Discouraged? Here’s How to Stay Motivated

Recently a reader asked me how to stay motivated to do the work after being dealt a number of setbacks. How do you keep studying when you’ve failed the exam three times already? How do you keep sending resumes when you’ve been turned down after each interview? How do you persist when all you experience is failure?

This is a problem I’ve thought a lot about, both intellectually and personally.

Intellectually, the role of setbacks in motivation is well-understood. Progress is one of the most reliable motivators in our work. And setbacks aren’t just negative progress—research by Teresa Amabile finds that setback experiences are roughly three times as negative as progress is positive.

Similarly, it’s long been understood in therapeutic contexts that lacking self-efficacy can create a self-fulfilling prophecy: when we have an irrational fear, we avoid exposing ourselves to scary situations, even if they might provide evidence our fears are overblown. Likewise, if we feel like everything we try ends up in failure, we don’t put in the effort to make it succeed.

I’ve been there. I’ve experienced many moments of feeling completely stuck, where everything I try doesn’t seem to work. It took me over five years writing before I found a way to make a living from it. My motivation to keep going was often mixed in with a considerable amount of self-doubt.

Thus, even beyond an intellectual interest, trying to resolve the problem of motivation in the face of setbacks has had enormous practical consequences for my life, as I’m sure it does for everyone.

Is Giving Up Actually Irrational?


A lot of self-improvement advice takes the perspective that persistence is an unqualified good. In this view, staying motivated is hard, but it’s always the right decision when faced with challenges in life.

Frankly, this is false. Giving up is the correct answer in many situations. If anything, human beings have a tendency to persist too long in many pursuits. We fail to exclude sunk costs when evaluating our decisions. We allow initial conditions to frame our future decisions. We take unnecessary gambles to win back losses.

 In many situations, then, quitting is the right move. Our motivational circuitry is, in some sense, responding to the situation we perceive in the environment. Experiencing a lot of failure doing one thing is life’s way of telling us to try something else.

I bring this up because, even though we all can struggle to deal with the emotional and motivational aspects of persistence, we need to start by answering this question as objectively as possible: should I keep going?

Only if you can give yourself a good answer in the affirmative—that yes, continuing is still the best option, in spite of the previous setbacks—does it even make sense to try to resolve the emotional and motivational problems of persisting.

When Should You Keep Going? When Should You Quit?

In general, continuing is the right answer when, looking at all the other alternatives, it’s still the most beneficial course of action.

Say you’re studying for an important exam, which you’ve already failed three times. Should you continue?

The answer depends on

• (a) what’s the chance you can still pass if you work hard,
• (b) how much time and effort do you need to invest, and
• (c) what other opportunities would you have if you didn’t go for it.

Having failed three times in the past is evidence, at the very least, that the exam is harder than you thought. Thus, the probability of succeeding is probably lower, and the effort required to succeed is higher than you might have thought before you attempted the exam.

However, the main factor here is actually (c), your other opportunities. If passing this exam doesn’t have a major influence on your future career or professional life, or if you have a really good fall-back opportunity available to you, then persisting might not make sense. You’d be better off spending that time and energy tackling other projects.

 If, instead, this exam matters greatly for your future career, and failing it leaves you with much worse professional opportunities, then it might still pass the cost-benefit test to study for it, even if you have to revise your probability of success downward and your effort upward.

Whenever I’m facing setbacks in something, whether it’s a major goal in life or simply one of my ongoing projects, I like to do this kind of rough analysis to get a sense for whether persisting still makes sense. 



This kind of analysis sounds almost depressing. Isn’t this just a way to reinforce poor self-esteem? Wouldn’t a pep talk work better?

In practice, however, I’ve found the opposite is usually the case. Either I get the clarity that giving up is actually the right decision, or I realize that, despite the recent setbacks, it’s still in my best interest to persist. Either way, I can move forward decisively.

Rebuilding Motivation

Supposing you go through this exercise and you determine that, despite your recent frustrations, continuing with your current pursuit is still the right decision. How do you rebuild your motivation to actually pursue it?

Once again, I disagree with a lot of advice given in this space. People are told to repeat positive affirmations to themselves, thump their chest or otherwise hype themselves up. This may work momentarily, but the effects wear off quickly and leave you vulnerable to future setbacks you’ve convinced yourself won’t happen again.

I think the key to rebuilding motivation is to have a clear plan that you honestly believe will work.

Take the exam example again. Suppose you’ve decided that it’s going to take you another six months of studying full-time to prepare for the exam, and even that only gives you fifty-fifty odds of success. However, you believe this is still a better opportunity, all things considered, than what you might do in those six months otherwise.

To rebuild your motivation, you need to create a plan that you feel, deep in your bones, would work as advertised.

Sometimes this involves making a plan that would definitely work, even if it requires a large amount of effort. For instance, if you’ve only put in ten hours per week studying, you might be able to convince yourself that studying full-time for a stretch would definitely work. If so, then drafting up this plan and committing to it can help overcome the past disappointments.

Other times, the plan may not be guaranteed, but you still believe it would be worthwhile, either because the probability of success is acceptably high, or because you believe the information you’d gain from your attempt would make that attempt worth it.

For example, if you’ve been struggling with finding a job—failing to land a single interview despite sending out a dozen resumes—then a project to send out two hundred resumes won’t guarantee success. But it does tell you that whatever you’re experiencing in the job market isn’t just bad luck, rather it’s a pretty good indicator that your resume isn’t sparking much actual interest.

Motivation tends to falter when we have plans that we don’t honestly believe will work. Success should look like a logical progression of doable, step-by-step actions that will lead to the desired result. If there are steps in your plan that require a miracle to succeed, deep down, you won’t believe in the plan, and that lack of belief will undermine your motivation.

If you can’t come up with a plan you believe in, the best first steps are either to do some more research to come up with such a plan, or to adopt a more exploratory mindset by trying out various things with the goal of finding a path that might work.

For instance, if you’re trying to succeed as an entrepreneur, it may not be clear what’s necessary to create a product people will want to pay money for. But you could decide it’s still worthwhile to spend six months experimenting with prototypes and talking to customers to see if you can find an offering that might have potential.

In the end, the motivation to persist is less about willpower than it is about rationally assessing your situation and crafting a strategy and plan you can believe in. If you can do that, the emotions needed to keep going tend to follow.