How to Make Deadlines Work Using Hofstadter’s Law

Hofstadter’s Law ^[1]: “It always takes longer than you expect, even when you take into account Hofstadter’s law.”

This little recursive nugget of wisdom can be stated simply as, “It always takes longer than you think.” That’s an unfortunate truth both in planning projects and setting goals for your life. When you don’t have all the information available, it becomes almost impossible to predict how long you will take to finish.

But how do you set deadlines when predicting the time you need is almost impossible? I don’t believe you should abandon deadlines entirely. Although some people work well without constraints on timing, I would say they are in the minority, not majority. I’ve already written about some of the benefits of using deadlines in this article. Now I’d like to tackle how to plan deadlines when timing is unknown.

Using Deadlines as a Creative Constraint

Coming up with ideas for articles is difficult. Not because I have too few ideas, but because I need to put each through a ruthless threshold of constraints before I start writing. I could come up with hundreds of article ideas and only have one or two that pass. Most creative people I know work the same way with an endless volume of ideas and a brutal filter to eliminate 99% of them.

Deadlines are a good aspect of that filter. They can cut off ideas that sound good but don’t fit into a practical timeline. Deadlines can be an extra layer to the filter you use to implement ideas.

Deadline Before Planning

The way to stop Hofstadter’s ever expanding project size is to set a firm deadline before you start planning how to do it. By deciding you want a certain outcome by a particular time, you immediately narrow down the base of ideas. Cutting out the frivolous and lengthy ideas.

Whenever I start a big project that will take months, I start with the deadline. I set a firm six-month deadline for this software program, and I had less than a month when completing my e-book, How to Change a Habit ^[2]. Whenever you have considerable complexity in a project, a hard deadline focuses your ideas.

Look Out for the Impossible Deathmarch

But a hard deadline can quickly turn into a deathmarch. Where the work expected doesn’t fit into the small container set out by the deadline. Instead of just containing the project, the deadline strangles it.

This is particularly true of goals that have limited flexibility. Setting a goal to double your income in a year might be almost impossible. You may get a creative insight, but you might not. I used to set traffic goals for this website until I realized that it wasn’t worth it. There were no magic solutions that a strict deadline could create.
My rule of thumb deciding when to set a hard deadline is to examine the flexibility I have. Completing a project like a book or a piece of software has enormous flexibility. A hard deadline can reign in your ideas. A traffic goal has less flexibility so your patience with shifting deadlines needs to be greater to compensate.

How to Make Use of Hofstadter’s Law

Here are some tips to consider when planning goals or projects:

1. More flexible projects means more rigid deadlines. These are inverse qualities. Deadlines only work because they provide a creative constraint, filtering your ideas. Here are a few possible goals listed from least to most flexible:
   1. Weight Loss – Low flexibility, so be patient and have a softer deadline.
   2. Income, Employed
   3. Website Traffic
   4. Income, Self-Employed – Medium flexibility, set a deadline but don’t let it burn you out.
   5. Learning a Subject
   6. Writing a Book
   7. Creating a Software Program – High flexibility, keep a strict deadline.
2. Separate your “needs” from your “wants”. When have you accomplished your task? A strict deadline needs strict rules for completion. Is your software completed when it goes for sale? When it reaches beta? When you’ve finished major components? Clear rules make better creative constraints.
3. Conduct a brain purge. Spew the contents of your thinking on paper. When brainstorming within a strict deadline, come up with as many ways as you can to reach your goal faster. I regularly spend an hour or two brainstorming ideas every week or two.
4. Cultivate patience. It’s easy to burnout and quit because things are getting difficult. You need to be willing to go for the long-haul. I fully expect it might take several years before I can earn a substantial income off this website. But expecting to change the world in a month is a recipe for failure.
5. Know when to reschedule. For “softer” deadlines, learn to reschedule them if they no longer motivate you. If you begin to realize they are an impossible deathmarch, retune them to meet reality.
6. Work on minor deadlines first. Break down monthly and annual objectives down to daily actions. Big goals aren’t important if they don’t translate into changes today.
7. Tweak for performance. When I lift weights at the gym I am careful to pick a weight and amount of reps that will be difficult, but possible. Too light and I don’t get any benefit. Too heavy and I give up. Practice finding what deadlines motivate you best. Pick ones that are tight, but don’t cause you to give up in frustration.

Practice Patience on Soft Deadlines

If your goal has a more rigid path to completion, cultivating patience when pursuing your deadlines is what matters most. This is at the heart of Hofstadter’s Law. Goals have a lot of uncertainty and it can take longer than expected. Work on your patience in these moments and focus on actions over results.