Cried But Did The Thing Anyway – Advanced Schedules and Deadlines (2)

cbdtta_tiny[Click here for other posts in the series Cried But Did The Thing Anyway – Life of a Freelance Writer]
Part the Third, Continued –
Advanced Schedules and Deadlines (2)

Last week, I talked about some ways of scheduling that are less likely to drive you bananas than some other ways. But as far as deadlines go, setting them is just the beginning. You also need to know how to keep them… and how to fail them. Yes, you read it right. Failing deadlines is an important element of AS&D. I’ll get to it. (Hey, no skipping ahead, you there.)


Discipline is choosing between what you want right now and what you want most.

~ Unknown Author

Discipline is writing this dumb blog when all you want to do with your Sunday evening is play Fallout.

~ This dumb blog’s author

Keeping Deadlines
When it comes to keeping deadlines, the first thing I want to talk to you about is discipline. Actually, I don’t. I just came back from bridesmaiding at a wedding weekend, and next week promises to be packed, since I’m at least a thousand words behind on my writing goals, five pages behind on my translation gig, and about eight hours behind charity work. And instead of either catching up on any of the above or enjoying my last few hours of freedom, here I am, performing a feat of spectacular irony and writing a blog about keeping deadlines.

…But in a way, I suppose this is the point of it all.

Prioritizing Your Deadlines
Most of us in the freelancing world are working on several things at once. You may be balancing paid work with personal projects, or juggling the work you do for several customers. Even if you don’t need to worry about the money at this time (you lucky bastard), you probably have several projects in the pipeline, and, at the very least, have to balance them with social/family life. And if you’re in total control and ownership of your life, and dedicate all of your time to one masterpiece, chances are that your magnum opus requires several types of work. The point I’m trying to make – we tend to multitask and juggle several schedules.

Now, if you look for advice on prioritizing your work, you’ll be told of the wonderful principle called Due First = Do First. I’d like to add my two cents to it.


Seriously, it doesn’t take a life coach to figure out that if you’ve got Deadline One tomorrow morning and Deadline Two a week from now, then work on Deadline One takes precedence. But oversimplifications like that (just like ‘work smarter, not har– *book to the head*’) have two problems. They (a) don’t care about the nature or origin of either deadlines or work; (b) assume that a human is a machine without motivation problems.

Is Project One due tomorrow because you’ve been procrastinating on it for days, or because it was dumped on your head an hour ago, with promises of great rewards for success / threats of grievous bodily reputational harm in case of failure? Is Project Two a revised manuscript you promised your editor, and Project One a guest blog for a friendly writer? Is One a paid gig that you hate, and Two a piece of art that keeps you going?

The ultimately sensible thing to do is to discard any and all such considerations, and proceed to do the work in order. Alternatively…

Put Internal Deadlines First

This may sound counter-intuitive, but years of practice have taught me to put my own projects before any work I’m doing for someone else. I do this because I’m very responsible before other people, but much less so before my own aspirations. I often stay up until ungodly hours to deliver a project on time. I have done so in the past, and I will do so in the future. But my own work? If I’m already tired from other stuff, I’ll find a million excuses to dodge it.

My brain doesn’t work well at this late hour! (says a chronic nightowl)

I’ve got zero inspiration right now, anything I write will come out as crap anyway! (says a novelist writing her first draft)

I’ll do more tomorrow! (says a freelancer with the next week planned to the minute)

What’s one day in the long run? (says a mortal human being)

Even when I overcome any of the above excuses, and 999,996 more, I find myself looking at the clock all the time, and quietly despairing at the fact that I’ve been up for, what, fourteen, fifteen hours now, and WHAT have I got to show for it, oh, wow, two hundred words down, real impressive, let us all slow clap now…

That feeling, more often than anything, becomes a reason to quit for the night, and go to bed, feeling worthless and promising to do better tomorrow.

On the contrary, on days when I did my own work (which usually means writing) first, I don’t mind staying up till whenever to meet an external deadline, bathing in a vague sense of pride because I DID IT. I made myself do a thing without anyone standing over me with a stick, and I’m one day closer to my goal. It’s a bit like that feeling you get when you get up without hitting snooze, even though you know you can sleep for another hour without missing any appointments or planes.

So, put internal deadlines first whenever you can afford to. (Hint: when you try, you’ll find you can afford it much more often than you think.)

Scale of Schedule vs. Size of Project
Let’s say you’re completely the boss of yourself and all your deadlines are internal. You are working on several projects of different size, and you’re the only one deciding on your delivery dates. You don’t even have a kickstarter to answer to.

…You RECKLESS creature.

But if that’s the case, I say you should prioritize large to small. The longer a job takes to complete, the higher the chance that you’ll lose interest in it halfway, and without an external deadline to answer to, you might proceed at a snail’s pace, or abandon ship altogether. With this in mind, when deciding what to do first on your work day, pick that day’s allotment of The Big Thing and get it out of the way. After that, everything else.

