My Favorite Time Management Tools for Freelance Writers

8 min. read

Photo by Green Chameleon on Unsplash

This past December marked my first full year as a freelance writer — a gig that turned out to be both easier and harder than I thought. After spending the first few months spinning my wheels and massively burning out, I realized that I was squandering my most valuable resource: time.

Instead of brilliant ideas, semi-rhetorical questions occupied my stream of consciousness. ("Should I build an invoice template? Did I follow up with that one person? Will I ever understand the self-employment tax?") Very little of it had to do with writing. If you call yourself a freelance writer, that's a problem.

When I finally got a few clients, whatever free time I had disappeared entirely. So much for the stock photo of a latte-sipping freelancer chilling on a Tuesday.

Luckily, time management problems no longer have to be resolved in a spreadsheet. Over weeks and months of searching for a better way to work, I slowly collected an arsenal of tools that helped me win back precious minutes from mundane tasks.

I decided to share some of them here, in case you, like me, are also trying to get more done in 2022.

Note that all of these tools (besides Rev Transcription) have a free version. Also, note that this is not a sponsored post.

Up first, my favorite scheduling tool.

Calendly (free version)

I heard about Calendly on a podcast for freelancers and immediately created an account. Usually, I take my time getting to know a new tool, but in this case I jumped on the bandwagon instantly. I was too tired of reading and writing emails like this: 

“Oh, are you available at 1 on Tuesday?”

“No, but…”

“Is that Central time?”

Most of my conversations with clients happen via email, so important threads get drowned out by this kind of stuff. Not to mention, triple-checking that I didn't misspell or mistype something out of exhaustion drains my mental energy. 

Calendly is a scheduling tool that promises to make all that pain go away. And as far as I can tell, it delivers.

Here’s how it works. Choose an event type (e.g. a 30-minute meeting) from the dashboard and set your availability on the booking page. When you need to schedule a meeting, go to your account and email the other party a link to your event.

Your invitee can choose a time that works for them within your available hours. Once they schedule a meeting, you both get a notification. That time is now booked and not available to others. 

I integrated my account with Zoom (which you can do on the booking page) so that an invite is automatically generated when someone picks a time. Calendly also integrates with Google Meet and MS Teams, or you can add your number and schedule a phone call. 

My favorite feature? Automatically updated time zones. Invitees see everything in their time zone, while my brain can keep cruisin’ in the PST. It’s a small thing, but when I’m feeling fried, adding those +3 (or is it +2?) hours feels like a lot of work for some reason. 

Calendly saved me hours in back and forth emails over the past year. About three hours per week to be exact, which I spent on productive things like writing (yay!).

Trello (free version)

I first started using Trello a few years ago as a volunteer writer for an animal welfare org. It was the first tool I set up when I began freelancing.

Trello is a project management software. It’s web-based (great news for my long-suffering hard drive), and the free version offers plenty of features for a company of one. Everything is organized in project boards. (There’s a free guide in case you want a more in-depth explanation.)

Each project board is divided into different columns. For example, if you’re a writer, you may have a Q1 Projects board with Researching, Writing, First round of edits, Second round of edits, and Final as your columns. 

Underneath the columns are cards, which are assigned to individual projects. As your projects move through their various stages, you get to drag the cards from column to column, until you reach the glorious “Final.”

I love Trello because it gives me a bird’s-eye view of my work. Whenever my day begins meandering, I come back to my Trello board and see if I’m spending too much time on something.

It also hits my inner middle school student tendencies in the best way — there’s color-coding, index cards (albeit in a digital form) and the ability to shuffle them around like you’re studying for a spelling test. If you’re like me and still buy highlighters in all colors of the rainbow, this may be your kind of project management software.

You can create checklists, and add links, attachments and notes within the cards. If you’re working with a team, you can share your board and edit it in real time together. I find this to be particularly useful with clients who don’t use a project management tool of their own. 

More features are available through the paid versions.

Rev Transcription ($0.25 per minute for AI-generated transcripts)

Raise your hand if you enjoy transcribing interviews. “Does not raise hand.” I know my strengths, and transcribing isn’t one of them. It takes too long.

That’s why I went looking for an affordable transcription service. Rev seemed like the most economical and least confusing tool for me.

