How to overcome failure

NB: Before we begin: this is the latest article in a series on modern leadership mastery. The series overview and links to previous articles can be found here. 

Sophomore year of college, 2005: I just got the worst grade I’ve ever received in my life. Worse still, it was on a high stakes Spanish exam. Though I am a generally an A-minus/B-plus student, I failed that exam hard.

After class, I nervously asked the professor if I could retake the test. She snickered and said, “No.”

Feeling small, I asked, “Well, what can I do for extra credit?” She responded, “I don’t offer extra credit.”

Finally, with my tail between my legs, I said, “I want to get at least a B in your class. What can I do?”

She looked at me as though she were about to drop the secret of life into my lap and said, “Jason, when you fail, you’ve failed. That’s just how life goes.”


School teaches us a lot about failure. We learn that failure is real. We learn that it’s shameful and bad. We learn that you can’t recover – at least not fully – from failure.

Only one problem: failure isn’t real. It’s a toxic myth that the education system has brainwashed countless people into believing.

Brainwashing the innocent

Over the course of your education, you took hundreds of tests, quizzes, and exams. Each time you did, you got a grade.

Unless your teacher was particularly enlightened, your grade was fixed. If you got a C but was aiming for an A-minus there wasn’t a lot you could do about it.

Sure, some teachers offer extra credit or makeup exams, but it’s hardly ever for full credit.

In other words, even if you learned the material and mastered it after the exam, you would still be punished for not getting it right the first time. You might be able to bring that C up to a C-plus or maybe even B, but not an A.

The end result is brutal: during some of the most formative years of your life, you had countless experiences teaching you that if you don’t get it right the first time, you’ll never be able to fully recover.

Though this lesson is consistent, it is wildly divorced from how the world works. In reality, when you try something for the first time, no one expects you to get it right. And when you inevitably make a few mistakes along the way, no one holds it against you.

If you believe that you have to get it right on your first shot, you’ll never start. If you do manage to start you’re going to quit pretty quickly because of the pressure.

We are shamed for failing 

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that’s why I succeed.” – Michael Jordan

Every single person who is succeeding has also failed. A lot.

One of the surest ways to succeed is to try different approaches as you search for the one that works for you. Inevitably you’ll “fail” a few times along the way.

Which presents yet another problem: we’ve been brainwashed to view failure as a shameful thing.

When we don’t do well on an exam, our teachers tell us to study harder, because if we don’t learn the material, we risk harming our future selves (heaven forbid future Jason can’t conjugate Spanish verbs!).

Anyone who has ever been a student in the traditional education system knows that pit-in-your-stomach feeling of shame when you didn’t do as well on a test as you’d hoped to.

Put bluntly: we are taught to feel inferior for our failures. We learn to feel shame and guilt for our failures.

Never are we told, “Hey, as it turns out, you just don’t have a knack for Spanish. No biggy. You still have huge amounts of potential, and we’ll work together to find what you’re good at.”

What we never learn is the greater truth: failing is an integral step to success of all sorts.

We learn to fear taking action on what matters most 

From here, the logic and tyranny of education becomes clear: we have learned that when we try something, we will either pass or fail. We have learned that regardless of the results, we wont have much of an ability to change the outcome. We have learned that to fail at something is bad, and may go on to make our future worse, not better. We have learned that failure is shameful and makes us inferior.

The lessons blend together to teach us to be afraid of taking action, especially on the things we love most, because those are the highest stakes.

The end result is a surreal form of paralysis: many people feel that it is safer to never take action on their dreams, than it is to attempt to live them. And while that logic is tragically flawed, it’s easy to understand how one gets there.

The bigger truth: failure is a myth 

Hidden behind the brainwashing, rests a quiet but stable truth: failure doesn’t exist.

All that exists are actions and results. You perform an action and you get results. When we like the results we call that “success.” When we dislike the results, we call that “failure.”

You wanted to raise $1,000,000 but only managed $30,000? Fail!

You wanted to ease hunger in your community, and you fed 1,000 people? Success!

