How to Know When to Quit

You know the dilemma.

You’ve been doing something for awhile, but it doesn’t seem to be working. Should you keep going, and push through with it? Or quit and do something else?

There’s no right answer to this.

Sometimes, sticking through will be the right answer. My business took off after five years of work, and after a disappointing two years which were bad enough that I was nearly at the quitting point.

Other times, quitting early will save a lot of pain. I spent over a year in a project in university when it became clear it was a toxic environment with an ethically-questionable advisor. I stuck through, but part of me regrets not stopping a lot earlier.

The decision of when to quit isn’t just for big life-changing decisions. When you step on the exercise bike, start studying or decide to meditate. All of these will push you to ask whether you should keep going a few more minutes, or give up and do something different.

The Commitment Muscle

Sticking through things longer builds resilience. Not only do you increase your endurance, you start to trust that you are able to keep the promises you make to yourself.

However, sticking through on a bad idea, project or effort can lose you years of your life. If the environment around you was rotten, this can scare you away from anything similar in the future. Quitting ahead of time in a bad relationship, bad job or bad project can be the very thing you need to improve your ability to stick to good ones.

The goal is to increase your ability to sustain commitments you make to yourself, without undermining those commitments by over-committing to the wrong things.

Decide Your Quitting Points in Advance

How do you overcome this?

Simple. Choose your quitting points before you start. These are pre-specified periods of time, effort or stress that you decide you’re willing to endure before you step back and re-evaluate.

When I started setting new habits for myself, one of the best ways I learned was a thirty-day trial. The benefit of setting a new habit over thirty days isn’t that after one month everything will be on autopilot. Rather, it’s that thirty days is a good amount of time before you set a quitting point. Even a habit that is inconvenient and ultimately unworkable is worth thirty days of testing.

Similarly, when you set big goals, choose the points in time when you’ll be able to step back and re-evaluate.

In my business, for ongoing commitments to new projects, I usually aim for one year to test things out. That’s not enough to necessarily reach success with those projects, but it’s enough time to decide whether it’s worth continuing or whether I want to try something different.

How to Pick Your Quitting Point

There’s three ways you can pick your quitting points:

1. Set shorter lengths of projects.

The easiest way to do this is to simply set projects that are short enough that committing to them all the way is easy enough to do. Most big projects in work, health, learning and life can be broken into chunks of 1-3 months which aren’t too much to commit to.

2. Set re-evaluation points for ongoing habits and goals.

For things which you expect to pursue for a very long time, you may want to set up junctures for re-evaluating your progress. Here, the goal is to put in quitting points that are sufficiently far out so that you’ve gotten enough information before you decide to switch. They should also be spaced out enough so that day-to-day frustrations don’t turn into abandoning the whole project.

At the same time, defining these points in advance also gives you some freedom. It means, when things get bad, you know when to re-evaluate them in the future.

3. Based on impact to other areas of your life.

Time is the most straightforward way to manage quitting points, but you may choose other metrics. One way might be to look at how those things impact your life. You may decide to work on one goal, so long as it doesn’t start interfering with another area of your life.

This one is harder to do, because many of these boundaries are going to be subjective. However, you might decide, in advance, that a certain project is something you’re going to work on for a point, but you’ll put it aside if it gets too stressful or if you stop enjoying it.

The value of deciding this in advance, rather than simply quitting when things become unpleasant, is that you’re exercising your ability to set an intention to commit to a certain level and stick with it. If you want to be able to achieve goals that require pushing through some discomfort, you need to be able separate those commitments from ones you’re pursuing just for fun.

Making the Decision

Ultimately, picking your quitting points doesn’t help you answer the question of whether to continue or quit. There’s no general “right” answer that will cover all cases. But, by picking your quitting points in advance, you give yourself the ability to accomplish a lot more things.

How to See Reality as It Is

People often get accused of seeing the world the way they want it to be, rather than how it is. This kind of optimism-bias, is supposedly pervasive, and it takes bold truth-tellers and skeptics to show people the light.

I’m not sure I agree.

It’s certainly true that we don’t see things exactly as they are. I’m not denying that.

Rather, I’m skeptical that optimism is the fundamental bias that most people exhibit.

Far more people, to me, seem irrationally anxious than optimistic. For every person who is blissfully unaware of the impending danger, there’s a dozen who are nervous wrecks over all the things which probably won’t happen but they can’t stop thinking they will.

Evolutionary biology, too, suggests that it would be quite odd for nature to fashion an overly-optimistic creature. If anything, we should be biased towards anxiety and pessimism. A threat unnecessarily-prepared for is much better than a hidden-danger that was gleefully ignored.

Instead, I believe the fundamental distortion of our perception is caused by something else.

Learning How to See

One of my favorite books on drawing is Drawing on the Right Side of the Brain. Despite the somewhat outdated right-brain, left-brain psychologizing, the book has quite good drawing advice.

The basic contention is that the problem most people have with drawing isn’t a problem of moving the pencil, but not knowing how to see.

Our minds, in their incessant categorizing and conceptualizing, don’t really look at the world. We see a table, and immediately our brain tells us what a table is like: four equally-sized legs, with a flat surface on top.

As a result, many people, when drawing a table, make four equally sized legs. Except it doesn’t look right because, at most angles, foreshortening will mean that the legs aren’t all the same length.

This is also a major obstacle in drawing faces. Our brains make detailed assessments of eyes, mouths and noses, which convey important information for our social lives. So much so, that we don’t notice that they only take up a much smaller part of the head. As such, novice portraitists draw awkward faces where eyes are at the top and mouths near the bottom (eyes are actually in the middle of most people’s head).

To learn to draw, you first must learn to see.

What Drawing Failures Teach About Reality

The distortion we have with reality is not that we see things optimistically or pessimistically (although there may be cases where such biases exist). Rather, the problem is that we see reality through our impressive structures of concepts and categorization.

The reason drawing is hard, especially for familiar objects, is that we already have a lot of knowledge about the physical world as a three-dimensional space which interferes with the ability to translate that space into two dimensions.

Reality is incredibly noisy. At any given moment, millions of impulses from your nervous system are coming in simultaneously. To process them, those signals need to be filtered, processes and reorganized into something sensible. Random smatterings of brown on your retina become a dog. A familiar pattern of dots becomes a face.

This process is a good thing. To see reality without those filters isn’t to see some deeper truth, but simply chaos. Without any lens of ideas filtering our perception, there’s not much useful we can do with it.

The problem is in recognizing that this organization is often constructed for a particular purpose, and for it to be useful for some other purpose, often the same signals and information will need to be reinterpreted differently.

The challenge of learning to draw, therefore, is to take the rather automatic process of ignoring what things really look like and focusing on what things really are (a chair, dog, face, etc.), and refocus your attention back onto the shapes and splotches that impinge on your retina. To see things as two-dimensional, even though your mind is racing ahead to turn them from shapes into things.

Retraining Your Vision

While this process of conceptualizing and organizing is fantastically useful, occasionally it can get stuck. A pattern of thinking which was useful in one moment, can crystallize into a dogma from which it is impossible to break free.

In these moments, it’s often necessary to take a step back. See things for the fuzzy splotches that they are, and start noticing them in a different way. From there, you can start to try seeing them in a different way, a way that is more useful for your current purposes, even if just temporarily.

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