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5 Tips for Meeting Deadlines, Even When They Seem Impossible

Productivity is a freelancer’s best friend. When you’re self-employed and paid on a job-by-job basis, your ability to meet deadlines and move on is vital to your success. The trouble is, deadlines are relentless. The more successful you become the more they pile up, until you’re wishing you could create a human clone or go back in time to extend that delivery date.

If you find that you’re frequently behind, it may be beneficial to reassess how you work. Keep these five freelance best practices in mind to help you meet your deadlines, every time.

1. Set project milestones in advance

Give both the designer’s and client’s deadlines equal weight in the proposal and you’ll be better able to convey how mutually dependent they are to avoid a logjam.

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Before a deadline can get out of hand it first has to be created, and going back to that starting point reveals a method of maintaining control. Over the course of the 12 years that he’s been running Ann Arbor, Michigan-based Hammond Design, freelance publication designer Don Hammond has found the best way to do this is to set milestones with the client early on.

When Hammond puts together a proposal, he works backwards from the delivery date and creates a detailed schedule of benchmarks that he and the client will meet together. This way, the client knows which materials he or she must to provide in order for the designer to work, and exactly when the designer will need them.

“This is absolutely critical,” Hammond, whose ongoing projects include the University of Michigan’s School of Public Health magazine Findings, says. “It’s important from the standpoint of helping clients who might not be totally knowledgeable about how the work gets done, but also if there’s ever a point in the process where fingers are pointed, it’s always valuable to be able to say look, I needed such and such in order to meet deadlines.”

2. Become your own project manager

Prioritize your jobs and pick the organizational method that works best for you. If you commit to managing every project, there’s little chance that a due date will slip through the cracks.

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Even with a set of approved milestones to work with, it’s easy to fall behind. The solution? Become your own project manager to pilot your jobs to completion.

Mike McGowan, a freelance designer who also works out of Ann Arbor, recommends ranking deadlines by order of importance. “A project of minor importance should not delay a more important one, even if it’s due first,” he says. McGowan also stresses the value of analyzing the deadline you’re given to see if there’s any wiggle room, which can be very useful if you’re juggling multiple due dates. “Is (the deadline) artificial or actual?” he says. “If it’s arbitrary, try to discover the actual deadline, and what’s driving that decision.”

Like project managers, freelancers benefit from being supremely organized. Whether your calendar hangs on a wall or resides in an app on your smartphone, you’ll want to add every key date and deliverable to your schedule. Tools like Wunderlist  and Google Task, which is part of Gmail, can help you manage your workload and meet deadlines by creating to-do lists complete with critical details and dates. For many, the satisfaction of checking a box every time a portion of the job is finished is enough to keep production moving at a steady pace.

3. Maintain communication

A request for an extension is much easier to stomach when it comes two weeks before the deadline, rather than at the 11th hour.

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When you’re on a tight deadline and need to catch up, making work a priority is only logical. Still, it’s important to put time aside to reconnect with your clients along the way. This gives them the chance to adjust those milestones if they aren’t holding up their end of the bargain.
“Every designer has had a client from hell, and one of the defining characters is the client who doesn’t meet deadlines but expects the designer to,” Hammond says.” That’s when the pressure and the tension really gets bad.” By keeping in touch, however, you can manage the client’s expectations as soon as you realize you may need more time. Checking in with the client about the schedule and making corrections as needed is good for everyone involved.

4. Drop everything and get it done

There are times when you simply have to work until you drop.

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Despite their best efforts, most freelance designers do at some point find themselves rushing to get a project completed. Christina Sweetman, a graphic designer based in Alberta, Canada, knows this well.

“There have been times when I completely underestimated the amount of work or the client’s expectations,” says Sweetman, who’s been freelancing since 2013 and currently works with a regional library and an oil and gas company. “I now work with the client as closely as possible, and emphasize that I’m the expert. Most are willing to let me inform them about how long it’s going to take to get a good design and something that they’re happy with.”

And if she still needs more time, Sweetman — who works from home and has an infant — drops her baby off at her parents’ house and toils for as long as it takes.

Hammond agrees that there are times when you simply have to work until you drop. “I can get by with three hours of sleep if need be and get back to it again,” he says, noting that he learned self-discipline while in architecture school at the University of Michigan in the late 1970s, which he attended before switching to U of M’s School of Art & Design. “That was like being in military boot camp. The number of hours we had to put into the program were mind-boggling. That trained me to keep at it.”

5. Enlist some help

Don’t be afraid to bring in some backup if you really can’t meet your client’s deadline demands.

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If all else fails and you know there’s no way you can meet deadlines, it may make sense to bring on another freelancer to help you get the job done.

Splitting your work — and your profit — with a peer may not be ideal, but when your reputation and relationship with the client are at risk, it’s a practical fix. You may even find that an ongoing collaboration frees both of you up to accept more projects overall, and leaves the client more than satisfied. As McGowan points out, “There are very few joys in life that can equal a deadline met and a happy client.”

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