Writing Tools & Tips – Jessie Kwak

[Infographic] Get Unstuck! How to deal with writer’s block.

Post published:August 5, 2022

A quick note: I wrote this infographic to go with my presentation at the Willamette Writers Conference this weekend. If you’re attending, I’ll be talking about Joyful Productivity for Writers at 9am on Saturday (in person) and 8am Sunday (virtually). I can’t wait to see you there!

A lot of professional writers say they don’t believe in writer’s block — but I totally do. I’ve been there, staring at the computer screen, knowing I should be writing but feeling totally, completely stuck.

However, as a professional writer, I’ve also had to learn tricks for pushing past that writer’s block in order to get those words flowing again. After all, when you’re up against a deadline you don’t have (much) time to wait for the muse to grace you with her presence.

Here are 15 quick tried-and-true ways to get yourself unstuck and back in the groove with your writing.

(Infographic text copied below for accessibility).

1. Interrogate why you’re stuck

Every trick in the book won’t help get you writing if you are stuck on something bigger than not knowing a plot point. Free write to tease out the problem. Are you afraid to write something too true, or too close to you? Have you grown out of this project? Are you writing the wrong thing? This can be a scary exercise, but it’s better than continuing to work on the wrong project.

2. Change your environment

Switch things up by writing from a new location. Even if going to the usual favorites (coffee shop, bar, or library) is not in the cards right now, try moving to a place you don’t normally write in the house, or even take a drive somewhere with a good view and sit in your car.

3. Go for a walk

Getting up and moving can help break you out of your rut. Go for a thirty-minute walk around your neighborhood—you can either let your mind wander, or go with the intention of mulling over whatever specific thing you’re stuck on.

4. Go for a dictation walk

Take your phone on your walk, and record yourself thinking through whatever issue you may be having. Use a program like Dragon Dictation, Just Press Record, or Otter.ai to transcribe your thoughts afterward.

5. Remember your “why”

What was it about this project that you are most excited about? If you’ve been stuck for more than a few sessions, this could be a good way to help you find momentum again. Free write on what excited you most about your project initially, and what you’re most passionate about now.

6. Try writing gibberish

Try writing deliberately badly. Set a timer for 10 minutes and force yourself to write total, complete gibberish. This will help you get out of your head so you can get back to writing real words.

7. Set a timer

This is one of my favorite motivational methods. Set a timer for 25 minutes and tell yourself that’s as long as you have to work on the project. Once the timer is up, you can get up and do whatever else you want to. Chances are, though, once the timer goes off you’ll be in the groove.

8. Writing sprints with a friend

Meet up with a friend in person, or set up a video call to do some joint writing sprints. A good format is 25 minutes on, 10 minutes to chat, for as many cycles as you’d like. You could also join an online write-in with other authors for accountability.

9. Create a “swipe file”

Start a swipe file of things related to your work that inspire you. It could be passages from a favorite author, short movie clips, a soundtrack of inspirational music. When you’re feeling stuck, spend ten minutes with your swipe file to get inspired.

10. Skip ahead

Are you stuck in one location of your story? Try skipping ahead. There is no rule that says you have to write linearly. Plus, if you’re stuck because you’re bored of a scene, you may find the scene isn’t necessary, and your readers would be bored by it, too.

11. Get rid of distractions

Use an app to block your access to the Internet, write on a device that isn’t connected, or turn on your noise canceling headphones. It could be less that you’re stuck, and more that you’re letting yourself get distracted.

12. Create a border crossing ritual

When I put in my noise canceling headphones and turn on the sound of a thunderstorm, my brain switches into writing mode like a Pavlovian response. Find your own combination, whether it’s a white noise app, a special “writing time only” tea blend, lighting a ritualistic candle, or something else.

13. Write in a different medium

Our brains work differently depending on what are using, which is why brainstorming with pencil and a spiral-bound notebook can be so freeing if you’re stuck in the more formal writing mode of your fingers on your keyboard. Shut off your computer and write longhand in a notebook, try dictating, use crayons—whatever will make you feel a new spark of creativity.

14. Box yourself in

Try giving yourself limitations to get the creative juices flowing. Try using a writing prompt, telling yourself you won’t use words with the letter L, or whatever parameters you can think of to force yourself to be more creative and playful about your writing.

