5 Email Tools That Will Change Your Life

This post originally appeared on our sister site, Contently’s The Freelancer.

Ever feel like your inbox is out of control? Join the club. Most of the freelancers I know—myself included—spend an inordinate amount of time each day scrolling through press releases, writing pitches, following up with editors, and scheduling interviews. We may not have as much face-to-face contact with colleagues, which makes email such an important component of what we do. And since email is so ubiquitous, default services don’t quite cater to our self-employed needs.

However, there are programs out there designed to simplify our email responsibilities. Here’s a look at five free tools that can help you manage your unruly inbox.

1. Boomerang

There’s email protocol we all have to abide by. You wouldn’t call a colleague on the phone at midnight and just leave a voicemail. Likewise, you shouldn’t email someone at odd hours if you want to make sure your message gets read.

If it’s late at night and you finish a pitch, it can feel cathartic to just send it right away. Boomerang gives you that catharsis by letting you schedule future emails so you don’t forget them in the drafts folder or send them at the wrong times.

This Gmail extension has vastly improved my email experience, and New York-based freelance travel writer Lilit Marcus agrees. “I travel a lot, which means I often keep strange hours and I might be replying to important work emails at 4 a.m. New York time,” she said. “I use Boomerang to make sure that my emails get sent to editors at the hours they’re most likely to see and respond to them, which makes both of our lives easier. I will also Boomerang follow-up emails and send them at a later time if I’m worried about looking overeager.”

Boomerang also offers functions for click tracking and read receipts. The basic version is free and comes with 10 messages per month, while monthly subscriptions start at $4.99 for unlimited messages.

2. The Email Game

Working with Gmail and Google Apps, The Email Game challenges email addicts to process emails more efficiently through gamification. Earn points by racing against a timer to work through your inbox, deleting, replying, forwarding, archiving, and so on. I’ve used The Email Game first thing in the morning when I have the most unread messages during the day, and the software offers feedback on how I could manage my email more efficiently and reports on the average time spent on each email. At one point, I got my average down to nine seconds, omitting messages that required a thoughtful reply and focusing on the low-hanging fruit.

3. Sidekick

Sidekick is like the little fly on the wall you always wish you had. It lets you track email opens and clicks, plus it can generate reports about open rates and click rates over time.

For Liz Alton, a Boston-based freelance writer, the best part about Sidekick is the ability to see when emails have been opened so she’ll know for sure a client received an assignment from her. “As a data point, it also helps me anticipate when I might be receiving responses to certain messages throughout the day and gives insight into when a follow-up might be appropriate,” she explained.

Alton also likes the ability to see if a user is clicking links within an email. “If your pitch letter includes links to your portfolio or stories, you’re able to gauge a potential client’s level of interest by looking at that activity,” she said. “In some cases, prospects have clicked links multiple times during a certain time window. These are generally great times to send a quick follow up reiterating your interest. I’ve used this technique to successfully launch conversations that have led to ongoing assignments.”

The free version of Sidekick comes with 200 notifications per month, while the premium version costs $10 per month per user and offers unlimited notifications. And if you refer a friend, you can earn a free month of the premium service.


Deleting emails can feel like a game of Whac-A-Mole—drag one message to your trash, and two more pop up in its place. As Alton points out: “What I find is that through networking or interactions with sources, you often start receiving people’s newsletters that you’re not truly interested in following,”

Now, Alton and I both use to mass unsubscribe from unwanted email lists. The site also has a feature that lets you “roll up” the subscriptions you want to keep into one daily digest so you don’t have to process individual emails. It’s essentially a newsletter for your newsletters.

5. Streak

This Gmail plugin has a lot more bells and whistles than some of the other tools we’ve mentioned. Streak lets you manage timelines right in your Gmail account, so, for example, a freelance writer can track a project from pitch all the way to payment.

Deborah Snoonian Glenn, a former magazine editor and now a Los Angeles-based freelance writer, needed a system that would help her monitor the progress of multiple assignments like a CMS. She uses Streak’s boxes feature to create a workflow for each story she wants to pitch. “Instead of scanning my draft emails, which is where I write pitches, I make a box for every idea, and it collects all of my ideas in different stages of the process,” she said. “It’s helped me get pitches out faster and prioritize my time a little easier.”

Final Thoughts

For most of us, trying to maintain inbox zero is a struggle, if not an impossibility. But as I’ve outlined above, there are creative (and free) ways to tackle email. Just as we might clean a desk with organizers and folders and shelves, we should take the same approach to our inboxes. They’ll will still get out of control from time to time, but these tools can help freelancers spend less time worrying about communicating and more time actually working.

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