How to Overcome the Fear of Failure

One of the most common causes of procrastination is the fear of failure.

Let’s imagine we have a task to do and we feel negative about it for some reason.

Negative emotions are like a hill

That makes it harder to do, but we can make it even harder. Much harder. How?

We might think we cannot possibly make a single mistake.

Maybe we adopted this attitude from our parents or our teachers in school. Whatever the reason, many of us fear failure and don’t see it as a natural part of the process.

So, failure turns from something natural, though unpleasant, into a lethal threat. Every simple task becomes a tightrope walk over a deadly chasm.

Fear of failure is like a chasm

No wonder the fear of failure is so paralyzing. When we perceive every mistake as a possible death (or sacking, or dropping out, or a proposal rejection), it raises our stress levels and we try to relieve them by procrastinating.

We make ourselves into a tightrope walker.


What a tightrope walker believes

If I fail, I’m worthless and destined to die

If this business fails, I’m clearly someone who can’t have any kind of business.

If this book doesn’t hit the bestseller list, I’m clearly not a good writer.

If I don’t pass this subject, I’m clearly never going to be good at it.

Some of us have a tendency to view failure as a fatal verdict.

If I fail, I’m clearly not good enough.

When we fail (which we inevitably will at some point), we can take it as the end. We get crushed.

Well, better do something else.

The thing is, everyone fails. We lose money, we lose partners, projects fail… but not all of us react in the same way.

Different reactions to failure

Most of the time, failure isn’t a fall off a cliff.

We humans have an uncanny ability to recover from all sorts of mistakes, if we allow ourselves to.

It’s foolish to expect that we'll be good at everything we try and won’t fail ever.

Let’s update our view of failure.


When I fail, I’ll get back on my feet

Everything doesn’t depend on one single performance most of the time.

When you look at the lives of successful people, we see that they failed many, many times.

Legendary investor Ray Dalio at one point lost all his money. Entrepreneur Elon Musk at one point didn’t have enough money for rent. Apple founder Steve Jobs was at one point kicked out of the very company he started!

If these people took those failures as fatal diagnoses of their worthlessness, neither one of them would build billion dollar companies.

They learned from their failures and got back into a ring.

Failures big and small happen all the time. The important part is recovering, learning from them (so then they don’t repeat) and taking them in stride.


Performance = my self-worth

As with perfectionists, people who fear failure identify with their work.

New project? If it doesn’t pan out, I’m a failure.

Test in school? If I get an F, I’m an idiot.

If I’m not first, I’m below average.

Self-worth tied to an outcome

Failure is not a fatal diagnosis. One F doesn’t make someone an idiot, it simply points to their current level of mastery of the subject. And that level can improve with effort.

Failure is not a diagnosis of worthlessness.


Performance = current level of ability, I can always improve

You’re at a competition and you lose.

You’re taking a test and you hand in an empty test with just your name.

You make a presentation on the wrong topic.

Happens to everyone. You can’t win every contest and succeed with every project for the rest of your life.

So why not take a particular performance (presentation, project, test,...) as just one performance at one point in time?

Every product of our effort is a clue whether we’re going in the right direction or not.

Bad performance? Okay, what do we have to change? How can I get better at this?

Good performance? Awesome, let’s go full steam ahead.


Mindset shifts

To summarize, here are the 2 main mindset shifts to take away:

Now let’s take a look at some tools and exercises that can help us manage and reduce the fear of failure.


Hi there! This is a free sample chapter from our book.

If you want to get a whole comprehensive guide about procrastination and learn about each fear deeply, check out our handbook.

We put hundreds of hours of research into it, so you don’t have to. And also we keep updating it often to give you the best, most concrete strategies for dealing with procrastination.

1. Put the fear of failure into perspective

Negative visualization

Negative visualization - difference between tragedy and inconvenience

Whenever you feel you’re procrastinating because of the fear of failure, we recommend you to do this exercise.

What really happens if I fail?

People often avoid philosophy because they don’t consider it to be practical, but there are some branches that are useful in everyday life.

For instance, in stoicism there’s a practice of negative visualization.

It’s simple:

you imagine the worst case scenario you can and then imagine how you’d deal with it.

What if you were fired tomorrow? What would you do? What if you failed all tests this semester? What would you do? What if your computer with your thesis on it burst into flames? What would you do? What if your new project failed miserably and publicly? What would you do?

The goal of this exercise isn’t to make you depressed. It’s to acknowledge that all those terrible things that float through our consciousness might happen, but they wouldn’t be the end of the world…

Once you describe the fear you have in detail, it’s usually not that scary. And even if it is, negative visualization can help you prepare for these worst case scenarios and stay cool if they ever play out.

What if they kick me out of school?

I could go abroad and teach English. I could help out in a restaurant to save up for a gap year. I could ask friends about any jobs or help that guy I met last week with marketing. I could also start learning more about programming...