15. Check your expectations

Do you have unrealistic expectations about how fast you are working? How many words you’re writing in a day? The quality of your first draft? Identify those, acknowledge them, and then set them aside to give yourself space to write in your own way.

Jessie and the Dictator: an Update

Post published:June 1, 2016

Since I wrote my last post on using Dragon Dictation for writing, several of my friends and internet acquaintances have jumped on board with the software. More and more people are seeing dictation as a way to live a healthier, more productive writerly life.

It can still be a pain in the butt, though, as I outlined in my last post.

I’ve been using dictation more and more as a tool in both my fiction and in my freelance work over the last six months. Despite my initial frustrations and the steep learning curve, I’m starting to be quite happy with the results.

If you’re just starting out and as frustrated as I was, take heart. There’s hope!

Here’s what I’ve learned so far:

Fiction

When I first started dictating, I had a tough time making it work for fiction. I think in part by typing, and it was awkward to force my thoughts to flow as I spoke them. I could puzzle out plot problems, but I couldn’t draft a scene.

In the last few weeks, though, I’ve actually switched to where I’m dictating my first drafts more often than typing them. One reason for this is that I’m feeling easily distracted these days. Even when I turn on Freedom and turn off my phone, I still have a hard time sitting down and doing the work.

When that work is drafting a new scene, I’ve found the fastest way to get words on the screen is to take myself on a distraction-free walk and just talk it out.

Originally, I felt like the first draft quality of a dictated draft was pretty terrible. But as I’ve gotten more accustomed to speaking my scenes instead of typing them, the quality has improved drastically. I’m now really happy with the scenes, and they require only a small amount of editing.

I’ve also gotten waaaay better at writing a scene from scratch, imagining it as I go rather than having to dictate a scene where I already know what happens.

(I almost always outline my books, but at the scene level I often feel like I’m wandering in the dark. Outlining will definitely be a topic of another blog post.)

Freelancing

While dictating fiction turns out to be a good way to get away from my desk for a while, when writing for clients I’m normally still tethered to my computer as I dictate. That’s because I need to have my research, interviews, and reference materials in front of me – unless I’m dictating an opinion-based blog post or something that I can fabricate out of the information that’s already in my head.

This was already going well in the last post, so I’ll just say it’s continuing to be a productive way to write non-fiction for me.

The software

Some of the frustrations that I had using Dragon Dictation came from my own quirks, and those are mostly all ironed out.

Mostly.

Here’s a few tricks I’ve learned along the way that will hopefully make the process easier for you, too.

“New Line” vs “New File”

For the longest time I’ve had a problem where Dragon would open a new file about 30% of the time I said “New Line”. It would drive me batty, but I finally realized just yesterday that you can disable built in commands.

Just go to Manage Commands in the menu, search for the command you hate, and click the box that says “Active.”

Hopefully that will solve my “new file” problem.

The right microphone increases accuracy

I mentioned in my last post that I was going to buy a new headset and see if that helps. I ended up getting the Andrea NC-181VM USB On-Ear Monaural Computer Headset, and that helps tremendously. According to the internet, the USB connection provides way better accuracy, and the Andrea NC-181VM seemed to offer the best quality for the cash. (It’s $32 on Amazon.) It’s relatively comfortable – even while I’m wearing my glasses – and seems to do a good job of recognizing my voice.

Plus, it makes me look extremely professional.

Jessie wearing headphones — How may I take your order?

Quirky capitalization and punctuation

I often edit as I’m going along, if I’m standing in front of my computer. For that reason, where the cursor is on the screen doesn’t always correlate to where Dragon thinks the cursor is.

It took me forever to realize this.

For example, if you tell Dragon to correct a word and then manually move the cursor back to the end of the line, Dragon still thinks it’s back in the middle of the sentence. Therefore, if you say the word “period”, Dragon will add a period, then automatically attempt to capitalize the first letter of the word it thinks is still to the right of the cursor. If you notice this happening, simply commands Dragon to “go to end.”

Rampant running backwards

This still happens from time to time if I try to correct a word, especially once the document becomes large and cumbersome. If any of you know how to stop this, let me know. It makes me crazy.

It’s worth taking the plunge

Overall, Dragon has really been a worthwhile investment for me, both in terms of getting myself up and moving, and also in how productive am able to be when I’m writing. It still has its quirks, but it’s definitely worth it for me.

