The Born Freelancer on the Sanctity of Deadlines, Part 2

This series of posts by the Born Freelancer shares personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? We’d love to hear from you in the comments.


In my previous post I talked about why deadlines should be considered sacrosanct.

Today I want to talk about how to ensure you always make deadline. Everybody will develop different strategies; these are a few of my own.

When is it due?

When a deadline is given, you can accept it or attempt to negotiate it. In many cases a deadline is set in stone; in others there is room to manoeuvre. It will depend on many external factors that your employer may have no control over.

Ultimately, only experience will tell you how much time you will need. 

Some freelancers work fast. Some require multiple time-outs during the process. Others will plough through in a mad fit of productivity. Only you know your own needs. You must learn to assess a project before you begin it to roughly determine how long it will take you to complete. If you don’t, you won’t last long as a freelancer. 

If you can negotiate the deadline, always ask for more time than you think you need. First, it is a useful tactic as they may come back to you with a revised deadline more to your liking but still less than you requested. Secondly, it gives you built-in cushioning for unforeseen developments.

As a freelancer you always have to expect the unexpected.

Sometimes the unexpected will be organic – you will find new sources, etc. Other times they maybe wholly unwarranted – like one assignment I had when the boss ordered multiple minor changes. Why? Because their spouse requested it.

And all by the original agreed-to deadline, of course.

Curiously, I have rarely found any benefit in getting my work in before an agreed-to deadline. You may think an employer would be grateful and think more highly of you but in fact it almost never works out that way. Most employers can’t actually use your work before the agreed-to deadline. It will probably just sit in their inbox.

As for being grateful, forget it. It will more than likely result in them thinking the work was too easy and that you were asking too much time and money for it. Your next assignment may reflect this revised opinion.

Get your work in on deadline. Not a moment later. But rarely ever earlier.

Get the deadline clear in your mind

Once the deadline has been agreed-to, use whatever methods and technology to imprint it in your mind. 

I still use multiple old-school wall calendars that show me visually at a glance deadlines and estimated dates by which I should have achieved various goals – rough drafts, first drafts, etc. 

That way I can judge day by day if I’m on my estimated schedule or slipping behind.

Start it right away

It doesn’t matter if it’s just a rough outline or a preliminary interview. I find it important to begin a contracted project as soon as possible. It starts a timer in my head that helps me to sense how much time I need versus how much time I have left. Of course, I’m not going to finish it right away (well, rarely, anyway). But beginning cements a project in my mind as something real. Until that point it remains abstract. 

As deadline approaches

For many of us, the ticking clock is an amazing motivator. It focuses the mind and forces concentration in a way no other factor can. I have previously referred to a deadline as both a hated bully and beloved muse – and for many of us it is exactly that paradoxical combination.

But sometimes there are circumstances beyond our control. 

You must learn to adapt, improvise and roll with it.

I once had my home computer literally melt down on me late one evening – it had seriously overheated – and I had no choice but to spend a completely sleepless night rewriting by hand from memory my entire segment of a television script which was due the next day.

Needless to say, they weren’t thrilled when I came in very early to the studios with everything in longhand still needing to be input (which I did). But I still made my deadline – despite a totally fried computer and a night without sleep – and that was all that mattered. Nobody thanked me for just doing my job.

What if I get sick? 

Generally, especially working from home, you should be able to work through most illness. I’ve typed away at screens I can barely see when high temperatures caused perspiration to fill my eyes.

If it is bad enough to get a doctor involved, you should inform your employer asap. They may have insurance to cover such delays and other freelancers who can pick up the slack.

Don’t expect to be in their good books for a long time unless you already have an excellent track record.


If you are doing a regular assignment or “beat” try to stockpile a couple assignments in advance. You’ll be amazed how they can save you during some unexpected calamity. The trick is to ensure they are still relevant without being too timely so they won’t expire on the shelf. Best to use them up every so often and replace with newer ones so they don’t get too outdated if you haven’t needed them.

Motivate me!

The knowledge you are engaged in a project that you will be proud to see in print/on air one day should be enough motivation for any true professional. (OK, that and getting the check!) But the truth is all of us hit the wall from time to time and seem unable to proceed as a deadline approaches. 

I’ve heard writing described as akin to removing an elephant from your keyboard. As deadline approaches closer and closer make that a whole herd. 

Music can prove helpful. Bouncy pop tunes playing in the background may provide a useful lubricant for creative logjams. (Me, I prefer jazz or classics as I get too easily distracted by lyrics). 

But sometimes even a complete symphony orchestra can’t help. 

Treat yourself

My ultimate, never-fail secret when it comes to motivating myself when up against a looming deadline? 


It’s never let me down.

For example, I might say that I’ll treat myself to that piece of pecan pie as soon as I’ve done the outline. Or some of my favourite potato chips as soon as the first draft is complete. And so on. It’s amazing how often food is involved! I don’t know if it’s specifically endemic to work-at-home freelancers or just me. 

Perhaps for you it will be a sneak-peek on Netflix or a short round of your favourite video game. Whatever. 

You’ll be amazed at how productive you become if you break up your work process with quick small rewards the next time you’re stuck and on deadline. 

Also how much extra weight you put on.

The takeaway

The ability to consistently make deadline is one of a freelancer’s most valuable assets. Your employers won’t really care how you manage it, just that you do it.

May these tips help you always make it with as little self-inflicted torment as possible.


Posted on March 22, 2017 at 9:00 am by editor · · Tagged with: , , ,

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