But those successes and failures are merely judgments. There is nothing that makes them intrinsically true.

When you start looking at the results of your actions as just that – results – you’ll see that neither failure nor success are permanent states. Instead, they are fluid things that you can influence and manipulate. If you don’t like the results you’ve created, you can create new ones by taking a different course of action.

Overcoming the illusion of failure 1: replace judgment with curiosity

 The easiest way to overcome the illusion of failure is to create an opportunity to learn by replacing judgment with curiosity. By being curious you’ll find blind spots, areas for improvement, and new paths forward.

When you get results you don’t want, ask:

  • What went well?
  • Where was there was room for improvement?
  • What were you right about?
  • What were you wrong about?
  • What was counter-intuitive?
  • What did you learn?
  • What will you do differently next time?

If eliminating judgment is more aspirational than realistic for you (as is for me), then try this: when you feel as though you have failed or you’re frustrated, let that feeling be a cue that it’s time to become curious.

Overcoming the illusion of failure 2: tweaking variables

Another approach to short-circuiting failure: tweak a variable and try again. When you get results you’re not wild about, change a part of the process to see if it will produce a different result.

Trying to get sales for your business, but no one is returning your calls?

Call at a different time. Or change the voicemail you’re leaving. Or use email. Or knock on doors. Or get sales training.

Not enjoying the quality of your social life? Be more proactive inviting people to hang out. Or move to a town with a better scene. Or join a meetup group. Or improve your people skills.

Keep tweaking variables again and again until you get the results you want.

Overcoming the illusion of failure 3: more strategies for getting better results

At times, you’ll feel as though you’ve tried everything and you still you can’t seem to get the results you want. I know the feeling. Here are three ways to jump-start your progress:

1) Brain storm. Focus a brain storming session on actions you can take to help you achieve the desired results.

2) Ask for help. If you’re really stuck, start asking people for help. Most people will turn to experts for advice. This works, but don’t discount asking people who know little about the subject matter too. You’ll be surprised to find that novices can come up with amazing solutions to problems they know little about. (This happens because their thinking isn’t limited by industry norms, and while this will generate plenty of oddball ideas, it also periodically strikes gold).

3) Talk it out. My favorite strategy is to call a friend and talk through the issue. I ask them to listen as I explain my thinking. Often, midway through the monologue, the solution becomes clear. When this doesn’t happen, sometimes the person I’m talking to will be able to point me in the right direction or ask a useful question.

How to make success inevitable 

Each step of the way you’ll have an opportunity to “succeed” or “fail.” As you move forward, you’ll be surprised by how often you’re swept away by the momentum of creating your dreams. Of course, from time to time you’ll get results that you’ve been trained to think of as “failures.” If you accept failure at face value, you’ll never achieve your dreams for yourself, let alone the world around you.

When you realize that success and failure are little more than passing judgments, and all that really exists are results for you to accept or reject, you start to become powerful.

And the real trick to all of this is simply to refuse failure. When you do, success will become inevitable.


Photo credit: Michael 1952, “First Grade St Bridgets Chicago 1958-59”

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4 COMMENTS ON THIS POST To “How to overcome failure”

  1. Duane covrig December 14, 2015 at 11:35 am


    As always. I look forward to your insightful and well written blogs. You know how to take truth about leadership and weave it into the most enjoyable prose.

    This one hits close to home on two of my most intense experiences and frustrations-teaching and leading others.

    Thanks for the deep encouragement to keep working through the “setbacks” and make better judgments about “failure” and success.

    Keep writing!!!!

    I judge your blogs to be a success. But that is not as importamt to your commitment to keep writing!!! Thanks for this good truth!!

    Department of Leadership

    • Jason December 14, 2015 at 7:29 pm

      Wow. Duane. I can’t tell you how much I appreciate you taking the time to share this. You’re encouragement to keep writing is wayy better timed than you realize. Though I haven’t officially announced it, after Feb, I’m going to take a long break from the speaking circuit to focus exclusively on writing. It feels totally right to do that, but also, I’m nervous. Your note pushes me in the right direction. 🙂

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