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Turn Hard Deadlines into Soft Limits

For freelance editor and writer Louise Bolotin, it all ended in tears. Writing on her blog in 2007, she described how after putting in a series of 12-hour days on a handbook, she emailed the production editor to explain that she was going to have to miss the deadline. A slow exchange of emails failed to solve the problem and frustrated, anxious and stressed, Bolotin burst into tears. A calm, diplomatic phone call later, her deadline was extended and some of the “drudgery” was outsourced to someone else.

It’s a feeling that’s familiar to anyone with freelance experience. Among the hundreds of jobs that we negotiate and accept each year, we’ll get some of them wrong. We’ll underestimate  the amount of time the project will take to complete or something more urgent will come up before the work is finished, taking a chunk out of the time allocation that we never seem to be able to put back. Without warning, the deadline is suddenly upon us. Often some extra-long days are enough to solve the problem but occasionally, it’s too late. There’s too much work and too few hours.

At those times it would be great if the deadline wasn’t actually a deadline at all but something more like a soft limit, a recommended time by which to return the work if at all possible. A kind of “best offer” that the client would accept on a “more-or-less” basis.

When you’re up against the clock, there are a few things you can do to turn the wall of a deadline into a cushion that can provide a soft landing.

  1. Spill the Beans

The usual advice given to freelancers struggling to meet a deadline is to tell the client as early as possible. That’s sound, sensible and usually impractical. We don’t really want to tell the client we messed up our timekeeping unless it’s absolutely necessary, and if we could always accurately estimate our productivity then we wouldn’t be in trouble in the first place. It doesn’t help that as the deadline approaches, productivity increases: nothing creates focus more than a fast-impending deadline, making us believe that, despite the panic, we can actually get it done.

But there does come a moment when you know it’s not going to happen. That’s the time to spill the beans. Usually an email laying out the problems, apologizing and offering a new, more accurate deadline is enough to solve the problem but, like Louise Bolotin, you might need to make a phone call. Keep the conversation calm and professional. Most clients understand that problems happen in every business. They won’t be happy but they’ll be less sad if you also come with a solution in hand — usually, the softening of the old deadline and the creation of a new one.

As a strategy though, honesty might be the best policy but it does carry risks. When artist Caanan Grall told a publisher that he wasn’t going to be able to meet the Halloween deadline for a monster comic, they ditched the title.

  1. Create Your Own — Earlier — Deadline

One strategy requires a bit of willpower. When you receive a deadline, set your own soft limit about ten percent earlier than the time you actually need to return it. If you have a month to complete the work, for example, then instead of aiming to deliver at the end of the last week, aim to deliver at the beginning or the middle of that week.

It’s a good strategy to follow regardless of your timekeeping. If, by some miracle, you do manage to complete the work according to your own soft deadline, you’ll be able to let it sit for a few days before reviewing it and sending it on, reducing the chances that you’ll be asked to make revisions and corrections. And if, as is more likely, you miss that deadline, you’ll still have a few more days to finish things off.

It’s a good habit to get into it but it does require discipline and a willingness to gamble with your competitiveness by offering a time limit that may be longer than necessary. If you are finding that you’re struggling to meet deadlines though, it’s a good way to give yourself a bit of breathing space right from the negotiations.

  1. Deliver as You Go

Milestones are always a good way to reduce the risk in any freelance project. For the freelancer, they assure that you don’t lose all of the fee if the client disappears, and for the client, they ensure that the work is being done and at the right quality. But milestones also have the advantage of keeping both sides informed of the progress of the project — and they’re relatively flexible. Miss a milestone and there’s always the feeling that you can make up time by completing the next stage faster. Once it becomes clear though that isn’t happening, the client starts to prepare for the possibility that the final deadline will be missed. He comes to think of that deadline as being the preferred date for completion but has a contingency plan already in place in case it doesn’t happen.

In effect then, milestones have the effect of slowly softening a deadline as you approach it at high speed.

And you don’t have to set too many milestones. Commenting on Graphic Design Blender, a site for designers, website builder Ramona Iftode says that for small jobs, she uses just two milestones: the mock-up design and the coded template. For bigger projects, she inserts more. Milestones can be far more flexible than a single deadline.

In an ideal world, every freelance project would end on time, clients would always pay their bills, projects would always be interesting and well-paid, and the workday would always end at five. Freelance work though takes place in the real world where time estimates aren’t always accurate and urgent items often pop up, overturning even the best-laid plans.

Deadlines look scary and it’s good that they do. It’s the fear they inspire that keeps our fingers on the keyboard long after we’d like them to be wrapped around the remote control. But they’re also not monsters. They can be softened if approached carefully and (don’t tell anyone this) the world doesn’t end if they’re missed. You might lose a client, which is always painful, but unless it happens all the time, you won’t lose a career. As Douglas Adams once said: “I love deadlines. I like the whooshing sound they make as they fly by.”


  1. Louise Bolotin Says:

    I'd have appreciated you contacting me first to ask me if it was ok before deciding to lift my story for your own blog - it's unethical to do that, especially as you used my real name instead of the blogging name I used for that particular blog. It was a bit of a shock, to say the least, to discover this post through Google Alerts early this morning. Now I'm stuck with the fact this page will be cached forever and I am definitely not happy. I think you owe me an apology.

  2. alex Says:

    Hi Louise,

    We're sorry if you're not happy but we reject the accusation that we acted unethically. We didn't "lift" your story; we described a post available to anyone to read on the Internet, commented on it and linked to it so that readers could see the source for themselves. This is usually how blogs discuss issues. Nor, in using your real name, did we reveal anything that wasn't public knowledge already. Your own blog identifies you as the author of diaryofawordsmith, a fact we, as readers, couldn't have known otherwise. As I say, we're sorry if you're unhappy but in highlighting an interesting story already on the Web and repeating information already known, I don't think we acted unethically or unfairly.

  3. Louise Bolotin Says:

    I think you're missing the point. That blog was totally anonymous until just over a year or so ago when I outed myself, and the experience I described was written on that anon blog precisely because I didn't want my own name publicly linked to it - if I had, I've stuck it on my other blog, which *is* linked to my real name. I had very good reason for blogging that story anonymously, because the company I was working for could not be identified. And not only that, I don't want to cast aspersions on my own professional reputation by admitting under my own name that I have periods of such weakness - ok, we all do, obviously, but that's why we tend to blog about them anonymously. I'm amazed you don't seem to get this.

    And you know what, if I were in your shoes and stumbled across an interesting story from 3 years ago I would definitely have contacted the blogger to check it was ok to quote and link - firstly because it's the ethical thing to do and secondly because a lot can change in three years and the person who wrote the original piece might have very good reasons for not wanting it reproduced so much later on. Plus, if permission *were* given, I'd have used the blogger's blogging name - you know, the one they wrote it under, instead of tracking down their real name and using it, which stinks.

    But hey, thanks for being so unapologetic and refusing to be understanding. What I'm going to do now is remove my blog post and put something totally different there to wreck your URL to it.

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