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5 Reasons Why We Miss Deadlines (And How To Never Miss One Again)


Barnaby Lashbrooke

Founder and CEO of Time etc, author of The Hard Work Myth

9 minute read

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There are few things as stressful as watching a deadline approach and realizing you won’t finish on time. The feeling that you're going to let someone down, or knowing there’ll be repercussions for not completing on time, can be pretty debilitating.

But whether we like it or not, as entrepreneurs, deadlines are an unavoidable aspect of doing business with other people.

If we want to avoid missing deadlines, it is important to understand why this happens in the first place. Once we know the causes, we can take steps to prevent it from happening again and set ourselves up for future success.

Why should we avoid working under pressure?

Pressure can be a solid motivator for some people, but there are a number of downsides associated with working under these conditions.

When we’re rushing against the clock, we risk compromising the quality of our work just so we can get it done on time. It becomes a case of “That’ll do” instead of something we’re proud of. Rushing can also lead to a higher chance of making mistakes than if you had more time to be careful and considered in your task.

Lower quality aside, leaving important work until the 11th hour also runs the very real risk that you still won’t be able to complete it in time. This can have serious consequences, including negative reviews or feedback, losing out on opportunities with future clients or customers, and financial losses.

And not just your professional life, working under pressure can also lead to issues with your physical health. Stress can cause a whole host of problems in the body, such as increased susceptibility to colds and illnesses, migraines, and even heart attacks and strokes. This is another reason why it’s crucial to learn how to manage the stress of deadlines so that it doesn't take a toll on your body or your life.

Why We Miss Deadlines

1. Planning

According to experts, there exist two cognitive biases which often work hand-in-hand to derail our organizational planning. I’m willing to bet that almost everyone on earth (yes, you too!) has fallen victim to the planning fallacy and optimism bias at least once in their lives.

In basic terms, the planning fallacy is the human tendency to overestimate how much time we have to complete a task even if it goes against our previous experiences. Optimism bias is the tendency to believe that everything will go smoothly and there’ll be no obstacles or hitches along the way. As great as that would be, as we all know, unfortunately, it’s not always the case.

So if issues with planning are your biggest hurdle, here’s how we can tackle them:

  • Don't let the potent cocktail of planning fallacy and optimism bias lull you into a false sense of security and create a “This time will be different” mindset. Ask yourself objectively, how much time and effort have similar tasks or projects required in the past?
  • No matter how hard we try, there will always be factors outside of our control that can spring up when we least expect them. Conduct a “premortem” to determine all the things that could potentially set you back so you can make a more realistic and less biased estimate for completion.
  • While efficiency and finishing work as quickly as possible is a desirable trait, scheduling some extra “buffer time” on top of your estimate means you’ll be even less likely to be impacted by any unforeseen circumstances or distractions that may arise. You might not need that extra buffer time in the end, but getting it done early is always better than being late.

2. Disorganization

It’s hard to meet a deadline when you’ve forgotten you had one! To put it lightly, life as an entrepreneur can be very hectic. When you have so many things to be thinking about at any given time, it can be all too easy for things to slip our minds, or for time to run away from us completely.

But all tasks – big and small – impact your business, so how can we stop things from falling through the cracks?

  • Luckily, there are hundreds of apps on the market for this exact purpose. You may be familiar with popular tools like Remember The Milk, Todoist, and Trello to name a few, but it’s worth shopping around to find the one that works best for you.
  • Another useful tip is to create a document that lists all your deadlines in order of due date. Having everything in one place will help you avoid scribbled notes getting lost or important details getting buried within multiple notebooks, documents, or programs.
  • For the more visual learners among us (*raises hand*), a simple list of dates doesn’t always help you gauge just how much time you have between now and your deadline. You may find it useful to have a physical, printed calendar in your workspace that you can quickly and easily refer to, and give you a clear visual understanding of just how many days or weeks are left until your deadline dates.

3. Procrastination

Many people miss deadlines because they struggle to start in the first place.

If a task feels too daunting or overwhelming, or we subconsciously dread the amount of mental effort and energy we will have to spend on it, we may put off working on it for as long as possible. This can lead to us feeling even more stressed and anxious about the situation, which can make it even harder to start working on the task.

