Do you finish early?
Putting the DEAD in deadline đź’€
3 October 2025
This week is all about meeting deadlines. Call it project management, life admin, or “finally getting your sh*t together” – whatever label you go with, it comes down to the same thing: delivering on time.
One sassy reader suggested I should cover this topic after missing a couple of WIWILAS newsletters (ok, three) in August. Touché!
Delivering when you say you will is one of the most underrated life skills out there. And it’s not just about being trustworthy and reliable. Research shows that sending your work after the cut-off leads people to judge it more harshly, even if only slightly late. (Strangely, delivering early doesn’t tend to win you any extra points – so don’t kill yourself trying to be the teacher’s pet.)
School taught us about deadlines by dangling fear over our heads: setting homework and coursework, with the threat of detention if you messed it up. We were never given concrete strategies. No one taught us how to manage projects in a way that makes deadlines doable.
That schoolwork could have been practice for building those time management muscles. Instead, most of us just learned to dread the ticking clock. At least, I know I did!
I was terrible at it. Rushing essays the night before they were due, riding the wave of adrenaline because I couldn’t start until the pressure was unbearable. It seemed to come naturally to some of my friends. But I always felt like I could have used a bit more specific instruction. Not just “you better not be late,” but “here’s how you actually break something big down into pieces that won’t crush you.”
When I started freelance copywriting, I had to rewire my perfectionist brain. I was always drawn to writing because it allowed me to fuss over my words until I was happy with them. I used to think I’d have all the time in the world to get them right. In reality, clients want something on their desk by tomorrow, not your magnum opus in three weeks. I had to learn that useable and on time always beats perfect but late.
A metaphor I find helpful: picture your time as water dripping from a leaky bucket. You don’t notice it going, but eventually it’s gone. You can’t plug the bucket. But you can learn how to use what you’ve got before it disappears.
Below, I’ll share the strategies that have worked for me, a few of them pinched from the world of ADHD (because nobody knows what it's like to wrestle with deadlines more than people with ADHD). Some of these tips I covered in my July letter on getting sh*t done, so if you missed that one, that’s worth a look.
Note: I’m writing this newsletter during a week away with family on a full digital detox – no phones, no laptops – which makes sending it out a little trickier… But it also gave me the perfect excuse to practise what I’m about to preach.
Don’t bite off more than you can chew (Set Expectations)
Overextending yourself is a killer. All it takes is one “innocent” extra line in an email and suddenly your project has doubled in size. The only way to survive is to be upfront about what’s doable, and involve whoever else is on the hook – your client, your boss, your teammate – so they’re in on the decision. It helps to strip things back to the essentials: what’s the minimum viable version here? When the clock’s ticking, it’s good to know exactly what can be cut. My personal pitfall is people-pleasing: I overpromise, then scramble to deliver. Learning to say no – or at least underpromise then overdeliver – is the only way I’ve managed to stop drowning myself.
Work backwards from the end (Overarching Timeline)
Let’s put the dead in deadline. Before you even start, run a pre-mortem: imagine what could go wrong and kill the project before it’s finished. Then plan for those scenarios up front. Once you’ve spotted the weak points, take the final date and work backwards. What has to happen one week out? Two weeks out? What needs to be in place tomorrow? When you’ve sketched the bones of a timeline like this, deadlines stop being a foggy cloud of doom and become a series of stepping stones.
Shrink the monster (Micro-Deadlines)
Big projects can feel like a giant beast looming over you, but the trick is to cut it up into something you can actually face. Set yourself daily or weekly quotas, tiny deadlines that add up. It’s like marking levels on that leaky bucket: suddenly you can see where the water’s at instead of guessing. Every milestone becomes a mini-victory, and those wins quickly add up to real momentum. If you’re bad at breaking things down yourself, there’s a handy GoblinTool that will do it for you.
One thing at a time (Timeblocking)
If your bucket leaks no matter what, then the only thing you can do is use the water wisely. Nobody has unlimited focus – even Darwin and Dickens only managed about four concentrated hours a day – so knowing when you’re sharpest is key. Make sure you use those productive hours for deep work, not emails. And forget multitasking – it doesn’t exist, it’s a myth! Instead, grab a timer and set yourself a 25-minute challenge: pick one of your micro-deadlines, and do everything you can to reach it before the buzzer goes off. A visual timer works well for me because you can literally see the time leaking away. If you’re prone to distractions (guilty), keep a pad of paper nearby to scribble down stray ideas so they don’t derail your work.
Lie to yourself (Artificial Deadlines)
Here’s a sneaky one: give yourself a fake deadline a day or two earlier than the real one. That extra buffer will give you some extra breathing room to polish, tweak, fix mistakes, and send with confidence instead of panic. The other side of this is aiming for a “good enough” first draft fast. Get something workable down early, then give yourself permission to refine it later. Better an ugly duckling draft on time than a perfect swan that never arrives.
Tell someone, then do the thing (Social Accountability)
When someone else is relying on you to deliver, the pressure’s built in. But with personal projects, the stakes can feel lower. Nobody’s marking you down if you don’t deliver. That’s where social accountability comes in. Tell a friend, post it publicly, promise someone you’ll send it by Friday. That’s why this newsletter goes out at all: the world won’t end if I skip a week, but knowing you’re waiting for it gives me the kick I need to hit send.
The Deadline Debrief (Post-Mortem)
Once the dust settles, take a moment to look back. What went right? What went wrong? Did the water leak out quicker than you thought? Next time you’ll have better info to estimate with. My favourite version of this is the super-simple + – →: write down the positives, negatives, and what to do next. It takes five minutes but can save you hours the next time around.
So there you have it! A newsletter all about how to deliver on time, delivered on time…
Meeting deadlines isn’t about locking yourself into some military-grade routine, optimising every second so tightly there’s no room left to breathe. It’s about having the right strategies in place so you can build momentum and actually get the work done on time.
I didn’t use all of the tricks above to get this newsletter out today, but I did manage a few: working in 25-minute chunks when I could (timeblocking), getting a sendable draft ready the day before (artificial deadline), and – most importantly – having you, my eager audience, waiting to receive this message (social accountability).
Yes, I bent the detox rules this week and got a sliver of laptop access to send this out. But most of it was scribbled on paper first, then quickly typed up later. Quite nice to work like that sometimes!
You can refer back to these tips whenever you’re staring down a deadline… or you can just print out this Deadlines Cheatsheet. It’s in a quick-fire question checklist format, designed to fold into a little zine if you’re into that sort of thing.
I’m also toying with the idea of building a tool – something like this one mentioned above, but geared specifically towards meeting deadlines. What would help you most? Breaking projects into milestones? Reducing the scope? Making yourself accountable? I’d love to know which parts of meeting deadlines you struggle with, and I’ll see what I can come up with.
PS. This extra tip just landed in my inbox, right on time:
Advice for big, daunting projects: do something right away.When a major project lands in your lap, perhaps with a deadline weeks or months away, make it your business to take some kind of concrete action on it as soon as you can, even if you won’t get to the majority of the work until later. The longer such a project sits on your plate without being engaged, the more intimidating or resentment-inducing it’ll grow – and the more mental energy you’ll expend either on fretting about it or trying to avoid thinking about it. On the other hand, taking action forges an inner relationship with the task that saps it of its power to intimidate, while also allowing your subconscious to get to work on it in other ways.