How to Wrestle Deadlines and Win (Even When You Think You Can’t)

How to Wrestle Deadlines and Win (Even When You Think You Can't)

You don’t get to be on big-name sites like Men with Pens, Copyblogger, Problogger and Daily Writing Tips by fluffing deadlines like some flaky moonlighter. And Ali Luke (yes, she’s back!) knows that very well.

Unfortunately, meeting deadlines is still a huge issue. Writers aren’t known for their planning and scheduling skills, after all – but nail deadlines, and you’ve turned yourself away from flaky and straight onto fantastically competent. (Keep reading to learn how.)

By the way, if you’ve become one of those deadline vigilantes who always gets work in on time, come share a secret or two in the comment section – or tell the story of the Deadline from Hell that made you swear never again.

Nasty creatures, deadlines. They creep up on you slowly but inexorably, a bit like zombies on the march.

And then they loom, larger and larger, until they’re blotting out all the light in your world.

By the time you realise that you have a monster in your world, it often seems like it’s too late to hit that deadline. You’re a writer, not a warrior! You just want to curl up under the duvet and pretend that deadline doesn’t exist at all.

Hey. Take heart. You can fight that deadline – and win.

Step 1: Spot Your Monster Early

Deadlines move at a constant rate. You can see them coming closer… and closer…. and closer. So when you realise that your deadline’s becoming a monster, do something.

Don’t turn your back. Don’t cross your fingers and hope for a last-minute miracle. Acknowledge that deadline. (Give it a little wave, if you like.) Let it know that you are in control.

How can you spot a monster deadline creeping up on you?

  • You thought the first draft would take ten hours. It’s taken twenty already – and you’re still not finished.
  • You wake up with a sinking feeling in your stomach when you think about how much work you still need to get done.
  • You find yourself procrastinating – chatting on Twitter, watching re-runs of The Simpsons, playing Flash games…
  • “Write mega-huge client project” keeps slipping down your to-do list.
  • You don’t have any slack in your schedule. And you know you need to write every single day to hit this deadline.

You’re looking that deadline square in the eyes. And you can feel the panic bubbling up…

Step 2: Win the Psychological War

It’s easy to lose perspective when you’re facing a nasty deadline – and especially when you panic. It’s almost impossible to write.

Take a deep breath.

Remind yourself that no deadline, however monstrous it may be, can kill your career. You’re a good writer. You’ve turned in great work before, and you can do it again.

To quell that sense of panic:

  • Ditch everything on your to-do list which isn’t urgent and essential. Your email inbox won’t implode, don’t worry. Just focus on the project at hand.
  • Write a quick outline if you don’t already have one. When you can see where you’re going, it’s easy to keep writing.
  • Tackle the easiest sections first – the ones where you’ve already done the research, where you have a good idea of what you’ll write.

Once you feel calmer, figure out how much time you have left. Deadlines creep closer every minute, so you need to keep up your momentum.

Step 3: Set a (Sane) Schedule

It’s Monday. You have five days to finish an ebook of 20,000 words. You have an outline, you’ve done all the research, but you’ve only written a paltry 500 words (and you’re pretty sure you’re going to scrap those).

Five days. 20,000 words. That’s an average of 4,000 words per day.

To create a sane schedule, do this:

  • Allow for some slack at the end. Aim to write 5,000 words every day so that you have Friday to catch up if necessary.
  • Write at your best time. For me, that’s in the morning. It could be afternoon or evening for you. Refuse to allow other commitments to sneak into your best writing time.
  • Work in short bursts – maybe 45-60 minutes – with breaks in between. Don’t plan to write for hours in a marathon.
  • Make sure you get some down time. Give yourself something to look forwards to mid-week – perhaps a movie or a meal out. You can afford to take a proper break, because if you don’t, you’re probably going to end up making silly mistakes that cost you more time.

If all that isn’t enough – if you can see there’s no way to beat that deadline – then move the goalposts.

Step 4: Get an Extension

Deadlines are rarely set in stone, and most clients or editors can be flexible if necessary.

However, this is a last resort. Flaking out on deadlines gives you a bad name, and while your clients may be accommodating the first time it happens, they’re not going to put up with a flaky writer for long.