My biggest takeaway over the past few months is that it’s worth it to make the investment in a good microphone, and to take the time to get up the learning curve. You’ll be grateful you did.

Jessie and the Dictator—Increasing Productivity with Dragon Dictation

Post published:March 2, 2016

About four months ago I finally bit the bullet and threw down the $150 for a copy of Dragon Dictation by Nuance.

It seemed like every writing podcast I listened to was extolling the virtues of using dictation software.

I was going to write 5,000 words an hour.
I was going to be 1000% more productive.
I would never have wrist pain again.
I was going to lose weight, and probably live longer.

It sounds like a lot to ask from a speech-to-text program, and if you’re anything like me, you’re probably as skeptical as I was as I typed in my credit card information. Would using Dragon Dictation really cause a magical unicorn to appear in my office and put rainbows in my coffee every morning?

(No. The answer to that is no. Sorry.)

Well, I’ve been using Dragon fairly regularly since I bought it – both for my freelance writing and for fiction – and I have some thoughts to share.

First up, dictation is pretty rad. But it has its challenges.

All the things that people say about dictation are fairly true. It does make you more productive, and reduces the physical strain of typing. You can use it while you’re out on walks. I’ve dictated blog posts and scenes from my novel while cooking dinner.

There’s also quite a big learning curve, and sometimes Dragon becomes infested by gremlins that are incredibly frustrating.

(Gremlins, but no unicorns? Get your priorities straight, Nuance.)

Nonfiction vs. Fiction

Because I’m using dictation for both freelance copywriting and for fiction, I’m basically having two different experiences with it.

Nonfiction

When it comes to my freelance work, dictating is faster. I can definitely speak faster than I type and so long as the dictation software gets it right the first time, it saves me time. Because my freelance client work is mostly fairly analytical – I’m writing about things like adaptive learning software and sales CRM software – I’m finding it fairly easy just to gather my thoughts and say what I want to say.

My freelance clients are pretty specialized, so there’s always a bit of a learning curve for the Dragon dictation software to pick up new industry jargon and terms. I’ve found it’s pretty good, but when it comes to proper names – like my clients’ company names – I’ve had a hell of a time training it to type certain things. In that case, I just develop shorthand and then use the find and replace function during the editing process.

The other aspect that I’ve found dictation software to be helpful in is transcribing interviews. If you’ve ever tried to transcribe an interview and you’re not a pro at it, you know that it sucks. You spend a lot of time tabbing back and forth between your document and your audio file, rewinding, typing, rewinding, typing….

Previously, I had budgeted at least twice the amount of time as the interview itself in order to transcribe it. So that meant a 30 minute interview would take me an hour to transcribe.

Now, with the dictation software, I just put on my headphones, play the audio file, and speak along with the person that I’m interviewing. I still have to rewind from time to time, but it normally only takes me about five minutes longer then the interview itself. It’s become a huge timesaver.

Fiction

Using dictation with freelancing is been really great, but I’m not having is easy time using it for fiction. It slows me down in ways I, frankly, expected it to.

What I mean is this. Sometimes it seems like when I’m writing fiction, my best work pours straight out of my fingertips, bypassing my brain and thought process altogether. (You know what I mean, right?) When I’m dictating, I think a lot more about what I’m trying to say, and have a tough time getting into that creative fugue state.

In a recent podcast, Joanna Penn talks about her experience dictating the first draft of her latest novel. She’s just been getting started with Dragon, too, and I resonated with her observation that dictating produces a poorer quality first draft than she’s used to.

But I also think that learning to write fiction via dictation is just something that will take time. Some days it seems to work, and some days it doesn’t. I don’t think I’ll ever completely stop typing up first drafts, but I am committed to getting better at first drafting by dictation.

Why bother with dictation?

For me, dictation has two main benefits.

The first is that I can often the get first draft done faster then if I type it out – with my freelance work at least. I don’t have to wait for my typing skills to catch up with my thoughts – especially when I’m typing a lot of jargony technical words that I may end up getting my fingers twisted around. I haven’t found it to be a timesaver in my fiction yet, but in freelancing – and in blogging – it does save me time.

The second benefit is increased activity. I dictated the first draft of this blog post while out on a walk. I’d been staring at a computer all day long, and was starting to get what I call “screen sickness” – that slightly nauseous, glazed feeling when you’ve been staring at a screen too long.

