Earlier this fall, I was contacted by a prospect for a potential project. He runs a marketing/advertising agency, and we’d worked together for a third party on a project earlier in the year. This was my first chance to do some work directly for him, so I wanted to make it count.
We had a 30-minute Zoom call to discuss the scope of work, and it sounded like a good fit. I crunched the numbers and sent him an estimate the next day. He said he’d discuss it with his team and get back to me.
As it happened, my wife and I watched the movie Swingers over the weekend after I submitted the estimate. If you haven’t seen the movie, it’s a snapshot of the mid-1990s featuring a young Vince Vaughn and Jon Favreau. If you have seen it, you’ll recall the agonizing scene where Favreau’s character Mikey leaves a string of increasingly desperate voicemail messages on a girl’s answering machine — against the advice of his buddies, who tell him it’s smarter to wait a few days before calling. (Or even, one suggests, till the next Olympics.)
So I waited. And waited some more.
A week turned into two and into three.
At this point, I was assuming that it wasn’t going to happen, whether I had priced it too high or they had decided to do it internally, or to scrap it altogether.
Then, at the beginning of week four, I received this email: “Estimate sounds good, let’s get started!” I was both excited and relieved, not necessarily in that order, and the project (which wrapped up a week ago) was a success.
In retrospect, I’m glad that I stuck to my Swingers principle of being patient. Even when you’re excited about a project, it can come across as too eager or even desperate if you push someone to a decision when they haven’t had enough time. From personal business experience, a “Just following up” subject line is a huge turnoff.
In retrospect, however, I would have done one thing different: When I emailed the estimate, I could have simply asked, “When do you think you might have a decision?” or something similar. That would have given me a reason to reach out after a specific number of days or weeks, without feeling like I was being pushy—and also without having to wait till the 2026 Winter Games in Italy.
Jake Poinier made the leap into freelance writing and editing in 1999 after a decade of positions in the publishing industry, giving him key insights from both sides of the desk. As the founder and owner of Boomvang Creative Group, he has worked with a diverse array of Fortune 500 and small businesses, consumer and trade magazines, and independent authors. Jake is committed to helping freelancers improve their businesses and shares his knowledge and experiences frequently as a speaker at industry conferences, through webinars, and on his blog.
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