When you were working for Client X, communication was simple! You emailed them, they emailed you; they gave you assignments, you finished on deadline. The rules were clear.

Then you finished up your work with them, submitted your final invoice, and wrote a “thanks for everything” email. They, in turn, thanked you – and said, breezily, “Keep in touch!”

And now here you are, hunched over your keyboard, sweating neurotically. It’s like writing to an ex-boyfriend or ex-girlfriend that you want to reconnect with; how do you sound sane and friendly, while also expressing your interest?

Savvy freelancers know that the best clients are repeat clients – and that it’s much easier to reconnect with a previous contact than it is to establish a completely new connection. But “keeping in touch” is easier to say than do; how often should you check in with old clients? How do you touch base without sounding desperate?

Here are a few tips for keeping those overtures breezy, relevant, and productive:

Do your research

Before you write to Client X, snoop around Google, their website, and LinkedIn pages. Find out what their company’s been up to, and (if you can) if there’s been any staff turnover; nothing’s more awkward than asking your contact to “say hello to Bill!” if Bill was fired a year ago for verbally abusing Santa at the holiday party. If there’s been positive news, that’s an excuse to write to your client – and a good way to show that you’ve been keeping track of their work: “Congratulations on the Hoover Dam project! I wondered if you might need help plugging the leaks?”, etc.

Use the excuse of special occasions (or new offers)

Have you expanded your skill set since you last worked with Client X, you clever creature? Do you now do social media as well as web content, or coding as well as graphic design? That’s a great excuse for sending out a friendly little update email to your former client. Think of it this way: you’re just informing them that if they happen to need an editor who ALSO moonlights as a juggler, you can now fulfill both needs!

I also like to take special occasions, especially major holidays, as an excuse to stay on a client’s radar. Nobody objects to a nice “Happy Holidays, thanks for a great year!” message. If no major holidays are forthcoming, you can also invent your own special occasion – a kind of freelance event. What’s a freelance event? Why, it’s a special deal on project pricing you are offering to select clients, for a limited time – and wouldn’t you know it, they’re on that list?* You’re just writing to let them know about it! Aren’t you considerate?

*The point with this is not so much that they take advantage of your (modest) one-time deal; it’s to remind them that you exist. Don’t undercut your own prices, and make sure that you build in a deadline for clients to take advantage of any discount.

Keep it short

How many emails do you get a day? How often do you closely read the long ones?

Keep it short (3-5 sentences), keep it friendly and casual, keep it germane. Again, you’re just reminding Client X that you’re alive and that your services are available. You’re not sending out a digital newsletter – that’s a whole ‘nother animal. Newsletters are perfectly viable tools with their own tricks and traps; these strategies are for personalized emails to select clients.

Don’t expect a response

Sometimes you’ll send a carefully-crafted, researched email into the ether… and never hear back. Sometimes you’ll get a two-word blurb in response. Sometimes you will be deafened by the silence.

And sometimes, they’ll offer you a gig.

Don’t wait on tenterhooks for a response (and don’t take it personally if you don’t get one at all). It’s not necessarily a rejection! The point is more to keep in long-term contact than to land a short-term project. Make sure the email you send gives Client X your most current contact information and an invitation to get in touch; the ball is now in their court.

With a few tweaks, writing this kind of “how-are-you” fishing email can transform from a queasiness-inducing endeavor to a perfectly casual, painless experience! It’s smart, it’s professional, and yes – it’s relatively easy. Just keep in touch!