3 Proven Strategies to Help You Overcome Fear of Failure

I sat down yesterday to write a blog post about successful people who have failed in big ways. There’s certainly no shortage of famous examples:…

I sat down yesterday to write a blog post about successful people who have failed in big ways. There’s certainly no shortage of famous examples: Michael Jordan (cut from the varsity basketball team his sophomore year), Steve Jobs (fired from the company he founded), and Oprah Winfrey (fired from her job as a television news anchor), just to name a few.

But that’s not what this post ended up being about.

Rationally, I know that failure is nothing to be ashamed of. It’s an inevitable part of life and even a necessary step toward success and innovation. Irrationally, I still fear failure. And I know I’m not alone.

As I began doing the research, I got to thinking that these failure-before-success stories aren’t exactly a secret. From elementary school on, we’re bombarded with variations of “what doesn’t kill you makes you stronger” and “if at first you don’t succeed…”. Our classroom walls are plastered with inspirational quotes about overcoming defeat and learning from your mistakes.

Rationally, I know that failure is nothing to be ashamed of. It’s an inevitable part of life and even a necessary step toward success and innovation. Irrationally, I still fear failure. And I know I’m not alone.

At some point or another, almost all of us have experienced nagging self-doubt, made negative comparisons between ourselves and those around us, or felt like we’re not talented, smart, or disciplined enough to reach our goals.

The irony is that these fears tend to become self-fulfilling prophecies. Research has shown a connection between the fear of failure and procrastination. That means that the more anxiety we feel about failing the reach our goals, the less likely we are to take action toward achieving them. It’s a completely irrational reaction, but — as anyone who has experienced this kind of paralysis can tell you — it’s a hard one to resist.

So instead of putting together yet another inspiring list of people who failed and went on to succeed, I decided I wanted to answer a question: What can we do overcome fear of failure?

There are a lot of articles out there on the subject, but most end up being variations of the same cliches we’ve heard all our lives. For the record, it is not at all helpful to tell someone who fears failure to “think positively” or “be more assertive”. If it were that easy, we wouldn’t be googling “how to overcome fear of failure” in the first place!

For this post, I combed through pages of TED talks, blogs, and podcasts to find the best, concrete, proven strategies for overcoming fear of failure.  They’ve all actually worked for people who wanted to break the cycle of self-doubt and avoidance. I’ve even used them myself, and I hope you find them as useful as I have. They can be summed up as follows:

Face it.
Externalize it.
Ignore it.

1. Face it.

“Face your fear” isn’t exactly a new concept. However, it’s a lot more straightforward to face a fear of heights or spiders than it is to face a fear of failure. I wanted to share a story I came across of someone who gave this strategy a new spin and made me think differently about how I can face fear in my own life.

Gamifying rejection

Jason Comely was a freelancer from Ontario, Canada and he had hit rock bottom. His wife had left him for another guy and for nine months he just retreated from the world. He didn’t go out. He didn’t really have friends. Here’s an excerpt from the Invisibilia podcast where I first heard this story:

"That Friday evening that I was in my one-bedroom apartment trying to be busy," Comely says. "But really, I knew that I was avoiding things...I had nowhere to go, and no one to hang out with...And so I just broke down and started crying."

He realized that he was afraid. "I asked myself, afraid of what?  I thought, I'm afraid of rejection."

Which got him thinking about the Spetsnaz, an elite Russian military unit with a really intense training regime.

"You know, I heard of one situation where they were, like, locked in a room, a windowless room, with a very angry dog, and they'd only be armed with a spade, and only one person is going to get out — the dog or the Spetsnaz."

And that gave him an idea. Maybe he could somehow use the rigorous approach of the Spetsnaz against his fear.

So if you're a freelance IT guy, living in a one-bedroom apartment in Cambridge, Ontario, what is the modern equivalent of being trapped in a windowless room with a rabid dog and nothing to protect you but a single handheld spade?

"I had to get rejected at least once every single day by someone."

And that’s exactly what he did. He asked strangers for rides and breath mints and asked for discounts before buying things.  He even created a product pitch and submitted it to Dragon’s Den Online.

Sometimes he would get a resounding “NO”, which actually meant he had “won” for the day. But to his surprise, most people were actually receptive to him, and in turn he began to be more receptive of others.

He even decided to write down each and every one of his rejection attempts on cards and turned it into a game called Rejection Therapy.

rejection therapy

So what can we learn from this exercise in willful self-humiliation?

That most fears aren't real in the way you think they are. They're just a story you tell yourself, and you can choose to stop repeating it. Choose to stop listening.