In the middle of particularly busy days it can be really hard to get myself out and go for a walk. I’m already behind my schedule by an hour today, and I know I’m not going to check everything off the list – do I really have time to go wander around an hour?

(This is the subject for totally different blog post, but the answer is a resounding yes. If you want to live a healthy, happy life you don’t not have time to go for a walk.)

But, with dictation, I can take a walk without falling even farther behind. On a brisk stroll through my nearby neighborhood rose garden, I can get a fairly serviceable first draft blog post of 1500 words.

Yeah, I may sound a little odd as I’m walking by people speaking punctuation, but hey, it’s Portland. I could be on a unicycle playing bagpipes.

Here’s a devils advocate thought for a moment, though: sure, it’s good for my body to go walk around, but I’m really giving myself a break if I’m forcing my brain to continue composing first draft materials as I walk? Would I be better served by leaving my phone and headphones at home, and letting my mind wander aimlessly?

Maybe. But that’s a luxury for a week less busy.

It’s just not not just walks in the park speaking into a headset though. When I’m dictating straight into my computer, it gives me more freedom of motion, as well. If I set up my computer up on my standing desk (a.k.a. my dresser), and use a Bluetooth headset, then I’m not tethered in one spot through the tips of my fingers. Instead, I can paced back and forth, do squats, dance around, etc.

My dresser – my standing desk. — My super-sophisticated home office standing desk.

What equipment do you need?

Beyond the software, I haven’t bought any other fancy equipment – and my results have been pretty good. I’m considering purchasing a better headset that’s really designed for noise canceling, etc., because if I was able to improve the software’s accuracy even more, it would save me even more time. As it is, I think the software is about 90 to 95% accurate for me.

Right I’m using either those white Apple headphones that come with every Apple product, or one of those dorky Bluetooth headset by Jabra, which I bought for about $20. The plug-in headset seems to be a bit more accurate, and from my research it looks like you have to spend quite a bit on a Bluetooth headset for it to match the quality. I’ve tried just using my laptop’s internal speakers, as well, and I find that accuracy rates goes down.

Hey, wait. Doesn’t my Mac come with dictation software already?

Yeah, yeah it does. And although it’s fairly decent, it was frustrating enough to me that I decided to drop the money on Dragon Dictation.

And I’m happy I did.

The Mac’s native software doesn’t have as robust an ability to correct mistakes or navigate through your text. Also, it doesn’t learn in quite the same way that Dragon Dictation does. Dragon will take things that you commonly correct into account, and can be trained both by you speaking, and by feeding it chunks of text that you’ve written with all of your industry jargon, etc. in it.

Also, the ability to dictate things while I’m walking and have it translate audio file has been really helpful – that’s a feature Mac’s native dictation didn’t have.

Is dictation always super magical?

No. Sometimes Dragon makes me want to throw my laptop through the wall.

Sometimes I’ll say something totally innocuous, and because the software for some reason thought that I said “Capitalize Grand Canyon”, the cursor starts scrolling madly through my document trying to find the phrase Grand Canyon – which of course, is nowhere to be found.

I haven’t figured out a way to stop this in mid-run, which means that I just have to wait it out – extremely frustrating if I’m in the middle of Deep Important Thoughts and the document is large. With Scrivener, I can just close out of the program and restart it. In Pages, however, you’re screwed until the curser gets all the way to wherever it’s going.

Nuance’s support is pretty non-existent, too. I’ve sent them a few support tickets when I had problems, and I’ve never once gotten a response. Googling solutions to specific problems normally revealed other people asking the same questions in forums – usually to be told that there is no solution to that problem. The software is constantly being updated, though, and it sounds like Dragon is getting better with every iteration.

Is dictation for you?

I don’t know. I can’t answer that for you. And, of course, purchasing Dragon is a big chunk of cash to plop down. If you’re curious to try dictation out and you have a Mac, you can always experiment with the native dictation program. Here’s how to set it up.

(Sorry, I don’t know anything about PCs.)

You might, like me, get addicted and want to pay for something better. Or you might figure it’s not for you.

Either way, Dragon offers a 30-day money back deal, so you can always give it a shot and see what you think.

Have you used dictation software? What did you think? I’d love to hear about your experiences in the comments.

(*Disclaimer: Nuance didn’t give me one red cent to write about this – I’m just sharing my personal experiences.)