On deadlines

And on my love-hate relationship with them.

You know the paradox about the shoemaker whose family walks around barefoot? Ostensibly because he spends all of his time making shoes for others, and has none left to devote to himself.

This is a situation many agencies fall prey to, despite their best efforts. Web design agencies that don't have websites, content marketing agencies that have no content, communications agencies that don't communicate. I won't lie, this is something that we, too, have struggled with. Devoting so much time and effort to creating assets and communicating on behalf of our clients, with no time left at the end of the day for our own digital properties. 

But we didn't want to be like the shoeless shoemaker. We devised a system to avoid just that. The idea was simple: every month, a Truesix team member would be tasked with writing a blog post for our own blog. No specific guidelines, just whatever was on their hearts. It’s led to some great pieces that I truly look forward to reading every month:

In June, it was my turn. And in true “me” fashion, I've let the deadline slip. I could, of course, shift the blame onto the long summer solstice holidays, the nasty bug I caught from my godson, or a heavier workload due to a variety of colleagues’ business trips and absences. 

But the reality is that we deal with tight deadlines all the time, and June would be no particular exception. Things are always happening, and the one thing we’re experts in, is adapting to quickly changing circumstances. 

An agency to-do list hits different

One thing my grade 11 American history teacher, Mr. Finn, once said to me, was “if you want something done, ask a busy person”. I was, of course, the busy person in question. Juggling a variety of tasks and projects for the plethora of roles I already held as a teenager (student council secretary, swimming instructor, Latvian school assistant teacher, member of the improv team, community theater actor, folk dancer, I could go on…) was a norm. 

When I think about it, there are many parallels with running an agency. 

  1. You get to work on a ton of different things, dipping your toes into different worlds and realities and get a taste for all of them
  2. You get to meet a bunch of diverse and interesting people
  3. The more you do, the more you’re given (think Mr. Finn’s allegory)
  4. There are only so many hours a day, and yet somehow everything gets done
  5. Without it all, life would lose its flavour

When working in an agency capacity, you’re working in this beautiful mosaic of chaos. Unlike regular jobs where there are ebbs and flows to the rhythm of the work cycle, a quiet period after an intense moment, in agency life, there is no ebb. There’s the next project, the next client, with their next emergency. For each client, their project is their big deal, and we treat every one with equal and appropriate enthusiasm. They deserve it. 

As such, as a small team of 5, we’re always on. And we manage to do a shit ton of work. From managing multiple conference comms and media relations per year, writing entire books (check out Treasures of Latvia if you haven't already), managing media campaigns for clients around Europe, working on EU-level projects supporting 120+ of Europe’s biggest deeptech scaleups, day to day client work, and a major major project that’s coming up (stay tuned), and that’s just the tip of the iceberg. 

This takes a certain kind of person to love (and thrive) in this sort of environment. I've said before that I believe that the most important characteristic for someone to work an agency job is: curiosity. But even with all the curiosity in the world, you can only do so much. When enthusiasm runs out, and when key team members get sick, you’re confronted with a reality: you’re only as good as the systems you can fall back on.

Fortunately, over 8 years, we’ve got this sorted out. 

Dreading deadlines

I've always had a love-hate relationship with deadlines. But deadlines can be diverse, as diverse as the tasks they accompany.

  • Hard deadlines – the kind that fill you with dread and coat you with cold sweat as they approach
  • Self-imposed – like these blog posts, which are all too easy to push back and defer to the above
  • Deadlines for clients – when you think you’re being smart by giving clients a deadline to submit their input so that you can get to work on time. But we all know will inevitably be ignored
  • Overly optimistic – often paired with youth and an overestimation of how long our work actually can take 

When staring down my list of tasks, I often feel a sense of camaraderie with one of my all-time favourite writers, Douglas Adams. When asked if he liked to write under the pressure of deadlines, he responded:

‍“I love deadlines. I love the whooshing noise they make as they go by.”

A prolific writer himself (you should totally check out A Hitchhiker’s Guide to the Galaxy, Dirk Gently, or anything else by him), it’s comforting to know that despite a productive career of writing words, he, too, can fall victim to speeding deadlines. 

But it used to be much worse. 

The perfect to-do list system

I spent much of my 20s trying every productivity hack under the sun (think standing desks, all the to-do apps, drinking beer at work, even inventing the 52/17 productivity ratio). Nothing really seemed to stick. In retrospect, I suspect a possible hint of neurodiversion, but now at the ripe ol’ age of 35, I've developed and implemented foolproof systems that work for my brain. I’ll share them here with you, lest they help others with a large and diverse workload and a wandering mind. 

  1. To do list setup

You start with the humble to-do list – a place to dump all of the things you need to do and capture them, all in one place. This is where you write down everything on your plate (particularly when feeling overwhelmed). This first task is very important, because you free your mind from the pressure of having to remember everything. 

Tools: This is up to you, it can be a notebook, a google doc, notes app, etc. Whatever works best for you. At Truesix, we use Motion, it works well for teams and personal tasks. 

  1. Monthly overview

At the beginning of the month, go through all of your tasks one by one, add any additional tasks that you know will be upcoming for the month. Some will likely have known deadlines, others might just be “asap” (or my favourite – “yesterday”). Others might not have a specific due date, but you just know that they should, eventually, get done. 

When going through each task, assign them a week of the month when you would want to have the task done by. The asap tasks would be week 1, the ones that don't have a deadline but need to be done could be week 3 or 4.

  1. Weekly overview

At the beginning of the week, go through your week’s task list, and add anything that’s come up since. Put them in order of most important/highest priority to the least. This will be the order you will do your tasks in.

That way, the most important tasks will always be done on time, and weigh less on your mind. 

Some tips:

  • Write down tasks into your task dump list as soon as they come in, and set them approximate deadlines. 
  • When tasks are completed, cross them out, and leave them in a place you can see. This is so satisfying, and it serves as a reminder that you are, indeed, crushing it.
  • If you can sync with your calendar. Motion does this for us automatically, but you could manually block out time in your calendar for when you’ll do each task.  This way you’ll have a visual reference for when you should be doing what, and how busy you actually are (and how realistic it is to actually get things done). 

Kill tasks that aren't working

You know that feeling when you’ve got this one to-do that’s been dragging along for far too long? You can't seem to bring yourself to do it, but you can't in good conscience just erase it (if that’s you, I assume you’re also the kind of person who can't stop reading mid-book). 

Throwing in the towel can actually be a very productive thing to do. 

If a certain task just isn't getting done, then it’s time to think about getting rid of it. No one needs that kind of negativity in life. 

Some great options for dealing with half-dead tasks:

  • Trade – If you work in a team, then consider trading tasks with someone else. Sometimes all it takes is a fresh perspective. And they might be getting rid of a task they, too, are struggling with
  • Adjust the task –  if it’s not working, consider changing up the format. For example, if your task is to write an offer for your dream client, and you haven't been able to bring yourself to do it, how about changing the task to “have a call with that dream client” to get a better idea of what they need.
  • Give it one last go – when everything has been tried and nothing’s working, tell yourself you’ll give it one last go, and if it doesn't work out, you drop it. You’ll know that you tried, and you’ll also give yourself the permission to let go.

“But Julia,” you’ll say. “What about this article? You’ve been procrastinating with this one, what’s the deal?” And you’re very reasonable in asking. 

It came down to finding stillness to think about what to write. In my case, it was a two-and-a-half hour flight with no wifi. I came out the other side with a (handwritten) working draft, ready for editing. 

And so that brings me to my last pro tip: sometimes all you need to do is to disconnect.