Pro tip: if you’re playing a long game (writing a novel, drawing a long comic book, composing a rock opera, preparing a series for an exhibition, or doing anything that takes several months or more to complete), it’s a good idea to do a small job on the side every now and again – if nothing else, for the sense of accomplishment in actually finishing something. Because somewhere around Day 134 of a year-long quest, that vague sense of pride I talked about earlier can be altogether too vague, to the point of transparent. At times like that, getting a small self-contained thing done can really boost your spirits (not to mention that when asked ‘so, how’s work?’, you can say something in addition to the usual grunt about that same damn book/comic/record/exhibition/solution to global poverty that’s taking so damn long).

With this in mind…

Pick One Iron-Clad Project
+/it helps/
With a(n Semblance of) External Deadline

Schedule A Thing to do every so often. And then do The Thing. No excuses.

Seeing as my main project right now is my novel, you’d think that’d be my iron-clad thing. But no, it’s not – because my novel is the guns I know I’ll be sticking to. It, and the series it is part of, is something I can soon start describing as ‘my life’s work… so far’, and I’m invested in it enough not to quit. Blogging, however, is something I’ve always wanted to do but never had the discipline to.

So I took the leaf out of the book of iiSuperwomanii, who, close to the start of her YouTube career, made a promise to herself and her audience that she would post a new video every Monday and Thursday. That was several years ago, and so far, to my knowledge, the number of weeks where she didn’t live up to that promise is ONE. She has now done over 300 videos and has close to four million subscribers.

Me, I’m on my fourth blog post, and strongly suspect I have an audience of under ten at this time, but I Intend To Keep Doing This Thing. (This is the point where I ask you, the reader – if you read this and like this, pretty please let me know, whether by liking this post, subscribing to get more, dropping me a note on twitter – anything will do. Don’t be shy, I promise I love every single one of you, and any bit of response makes me squee. Knowing that someone reads this crap I write is what keeps me going.)

Done with plug, back on track: Pick a thing, pick a time, and do it. Like I said, no excuses. If you’re conscious on the Day of The Thing – then do The Thing. (If you’re unconscious, I hope there’s someone who can take care of you.) Plan in advance if you must – if you expect to be away from your normal working environment or unable to work on The Day of The Thing, then do it a day early.

And if it so happens that you skipped The Day of The Thing – then do it a day late, do a smaller version than you would otherwise. But do it. Don’t write the day off and promise to do the thing the next time – because chances are, you won’t.

I can go on about this, but that might take me into the next week, and I fear that a post titled Cried But Did The Thing Anyway – Life of a Freelance Writer, Part Four: Advanced Schedules&Deadlines Part Three might land me with a cease and desist order from Fall Out Boy, so I’ll move on to the last part of the deadline life cycle, and that is…

Failing Deadlines

First off, this isn’t me being defeatist. I don’t think every deadline ends in failure. But if I wrote a section titled ‘Conquering Deadlines’, it would be limited to the word ‘PAR-TAY!’, which, while refreshingly brief, could be fairly superfluous.

So, let’s talk about the less fortunate option. Learning to fail deadlines is almost as important to a freelancer as learning to fall correctly for an ice skater or an acrobat. If you see the fall coming in advance, you might prevent it. And if you can’t avoid it, you can do your best to minimize the damage.

Finding Your Feet Again
This is something you can do if you budgeted some contingency time. There are two ways of straightening out a schedule that’s about to collapse – playing catch-up or picking up the pace.

If you can catch up on a chunk of work you missed in a fairly short time, do it. But remember that working extra hard for a few days in a row means you’ll be more tired on the days that follow. Plus, it’s quite disheartening to do a full day’s work, only to conclude that – yay, now you’re only TWO days behind schedule. If that’s the case, the second method might do better for you.

The second method is adding a much smaller chunk of work to each of the remaining days. Less disheartening in the short run, more so in the long one, as the accumulated work load leaves less time for whatever else you might have planned. Plus, this method can get out of hand if you slip more than once.

Personally, when trying to correct a slipping deadline, I use the first method with the condition that each catch-up day cannot have more than 150% work of a normal day (meaning, a catch-up day is equal to a normal day and a half). Sometimes, it also helps to space such days out a bit – let’s say, after missing ten pages once, I have a day when I do fifteen, then return to my normal pace for a few days, and then do fifteen again, maybe right before my day off, to have an incentive to push towards a pit stop.

Most of the time, if you keep an eye on your real vs. planned progress, catching up is a thing. But every now again, a fall happens. Then, your best chance is…

Trying to Land On Things Other Than Your Face
Maybe you misjudged the amount of work, or didn’t budget any extra time, or life and universe happened. Whatever it is, it’s X days to project deadline, and you’ve been playing catch-up for the last week, and your daily workload has swollen to double its size, but you press on, telling yourself you can still make it.

Maybe you can. Maybe you can afford to drop everything else, focus one hundred percent of your energy on the project, and limbo dance your way under the dropping deadline. And, hopefully, learn from it and schedule better in the future.

But maybe it’s been a few days since you told yourself you can make it, and it looks like the only hope for you is working ten twenty-hour days, and then you have one of the Days When You Just Can’t, and cry for two hours, and sleep for twelve, and then you’re up and the work is still there, and There Just Isn’t Enough Time…

In that case, this is what you do:
1. Stare at the pile of work in the hope that it goes away.