To stay on the client’s good side:

  • Contact them promptly. Don’t leave it until the day of the deadline and then email to say you need more time.
  • Be polite. Don’t imply that it’s their fault the deadline was too ambitious. (Maybe it was, but as the contracted writer, you should have let them know that up front.)
  • Offer part of the work. Tell them what you can do, not what you can’t. For example, say you can have 15,000 words of the ebook completed by Friday.
  • Suggest a new and more realistic deadline that you’re confident you can meet. Give yourself a day or two more than you think you’ll need – you can always turn the work in early.

Deadline nightmares don’t need to keep you awake at night. You just need to deal with the situation now and make sure you stay well away from more monsters in future.

Step 5: Avoid Monster Deadlines – Forever

It’s not much fun wrestling a huge deadline – though it can be exhilarating when you win. Still, you want to make sure that monster never comes back, ever again.

When negotiating deadlines:

  • Allow more time than you think you’ll need. Life gets crazy sometimes – especially when you least expect it or during weeks when you need every minute of your writing time.
  • Plan to turn in work early. Set yourself a personal deadline that’s a few days ahead of the real one. That way, you’ll feel calm and in control, and you can cope with last-minute problems.
  • Set milestones and agree on deliverables. That way, you’ll get started early (rather than leaving the whole project till the last minute), and if the client wants a slight change in direction, they’ll let you know sooner rather than later.

So – over to you. I’m sure you have plenty of thoughts on deadlines – and some horror stories to share. Comment away!

Ali Luke is the go-to gal for all things blogging. Check out her newest ebook, The Blogger’s Guide to Freelancing. It’ll teach you everything you need to know to be an awesome on-time, on-demand blogger they’ll love.

Post by Ali Hale

Ali Hale is the go-to gal for all things blogging. Check out her newest ebook, The Blogger's Guide to Freelancing. It'll teach you everything you need to know to be an awesome on-time, on-demand blogger they'll love.

Join the Discussion. Click Here to Leave a Comment.

  1. Ali, thanks for the great suggestions for getting your writing projects done! I have learned that consistency in all things – particularly when trying to make money on the Internet – is the key. All of the experts I have written about on my blog have consistency as a integral part of their success.

  2. I’m reminded of the Erma Bombeck quote “I love deadlines, the whooshing sound they make as they rush past” LOLOL.

    I could give you some horror stories, but that would just be talking about normal life since I’m a shocker for any form of deadline.

    The best thing I’ve done with deadlines is start using the Pomodoro Technique that has been mentioned on MwP before. It gets me focussed and productive.

    And blocking out time in my calendar.

  3. I always ask for a midweek or end of the week deadline if I’m not on a posting schedule. Since the weekday here starts on a Sunday, I’m covered even if I slacked the week earlier.

    I work on Sunday and get a head start on my week’s deadline.

    • I often set deadlines as Fridays and aim to hit them on Wednesdays — that way, I feel comfortable with the writing, and my client is impressed by having the work early.

      Being in the UK helps a little, too, cos most of my clients are 5+ hours behind in the USA…

  4. Love your intro Ali. Deadlines do feel like a lurking monster–especially in the middle of the night.

    You’ve named so many great hints, the only one I can add is when you’re tossing and turning at night–instead of just worrying–get up and work on your project.

    I found even an hour spent on it (even if it’s 3AM) helps me go back to bed, go to sleep, and often I get good ideas when blessed sleep occurs.

    That said, it does not help to get up at 3AM and just Twitter around. Then I just worry more and never get back to sleep.

    • Great addition! In my early (more anxious!) days of freelancing, it wasn’t unheard of for me to wake up in the middle of the night and work..

  5. Excellent article. What I have done to help beat the deadline monster is to post the following where I see it every morning when I start work: “What would you work on if you only had 2 hours today?” This is really just another form of your sugggestion – “Ditch everything on your to-do list which isn’t urgent and essential.” The added element is the reminder for concentration and focus during the working period. If I think I have lots of time, and think that every waking hour is available to help meet a deadline, then I eventually end up in a pickle, and lose my balance in life along the way. You point this out also when you noted that we should “Make sure you get some down time.” I have always thought that ‘nothing gets done without a deadline,’ but they need to be reasonable motivators, not generators of nightmares.

    • Thanks Bryan, that’s a great question to ask. I do something similar – usually “if I could only get one thing done today…”

      I think deadlines are motivating to an extent … but blind panic doesn’t tend to do much for anyone’s writing!

