Should You Set Deadlines for Your Goals?

Say you have a personal goal: you want to build a business, lose weight or learn a language. Does it make more sense to set a deadline for that goal (i.e. I want to speak conversational French in 9 months) or should you ignore it?

I think this is an interesting question because, on the one hand, a deadline can motivate action. By knowing you need to accomplish something in a particular period of time, you’re less likely to procrastinate on it.

However, a deadline can also be deflating if it turns out your goals’ natural timeframe isn’t in line with your projections. While you can often accelerate progress by working a bit harder, many goals have a natural timeline they will be achieved at. If you set your deadline much faster than that mark, you may end up frustrated when it looks like you can’t reach it.

When Do Deadlines Work Well?

In my mind, deadlines work well for your goals in the following conditions:

  1. You can be confident your deadline and the natural timeframe for the goal are consistent.
  2. You have a fair bit of flexibility with how much effort you can put into the goal.

With the first point, setting a goal which has a timeframe that is much longer than your deadline will inevitably lead to frustration. For instance, if your goal is to lose 30 lbs in a month, not only is this unlikely to be achieved but you might have to risk your health to accomplish it. Similarly, if you want to build a six-figure online business in six months, you’ll also probably be disappointed, no matter how hard you work.

The second point, however, is important too. Deadlines work because they can motivate action. But if constraints mean you really can’t invest more time and energy towards a goal, there isn’t much point.

For example, if you’re trying to learn Japanese and you can only invest three hours per week, a deadline doesn’t make much sense to me. Unless you are prepared to increase the investment or work harder when you’re behind on your goal, a deadline is just there to taunt you.

What Goals Shouldn’t Have Deadlines?

Conversely, I think goals shouldn’t have hard deadlines when:

  1. You don’t know what the natural timeframe is for the goal.
  2. Your investment into the project is relatively fixed.

If you have no idea what is a reasonable deadline to set for a goal, I’m not sure it makes much sense to set one. Unless, of course, you can be prepared to ramp up the investment of time and effort by a large amount, in the case that you’re not meeting your target.

Set a Period of Focus, Instead of a Deadline

A good alternative, I’ve found, to setting goals with deadlines is to set a period of focus instead. This allows you to constrain your time, so you don’t have a project that extends into infinity. But instead of setting a firm standard you need to reach by the end of the project, you just see how far you can go.

The MIT Challenge, had a traditional deadline: pass all the exams and do the programming projects in one year. When I was learning Chinese, in contrast, I had a period of focus: learn Chinese over three months and see how much progress I can make.

Starting with a period of focus can be useful when you’re not sure what the natural timeframe is for a certain goal. Then, as you’re working on the goal, and have a better sense of where you might end up, you can set a more traditional deadline to motivate action. Halfway through my Chinese learning experiment, I decided to write the HSK 4, since I felt it was reachable with the time I had left.

What do you do? Do you tend to set deadlines for your goals, a period of focus or neither? What do you do to stay motivated and avoid frustration when working on your own projects?


What’s More Productive: Counting Hours or Tasks Accomplished?

I’m a big fan of setting constraints to get work done. If you make work a scarcer quantity, you’re more likely to use time wisely and get things done than if it feels like an endless to-do list.

There’s two key ways you can do this: restrict your hours or restrict your workload.

Restricting hours is fairly simple: set aside a certain chunk of time for work and don’t work outside of it. This is a commonly advocated productivity method, from Cal Newport’s fixed-schedule productivity to Pomodoro’s for working in short bursts of time.

Restricting workload changes the equation. Instead of deciding on a set number of hours, you decide on a set number of tasks. You might decide to create a list of tasks for the day and keep working until you can get them finished. It also applies on shorter timescales when you might decide not to work until you get to a particular milestone and then call it quits.

I’ve gone back and forth over using both types of constraints over the years. This suggests to me that neither is a dominant strategy (better in all situations) but that both have their usefulness with different productivity problems.

When Should You Constrain Time?

The biggest advantage of constraining time is that it’s always unambiguous. If you decide to work for three hours and then stop, there’s no confusion there. On the other hand, if you decide to work until you’re finished an essay, there’s the chance that it might be done in twenty minutes or take three weeks.

This lack of ambiguity means that the constraint rarely fails because you were overly optimistic. It’s a lot easier to predict working a set number of hours than working until you complete a set number of tasks.

However, I’ve also found time constraints can encourage a sloppier attitude towards work. You might decide to spend all day studying in the library—but without tasks to constrain your productivity, you end up checking your phone or skipping hard problems to work on easier stuff.

My rule of thumb is that time constraints work best when:

  • It’s unclear the time and effort required to complete the task.
  • The work itself is ambiguous, and may require a lot of trial-and-error.
  • The work is continuous and can’t be easily divided into discrete chunks.

I tended to use this method during my ultralearning projects, because they often had long stretches of continuous work where it would be unclear how much time would be required.

When Should You Constrain Tasks?

The advantage of constraining tasks is that it focuses directly on the object of productivity: whatever you’re trying to accomplish. Done successfully, this means that it’s very hard to fool yourself into believing you’re working hard but you’re not actually accomplishing much.

The drawback of this approach is that tasks can often be ambiguous or hard to predict. If you fail to predict properly you might create to-do lists which are unachievable or those that are trivial. This can create more variability in your schedule, resulting in days when you finish everything quickly and days when you can’t finish it all.

I’ve found task constraints work best under the following conditions:

  • Tasks are discrete and fairly predictable.
  • You might be tempted to fill up time without making real progress
  • The tasks are frequently repeated, and therefore easier to estimate.

I’ve tended to opt for this method with a lot of my business and writing work. They tend to form discrete tasks that are fairly easy to anticipate how long they will take. Constraining the tasks encourages me to get them done quickly, with minimal delay and procrastination.

What Constraint Should You Use?

I find myself flipping back and forth between the two constraints. I tend to use task constraints as my default, since much of my daily life is filled with the small, repeatable tasks that are well-handled by that system. But I switch to having chunks of time for particular projects when it’s clear I’m not getting much done just setting up the tasks.

What do you use to control your productivity? Do you prefer making to-do lists and focusing on tasks? Or do you prefer to set a schedule and focus on hours invested? Share your thoughts in the comments.


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