Approach #1 – Acknowledge that a deadline cannot exist in a vacuum
Last updated on January 26th, 2026 at 03:20 am
How To Finally Overcome Your Problems Meeting Deadlines
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- How To Finally Overcome Your Problems Meeting Deadlines
Let’s be honest: you probably have more problems meeting deadlines than you care to admit.
Maybe you missed submitting that proposal you promised a client by Friday that didn’t get sent until the following Tuesday.
Or the quarterly report your accountant needed that you finally patched together at 2 AM the night before your taxes were due.
Or perhaps right now, you’re anxiously reading this blog post desperately searching for that magic thing that will help you with meeting deadlines. (Sorry, the deadline fairy is procrastinating)
Key Takeaways:
Instead of magic, here’s what you will get from this post:
- What is a deadline
- Why you struggle to meet deadlines
- Why meeting deadlines are important
- A practical method to help you actually meet deadlines
- Key approaches that help you meet deadlines
What is a deadline?
On the surface, we can think of a deadline as a specific date or time by which a task, project, or obligation must be completed.
In other words, it represents the final moment when something is due, after which it would be considered late or overdue.
In business it means more than that.
It’s a goal you set for yourself, the start of a relationship built on trust and how you organise your work to achieve these.
The effectiveness of deadlines often depends on them being realistic, clearly communicated, and having meaningful consequences tied to meeting or missing them.
Why meeting deadlines is important for small businesses
If you run a small business, deadline chaos isn’t just embarrassing. It’s expensive.
Every missed deadline is a chip in your professional reputation, a crack in client trust, and often a very real hit to your bottom line.
You know – Late fees. Rushed charges. Lost contracts. That sick feeling in your stomach when you have to send yet another “sorry for the delay” email.
But if you’re a service provider in particular, here are reasons you should want to meet deadlines:
Competitive advantage – In markets or niches where service quality is relatively similar, reliability often becomes the key differentiator. Clients will often choose a service provider who consistently delivers on time over one with slightly better quality but less reliable timing.
Trust and Credibility – When you are consistently meeting deadlines, clients develop confidence in your reliability. This trust becomes the foundation of long-term business relationships and often lead to them recommending your services to others.
Professional Reputation – In industries which depend on services, word of mouth is the key form of marketing. If you earn yourself a reputation for consistently missing deadline, this will spread equally fast. As to be expected, this will seriously impact your ability to win new business and retain existing clients.
Cash Flow Management – You are very aware that how (and if) you get paid is tied into agreements with specific delivery dates. Not meeting deadlines can delay payments, affect your cash flow and your ability to manage your own business operations effectively.
Avoid Creating Domino Effects For Clients – Your clients typically build their own timelines around your delivery dates. When you miss deadlines, it can create a domino effect that disrupts their operations, marketing launches, or other critical business activities. This ripple effect can be costly and damaging to their business. And yours as well.
Why you struggle with meeting deadlines
Following from above, there is no surprise that you would be constantly trying really hard to address this “deadline” problem.
You’ve downloaded the apps, bought the planners, followed the time management advice, tried the project management approach and even installed an accountability partner.
You swear you will be better next time and even thought of consulting an obeah woman.
Yet here you are, still scrambling. Still behind. Still wondering why nothing seems to stick.
And here’s why: these systems assume your problem is organization. That if you just knew what to do and when to do it, you’d do it.
And in that moment, they ignore the huge fact that you’re human. Really.
On that score, these systems fail because they don’t account for how humans actually experience time and work.
Here’s a sample of what I mean:
Humans procrastinate. Our motivation crashes. Unexpected emergencies arise in Our life. And what about personal issues?
We’re terrible at estimating how long things take. Psychologists call this the “planning fallacy,” and research shows we underestimate task duration by 40-50% on average.
We’re also terrible at maintaining motivation over time. What seems totally manageable on Monday morning when you’re fresh and caffeinated, feels impossible on Thursday afternoon when you’re tired and drained, 3 unexpected problems have popped up, and your kid’s school just called about a situation.
And we’re really terrible at dealing with perfectionism. How many times you didn’t start something because you didn’t have time to do it “right”? Or kept tweaking and revising long past the point of diminishing returns because it wasn’t quite perfect yet?
How to become better at meeting deadlines
The big question is: What is meeting deadlines really about?