  6. fun post ali!

    I reverse engineer everything from the deadline. works like a charm … if a client presents me with an absurd deadline from the get go, i either turn it down or say it will entail a rush charge. if money’s involved some deadlines suddenly end up being flexible.


    • Cheers Giulietta, it was fun to write!

      If a client wants something in a hurry, I explain that it’ll cost them more. I think that’s perfectly fair, and most clients are happy enough to either pay or wait a bit longer!

  7. This even applies to physical product deadlines. I experienced a lot of deadline hell doing private commission work in high end furniture. Love your suggestions and strategies.

    I know it’s a bit different in the virtual world, so avoiding setting any deadlines at all isn’t realistic, but that’s exactly how I moved past the nightmares with my deadline problems.

  8. Hi Ali, I think the two key things for me with deadlines (these are also endemic in my profession, namely translation) are agreeing a reasonable deadline in the first place, based on a reasonably accurate estimate of the amount of time it’s likely to take – whilst also leaving some time for other work so that I don’t have to turn all my existing customers away – and then starting promptly and making good early inroads, as time-complacency at the beginning can lead to overwork at the end, with all the stress and potential for error that entails.

    • I absolutely agree with you, both on getting a reasonable deadline (with some margin for error) and also getting going on it sooner rather than later!

  9. Great suggestions, Ali! I’ve always had friendly competition with deadlines. I challenge myself to beat the deadline, so I create a pre-deadline-deadline, and aim for that. That way, I never even get close to the deadline. Not a fan of the word deadline, either. It’s so ominous. I like the idea of a lifeline I grab onto and let it lead me to fun and success. 🙂

    • Hehe! Yeah, “deadline” isn’t a particularly nice word. And I like the pre-deadline-deadline idea — I usually do something similar. It’s always nice to be able to turn in work early!

  10. Miss Ali !

    It was a good post. I had made many mistakes in past but Now I only take projects which don’t have very hard to meet deadlines.


  11. Every time I have a nasty deadline, I say never again…but then next time, there it is again. The thing is, I often do my best work under at least a little bit of pressure because I’m not stopping every five minutes to look at news sites, Twitter, blogs etc.

    The best tip I have is for those of you that do article writing and need to get hold of sources: when they ask what your deadline is, never tell the truth. Always give a date at least four days before your real deadline. I find that the writing itself never takes that long, it’s messing around trying to get hold of people. So save yourself the angst.

    • Yes – great point about getting *other* people involved with your deadline. I always tell them a few days earlier … because there’s invariably someone who’s late!

  12. Like The Pomodoro Technique – there’s some great free online timers that help. is one

  13. Great post! They do loom like monsters. After years of wrestling with them and being scared of them, I decided to talk to them–and I’m very hopeful about the results! The conversation is on my blog.

  14. The best way to win a deadline is to choose projects wisely and then plan your work. Starting working on a impossible kinda project is the first thing that can blow you away.

    Choose projects wisely and then start working fast at the earlier stage. One can also set his/her own deadlines.

    Good work Ali. keep more coming 🙂


  15. Deadlines always cause me stress. Having the right state of mind can turn it into a powerful motivation, but I think that comes with a strong sense of determination and the decision to go from doing it someday to it being the priority. That feeling that you can’t get it out of your mind until you’re successful that feeling that this is what I must do versus I didn’t want to deal with this to begin with.

    Deadlines have helped me determine what is most important and to scrap the rest.

  16. My first employer in publishing — a writer himself — used to say that once a project had a deadline, the joy went out of it for him, and the project after it suddenly became exciting. His strategy, then, was to slog away at the current project, but jot down ideas about the next one as they occurred. That way, when the current project was finished and the next one became scheduled and lost its luster, the creative work had been done. This balance of duty (the current project) and fun (the next project) is sort of like promising a child desert once the peas are all eaten. Works for me.


  1. […] How To Wrestle With Deadlines And Win (Even when you think you can’t) – Oh how I needed this article. Thank you thank you thank you. “Deadlines are like zombies.” <— NO KIDDING! […]

  2. […] How To Wrestle With Deadlines And Win (Even when you think you can’t) – Oh how I needed this article. Thank you thank you thank you. “Deadlines are like zombies.” <— NO KIDDING! […]

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