If you want to get out of the vicious cycle that is procrastination, here are some simple things you can try:

  • Who says a tough job has to be done all at once? Try splitting these tasks into smaller ones that are easier and more manageable. This will make it seem much less daunting and will also help you to better focus your efforts.
  • Once your tasks are broken down, “eat the frog” every morning. In his bestselling book of the same name, self-development and productivity expert Brian Tracy introduced the ‘Eat That Frog’ technique as a method of tackling procrastination and getting more done each day.
“The key to reaching high levels of performance and productivity is to develop the lifelong habit of tackling your major task first thing each morning. You must develop the routine of ‘eating your frog’ before you do anything else and without taking too much time to think about it.” - Brian Tracy

4. Unable to focus

Picture this: you sit down to start a task that should only take a few minutes, but somehow, hours later, you're still not done. Sound familiar?

There are a million reasons why this can happen, but one of the main culprits is the endless supply of distractions we face on a daily basis. Whether it's work emails or social media notifications, it's easy to get pulled away from what you're supposed to be doing.

  • To avoid falling into this trap, you must aim to eliminate any and all distractions as much as possible. Where do you find your attention is lost the most?
  • For example, many people struggle to concentrate when there is a limitless source of information and entertainment at their fingertips. Switch your phone onto "Do Not Disturb" or “Focus” mode, or put it away in a desk drawer so you don't have the urge to check it. Out of sight, out of mind! If you’re distracted by noise or conversations and don’t have access to a quieter location to work, a pair of noise-canceling headphones or earplugs is a worthy investment.
  • Block out time in your schedule for periods of uninterrupted deep work. Close your office door, switch off any notifications, and just allow yourself to be fully immersed in the task at hand. You’d be surprised at how much you are able to get done when you’re in the zone and there’s nothing to pull you out of it

5. Lack of time

Last but certainly not least, the scenario which I’m sure all business owners will have felt the pain of. Too many responsibilities on your plate, and only so many hours in a day. Let’s be honest, you’re only one person, and it’s just not physically possible to meet all your deadlines when you have so much to deal with.

It can be incredibly frustrating when you feel like you're working as hard as you can but you’re still falling short, and this is an issue that all entrepreneurs must overcome if they want to achieve their goals.

  • To make the most of your available time, it is absolutely crucial to prioritize the most impactful work that will get you over the finish line. If a task or project will have a significant effect on growing your business or generating income, you mustn’t be getting bogged down in the tasks that eat up precious time, consume your limited energy, and have the lowest return on investment. If this is what is stopping you from meeting vital deadlines, they need to come off your plate as soon as possible.
  • Offloading these time-consuming, lower-return tasks will allow you to reclaim valuable time to make sure all your essential work is done on time, and with the focus and attention it deserves.

What’s The Bottom Line?

Entrepreneurs have a lot of different balls to juggle, and sometimes it can be tough to keep everything in the air. Deadlines are one of those things that can easily slip through the cracks, especially if you’re trying to do too much at once.

But if you want your business to succeed, it’s important to make sure that deadlines are front and center in your mind, and you’re well-equipped with all the knowledge and know-how for how to meet them.

With an experienced virtual assistant in your corner, missing deadlines can be a thing of the past. They can take care of the small details and tasks that can often cause big headaches, and their support can relieve the pressure from your days so you can focus on the bigger picture and carve out your path to success.

Finding the best virtual assistant for your needs is crucial, and shouldn’t be left to chance.

At Time etc, our mission is to help hardworking and ambitious entrepreneurs achieve more by matching them with the best virtual assistants. We know your time is precious, which is why you won’t need to do any of the heavy lifting. To ensure that you have a great experience as well as great results, we have a rigorous 10-stage application process for virtual assistants looking to join us, with only the top 2% of VAs making it through, on average. Not only that, we offer all our users a lifetime happiness guarantee.

So if you’re ready to start doing more of the work that matters, try a skilled virtual assistant for free or speak to our expert team to find out how we can help you today.

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About the author

Barnaby Lashbrooke is the founder and CEO of Virtual Assistant service Time etc as well as the author of The Hard Work Myth, recently recommended by Sir Richard Branson. Barnaby is a Forbes Columnist on productivity and is also an accomplished entrepreneur, selling more than $35 million worth of services.

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