Deadlines can be a source of stress, or they can be the driving force behind structuring your work flow--it all depends on how you manage them. If you’re flying solo in your career, then you are--for better or worse--your own personal project manager. How can you manage your deadlines so they don't end up managing you?
Setting reasonable, obtainable deadlines is key. This is not a time for wishful thinking. Keep the scope of work in mind, and add a little padding to account for the unexpected. Missing a deadline is a lose-lose situation--you look bad, and your client is, at best, underwhelmed. Don’t be afraid to turn down work if your schedule is full. Being in-demand is a good problem to have, but it will go away quickly if word gets out that you can't keep a deadline.
Set a Schedule
A deadline is merely the finish line. There are inevitably smaller victories to be had before the deadline. Identify what these waypoints are, and put them on your calendar. Remember to consider "padding" time for unexpected obstacles, and schedule that in as well. Your client won’t complain if you beat their deadline, but they almost certainly will if you miss it.
Stick to It
Your schedule is only as good as your commitment to keeping it. Sticking to your schedule will insure that any unforeseen complications can be communicated to your client as they occur. Hitting your scheduled waypoints will give you the opportunity to ask your client any questions or request resources/data as the need arises.
Keeping your clients in the loop is important. The strategies above can all help contribute to managing your client’s expectations about your progress. In the event that you cannot deliver on deadline, your client is better off knowing sooner rather than later--no one likes unpleasant surprises! While certain objectives or functionality might seem trivial to you, they could be crucial to your client. So, before you narrow the scope of a project to meet a deadline, make sure you and your client are in sync when it comes to determining what’s necessary, and what’s simply icing on the cake.
Delivering the goods on time and as expected is what builds lasting client relationships and a solid reputation.
For more info on managing deadlines, check out these articles:
Change Order Blog - "Do or Die? Six Secrets for Managing Deadlines"
FlyingSolo.com - "Managing deadlines: Avoid deadline dangers"
OpenForum.com - "Use Deadlines to Become a Learning Organization"