Can You Succeed as a Freelance Writer if You Suck at Deadlines?

Yes, but only if you communicate effectively.

Artwork by the author.

Douglas Adams, The Salmon of Doubt

I am spectacularly good at missing deadlines.

So good, in fact, I have managed to blow deadlines by not days, but months.

This is not something I’m proud of. But I’ve tanked enough client relationships that I have figured out how to avoid doing that, to some extent. It’s not a perfect system, and hopefully you’re the kind of person who is reading this more out of morbid curiosity than to learn something that might be helpful.

If you’re part of the latter crowd, you can at least take some comfort in knowing that you’re not alone.

Procrastination and the anxiety death spiral

A year or two ago, I got an assignment from to write about Ahrefs.

This was exciting because I knew nothing about the software, and I applied for the project because it was an opportunity to learn something new while getting paid to write about it.

They gave me the assignment.

I should probably admit at this point that one of my major problems in life and as a writer is that I have perfectionist tendencies when it comes to writing.

I’m a literary snob and have high standards. The standards I try to hold my own writing to are impossible. There’s a little Nazi editor in my head that I try to ignore, but he’s a sneaky little bastard and more often than not, he’s running the show.

Here’s what happens when I’m about to miss a deadline: I increase the amount of work I feel like I need to do in order to make up for my transgression.

The idea is that if I write the best piece of content [insert publication] has ever seen, they’ll forgive me for being a few days, or a week, or a month late.

In reality, they just want the piece done so they can publish it and move on.

But my imagination is wildly overactive, and I waste a lot of time and energy constructing imaginary scenarios in my head.

Once I miss a deadline, I start to beat myself up about it. In order to protect myself from the negative feelings caused by, yes, myself, I come up with grand plans for how I’ll make it up by writing the best piece ever.

This never works out. The farther I get past a deadline, the better the work has to be and my original expectations were already impossible to achieve.

So, I get caught in the anxiety death spiral and end up hating myself, convinced I’m a failure.

How I learned what professionalism looks like in client-freelancer relationships

Last year, I attempted to start a business with a friend. It didn’t work out for reasons that I’ll discuss one day in a future post, but in the early, optimistic days before we realized the partnership was doomed, I outsourced a blog post to an experienced freelance writer I know.

While he was working on the piece, I would get frequent email updates that confused me at first.

He would email with a status update, explaining exactly what he was going to do and when. We got regular updates on the status of the piece, and while I thought this was unnecessary, it eventually dawned on me that this is how you should communicate with clients when you’re working on an assignment.

My tendency is to go AWOL (away without leave, if you’re unfamiliar with military jargon) and spend all of my time and energy frantically trying to figure out how to build a time machine in order to go back and not miss my deadline.

It usually doesn’t occur to me that I should probably give my client a heads up instead of going radio silent if I miss a deadline. (I don’t know if I’m a solipsist or an only child, but I often forget to put myself in someone else’s shoes to consider how they might be feeling.)

The experience of working with a freelance writer that has his shit together was eye-opening, once I figured out what was going on.

I realized that if I communicated with my clients the way this writer was doing with me, I would probably still be working with some of the people who had decided I was not the best fit.

I had been causing them undue stress by going MIA (missing in action) instead of just giving them a heads up about my current progress — or lack thereof.

If you can’t under-promise and over-deliver, you can at least communicate more often

One of the things I’ve been working on is the whole “under-promise and over-deliver” skill (because I have a tendency to do the opposite).

Recently, I sent my client an email with a status update. I said I’d be working on something that day and they would have it sometime in the evening.

At 2am the next morning, I still hadn’t completed the work, and the anxiety death spiral was looming. My inclination was to play ostrich: stick my head in the sand and pretend no one could see me.

Instead, I sent a quick email update. I let the client know I hadn’t finished the project quite yet, and they should have it in the next 24 hours or so.

This was the response:

Hi Jess,

These quick email updates are super helpful!

Thanks for taking the time to write them up and send them over.

And no worries about the deadlines spilling over. As long as you give us a heads up, then we can plan around it.

I’d rather have quality copywriting that takes an extra 24 hours vs. a rush job.

[Name Redacted]

By sending the email update admitting that I was not going to deliver on the timeline I originally promised, I succeeded in maintaining the relationship.

I almost didn’t do this, and I’m so very glad I did. I was able to get some rest instead of anxiously beating myself up until 7am about being a terrible person.

The next morning, with a clear head after a solid night’s sleep, I finished the project and got great feedback.

So, if you suck at deadlines and want to figure out how to not get fired, try being more transparent.

Clear communication is important when you’re working with people you’ve never met IRL. Given that the world is going to be much more open to working remotely than it was before the pandemic, this is a good skill to develop.

Writing about writing. And other stuff.

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