The Freelancer’s Guide to Setting Perfect Deadlines

Creative Commons License photo credit: elle_rigby

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.

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{ 10 comments… add one }
  • Giorgio Constantine August 28, 2009, 6:54 pm

    Very helpful guide. Thank you for the tips. it really helped alot.

  • Giorgio Constantine August 28, 2009, 2:54 pm

    Very helpful guide. Thank you for the tips. it really helped alot.

  • Marc Rohde June 29, 2008, 10:26 pm

    Good hints but I disagree with seperating project calendars from your personal. I recommend keeping one calendar for all scheduled tasks. By keeping personal and work items on one calendar you have an opertunity to plan all your time and be assured that you are keeping all your commitments.

    I would not be happy in social situations if I didn’t have the assuarnce that I had reviewed my work calendar first.

  • Sandi Johnson March 27, 2008, 6:41 am

    Great tips for setting deadlines! Personally I try to set 3 deadlines for any project. The first is my ‘early bird’ deadline – my own personal challenge deadline, if you will. The second is my “wow” deadline – the one that doesn’t challenge me quite as much, but still ‘wows’ the client for being ahead of schedule. The third deadline I set is the one I actually give my client. When I start a particular project, I set every intention of hitting the 1st ‘early bird’ deadline. Only twice in my professional career have I needed to go beyond my ‘wow’ deadline. Once was out of anyone’s control, the other was a client’s own procrastination in getting information to me. I guess my ‘system’ is similar to what you suggest for setting smaller deadlines for yourself. Great post!

  • Eric Eggertson March 11, 2008, 12:12 pm

    Love the photo! These are good tips.

    One thing that’s really important about deadlines is communicating with the client when you’re likely to miss a deadline (especially if it’s something beyond your control). There may be things they can do to compensate if they find out ahead of time. If you phone them five minutes before something’s due to let them know there’s been a delay, you’ll just piss them off and make THEM look bad (you already look bad).

  • Lee Newton March 7, 2008, 10:48 am