On Deadline

It’s a pretty safe bet that if you’re ever working on something, you’re on a deadline. If there’s no deadline, then it’s probably too enjoyable to be called work. (Yes, I suppose it can be enjoyable AND on a deadline) Managing deadlines is a critical and oft-overlooked aspect in writing and freelancing. Hell, even in a standard office space environment.

There are a few types of deadline out there. There’s the hard deadline: where a project absolutely must be finished by a certain date, no ifs ands or buts. This is typically because you need the project to finish before some other project can begin, or because completion is linked to some other event or release. There’s no much you can do about a hard deadline, outside of be smart about accepting the gig or not. It’s doubtful you have enough pull to actually get them to move or delay the item that your project is running up against, so all you can do is be wise enough to know your limits. Look at the project, work backwards from the deadline and estimate how long all the various steps will take you. Now add 25% more time on top of your estimate, to plan for emergencies. Will you still finish on time? Will you finish on time but hate every second of your life leading up to the deadline because you destroyed yourself trying to meet it? It’s something to consider.

If you’re lucky, the client will ask you when you feel you can have the project done. This is the ideal situation… but only if you handle it right. Too often, people are too eager to please their client and will quote a timeframe that they haven’t thought through. It’s not entirely likely that the moment someone says “How long do you think this should take?” that they expect an immediate answer and will settle for nothing less. Your automatic response to that question should always be, “Let me look into it and get back to you as soon as I have a solid estimate.” They’re not going to drop you and go with someone else because you want to give them realistic ideas of how long your work will take. In fact, in time, people will opt for you strictly because of this precision.

Then take a day or two to really run the numbers on your project. How long will prep take? How long will the body of work take? Review stages? Rewrites? Do-overs? Again, take that time, and boost it by at least 25%. That’s your number. If they say that that deadline is too far out, reduce your padding by a bit, that’s why it’s there. Ideally, you have plenty of time to do your work and if you wrap early, you’re a rockstar and they love you for being such a hard worker.

I like the idea of having milestones that you present to your client. As you complete pieces of your project, whether it be chapters or sections or features or whatever chunks you can break your work into, run them by your client and let them provide feedback. Their responses will help keep you on track and gauge their expectations, and it gives them a palpable sense of a working freelancer. No one wants to promise you money and then have you vanish into a cave for four weeks while they hope you’re not partying hard in Mexico with their funds.

Milestones, however, are something I would advise to not turn in early to your client. If you have your project broken into 10 stages at specific dates and for every single one of those stages you are 3 days early in turning your work in for review, what do you think the client will expect when your final deadline approaches? That’s right, an early completion. If you can only provide them “on time”, it’s a bit of a let-down, even though it shouldn’t be. Manage the expectations of your work. Be too early and too available and you run the risk of seeming overly eager or needy, and you also run the risk of feature creep. The client sees how fast you can crank work out, and maybe they start to request more and more, and soon even your padded timeline is useless.

Instead, use that extra time between milestones to either get a jump on later stages of the project at hand or, ideally, take a look at some personal enrichment. Indulge in your hobbies, practice some new skills, or just kick back and relax and recharge your batteries. Do not feel too guilty to take this time. You and your client have already agreed on an acceptable end date. Your time on how you get there is your own, as long as you meet your bottom lines. So, if you’ve been wise enough to schedule in leisure time, then you deserve to enjoy some leisure time. Besides, it’s precisely that time spent exploring other avenues that will make your skillset broader and give you more value to anyone who wants to work with you.

The last deadline is one I’m going to gloss over, because much of my thoughts on it are covered above. It’s the type of deadline that is mandated, but not drop-dead, as in the first sort. Your boss or client says “I need X done by Y.” You can say no. It’s a big thing for people to wrap their brains around. It took me years of experience at my company to reach the point where I could do it. But you need to learn to say “Nope”.

Of course, I don’t mean “No, I won’t do it” (unless of course someone is asking you to complete a task that you aren’t paid for or a task that someone else should be completing instead), I mean “No, it can’t be done by then.” I’m a manager now, so I can say with a certain degree of authority that when someone asks for something by a certain date, they have pulled that date right out of their butt. Unless they are actively involved in doing the work along with you, they don’t really know the time it will take to do what you have asked. So, if they say 2 weeks and you think you need 3 weeks… well… say you need three weeks. I can almost guarantee the response will either be “Oh, okay. Great.” or “Really? Why so long?” and then you can just explain your reasoning. People want things done right before they want them done fast. So don’t be afraid to tell them how long it will take you to do it right.

It’s important to remember when working on a deadline that fast work isn’t the same as early work. Earning a reputation for getting work done fast is great, but it will likely also be the cause of your first ulcer. Earning a reputation for getting work done early likely means that you are simply managing your time well. Both are equally attractive to clients, but one will result in a much happier worker.

Which leads me to my final thought for today: “Corporate Juice Pimps” is a great name for a band. That is all.

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