11 Things to Do When You’re Struggling With Deadlines

January 18, 2016


Deadlines are a daily part of life of a freelancer. Most clients will give you a due date, and if they don’t, you need to create your own. Meeting your deadlines is more than a basic requirement for  happy clients, especially when missing a deadline causes serious issues for their business.

If you’ve found yourself struggling with deadlines, you aren’t alone. I recently had the flu and was unable to work, but my work still had deadlines. I struggled to catch up once I was well, but along the way, I learned some valuable tips for how to handle daunting deadlines.

Learning these energy hacks got me in the right mental space, and then I went to work.

Now, I’m going to share what I learned with you. I’ll detail 11 things you can do when you’re struggling with deadlines, either chronically or in the short term.

1. Write a List of Everything You Need to Do

If you’re presently overloaded with work, write down a list of everything on your plate. Make a habit of starting your day by writing down what must be completed that day to keep your workload in check.

There’s countless “to do” apps out there, both for your OS, browser and smartphone. I’ve played around with many of the popular ones, and you know what I’ve discovered?

10 Million Small Business Owners Love FreshBooks – get started for free

Nothing beats a basic text editor.

Annoyingly, most apps I’ve used require too much time to open and close – and that’s time I need focused on work.

Of course, feel free to experiment and play around. I still do, even though I often end up right back at the basics. Sometimes simplicity really does work best.

2. Estimate the Amount of Time Needed

Once you’ve been working in your chosen trade long enough, you’ll have a rough idea of how much time each task will take.

In your Notepad or other to-do list app, also include a time estimate. It’s better to overshoot it than undershoot it, so aim high!

3. Organize Your Task List by Priority

At this point, you have a list of everything you must do to meet your deadline. Now, it’s time to become a priority-setting ninja and organize your list accordingly.

There are a few different schools of thought for prioritizing your list. Some prefer the ABCDE method, while others like “eat the frog” method. Discover which of these priority philosophies works best for you.



4. Find Opportunities to Delegate

You know exactly what needs to be done, you know how long each item will take and you have your priorities set. Now, what can you delegate to someone else?

You may wish to hire a virtual assistant or work with other freelancers with your same skill set. Sure, delegation means less total profit that reaches your pocket, but it will help you meet every deadline in your path.

In fact, the famed tycoon Richard Branson credits learning how to delegate early in his career to his present success. It allowed him to create strong companies, and put most of his focus into new ventures.

Learning how to delegate may result in your future 9-digit bank account balance. For now, it’ll help you manage your responsibilities.

5. Dedicate Chunks of Time to Get Tasks Done

Time chunks help you become hyper focused on the task at hand. In fact, one of the most popular time management systems among freelancers makes use of 25-minute time chunks, with 5 minute breaks. Known as the Pomodoro Technique, it calls for periods of extreme productivity followed by brief breaks.

You can create your own similar technique, but think in chunks and breaks – not in long stretches of time at your desk. Knowing that a break is only 25 minutes away, at most, will do wonders for you.

6. Remove All Distractions to Increase Focus

Most freelancers work from home. And, trust me, I know this from personal experience: It’s easy to become distracted, even with important deadlines on the horizon.

Removing distractions isn’t necessarily difficult, it just requires willpower. Turn off all other electronics and hide anything else you may be drawn to. Since you’ll be working online, you may need to employ a site blocker to keep you off of Reddit and Facebook.

7. Do the Hardest Tasks First (By Priority)

Attack the most difficult task that’s high up on the priority list. This is known largely as “eating the frog,” since everything else you do that day will seem easy by comparison.

Grab your coffee, warm up your hands and get at it. When you’re done, you’ll be coasting through the rest of your to-do list.

8. Set Milestones and Reward Your Accomplishments

Creating milestones will help keep you goal oriented, instead of task oriented. Task oriented is great in the short term, but you’ll need goals to meet those deadlines.

For each project you take on, break it down into milestones. Next, create simple, time-efficient rewards for yourself. Avoid rewards that will suck you into losing track of time, such as watching Netflix or playing video games. Instead, maybe take yourself out for a nice lunch.

9. Schedule Time Daily for Deadline-Based Work in Your Calendar

Most projects will span across multiple days. Using a weekly or monthly calendar will help you schedule time every day to meet distant deadlines.

Google Sheets templates provide you with a calendar with even greater flexibility, which will aid data-driven freelancers.

Make a habit of putting both deadlines, milestones and time chunks on your calendar. This will keep you on track and focused.



10. Reduce Stress to Avoid Burnout

Stress reduction is vital for self-employed freelancers.

Start a daily habit focused on stress release. Meditation and yoga have become the go-to methods for relieving stress for many freelancers, including myself.

Every day I begin with meditation, and then an hour into my day I do some light yoga. I’m not trying to break a sweat, just move around and break away from the laptop.

11. Find a Deadline Accountability Partner

Your client isn’t your deadline accountability partner. They want to hand off the project to you and forget about it. A deadline accountability partner can be another freelancer, a friend or family member, or even a virtual assistant.

The right partner won’t just ask if you’re working, they’ll hold you accountable for missing a milestone or slacking during a given day. Give them something to hold over you, like the power cable to your Xbox or calling you out on Facebook.

The Struggle Is No Longer Real

Struggling with deadlines will become a thing of the past by enacting these tips. You’ll stop procrastinating and develop a skill set that will help advance your career.

What have you done to help stay on top of your deadlines? If you already use any of the above tips, how have they helped? Is there anything you’d add to help others who are struggling with deadlines?


about the author

Freelance Contributor Chelsei Henderson is a content marketing consultant helping freelancers and entrepreneurs build successful companies in the digital world.