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In today’s office work, deadlines are the ultimate double-edged sword. On one hand, their mere presence invokes dread and stress as they present a cut-off date by which you have to deliver. On the other hand, they catalyze productivity and creativity. They force you to prioritize what’s critical and how to provide it with what’s available. This paradoxical love-hate relationship with deadlines is a familiar narrative for any knowledge worker. In this post, we dive into the heart of this contradiction, unraveling why deadlines stir a mix of fear and motivation while learning how we can make peace with them to get stuff done.

4 Pain Points Associated with Deadlines

Let’s start by listing and understanding some stress points deadlines generate. Doing this gives us a handle on how they cause us discomfort.

1. Highlights Our Inability To Plan

Even if you know deadlines are essential, getting them right is often problematic. Courtesy of the planning fallacy, our ability to predict accurate deadlines is abysmal. We often underestimate how long it takes to do things. As a result, when we run short of the clock, we burn the midnight oil to squeeze things in. And on the rare occasion that isn’t true, you run afoul of Parkinson’s Law, which states you will work as long as the time you allocated. In short, it’s rare to finish things before a deadline. So, why spend the energy to set one if you’re not likely to get it right:

Don’t ask me to predict the future. No one can.

2. Stifles Creativity By Unnecessary Pressure

It would be great if you could generate world-class solutions in an hour, but the harsh reality is that great ideas, designs, plans, etc., take time. There is no formula to predict how long brilliance takes. Even if you engage in Deep Work, you don’t know whether your insight will come in 1 or 10 sessions. For ideation, you want to identify all the cool things you want to achieve. You don’t think about budgets or constraints. You want ideas to flow first before knocking them down with reality. A poorly set deadline can kill creativity prematurely (see above regarding planning fallacy), leading to:

Genius cannot be rushed.

3. Generates Performance Anxiety

Deadlines are about getting things done under the clock. When you know what you’re doing and have experience, the pressure can push you to perform your best. But if your tasks are new or complex, or you’re doing something familiar but in a new environment, chances are high that uncertainty and unfamiliarity will trip you up. Deadlines ramp up the stress and, unfortunately, can lead to making mistakes, which creates a doom spiral as you get more stressed and more errors happen. As they say:

Doing it right takes time. 

4. Risks Exposing Our Deficiencies

Fundamentally, deadlines are painful because they put a magnifying glass on your deficiencies and air them out in the open if you don’t make the due date. Consider the following: you already look bad if you don’t make your deadline. But if others depend on you to make their timeline, the damage amplifies since you cause them to slip on their schedule, giving people reason to blame you. Thus:

I don’t want to be embarrassed.

In short, deadlines feel like they create more opportunities for us to look bad than to help us move forward, or is that the case?

5 Benefits Deadlines Provide

So, if deadlines cause so much suffering, why on earth do we have them?

Are they simply a necessary evil?

The best justification I’ve seen comes from the culinary world, where Dan Charnas, in his book, Everything Has Its Place, stated:

Excellence is quality delivered.

Why is that relevant?

For context, I’m a scope-driven person who firmly believes that to do quality work, you should take the time to do it right. But imagine you’re at a restaurant and you’re hungry. Would it be worth it if they told you it would take 6 hours to deliver a 5-star meal? Probably not. The point is excellence has a shelf-life. If you take too long to produce something, even if it’s high quality, its utility diminishes with time.

In short, the power of deadlines lies in acknowledging that there needs to be a balance between quality and getting it out the door. Excellence depreciates with time. If you take too long to deliver, then you risk the value of your efforts diminishing the longer you take.

Thus, you need to rethink the role of deadlines to leverage their power. Don’t just worry about the pain they inflict, but assess how they can help you deliver. In this regard, there are 5 benefits that deadlines bring to the table.

1. Urgency Creates the Need for Efficiency

The beauty of not having a deadline is you can move at your own pace. But that is also a curse. You aren’t required to be organized, prepared, or plan well because there is no driving pressure. You do things as you need them. This situation sounds great, but unless you’re extraordinarily motivated or disciplined, you will lose focus, and your progress will stall. Having a hard stop forces you to think in advance about what you need when because if you don’t, you risk not delivering. So, deadlines act as a forcing function. In fact, you will find that the tighter the deadline, the more planning and preparation you have to do since your window for execution is shorter.

2. Timeboxing Your Investments Facilitates Opportunities.

When you engage in any goal or project, the tradeoff is you can’t do other things with 100% effort. By having deadlines, you impose a limit on your commitments. So even if you go all in, it’s for a set period. After that, you are free to move on to other opportunities. Without having that hard stop, you risk staying mired in a goal that may have gone past its expiration date.

