How to set (and keep) your own deadlines

Feb 26, 2014

by Katherine Hamill

Clients’ deadlines are a freelancer’s bane – and blessing. They’re stress-inducing, but they can also force you to be productive when you’d otherwise be inclined to put things off.

But what happens when you have to set your own deadlines? If you’ve ever tried to write a novel, finish a painting, or put the final tweaks on your personal website, you know that it can be easy to put off doing your own work indefinitely.

With that in mind, here are 4 simple ways to set and keep self-imposed deadlines, even when you get busy.

1. Build in a rewards system

Ever try to convince a toddler to pick up his/her toys? Bribes. Bribes are key. The same is true for your inner child; positivity and small rewards goes a long way.

Freelance writer Bethany Bryan (check out her very funny stuff here), like so many of us, builds in tiny kickbacks along the way:

“I try to give myself words of encouragement like, ‘Hey, you. We’re gonna do this today. Does that sound all right? Would it help if I offered you a brownie first?’ Then, I surprise myself by doing stuff.”

2. Alternately, build in a punishment system

Yes, okay, this is extreme – but it’s necessary for the world-class procrastinators among us. And research shows that punishment can motivate more than rewards.

Whenever I’m trying to finish a project that I’ve put off for the umpteenth time, I write a post-dated check to my no-nonsense friend. If I don’t send her a draft by the set date, she gets to cash it. Yikes.

If you don’t have a friend you trust to lay down the law, try motivational website stickK, which allows you to bet money that you’ll reach your goal. If you don’t achieve the goal, that money goes to a cause you support – or a cause you DON’T support (i.e. a politician you loathe, a group you can’t stand). It’s the ultimate motivational ‘nuclear option’.

3. Make sure your deadlines are realistic

Trying to do too much, too fast is setting yourself up to fail – and that leads to even more procrastination. Think, first, of how fast you could ever realistically finish your project; then think of how slowly you fear it could go. Pick a deadline that falls somewhere in the messy middle. Then, set online reminders to give you a poke now and then.

4. Be accountable to others

As support groups have known for years, people are more likely to accomplish goals when they’re exposed to a bit of peer pressure. Look into joining a creative community, such as a shared working space or writers’ group; you’ll be surprised by how motivated you become. Try Give it 100!

If no existing group strikes your fancy, contact a friend about being ‘accountability partners’ – write down lists of goals and check in weekly to see how each of you is progressing. If you’re looking for someone in your field, consider checking out one of our Freelance 360 events to find new collaborators.

If all else fails, announce your self-imposed deadlines on social media. Once they’re out in the world, you’ll be much more motivated to finish on time.

5. Break it down

Many freelancers follow the 45/15 or 40/20 rule – 40-45 minutes of work for every 15-20 minutes of procrastination or creative work. It doesn’t matter what the structure is, as long as you build in some breaks.

Says Bryan, “I like to reward myself for two hours of work-work with 20 minutes of ‘fun’ work. Or I write when I wake up in the morning before it’s time for my day job to start.”

Ultimately, overcoming procrastination is its own reward – nothing feels better than getting your work done. These are just tips to get you on the right path!

What about you – how do you keep your self-imposed deadlines?