How to stop worrying and learn to love deadlines

How to stop worrying and learn to love deadlines


To be a freelancer is to live with the terrifying and tedious reality that sometimes you’ll have nothing to do and sometimes you’ll have 14 things to do (and in the time you’ve spent reading this sentence, it’s become 16 things – sorry about that).

An uneven workload is part of the gig, but tight deadlines have a tendency to make capable, productive adults feel like children late on a Sunday afternoon who haven’t started their homework yet. Deadlines needn’t inspire terror, however: when they’re not making you feel queasy, they give shape to what otherwise might be shapeless.

Without firm endings in sight, all of my work would take at least a third longer to complete. There are certain ghastly pieces from the start of my career that – if I hadn’t been professionally obliged to kick some sense into them – I might still be writing today.

As with most arduous things, the solution to meeting deadlines is boring and expected. There is no revolutionary diet, no one weird trick, just regular exercise and healthy food.

The best way to finish work on time is to plan effectively based upon your knowledge of the job in hand and an honest appraisal of yourself. Which tasks are urgent and which ones can wait? What time of day are you most productive? What slows you down?

To varying extents, we’re all blighted by a magical optimism when it comes to our own productivity, but you should know how long it realistically takes you to do certain tasks, either at your regular pace or at a sprint (if not, then there are time-tracking apps that can provide an idea).

This will help not just in planning how to meet a deadline, but whether it’s even feasible; the best time to negotiate a deadline is before you start a job, rather than hours before everything is due.

Likewise, if you know you’re not going to make it then it’s better to tell your client with a fair amount of time than to wait until the deadline floats past. Even if finishing a task takes just as long, it’ll cause less consternation to meet an extended deadline than to miss the original one.

The ‘portion control’ solution here is factoring in a buffer period for the inevitable deto lays: your schedule should not be so tight that a roguish broadband connection one morning will derail you entirely.

Missing deadlines has consequences, even if it’s just that someone is a bit grumpy. There are clients who will be understanding if you’re slightly late – they’re working with buffers of their own. But it only decreases the likelihood that they’ll want to use you again, not to mention that it’s hard to maintain the high ground about someone not paying invoices promptly if you can’t deliver your own work on time.

At every point in the process, clear and specific communication can avoid frustration: if someone has said the deadline is Friday, does that mean by the time they arrive in their office on Friday morning or by the end of Friday? And what is the end of Friday, anyway? Is that the end of the work day or 23:59?

These are all questions that are best asked and answered before Friday morning, whatever that may mean. The best practices can only help so much when time is against you. In those frantic situations it helps to focus on the work rather than the time you have left.

When my deadlines are at their most pressing, I squirrel away my phone and delete the clock from my desktop taskbar. Obviously, sometimes you will need to work longer hours, but even then, it’s better to allow for this possible outcome. If I have a lengthy job, I’ll try to make sure I don’t have major evening plans for the last couple of days, just in case.

An all-nighter can seem attractive when matters get desperate, but more often than not, you just get a few more hours and you lose most of the next day to sleep or sluggishness. As a piece of emergency kit, it’s a lifejacket under your seat: it might save your life, but you don’t want to end up in the position where you need it, as that means you’re about to drown.

The real problem isn’t the scheduling, of course, it’s the work. An honest appraisal of oneself entails being frank about procrastination. Everyone develops their own ways of putting off work – each day, I get through a bathtub’s worth of tea, so I can dawdle by the kettle, and my flat is ruthlessly clean, because I start tidying whenever I’m stuck (and I’m almost always stuck). 

Social media is a massive time drain: it’s difficult when the machine that facilitates your work also happens to give you immediate access to everyone you know, all human knowledge ever and videos of corgis playing swingball.

Scheduling can be dangerously close to procrastination too, an activity that merely looks and feels like work. For my first book I created an elaborate planning spreadsheet that was beautiful as a digital organisational worksheet can be, but I barely referred to it.

Now I plot out my days with a bullet journal, eschewing the gorgeous, ornate designs that online articles suggested in favour of something that was quick and clear, and designed to be used rather than admired.

To combat procrastination, willpower can’t be taken as a given – it’s more pragmatic to admit the ways you distract yourself and ensure they’re not readily available when you’re supposed to be working. Famously, Jonathan Franzen used to write while wearing a blindfold and earplugs, but it isn’t necessary to be quite so radical.

I recently added an extension to my internet browser which blocks specified websites during set hours of the day. I still find myself instinctively heading for Twitter whenever I can’t think of my next sentence, but instead of strangers arguing, I’m greeted by a black screen and a gentle reminder to get back to work. This usually does the trick, and if it doesn’t then at least my carpets get a good vacuuming.

By Jason Ward