For $0.25 per minute, you get a “rough draft” generated by their AI program. Rev claims 80% accuracy for clear audio, and in my experience, it’s pretty close. 

Most of my interviews are 30 minutes, which leaves me with $7.50 per transcript. It’s low enough that I don’t feel uncomfortable adding it to my project rate. Rev offers a free trial for the first 45 minutes.

Most of the time, I upload an audio file from a Zoom recording to their system, wait five to ten minutes for the software to finish transcribing, make some edits, and then download the finished transcript as a pdf. The entire process never takes longer than 15 minutes. 

You can also opt for a human-generated transcript for $1.25 per minute (as in, a human being will type out your transcript for you, with presumably fewer errors). They also offer caption and foreign subtitle services, which I haven’t used.

Boomerang for Gmail (basic version is free)

Boomerang is another tool that came highly recommended by other freelancers, and after a few days of using it, I could see why. 

It’s an email plug-in and generally exists to make your life easier. There are a lot of features that make Boomerang great, so for brevity’s sake, I’m going to stick to my favorites here.

Let’s start with response tracking. 

Every time I send an email, I have the option to schedule a follow-up after a certain period. Boomerang will remind me if I have to follow up with someone every day. Gmail does something similar, but it’s not nearly as reliable, and I wouldn’t be able to maintain a customized follow-up schedule. 

Having a clear list of follow-ups waiting for me every morning saves me precious minutes I would've spent sifting through my sent folder.

Another favorite of mine is link-tracking. I don’t send as many cold pitches as I probably should, but when I do, I like to see if people viewed the clips I sent. Boomerang lets me know which links in my email got a click. 

As anyone who ever emailed a cold pitch knows, the radio silence is tough. You may never hear back from the person you pitched, which makes you feel like you’re yelling into a void. Simply knowing that someone looked at a link in my email gives me some feedback. If someone spent time on my website they were probably curious about me as a writer and it would make sense for me to follow-up.

Now, let’s get to the favorite of the favorites — inbox pause.

Do you consider checking your email a break from “real work?" Because I do. In between projects, on walks and vacations, I take email "breaks." They lead to stressed scrolling, which I convince myself counts as productivity.

Inbox pause keeps new emails out of my inbox until I’m ready to see them. That means when I’m done working for the day, or skipping town without my laptop in tow, I can simply set an out-of-office message and see NO new emails until I’m back at my desk. Even if I do end up checking my email, there's nothing new to see. No carrot to reward a toxic habit.

These are just a few of my favorite features. I have the basic version for Gmail, which is free but limited to ten message credits per month. I use those judiciously to schedule follow-ups for the most important emails, and for a one-person operation, it’s more than enough.

Good ol’ Pomodoro (free!)

Photo by Marcelo Leal on Unsplash

I’m lucky. I get to write every day, which I enjoy. This general satisfaction doesn't make me immune from a bad day. Sometimes I take "meh" moments as a sign that I need to redirect my energy. Sometimes I take a break. And sometimes I suck it up. 

The thing that helps me suck it up is setting a timer. In other words, the Pomodoro method.

Developed by the Italian productivity guru Francesco Cirillo in the eighties, the classic Pomodoro method works like this: set a timer for 25 minutes, work on a task, take a break for ten minutes, repeat or move on to another task.

I’ve been using some version of the Pomodoro since college. It's the best, and frankly, the only way I can get myself started on assignments I dread. Even if I only work on something for 25 minutes, I’m always surprised by how much I get done. The timer goes off, and somehow the Google Doc in front of me is filled with words instead of nauseating white space.

It also works great for setting boundaries — putting a limit on how much effort I'll give to a task, prevents me from burning all my energy on one project.

There are plenty of Pomodoro timers online, but any way you choose to time yourself works. 

That being said, I recommend setting a timer on your computer rather than a phone. In fact, leave the phone out of the equation altogether and make checking it a reward after completing a solid stretch of work. Seriously, try it. You may be shocked by your efficiency.

Last few thoughts

If you’re new to freelancing, don’t beat yourself up for not having the perfect system to do something right away. One, perfection doesn’t exist. Two, it takes time to develop a way of working that serves you, and as you grow and change, your freelance business should grow and change too. 

Let me know if you tried some of these tools too, and if I missed any of your favorites.