The real answer is: It’s about starting earlier, planning realistically, and dealing with the psychological barriers that make you avoid the work in the first place!
Therefore, what you need is a combination of actionable methods and realistic approaches which can improve your capacity to meet deadlines.
Let’s begin with a practical method…
Backward deadline mapping with buffer zones
Hey…unroll your eyes and let me explain the method and break it down for you.
It is also referred as “backward planning” or “reverse scheduling.” Basically, it’s a form of “begin with the end in mind and work backwards.”
Here’s a simple example of how it works.
Say you need to submit a grant application by November 15th (I’m wearing my not-for-profit hat for this example) here are the steps involved.
- List the steps involved in submitting the application
For our example these could include:
i. All required fields on the form completed as required
ii. 1-page project description
iii. Budget formatted as requested
iv. 3 reference letters acquired
2. Define ‘completion criteria’
Completion criteria let you know when a step is completed. I like to include it in the listed steps like I did above. It controls that need for perfection that leads to not meeting deadlines.
It is important to note this: The criteria for submitting a grant proposal is that it is submittable. Not perfect, not impressive, not award-winning. Just submittable.
3. Determine completion time for each step (with buffer zones)
In this step, you carefully calculate the time it will take to complete each step and add an additional 40% as a buffer zone. This means that if for example, ‘writing project review’ is 6 hours, with the buffer zone it is now about 8.5 hours.
4. Calculate total working hours and calendar time
Calculating total working hours is easy. You just add up the “buffered” hours for each task. Calculating calendar time can be more complex. It is determined by how many hours a day you will work on the project and if you will work on weekends, etc.
5. Work backwards from your deadline to determine your start time
Let’s say your total working time is 20 hours which you have determine will be spread over 3 weeks. You now know the latest date you can begin working on your project is October 26.
6. The last step is to assign hard start and end dates for each step
E.G. Budget: Start by October 28th. On November 3rd, spreadsheet is DONE, perfect or not.
Use your judgment in applying this method. Every deadline will not require the use of this method; some will just require you to be mindful of the approaches below. But here’s a good rule of thumb: If missing the deadline would be painful (financially, professionally, or emotionally), it’s worth mapping backward.
Reminder: The method scales to the task. A 2-hour project might just get a 45-minute buffer tacked on. A 2-day project might get an extra morning. A 6-month project needs the full treatment with milestones and structured buffers.
Why This method actually works (and the science backs it up)
It Transforms Your Cognitive Bias Into a Tool. Remember the planning fallacy—how we underestimate time by 40-50%? Instead of fighting this, the buffer zones harness it.
It Destroys Perfectionism Before It Destroys You – You can always make the parts of the process better if you finish early and have buffer time left. But first, you have to ensure that the standard is “submittable.”
It Creates Psychological Safety That Unlocks Action – Here’s something they don’t tell you about procrastination. Often, we’re not avoiding the work itself. We’re avoiding the feeling of not having enough time. Adding buffer zones avoids this.
The backwards mapping doesn’t create the time problem—it reveals it.
And now for some approaches…
Approach #1 – Acknowledge that a deadline cannot exist in a vacuum
I am amused when people try to live their lives in silos.
You want to leave your “home problems” at the door when you enter work and leave your “work problems” at the door when you get home.
Really? Try that when work and home are in the same location…
And just imagine: you’re caring for your sick mother, your son just lost $50,000 in his business and your partner is having a midlife crisis.
I don’t know about you, but that’s enough to kill my feelings for working, far less for meeting deadlines.
So if you’re one of those people who believe that you can be productive 100% of the time, regardless of your personal issues, congratulations!
For the rest of you, understand that your life is made up of many parts.
Therefore, to meet deadlines consistently, you must consider all parts of that life when you set those deadlines, if you want a meaningful chance of meeting them.
Stated more bluntly, meeting deadlines cannot exist in a vacuum.
Approach #2 – Pay attention to your energy levels
If I know you, you lead a high-stressed lifestyle, as most small business owners do…going, going from morning until night.
And when you’re already tired and have one or more deadlines to meet, you will have problems meeting deadlines…fuh real.
On the other hand, what if you live a harmonious life? You eat well; you make time for exercise and support all this with “me time.”
In this scenario, your energy levels are consistently high.