3. Sunk Costs Are Mitigated.

Having an end date also means that should you find the tasks for the goal pursuit unpleasant, you know the pain will be finite. In addition, for many long goals and projects, there is a point of diminishing return where you need to put in increasingly more effort for marginal gains in quality. A deadline puts a bound on sunk costs.

4. Antidote to Perfection.

When you have no deadline, you can continue working on something in perpetuity. The problem is that the world continues to march on, so new things are constantly happening. Knowledge and technology are great examples of things that change with time. So, if you’re continually improving and perfecting vs. getting stuff out the door and receiving real-world feedback, you incur all the costs of getting it “right” but never experience any of the benefits of getting it out. You don’t want to see all your blood, sweat, and tears amount to nothing because it’s always a work in progress. (Consider it took Henry Ford 20 iterations before he was satisfied with the Model T car. His business, later known as Ford Motor Company, would have gone bankrupt if they hadn’t sold their first Model A.)

Set a deadline so you can get the value of your invested efforts. If you’re afraid things aren’t ready, consider a soft release (not the final version), gather feedback on what needs improvement, and try again. But get it out there.

5. Some Stress Improves Creativity and Productivity.

While it may not feel like it, stress is good according to the Yerkes-Dodson Law. This states that performance is a bell-shaped curve with regard to stress. We know it deteriorates at high levels, but performance steadily increases with pressure at low to mid levels.

The same can also be said for creativity. When you feel you have insufficient time, you know that doing it the standard way isn’t going to work. So, you are more open to problem-solving and think out of the box to reach your goal.

These points highlight that deadlines can be valuable and used to your advantage rather than viewed as a necessary evil.

So, how does one go about setting up deadlines and mitigating their pain point costs?

3 Tips To Leverage Deadlines to Work For You

Oddly enough, before you algorithmically try to figure out how to set deadlines, you must understand what terrifies you about them. Assigning a due date isn’t enough if you don’t address the underlying concerns. It’s not sufficient to use pure willpower to “Just Do It.”

As stated earlier, two common complaints about deadlines center on the fears they negatively impact creativity and execution. Let’s examine some ways to address these concerns.

Tip 1: Budget for Ideation.

Great ideas take time. But there is no way of knowing when that critical insight will strike, and you don’t have infinite time to wait it out. The best bet is to timebox this stage and understand that you will miss something, and that’s ok. One issue with creativity is that you don’t see flaws in your concepts until you start implementation. Then, reality hits theory, and you begin to see things that you hadn’t considered or matters that you thought weren’t critical, start to raise their head. So, by limiting how much time you spend thinking, you transition to execution earlier. This step is crucial, as you can’t solve a problem you’re unaware of and don’t know that until you get something out the door.

Tip 2: Need Feedback For Execution.

When you work against the clock, you worry your performance will suffer because you haven’t perfected your actions. While it’s true that you can improve fluidity with practice, real-world exposure is the actual test of your skill mastery. At some point, you just have to go out and deliver. If you stumble, then incorporate that as a lesson learned. It’s important to be self-compassionate, as being self-critical doesn’t lead to a constructive solution. The combination of practice and real-world feedback leads to expertise. If you focus on only training, you’re wasting time since you’re short-changing yourself by avoiding real-life messiness.

Tip 3: Use 1/3-2/3 Rule to Balance Ideation and Execution Time

If there is a group of professionals who have to operate under conditions of high uncertainty and confusion, it’s the military. Wartime situations are the acid test of performing under less-than-ideal circumstances. It’s common to have incomplete and sometimes contradictory intelligence and work under unfamiliar conditions. While gathering more information is always desirable and more training preferable, combat’s fluidity creates a narrow operational window. Wait too long, and things can get worse. Thus, the United States military has a rule of thumb called the 1/3-2/3 rule. Given the time available, they try to cap the planning to 1/3 and use the remaining 2/3s to carry out the mission. This division allows a balance between ideation (planning) and taking action (operations). It gives sufficient time to think about what needs to happen but also recognizes you need to perform.

While the specifics may change depending on your situation, you need to partition both your plan’s ideation and implementation parts when setting the deadline. You also need to recognize that there are events that will upset your forecasts – you can’t know what you don’t know – so allow for some buffer.

The next takeaway provides some best practices for guesstimating deadlines and their alternatives.

3 Suggestions for Forecasting Deadlines and 2 Workarounds

One of the significant challenges in goal pursuit (and project management in general) is accurately predicting how long things will take. In an ideal world, if you nail the due date right, you can optimize your execution since you know what you need when.

Unfortunately, deadline forecasting is more art than science. However, the following techniques minimize the uncertainty as much as possible.