"Don't even bother trying to be cool," Jason says. "Just get out there and get rejected, and sometimes it's going to get dirty. But that's OK, 'cause you're going to feel great after, you're going to feel like, 'Wow. I disobeyed fear.' "

I can say from experience that this quirky method works. Though I haven’t fully committed to the one-rejection-a-day game yet, Jason’s story has already helped me change how I think about rejection, particularly in my professional life. Whenever I hesitate to share an opinion or idea to a colleague or to reach out to a potential mentor for advice, I think about Rejection Therapy. It gives me the perspective I need to go for it. They might just say “no”, in which case I win anyway. :)

(By the way, this technique helped me send the email that led me to my current job. It’s powerful stuff. Thank you, Jason!)

We may not be social recluses like Jason was, but a fear of rejection and failure can still keep us from fully embracing, or even creating, opportunities at work or in our personal lives.  Here’s one concrete thing you can start doing today to change that:

Action step:  Embrace your inner Spetsnaz. You don’t have to go as far as Jason did. Start small. Try to get rejected just once this week.  Strike up a conversation with a stranger. Ask a colleague for coffee. Speak up at least once in your weekly team meeting.

If you do, please consider leaving a comment below. I’d love to hear how it turns out. 

2. Externalize it.

Sometimes, overcoming fear is a losing battle.  No matter how much we try to face it or will our way out of it, the voice of doubt and negativity won’t go away. This second strategy is less about getting rid of fear and more about learning to live with it.

Giving your fear a voice, or at least an email address

On the outside, Paul Ford had a completely normal life. On the inside, he felt like he was walking around with a perpetual rain cloud of worry, doubt, and negativity hanging over his head. Here’s how he described it in this interview with PJ Vogt at the podcast Reply All:

I mean, it's the same little voice all of the time. This little guy just sitting there going, like, god, you're garbage. You're garbage. You're garbage. I don't know why he sounds like a Brooklyn construction worker, but he does right now today.

I was stressed. And I was anxious and overweight and terrified. And I was just like, holy [BLEEP]-- kind of like, I got to do better. And then the anxiety would be like, oh, hey, wow, I'm dying. No, wait, I'm covered with worms. No, I'm never going to get anything done. I'm a bad person. I'm a failure.

At some point, he decided he’d had enough. He had to do something. He also happened to be a computer programmer.

For me, it was just like, what is this weird force that is now running a chunk of my life and making me feel weird and bad all of the time? And so I went off, and I made this thing called AnxietyBox.

The way it works...you go to the website and you put in your name and your email, and then you put in what your anxiety is. So it's like, I'm really anxious about finishing my book. I'm really anxious about losing weight. And you can keep adding anxieties. And it saves all of that to a database. And then like 12 times a day, but kind of random, it just sends you these emails from your anxiety.

Just to be clear, these were not comforting, uplifting emails about his anxieties. These were emails from his Anxiety. Here’s a nice little example of what Paul would randomly receive in his inbox 12 times a day:

Subject: history will forget you because history forgets people who are unable to finish anything

Dear Paul,

So you're probably used to being at the front of the class, and this is a wake-up call that you're not even in the middle. Inform me, are you ready?


Your Anxiety

Or this:

I respect that you just live your life and don't care if people think you are childish and disgusting.

Or this:

Your mom and dad would never say anything, but they so want to know why you would choose to be unlovable and not smart.

Or this:

People on Facebook look at your picture and think, in possession of a weird nose.

You get the idea.

What was the point of this apparent psychological self-torture?

...building this little emulator, this anxiety simulator, made me go, oh, this part of me is incredibly stupid. It says the same things over and over again. And it really is like that is what my anxiety looks like. It's not smart. At some level, it's like a little robot that just screams. What this let me do is look at the robot.

It was immediately effective. And seeing it actually externalized as 20 messages in a Gmail inbox, it was so much like what my brain was producing. Seeing it was really funny. It turns your entire emotional freak-out into this relentless form of comedy.

It turns out that you're not as important as you think you are, nowhere near as terrible as you think you are, and actually fairly ridiculous. It's just so ridiculous to scream at yourself all day long, and yet there it was. There was the evidence of it. And so it was like, oh my god, I've been wasting a lot of time with this little son of a bitch.

In other words, hearing his fear and self-doubt from an external source allowed Paul to evaluate it with fresh eyes.  His negative thoughts, while still there, were no longer overwhelming in the way they had been. They were something he could even laugh at.

You don’t have to have a computer program to externalize your fears (although it is a pretty neat trick). After hearing Paul’s story, I immediately thought of The Oatmeal’s “Blerch”, the comic personification of every lazy, negative, soul-sucking thought you have that keeps you from getting out and exercising. The Blerch is now how I visualize my Anxiety. Whenever I find myself running a loop of negative self-talk over and over in my head, I imagine this ugly little guy telling me all of those negative things.  It makes it a lot harder to take them as seriously as I did before.