2. Accept the fact that it won’t.

3. Consider the original deadline.

4. Consider the amount of work left – carefully!

5. Figure out how long it would take you to do it at your usual pace – realistically!

6. Take about three quarters of that time (this means you’ll be working a bit harder than you would otherwise).

7. Make a new deadline by adding the time from (6) to wherever you are.

8. Add one more day to that.

9. Compare the result to your original deadline.

If delivering your project on your new deadline means being no more than 10-15% late (11 days instead of 10, or ten weeks instead of two months), you’re okay. No, really, you are. That rule about planning 25% of extra time I wrote about before, I didn’t invent it arbitrarily. That figure is the bread and butter of time management in the professional world, meant to accommodate for various screw-ups. It doesn’t feel good knowing that this time, the screw-up in question is you, but such is life. If it’s any consolation, I can promise you that you’re not a singular glitch in an otherwise perfect clockwork of a project. Chances are, you’re only one of many people currently mucking things up. Because that’s what people do. People trained to work around this are called managers and paid a lot of money.

If you’re more than 10-15% late, well, you can feel a bit bad about yourself, see if there are any corners you can cut to trim your time down… But if you can’t, then your new deadline is a fact of life, and something both you and your client will have to deal with.

10. Stare at the new deadline in despair, wishing you were a better, more disciplined person without any organization problems or any need for sleep.

11. Calm down and write a message to your customer, informing them about the new deadline. Do your best to be polite, but assertive. Asking ‘can I have X more time on this project?’ leaves them the room to say ‘no’. Saying ‘I’m very sorry, but completing the project will require X more time’ gives them the facts, which they may not like, but have very little control over.

12. If pressed to negotiate the new deadline, HANDLE WITH EXTREME CARE!

Adjusting a deadline once is a thing that happens. Having to adjust it a second time is… cringeworthy. So once you set your new deadline, you HAVE to keep to it, come hell or high water. But here’s the kicker – if you ask for a new deadline, and the client talks you down to a middle ground between the original one and your proposal, and THEN you fail to deliver to that one, the only thing they’ll remember (or make a point to point out) is that you were given more time, and STILL you failed. So, stand your ground as hard as you can. If your client is known to always try to trim a few days, plan for that, and give them a more generous estimate to start with.

13. If offered extra payment to finish sooner, HANDLE WITH EXTREME CARE!

Hey, it can happen. Maybe they’re understanding of your time problems, but they really do need the project on time, and they’re ready to pay extra for it. This is an even more precarious situation, because if you agree to take the extra money and then miss the date… No, man. Just no.

14. If told to send the project in ‘as is’, for someone else to finish, send NOTHING until the financial side is sorted out!

I know, you feel bad about yourself. I know, you feel like you don’t deserve to get paid a single penny for this horrible, disgraceful failure. I know. I know. But you did a chunk of the work, and once problems appeared, you were upfront about them, and you need to eat. So if your extended deadline notification gets a response that’s the freelance equivalent of ‘YOU’RE FIRED’, don’t rush with the reply to that one.

I’m not going to go into detail here, to avoid this post turning into Freelance Customer Negotiation 101 (hey, new post idea!). But, however crappy you may be feeling for being taken off a project you can no longer deliver, stuff your self-loathing for long enough to make sure you can continue feeding yourself.

15. (assuming you didn’t get dropped off the project) Get started on the new deadline – and, for the love of god, DELIVER.

But first! Remember that extra day I had you plan for? That’s the day on which the rescheduling and painful conversations with the client happened. Feel free to spend the rest of it digging yourself out of the pit of self-loathing. I recommend spending some time with a friend watching Disney movies.

We Are Not Interested In The Possibility of Defeat…
I’m fully aware there are some deadlines that cannot be failed, because failing them will result in grave consequences to your professional reputation and career, letting people down, and many other unpleasant things. For those cases, my range of solutions is limited to copious amounts of caffeine as an interim measure, and much, much better planning in the future. If you think you have no room for failure, plan accordingly. Alternatively, instead of signing up for a ridiculous deadline on a highly important project, explain your current time situation to your customer. In the majority of cases, a more accommodating schedule can be worked out. In a sad minority of cases, they’ll go look for someone else. It sucks, but if they remember you as a responsible person, they might approach you again. If you take the job and then fail to deliver – not so much.

Gloriously Meeting Deadlines
I know I said I wasn’t going to write about this, but this post got depressing as hell towards the end. So, here’s my instructions for when you’ve met a deadline. It is very important that you follow them religiously. The success of your next project depends on it.



Filed under Cried But Did The Thing Anyway

4 responses to “Cried But Did The Thing Anyway – Advanced Schedules and Deadlines (2)

  1. Pingback: Cried But Did The Thing Anyway – Playing Office | The Coffee Clef

  2. Riibu

    Oh, I am reading these posts! And I am considering their insights. 🙂

  3. Pingback: Cried But Did The Thing Anyway – Readers’ Questions Week | The Coffee Clef

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