Deadlines
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The Freelancer’s Guide to Setting Perfect Deadlines

This post was helped along by tips from amazing (and punctual) designer Grace Smith of PostScript 5.

I’ve struggled over the years as a freelancer trying to find the best way to gauge a deadline. It’s safe to say that creating an attainable deadline is more than just picking a date. There are lots of factors that go into projects, and gauging how long they will take is a hard thing to do. The more complicated a project is, the harder it is to create realistic deadlines. Have you ever known a contractor to finish construction of a house on time? It’s a rare thing, my friends.

No matter how much experience you might have, you just can’t plan for every delay. Strange things happen when working on deadlines. Much like you can’t predict the weather, you can’t know everything that might cause a hitch with finishing the project on time. And hitches will happen. But you can still create an attainable deadline with lots of unknowns too.

Perfect deadlines, (at their core), consist of 3 factors: Full understanding of the project at hand, realistic assessment of skills/tools needed, and proper time allotment. If you can get these factors aligned, you’ll be well on your way to creating a perfect deadline. Here are some ways to really assess a project and give ample time to finish it.

Know your specs inside out

Knowing everything that needs to be done on the project is absolutely critical. Make sure you and the client agree to everything that has to be done in writing before you even start to think about timeframes. Hashing this out right from the start clears up any confusion later on.

Leave no stone unturned

Getting to know the client a little bit can be helpful in not only deciding whether or not you want to work with them, but also for getting a feel of their preferences. Grace uses a client worksheet that really allows her to get a deep understanding of who she’ll be working with and what they expect. There’s no such thing as getting too much information about the client and the project.

Overshoot

Not giving yourself any wiggle-room on a deadline is just plain crazy. I don’t think I’ve ever had a project that went without a hitch. There’s always something unexpected that goes wrong, from sickness to equipment malfunction. (Ever heard of Murphy’s Law?) Make sure to give yourself plenty of padding. Both you and your client will be glad you did.

Be a pessimist, but only when making deadlines

The worst thing that you can do is to be an optimist when planning deadlines. If you see a possible hiccup, plan for it to happen. It’s better to be surprised when bad things don’t happen than when they do happen.

Plan to the smallest detail

There’s a quote from the movie The Patriot that I love. Mel Gibson’s character is reminding his sons that when shooting a gun they should “aim small, miss small”. If you can “aim small” by planning every detail that needs to be done, your proposed completion date will be much closer to the mark.

Constantly review what needs to be done

It’s easy to miss little steps throughout the duration of the project. However, if you’ve planned to the smallest detail, it’s harder to miss small elements. This also ensures that everything is done in order, without missing any steps.

Create smaller deadlines for yourself

By creating project milestones for yourself, you can ensure that the work gets done without too much procrastination. I’ve found that if I don’t impose small deliverables on myself, I just drag my feet and create stress for myself.

Keep a separate calendar for projects

Don’t try to fit all of your self-imposed deadlines on your personal calendar. You’ll need as much space as possible to put all the project information on there. You should never mix business with pleasure 😉

Be honest with yourself

Being realistic with our abilities and work paces is incredibly important when creating deadlines. Knowing what you’re capable of will allow you to only pick clients that really fit your expertise, and allows you to gauge the time needed to complete the project.

Know your pace

It’s human nature to think we can get projects done faster than what we’re capable of. For me it’s an issue of pride. I reckon I’m an efficiency monster, when I’m really not. If I swallow the pride and give myself some realistic deadlines, it works out better for everyone. I don’t put out shoddy work due to running out of time, and the client isn’t upset because I’m late on the deliverable.