Again, at the root of this strategy is the fact that our fears are not reality. They are the stories we tell ourselves, the thoughts that we repeat over and over again.  We may not be able to control our thoughts, but imagining fear as an external force can help us decide not to believe them.  Here’s some concrete suggestions on how to do it:

Action step: Next time you find yourself putting things off because of fear or self-doubt, find a way to put some distance between yourself and your thoughts. Write your anxieties down and read them back to yourself. Find your own version of the Blerch and imagine it telling you your negative thoughts.  And then tell it to shut up.  Or sign up for the waiting list for AnxietyBox (Paul is currently rebuilding it to handle more traffic).

3. Ignore it.

The first two strategies for overcoming fear — Face It and Externalize It — involved ways to change how we think about and react to our anxieties and self-doubt. But sometimes the best thing you can do is ignore it.  Let go of worrying about what people will think or your own expectations, or even thinking about the outcome at all, and just focus doing one thing.

I want to share two quotes from two of the best productivity blogs around that do an eloquent job of summarizing how to break out of the vicious cycle of negative self-talk and procrastination:

In his article Getting Lost in Just Doing, Leo Baubata gives the following advice:

Just pick something to work on. Write something, draw something, program something, animate something, sew something. It doesn’t matter. Anything that your heart is drawn to.

Set an intention for this activity: I’m doing this out of compassion for others, out of love for myself, to meet my commitment to so and so.

Now get started: begin actually doing it. Don’t worry about whether you’ll do it for 10 minutes or an hour. Don’t worry about how good you’ll be at it, or what people will think of it, or whether you’ll succeed or not. Those are not relevant to the task.

Similarly, James Clear urges us to set aside self-judgement and our constant comparisons to others’ work and learn to embrace the process of creation:

No matter what you spend your days doing, every morning you wake up and have a blank piece of paper to work with. You get to put your name at the top and fill it with your work.

If what you write on your paper doesn’t meet someone else’s expectations … it is no concern of yours. The way someone else perceives what you do is a result of their own experiences (which you can’t control), their own tastes and preferences (which you can’t predict), and their own expectations (which you don’t set). If your choices don’t match their expectations that is their concern, not yours.

Your concern is to do the work, not to judge it. Your concern is to fall in love with the process, not to grade the outcome. Keep your eyes on your own paper.

Making a conscious decision to ignore fear may not sound like the most exciting strategy, and it certainly isn’t the easiest. We have evolved to pay attention to our fear and anxiety. Imagine what would have happened if our ancestors had said, “You know what, I’m just going to ignore my fear of that saber-tooth tiger over there and focus entirely on the beautiful rock art I’m creating.”  Our species wouldn’t have survived for long.

But in the modern world, fear often harms us more than it helps.  Actively choosing to ignore  that fear and focus on the task at hand is a powerful strategy to keep moving forward. Here’s how to get started:

Action step: In his article “Productivity Tricks for the Neurotic, Manic-Depressive, and Crazy (Like Me)”, productivity guru Tim Ferriss outlines each step of his own ritual for dealing with doubt and negative self-talk. It’s a simple, yet effective way to get clarity and momentum when you’re feeling overwhelmed by your own expectations or those of others.

1) Wake up at least 1 hour before you have to be at a computer screen. E-mail is the mind killer.

2) Make a cup of tea (I like pu-erh) and sit down with a pen/pencil and paper.

3) Write down the 3-5 things — and no more — that are making you most anxious or uncomfortable. They’re often things that have been punted from one day’s to-do list to the next, to the next, to the next, and so on. Most important usually = most uncomfortable, with some chance of rejection or conflict.

4) For each item, ask yourself:

– “If this were the only thing I accomplished today, would I be satisfied with my day?”

– “Will moving this forward make all the other to-do’s unimportant or easier to knock off later?”

5) Look only at the items you’ve answered “yes” to for at least one of these questions.

6) Block out at 2-3 hours to focus on ONE of them for today. Let the rest of the urgent but less important stuff slide. It will still be there tomorrow.

7) TO BE CLEAR: Block out at 2-3 HOURS to focus on ONE of them for today. This is ONE BLOCK OF TIME. Cobbling together 10 minutes here and there to add up to 120 minutes does not work.

8) If you get distracted or start procrastinating, don’t freak out and downward spiral; just gently come back to your ONE to-do.

This certainly isn’t an exhaustive list of ways to overcome a fear of failure, but these three strategies - Face It, Externalize It, Ignore It - are a great place to start. Have you tried any of these strategies before? Are there others that work for you? Please consider sharing in the comments below.

Let Todoist take the mental load

Join millions of people who enjoy peace of mind, and getting things done.

Get started for free