It’s so easy to forget all the bad things we dealt with in the past. All the mistakes, mishaps, missteps,... When we think vaguely about failure, it stops us in our tracks. But when we start thinking concretely and prepare for the possibility, we realize it might not be the end of the world after all.

How to do negative visualization:

  1. Imagine the situation you fear regarding a task or a decision.
  2. Ask yourself: what is the worst thing that could happen?
  3. Describe what would happen (in your head or on paper).
  4. Ask: Would it be bad? What would you do if it happened?

How to overcome fear: Understand your options

We sometimes think that our situation is one big dead-end.

We might have a job we depend on and be unable to do what we want because it would mean losing it.

Or we might have one big project we’re working on that would sink us deep into debt if it didn’t pan out.

The problem with scenarios like this is that they put tremendous pressure on us.

And we try to ease it off by procrastinating.

If we have one thing to do and its failure would mean the end of the world, every step we’re unsure of becomes a tightrope walk.

One email or a blank page of a document turns into the possibility of apocalypse.

Who wouldn’t be stressed in a situation like that?

What if we could ease the pressure a little more?


Plan B and Z

Plan A, B, and Z

Plan B and plan Z show us that we often have a choice when it comes to our future.

When we see that we have many options open to us at any given point in time, failure becomes much less scary.

Let’s look at plan B and Z.

Plan B
= what you’d do if plan A didn’t work out, using the skills and knowledge you have

Plan Z
= what you’d do if everything went terribly wrong


Plan A:
studying computer science and helping out at a company with design.

Plan B options:
If I get kicked out of school because I’m working too much, I’ll try to find an easier field to study and reapply asap.

If you get fired from work because of studying for exams and not putting in enough hours, I’ll try to freelance until I have a new opportunity.

Plan Z - when sh*t hits the fan

What if everything went horribly wrong? What if you couldn’t use your plan B for some reason?

What would be your plan Z - the last refuge?

For example, what if you were a programmer and had a brain injury that would make you unfit for mental work? You could still stock shelves in a supermarket or be a barista.

Or you could be a business owner and suddenly go bankrupt. You could probably become a consultant and teach what you learned (not what got you into trouble, understandably).

No one wants to use plan Z, but it’s good to have it ready in the back of your mind.

“Well, if everything goes to hell, I can always ______________________________.”

Knowing our plan Z allows us to understand that the world isn’t going to end if our current efforts fail.

What’s your plan B and plan Z?

2-3 sentences are all it takes. It’s worth taking 5-10 minutes to get a greater peace of mind.

Plan B




Plan Z




Win-win: make it impossible to fail


Sometimes the failure we fear is not fatal in the least. It might be 0 likes, or slight embarrassment, or simply no reaction. All those can hurt, but we can bear them on most days without a significant problem.

But even a slight failure is a failure - a win-lose situation.

How could we make the deal better? How could we make it win-win?

Imagine this scenario:

You have an idea for a podcast about your thoughts on various topics, you put a couple episodes on SoundCloud and can see that only about 10 people played the first, 5 the second, and 3 the third.

Is that a loss?

But what if along the way:

  • You learned how to set up a microphone to capture the sound best.
  • Learned to minimize noise, add sound effects, and edit audio files.
  • Learned what speech ticks you have and how to leave out the hmms and uhs.
  • Improved your writing by first putting your thoughts on paper before reading them.

Is that still a loss? Or have you acquired skills that you didn’t have before that could serve you in the future, and destroyed a mental block regarding audio recording ?

Even if no one reads our blog, we’ll have improved our writing.

Even if no one uses our app, we’ll have learned to create it.

Even if no celebrity answers our emails, we’ll have practiced the courage to reach out.

Even if we fail, we can still benefit from the effort.

How can’t you lose?

How can you make whatever you fear a win-win for yourself?

What will you have learned along the way?

Who would you have helped? Who would you have met?

How would you, or others, benefit, even if your endeavor ultimately failed?

  1. Write down the task, project, or decision you fear
  2. Write down 3 sentences starting Even if I fail, I will …





Use the fear of regret

Fear of regret outweighing fear of failure

Elon Musk estimated the odds of his success with SpaceX to be about 40%.

Jeff Bezos thought Amazon had about 30 % chance of succeeding.

How then could they make the decision to start? How come they didn't worry and dwell on those odds? How could Musk invest millions of his own money into SpaceX?

Because it was worth it.

Fear is only one side of the equation. Depression, regret, sadness,.. those are on the other side.

For Musk, the other side of the equation was profound sadness. If humanity couldn't go to Mars, that would be depressing to him on a fundamental level.

For Bezos, it was regret that helped him overcome his fear. He read that the Internet was growing 2300 % a year. That seemed like a great opportunity. But he already had a great job in New York, how could he leave it and start from scratch something risky?


Regret minimization framework

When I'm 80 and looking back on my life, would I regret not taking this opportunity?

