We all need deadlines.
Whether they’re self-imposed, or come from a client or collaborator.
Creative work is hard. We all feel fear, resistance, a sense that we’d rather be anywhere else doing anything else than working on our current project. Even if we’re excited by it, too.
Deadlines help us through that. They motivate us, impose a discipline, give us something to aim for.
For most of my working life, the only reason I finished any writing at all was a deadline – and I’d often just about scrape in on time, working late into the night it was due. Even if the delivery date was a long one.
Yet we dread them, too.
In a recent coaching session, a writer told me gloomily that she was behind on a book project, and feeling overwhelmed. She was considering cancelling her family’s summer holiday, and was turning down new work. Which also left her worried about money.
I asked about the book. It was fairly straightforward, on a subject she knew well. Then I checked the delivery date. It was March 2028. She had more than two years to write it. Yet the deadline was already looming, casting a dark shadow over her life.
She is not a writer who enjoys working on multiple projects at the same time. She prefers to immerse herself in one subject rather than skipping from job to job. But once we discussed it in detail, she realised she should easily be able to deliver the book on time if she dedicated at least a week-long block to it every month.
Every quarter, she decided to assess her progress, and see if she needed to adjust. But as she’d often be able to dedicate more than a week, she might even finish early. Without drama, doom, cancelling holiday plans or turning down other paid work.
I’m sharing this story because it’s not unique. Many of us, when faced with a deadline, either go into a doom spiral or behave like a trapped animal, willing to do ourselves serious harm to break free.
Why do we approach deadlines with such a sense of doom?
Perhaps the answer lies in the origins of the word.
Andersonville military prison was built in 1864 to hold Union prisoners during the American Civil War. It was a dismal place. Historians estimate that of the 45,000 prisoners of war held there, 13,000 died of disease, thirst or starvation.
The crude wooden fence would have been easy for soldiers to climb, so the camp’s commander, Captain Henry Wirz, ordered the construction of a ‘deadline’, marked by planks of wood 20 feet inside the outer fence. Guards in towers on the perimeter would shoot dead any prisoners who crossed this line, even for a second.
It was effective way of keeping prisoners contained. Although after the war, Wirz was tried for war crimes and hanged for this brutality.
Unsurprisingly, the idea of the deadline then disappeared.
The word was revived the 1920s, when newspapers started using it – most likely humorously at first – to mark the final time copy could go to the printers and still be included in that issue.
Now we all use it, but it has somehow never lost its threatening undertone for many of us.
But perhaps we don’t need to call them deadlines. In his excellent book I’ve Got Time, Paul Loomans suggests using the term “delivery agreements” instead. I like how collaborative and positive that sounds, and I’m finding it useful. Even when the agreement is mainly with myself.
I often think of my creative self as a toddler.
She’s delightful, surprising, playful and imaginative. She loves exploring, and sees the world in quirky ways. But she’s also unpredictable, easily overwhelmed, and prone to irrational tantrums.
Given a deadline, she immediately rebels. “I don’t want to! You can’t make me!”
Simply changing deadlines to delivery agreements tames my toddler/rebel, and reminds me that on the whole, I write because I want to. And being paid to be creative is a privilege, not a chore.
A few more thoughts about deadlines:
Delivery agreements are often negotiable.
It’s all about communication. When I was a magazine editor, I much preferred the contributor who called to ask more time to the one that simply vanished.
If you know that copy or images are going to arrive two days later than you’d hoped, you can often work around that. When you’re ghosted and you’re unsure it will arrive at all, that’s a much bigger problem.
Whenever you’re feeling under pressure with work, it’s always worth a discussion to see if there’s any flexibility. And the sooner the better: it gives more time for the other side to change their plans.
Sometimes just knowing you could have more time is soothing – and suddenly the work flows, and you find yourself delivering to the original agreement.
Work expands to fit the time available.
Constraints are important. Especially when you’re working on personal or speculative projects, where no one else is waiting for the finished thing.
I often use a timer to help me focus, to create a sense of urgency, and to know when I’m done for that particular writing session.
And it’s worth always defining, before you start, what ‘done’ or ‘good enough’ looks like, for this version of what you’re working on.
A rough ‘About’ page for your website, a quick post on your socials, a shitty first draft or a messy sketch can often be better than nothing at all. And you learn so much more from doing the thing than from over-thinking it. Or avoiding it altogether.
What we get from leaving it to the last minute:
I know I can write well under pressure. Some of my best work has come from an editor calling me in the morning and asking if I could deliver an opinion piece by 3pm for the following day’s newspaper.
I couldn’t do this every day. It wouldn’t be sustainable for me, and would quickly lead to burnout. But looking back on my career as a journalist, I realise that I often created this pressure myself because I was afraid of doing the work, forever fearful that this time, it wouldn’t be good enough.
Leaving it to the last minute somehow relieved that – I just had to do the best I could, in the time remaining, using adrenaline as fuel.
It also made life joyless, because I didn’t ever do anything fun in the time I was procrastinating. I got lost in busywork, admin, unnecessary ‘research’. Or just distracted myself with computer games, or internet surfing that wasn’t work, but wasn’t fun, relaxing or social either. Then worked late into the night, exhausting myself to hit the deadline.
Sometimes, done is better than perfect.
There will be times when you have to choose between meeting a deadline, and doing it to the standard you’d like.
If the delivery date can’t be stretched, aim to produce something that’s acceptable. It might not be your best work, but we can’t be exceptional every time. Being reliable has a value, too.
Even if the date is flexible, beware the endlessly stretched finish line. Delivering a serviceable result on time is still better than never delivering a brilliant one. Getting flawed work out into the world is always more useful than having lots of brilliant ideas you never execute.
How I deal with deadlines or delivery agreements now.
This is simple and probably obvious. But I didn’t do it for my first 25 years of journalism and book-writing, so I’m sharing it in case it’s useful to you, too.
1. Write all delivery agreements in your calendar.
Now estimate how long you think it will take to do each one.
2. Give yourself a buffer.
If you’re anything like me, you’ll be wildly inaccurate in your estimates at first, so add lots of extra time on. Even now, when I have a much better idea of how long an idea will take me to develop, I add 20% extra so I don’t feel rushed, or go off the rails completely when problems or interruptions arise. If I finish early, I can always take some time off, or I can choose to go onto the next thing.
3. Block out the time.
Working backwards from your due date, schedule the time you need in your calendar. When other jobs or commitments come up, you can always move these blocks around – provided you’re still doing the number of hours you committed to do.
4. Assess regularly.
With long-term projects, check in on your progress regularly. Then make any adjustments you need, to finish on time. I do this monthly, and make any major adjustments needed when I make my next 90-day plan.
5. When the work is done, close it out.
Make notes about what needs doing next and put all your materials together if you’ll need to do more work on it later. If it’s complete, archive everything properly. Tidy materials away.
If there’s anything you’ve learned, anything you might reuse, make a note of it and label it so you’ll easily be able to find it again. (With me, this is often a checklist, a little map or step-by-step guide on how to do tech tasks, because I’ll inevitably forget by the time I need to do it again.)
There’s something very satisfying about clearing your workspace after a major project, and making space for something new to emerge. But even after completing a short task, close the open tabs on your computer, put the papers or materials away.
6. Finally, take a beat before rushing onto the next thing.
Celebrate your wins. But even with smaller tasks, just breathe, stretch, make a drink. Then decide what’s important to work on next.
Your day will feel more spacious, less frantic. And you’ll also move onto the most important thing, or the thing your current level focus/energy will allow you to do properly rather than just jumping in on what looks urgent or is sitting near the top of your in-box.
What do you think?