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Let's say you've had an email exchange with someone who seemed interested in hiring you for a freelance gig that went on for a few weeks and then tapered off. This isn't a "cold call" or a stranger, but a former colleague, so there is some history.

If I email them to inquire how they are and if they are still interested in having me work for them after 3-4 weeks of no communication, would that be considered annoying? Is there something I can add to the email to encourage them to take action (like "my calendar is starting to fill up and I wanted to make sure I can be available if you need me")?

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In my experience the 3 - 4 weeks of no communication is not uncommon as people get busy and shove projects aside. I have often had good results shooting them an email that says something like your idea:

"I want to check in regarding this XYZ project because my calendar is starting to fill up and I want to be sure I have time clear for you assuming you're moving forward." or "I'm trying to juggle a few things on my schedule, when are you hoping to do ___..."

If the project is over and you just want them to remember you, I would not contact them every 3 to 4 weeks, but occasionally should not hurt. "Just checking in to see if I can help you with anything." Just don't overdo it because I think there is a psychology to it where if you appear to have a lot of free time, they don't want you as much, even if just subconsciously. (It's like dating...)

I think the "I'm super booked but don't want you to think you're not one of my priorities." approach is best, assuming it's true.

Or "I have a few people sniffing around, but May and June are usually my slower months, so if you'd like to get on the calendar..." You could even offer a discount, but I'd say it's due to business being cyclical so it doesn't look like you're not in demand.

I also sometimes send links to articles on a topic of interest as a way to remind people of my existence without bugging them asking for work. People forget - I've had more than one client that I haven't worked with for a couple years call to ask if I know anyone who can do exactly what I do. Hello? The remembered me but not well enough to remember that's exactly what I do. Sigh. (I'm actually terrible with follow up - do as I say, not as I do.)

BTW, on the opposite end of the spectrum, when you get so busy you can't handle all the client requests a great way to buy time is to send clients some questions about the project that they need to answer before you can do anything. That's usually good for a week to a couple months of breathing room...

  • I'm waiting for that day when I'm so busy I have to book months in advance. I'm also bad with follow up, but I need to get good at it. It feels like I'm back in the dating world, waiting by the phone. – Voxwoman Mar 11 '15 at 14:00
  • So true facts, I've faced same things some times recently. – ElusiveCoder Mar 15 at 12:54

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