Suggestion 1: Reference Class Forecasting

Developed by Nobel Prize winner Daniel Kahneman, this approach is a fancy way of saying, “Find a completed project that is similar to yours and see how long it took others to finish.” Use their duration time as a data point for your estimate. Ideally, you look for several examples to get a distribution of time estimates. Once you have the data, calculate the median or average and use that to guide your deadline forecast.

If you can’t find a similar project, look at your tasks and search for data on them or something similar. Sum up the individual task times and use that as your guesstimate.

Suggestion 2: Time Logging

This approach is more for future projects than the current one. In short, keep time diaries of your work tasks to get a feel for how long things take and their variability. Some apps like Rescuetime track how long you spend on different software programs, and you can use these logs to estimate future deadlines better.

Suggestion 3: PERT (Program Evaluation and Review Technique)

PERT is a formula used in project management to estimate how long projects might take. It calculates total time (te) based on 3 data points: 1) optimistic time (o), which is the smallest time needed to finish the activity, 2) pessimistic time (p), which is the maximum time required to finish, and 3) the most likely time (m), the best estimate of how long you think it would take under normal circumstances. It takes a modified average over the 3 variables for the forecast:

te = (o + 4m + p)/6

PERT tries to balance among the best, worst, and most likely scenarios if those times are known.

The above are time-centric methods, but some people like to focus on process instead. Specifically, they may feel uncomfortable figuring out how long things take but are more confident about how many passes they are willing to make on an effort. In short, they feel good about making progress via iterations.

The following 2 approaches have greater variance than traditional point deadlines but are powerful when you want to follow this second view.

Workaround 1: Work in Sprints

Adapted from the Agile software engineering practice, sprints are typically 2-3 weeks long. During this time, you define the minimum viable product (MVP) you can complete during the sprint. As achieving anything sizable during that period is rare, Agile is about progressing incrementally towards your goal over time. You must break down your target into smaller chunks or at different resolutions for this to work – in short, your MVP. At this stage, estimating how long you think these chunks will take and knowing how much work you can finish in a given day (your work capacity) is critical. During each sprint, you gradually build up to your MVP.

Your final product is the aggregation or evolution of MVPs completed over several sprints. So, in this case, if a deadline is set for you, you assess if you feel comfortable with the number of sprints that can be done by then. If not, you can push back or reduce the number of goal features that can be done by the deadline and see if that is acceptable. Or, if there is no deadline, you can set the number of sprints you feel should allow you to make substantial progress and revisit where things are at the end.

The power of this approach comes from the MVP. While not complete, it is a product that is good enough to go into the real world at the sprint’s end. The motivation for the MVP is that sometimes, for business reasons, products need to be shipped out “as-is.” This approach provides a back-and-forth mechanism between stakeholders and developers on what can be released by when – a compromise between completeness and deliverability.

Workaround 2: Use Design-Build-Test-Learn (DBTL) Cycles

Similar to sprints, Design-Build-Test-Learn (DBTL) cycles were developed in biotechnology to explore and find solutions again by rapid iteration. In each cycle, the effort is divided into workplan design, followed by its execution (build), testing how the design fares against the success criteria, and obtaining feedback to learn what can be used to refine the next design iteration. Given a block of time, use the 1/3-2/3 rule with DBTL to balance between the design element and the rest. The power of DBTL is when your goal or target has a lot of uncertainties and unknowns, you get your answers through experimentation. Hence, DBTLs are powerful if you are evaluating different work strategies towards a goal since the learn phase allows you to compare and contrast (Sprints also have a lessons learned component at their end, so you know what to improve upon for the next sprint).

The power of DBTLs comes from iteratively going through a workplan you feel secure about and making steady progress.

Regarding work duration, you can set a limit of 3-4 DBTL cycles, revisit your progress at the end, and decide whether it’s good enough to stop or continue.

Both sprints and DBTL cycles are helpful when you’re afraid setting deadlines will adversely affect quality. They also try to balance the constraint of getting things out the door with how much you get done. Each iteration has a hard stop but can be viewed as a milestone marker to a larger goal.


Whether you love or hate deadlines, they serve a purpose. They help us stay focused and get things out the door. It’s often the stress that they generate that we can do without.

The key is not to view deadlines as the enemy but as a minor kick in the pants to help us make progress on the things that matter. In this article, we cover 4 pain points deadlines bring and discuss the 5 benefits they provide if used correctly. With the 3 tips to leverage due dates and the 5 different forecast techniques and deadline alternatives, you can transform deadlines from an unnecessary evil to a powerful tool to motivate yourself across the finish line.

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