March 8, 2019

Freelancer procrastination and how to help yourself

Written by Ben Wilks

Dinghy Co-Founder

Procrastination is a malady suffered by many, which is only made worse by being in charge of your own time – i.e. a freelancer.

Throughout education, we’re compelled to be productive. The constant threat of consequence – for missing homework, turning up late, habitual social media use during class hours – hangs over our heads, giving some strong external motivation to not slack off. Then you’re out in the world, blissfully free of immediate repercussion – but it’s a slippery slope, isn’t it?

You go mad on your own power, scrolling through the same Instagram feeds for hours, devouring Buzzfeed articles, aggressively organising your various inboxes. You find yourself 7 pages deep into a Reddit thread about sourdough starter recipes… and then it’s 4.30, and there’s no point in starting anything. You promise yourself you’ll do better tomorrow.

The sourdough starter thing is particular to my personal procrastination but sound familiar? There are ways to help yourself though, and with practice, it gets easier.

Why do we procrastinate?

The best place to start with squashing any bad habit is understanding why we do it.

Back in 2013 by Tim Urban wrote a paper called ‘Why Procrastinators Procrastinate’ (which you can read here). In his paper Tim suggests that the primary motivation for procrastination is not laziness, but feeling intimidated by or inadequate for the task at hand. Referring to the self-sabotaging part of our brain as the Instant Gratification Monkey. Tim goes on to explain why we let ourselves delay work to the point of panic in his eloquent metaphor that untangles the act of procrastination itself. He also includes some dubious Paint illustrations to really drive the imagery home!

The idea of putting off a job because you don’t feel good enough resonates immediately, with many people. Freelancers – creatives especially – are incredibly self-critical and it is rife in the industry as a whole. Freelancing can also be very isolating, which gives your self-doubt room to multiply at an alarming rate if left unchecked. Effectively fighting those creeping, tenacious thoughts will get you a long way to winning your procrastination battle.

So how do you go about that exactly?

Start anywhere – it doesn’t matter if it’s crap

One of the toughest things you can be faced with is a blank Word document. Where to start? The answer is: literally anywhere.

Whether you’re a graphic designer, web developer, software programmer or copywriter, just start hammering something out. Editing material always feels easier than creating it because you’ve got a starting point to launch from. Give yourself something to work with, no matter how rough, and make your own springboard. If you have to write 500 words of utter brain-spew, then do it. Not only is it therapeutic, but you’ll find some great ideas while sifting through the debris that just needs a little spit and polish to shine.

Suddenly, the project not only feels possible but like you’re going to do a good job.

Do the stuff you hate first

Many of us, when presented with a plate of food, will save our favourite thing until last. We choose to get rid of the not-so-choice bits of the meal first so we can fully enjoy the main event.

Approach your work day like a delicious dinner. Do the thing you least want to do first. Don’t give it time to make you anxious – as soon as you start finding excuses to push it down the list, the chances of it getting done that day diminish drastically. Often, the things we put off have the most substantial consequence (filing a tax return, sending a quote you don’t think the client will approve, navigating a tricky-bordering-on-hostile email exchange) which makes them prime procrastination fodder. The thought of doing them is dread-inducing, but knowing they’re sat undone taints the rest of your to-do list, making nothing enjoyable.

Once you’ve conquered the worst bits of your day, the only way is up.

Break tasks down into manageable chunks

Sitting down to write a 2,000-word article sounds much more intimidating than sitting down to write four 500 word paragraphs or ten 200 word subheadings.

You’re still doing the same amount of work, but the semantics make it feel surmountable. Breaking your work down into chapters, wireframes, or sketches provides the same kind of starting point as the ‘start anywhere’ suggestion, but with the reverse action. Instead of picking gems out of rubbish, you’re fleshing out your idea-skeleton with the help of a plan.

The principle remains the same: just get moving.

Organisational Software

Being organised is absolutely key to making sure all deadlines are met without your mental health suffering. If you’re not systematic by nature, that can be easier said than done.

There’s a tremendous amount of choice online for free-or-very-cheap software designed specifically to help you stay organised. These tools are so good that they can help revolutionise the way you work. Asana, which is a souped-up online to-do list with a VERY satisfying ticking-off animation is a go to for many freelancers we work with. Meanwhile project management tools like Zoho and Trello are invaluable when working across a variety of jobs. Even using a simple shared Google calendar to liaise with clients can help to keep you both on the same page.

Slack is indispensable at Dinghy, if you don’t know it, Slack describes itself as a ‘collaborative work hub’. It can help you liaise with clients quickly if required and you can also join Slack communities to help alleviate some of that freelancer loneliness (not to mention its’ excellent range of gifs).

Let yourself slack off sometimes

You can’t move for self-care guides online but, despite the saturation, the core message is right. We live in a constantly-connected, demanding world that moves at 1000mph and expects you to keep up, but DO NOT FEEL GUILTY FOR HAVING A BREAK.

A combination of University mentality, intern culture and the glorification of London living have created this unhealthy stigma towards having a rest. Whether it’s skipping lunch or consistently working late, it’s not good for you, and your work will suffer. One of the real beauties of being a freelancer is being able to work on your own watch, so take advantage of that.

Allowing yourself some structured downtime means that when you come to do some work, you’ll bring your A-game. That, in turn, will allay any doubts that you’re not good enough, making you (almost) procrastination-proof.

Remember why you started this freelance journey in the first place. Freedom and flexibility are wonderful things just make sure everything is as balanced as it can be. If you need insurance for your flexible freelance life you can get no obligation quotes in less than 60 secs from Dinghy right here!

About Ben Wilks

Ben Wilks has worked in insurance and technology for over 12 years. Having seen the trouble freelancers had getting insurance to suit their unique lifestyle he set about solving it. Ben is passionate about business as a force for social good. When not making insurance better, Ben spends his time on water, whether liquid or snow state. In 2017 he co-founded getdinghy.com, a B Corp (pending) insurance provider that specialises in freelancer insurance.

Read more blog posts by Ben Wilks


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