It follows then, that in this state, your capacity to meet deadlines will be higher.
So try to bring some balance in your life – physical, mental, emotional and spiritual.
In this way, the energy will be already there when you need to rely on it for meeting deadlines. All you need will be a shift in priorities and to apply the method outlined above.
Approach #3 – Accept that how soon a client accepts your proposal matters
Are you familiar with this? I am…
You meet a potential client. The meeting goes very well. You send them the requested proposal. And on time. Then the time you set for a response comes and goes and you cannot hear from them.
After several attempts to follow-up, including using advice from Oren Klaff, you give up. And then it happens.
One afternoon, some weeks later, out of the clear blue sky, you get a call from the business.
They are calling because the problem they are experiencing, predictably has worsened, and now they want to know how soon you can start for them.
No Problem. But they still want you to complete the project by the date you had originally proposed.
Seriously? And when you review the proposal, it now seems as foreign to you as the Magna Carta.
Renegotiate that submission date fast!
Unless you do, you are creating a pressure cooker of a deadline not even the buffer zone method above might be able to handle.
Approach #4 – Allow for learning needs on large or complex projects
A few years ago, I was the Capacity Building Consultant on an Inter-American Development Bank (IDB)-sponsored project for a small organisation in the agriculture sector.
I have a strong background in the not-for-profit sector, especially in the capacity building niche, hence my selection.
On the other hand, apart from planting some pawpaw seeds and having the giant African snails eat the plants as soon as they were 0.7 inches tall, my background in agriculture was almost non-existent.
In designing a work plan for this project, I factored in the time I would need to learn the various aspects of the agriculture industry, relevant to the project.
This was to help me strategically align my capacity building expertise with the needs of the project to create meaningful deadlines and delivery standards.
In similar circumstances, don’t hesitate to take this approach. You will significantly improve your ability to meet deadlines.
Approach #5 – Be aware that money is a motivator in how well you meet deadlines
I don’t know about you, but I work for money.
Yes…I donate my services to deserving organisations, but I can only do this because I get paid for other services I deliver.
Now, even with my best effort, there are times when my available cash dips below my ideal balance.
In times like these, even if I have to call up my incredible will power and massive amounts of energy, I meet any deadlines I set. I don’t negotiate with myself.
On the other hand, when I have a healthy balance in my bank account, I feel I can buy just a little, little bit of procrastination.
You know what I’m talking about…don’t you?
This was hard for me – the high-level professional, the will-power boss – to accept.
So accept that at some level, how badly you need the money can impact how you set deadlines and how well you meet them.
When this happens, don’t rely on willpower alone. Apply the Backward Deadline Mapping with Buffer Zones method.
Having a method that reduces most of your psychological levers is extremely helpful in this situation.
Your next “meeting deadlines” steps…
Look, I know this might be a lot to take in.
And I know your instinct might be to bookmark this post, while thinking “I should try these at sometime,” and then go right back to your usual deadline panic spiral.
Don’t do that!
Here’s what you should do instead:
Think of something you need to deliver in the next 4-6 weeks and apply the Backward Deadline Mapping with Buffer Zones method to it. You might feel weird about building in all that buffer time. You might feel like you’re being inefficient or padding things unnecessarily. That’s expected.
Do it anyway.
Reflect on the 5 approaches especially any that particularly impact you. Carefully reflect on the “actions” in each approach and when faced with similar circumstances, be willing to vigorously apply them.
Look…you’re not being productive when you’re optimistic instead of being realistic about deadlines. You’re just setting yourself up for panic.
You’re not being efficient when you don’t build in buffers. You’re just pretending uncertainty doesn’t exist.
And you’re definitely not doing yourself—or your business—any favors by continuing to use methods that’s not quite working for you.
Because here’s what I’ve learned after years of missed deadlines, late nights, and stress-induced stomach aches:
the illusion of efficiency is not worth the reality of constantly scrambling.
My Belief?
If you really act on the information above, you’ll actually meet your deadlines without wanting to throw your computer out the window at 2 a.m.
Wouldn’t that be something?
Lorna Barrow
Lorna Barrow excels at leading small business owners to get the breakthrough they are looking for in their businesses! She unleashes her 25+ years of small business experience and knowledge on your business, which was developed from working with small business across the Caribbean and beyond. This ensures you get the solutions that are right for you and your business...
