report and find a thorny issue that takes two hours to work through.

What does matter is that it gets done. I always get interrupted. Sometimes I’m grateful I got the one thing done.

Once I finish the task, I delete it from the calendar. I find that having every slot filled in nagged at my subconscious, even when everything was done.

Then I circle back to the task list in Outlook, where I dumped the emails and I work at clearing those out for the day. Clearing can include anything from replying to the email to pushing it to the next day (i.e., reading).

Is this a perfect system? No! I still have chaos erupt and get overwhelmed. Sometimes this seems to go in cycles and there will be a week where I’m glad to get to the end. But because of this system, it’s no longer a default every week.

It also helped me with balancing my energy. I focused on doing tasks that required mental focus in the morning, and easier ones as the day wound down. Essentially, I didn’t want a task to have me going at warp speed right before I shut down.

I was much happier with it because it felt like just enough structure to keep me grounded.

But on the writing hustle side? I still had some lessons to learn there, too! My creative voice is notorious for disliking being scheduled.

But I ran into a problem. After I finished a story, my average release time was two years!

So I wasn’t honoring the creative side and getting the stories out.

Writing administration was a challenge for me. I hated doing it because when I did it, my critical voice nagged at me for not writing. And when I wrote, critical voice nagged me for not doing the admin. Gibbs head slap, anyone?

The Smashwords/Draft to Digital merger was a wakeup call. I knew from my day job that if the data didn’t match (data being covers, blurbs, prices, and even versions), then it would be a mess. One of those emergencies that was entirely controllable.

Enter Dean Wesley Smith’s Motivational Mondays. These are worth the money if you can afford it. In one of them, he talked about the importance of scheduling administrative time to publish.

Before, my focus had been on trying to get writing done. I had recently completed the Great Challenge, a short story a week for a year. I started out with good intentions, publishing some of the early stories. But I didn’t have any kind of plan (I’m pantser! What else did you expect?).

As the challenge aged, it got harder. I dropped off publishing them as I neared the halfway point. The stories got moved into my short story folder…and then nothing.

According to Dean, that can mess up any streaks you’re trying to do. So I was lucky that didn’t happen. It was a wake-up call that I needed to pay attention to this.

He recommended scheduling the admin. Just pick a day or two each week and do that instead of writing.

Ah ha! I could do the same principle as what I was in my day job.

In this case, I put it on my calendar as an all day event, and included writing in the same way on the other days. I picked the two days based on both my schedules. Thursdays because I have a writing meeting in the evening. I know I’m not going to get to writing that, but I can do something on the admin side. Fridays for the second day because if there’s going to be chaos at my day job, it’s likely to be Friday.

It didn’t matter when I did any of it, only that it happened. This is where the time management books fail. They focus on getting your most creative tasks done first thing in the morning when your energy is best.

Except that we have day jobs at that time, so we’re making do with the time that’s available, not the best time.

With the anchor of “this day is for—” it gave my critical voice a job. It was comfortable keeping me on track.

The advantage also of having the writing on the schedule means it’s a commitment to yourself to do the writing. There are so many things that can have competing priorities that if writing isn’t made one, it gets shoved aside and suddenly months can go by. Remember Heinlein’s Rule:

You must write.