That is what Jeff Bezos asked himself. He calls this the regret minimization framework. If he didn't start Amazon, he knew he would have spent the rest of his life thinking about "What if I had started that internet company?"

Musk would probably spend a lot of time thinking about how he could have been a space pioneer if he didn't start SpaceX.

We regret what we didn't do more than what we did do. Not asking that girl out, not asking for a raise in that meeting, not spending more time with one's grandparents,...

You can overcome the fear of failure by understanding that you'd regret not doing the thing you want to do for 50 / 60 / 70 years. That's a lot of haunting regret.

Is the thing you fear worth it?


2. Set yourself up to learn if you fail

As we mentioned before, failure is most often not fatal, especially when it comes to business or creative endeavors.

Yes, you might give a bad presentation. You might paint a lousy portrait. You might cause someone discomfort because your app didn't work. That happens. It's not the end of the world.

Failure doesn't feel great, but you'll survive. You'll get back up and try again.


"It might not work"

Seth Godin, a best-selling author and master marketer, often repeats this phrase:

"Do things that might not work."

Why does he do that?

This phrase acknowledges that in creative work you might fail, you might disappoint someone, you might feel bad, but you should still try. You should still try to innovate, to push yourself, to create.

So there's always some risk of failure, but a) the failure is most often not fatal and b) you can reduce the risk of failure.


Reduce risk by experimenting

The thing that is so easy to forget is that we can try things.

We don't have to create the perfect thing on the first try.

In many endeavors, you can try various things with little expense.

In your life, you can try exercising every day for 3 days.

In business, you can try running ads on Facebook, you can try creating a website for a product, you can try to help someone do something awesome.

In writing, you can try expressing an idea, you can try writing down your thoughts, you can try a new way of describing an old topic.

You. Can. Try.

You don't have to be right.

And here's an important thing:

You can try in private.

Private failures lead to public successes

In the chapter How to Overcome Perfectionism we mention that the author Neil Strauss starts his writing by creating the 1st draft of his work only for himself. No one else but him sees that draft. Not his wife, not his friends, not his fans. No one.

When creating the 2nd draft he shows it to the least judgmental people (friends and fans) and only the 3rd draft is intended to be shown to potentially negative or mean people. And with every draft, he makes the work better, reducing the risk of failure.

In other words, he first tries to create something for himself, privately. Then he gradually shows more people and incorporates their feedback.

Start experimenting, privately at first, then gradually publicly. Try things to make sure they work to increase your chances of success and reduce your chances of failure.

And one more point on this topic:

Jeff Bezos, the founder of Amazon, has said many times in interviews:
"One experiment can pay for a 1000 failures."

In business and life, if you fail 9 times but then find the 1 way that works, it can yield disproportionate benefits. Remember this.


Reflect on past failures

Now, even if you do experiments and fail, here's another important thing:

Every failure can make you better.

This is true if you do 1 crucial thing: reflect.

Pain + Reflection = Progress

The above is one of Ray Dalio's mantras. We mentioned that he lost all his money at one point in his investor career, but what we didn't mention yet is that the lesson he learned from that failure was what led him to enormous success.

He learned to not be arrogant and always questions himself by asking: how do I know I'm right?

As Dalio says, every failure is a puzzle. If you solve the puzzle, you get a gem - an insight into how the world or your mind work. And you solve the puzzle with reflection.

If you do fail, reflect.

Use the momentary psychological pain to reflect and form a strategy for how to do better next time.

Don't dwell on past failure, learn from them through reflection. Take a piece of paper, write down what worked and what went wrong. Ask yourself why. Solve the puzzle.

When you fail, reflect.

Failure is not fatal, it’s a stepping stone

Failures, mishaps, personal embarrassments,... they aren’t the end of the world even though it may seem like it at the moment.

Failure in the right direction is a good thing.

Exercises like negative visualization or plan B and Z help us prepare for potential catastrophes and also dispel unnecessary fear.

When you find yourself procrastinating because of the fear of failure:

  1. Put the fear of failure into perspective

    1. Negative visualization
      Think about the worst-case scenario. Imagine it vividly. What's really the worst case
    2. Plan B and Z
      Think what your plan B would be if you failed with A. How could you make a living then? And if sh*t hits the fan, create a contingency plan (plan Z). What would you do if everything fails?
    3. Regret minimization framework
      Ask yourself:
      When I'm 80 and looking back on my life, would I regret not taking this opportunity? 
      Use your fear of regretting something for the rest of your life to overcome the fear of failure and take the leap.
    4. Win-win
      Ask yourself:
      How would I win even if I failed?
  2. Set yourself up to learn if you fail

    1. Reduce risk by experimenting
      Try things in private, free of judgment. Test your ideas.
    2. Reflect on past failures
      Remember Ray Dalio's mantra:
      Pain + Reflection = Progress

These 6 tools will help you overcome your fear of failure and stop procrastinating. We hope you find them useful.

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