How to Fail: 10 Tips for Explaining Your Missteps

Everyone makes mistakes, but the difficult part is talking about them. The following ten tips will give you insight into how to explain your missteps in a way that’s both informative and inspiring.

I discussed 10 methods to brag about your achievements without seeming like a jerk in my earlier essay, “The Helicopter-Guide Jumper’s to Talking About Yourself.”

In this essay, I’d want to discuss the other side of the coin: how to speak about your professional mistakes without coming out like a train disaster.

This is a question that most of us will have to face at some point in our lives. We are confronted with a setback or loss, and we must then go on.

Then there’s the dilemma of how to speak about your experience or background when certain aspects of it may be perceived as a failure. How can you speak about your failures and blunders without being judged or denied future opportunities?

When it comes to talking about failure, I’m going to go against the grain today. I’ll explain why we need to modify the way we speak about failure. And I’ll show you how, just as discussing your successes, talking about your mistakes and disappointments can be beneficial.

Finally, I’ll provide you 10 specific techniques for discussing your failures, errors, setbacks, and liabilities in a manner that explains and contextualizes rather than making excuses.

Why “Don’t Talk About Your Failures,” According to Conventional Wisdom

Career counselors, parents, and friends have taught us to avoid discussing unfavorable prior events totally, particularly while looking for or applying for a job.

According to Martin Yate in Knock ‘Em Dead Objective Interview: How to Turn Job Interviews into Job Offers, your job is to “present your goods for possible consumers.” “Whether or not you obtain the job offer depends on how well you present your product and separate it from the competition.”

In other words, the traditional strategy has been to minimize any flaw or blunder that would cause us to be viewed as having failed or tripped in any manner, whether or not that impression is accurate.

When It Comes to Failures, Conventional Wisdom Is Completely Wrong

The issue with the old method is that it hasn’t kept up with the realities of living in the twenty-first century.

Do you consider your failures to be a well guarded secret? Reconsider your position.

Today’s society is more open than ever before. Often, all it takes is a short Google search to find out about our dirty laundry. The barriers to privacy have been dismantled. The President could go about the White House with a mistress a century ago, and the press would turn a blind eye. Our 24/7 media culture has an insatiable need for breaking news – the more sensational, the better.

The barrier between what is private and what is public has been blurred thanks to social media. Public foreclosure databases and court documents are now readily and freely available thanks to the internet. Employers investigate prospective workers online before employing them; in fact, over half of all employers utilize social networking sites like Facebook to do so, according to a new poll by CareerBuilder.


At the same time, the current economic crisis has resulted in a greater number of individuals having failed in the past. Personally, I don’t know anybody who hasn’t lost a job or had some other kind of professional failure in the last 5 or 6 years.

Why Should You Talk About Your Mistakes?

Talking about one’s failures has become much more normal and acceptable as a result of shifting attitudes about failures, increased openness and transparency, and economic hardship. There are a variety of reasons why you should discuss your shortcomings in particular situations.

A failure or a setback may be remembered in the same way that an achievement is, without necessarily damaging your reputation. Being open and honest about your flaws might help people connect to you more easily. According to some study, some attributes that are frequently considered liabilities, such as anxiety disorder, might actually help individuals become better leaders.

There are many reasons why you might consider disregarding common wisdom and discussing your failures, setbacks, and liabilities:

  • It might be beneficial to others to talk about your failures. You are not the first person to have a setback, and you will not be the last. You will assist people who come after you adapt and cope if you speak about it honestly.
  • Those who are distinctive are rewarded. It’s the purple cow, as Seth Godin would say, who gets all the attention. Plain old dull black and white cows pique no one’s attention. Openly discussing your personal shortcomings and disappointments is still new enough to set you apart from the herd.
  • Talking about your shortcomings might be therapeutic. Many individuals who share their shortcomings with others (rather than keeping them to themselves) claim that it relieves them of a weight. They are more free to be themselves since they are no longer afraid of their “secret” being revealed. This, in turn, may help you succeed in your work in a variety of ways.

So you’ve come to the conclusion that discussing your failures is a good idea. Then there’s the matter of how. Let’s have a look at the answer to that query.

10 Ways to Talk About Your Setbacks and Failures

Vintage businessmen looking at papers talking while standing up.

The difficulty in revealing your failures and liabilities is expressing them in a manner that explains the failure while still offering useful perspective. Here are some pointers to remember while discussing your human hiccups:

1) Have a humble attitude

Noah Kagan is best recognized as the creator of AppSumo today. However, his path has not been without flaws. When Kagan was abruptly dismissed, he was the 30th employee of Facebook, and he was slated to earn a compensation in the tens of millions of dollars when the business went public. “At the time, Facebook was everything,” Kagan adds. “I was heartbroken.”

You’d think Kagan would be a bit sensitive while discussing his Facebook experience. But he isn’t. He made a lengthy blog post on his dismissal, emphasizing the lessons he took away from it.


The piece was very well-received. “The post garnered over 200,000 views in 24 hours,” Kagan adds. Getting fired from Facebook, ironically, was such a good experience for Kagan that he now believes “everyone should get fired once in their lives” because it gives you perspective and humility.

2) Make a joke

Humor, like bragging about your achievements, may go a long way.

After a great career as a highly compensated comedy writer for Roseanne in the early 1990s, David Raether utilized his sense of humor to convey his traumatic story of being homeless. In his biography Tell Me Something, She Said, Raether says, “The first night you’re homeless, you feel like you’ve been smacked in the face by a slow child.” “It’s like if you knew he was going to strike you, but you can’t believe he really did it.” ‘Whaaaaat?’ you would think. ‘How did you get so close to me?’

During the dot-com era’s peak in the late 1990s, a buddy of mine worked for a dot-com. This business attempted to sell “smells via the internet.” Yes, it’s true. The technology existed — it would have been a gadget that sat on your desk and resembled a speaker with a fan inside that released various aromas. When you visited a website like Bath & Body Works, for example, the fan would turn on and emanate a lavender or rose-petal scent. (It’d probably smell like baseball gloves, whiskey, and Chuck Norris in the Art of Manliness.) I’m not sure about you, but I can think of a few websites where I’m delighted there’s no odor. As a result, it goes without saying that the firm did not survive.

My buddy has mentioned the incident, and he now laughs about it. Despite the fact that the firm failed, he does not take the setback personally. Instead, he chuckles at the absurdity of it, and you can’t help but smile with him.

3) Don’t point fingers at others.

Blaming others (such as a previous employer who fired you) nearly always reflects badly on you. Even if you had the worst boss in the world at a previous job, blaming that employer doesn’t seem good – other people don’t know and haven’t encountered that person.

“I had a person approach me for a job opening who had been fired and blamed it on his supervisor,” Kagan adds. “I despise those who place blame on others. It is much preferable to accept responsibility.”

4) Contextualize the Liability

If someone asks you about your failure, you should be able to provide a brief explanation that places it in perspective.

Instead of going to college, my buddy Colin joined the Coast Guard, and when it came time to find work, his experience was seen as a disadvantage since he did not go the standard path. His role as a Coast Guardsman was to stop illegal immigrants attempting to enter the United States’ maritime boundaries. His wasn’t a “failure” in the traditional sense, but his military experience was preventing him from landing a more normal career.


Colin ultimately figured out how to speak about his time in the Coast Guard in a manner that was both memorable and non-threatening. “I usually try to utilize empathy and analogies to persuade people to listen to what I have to say,” he says now. Respect, empathy, and context are the most crucial aspects. Make sure the audience understands what you’re saying in real time rather than in fantasy terms.”

Colin has been able to communicate the event in a manner that is more understandable and less of a liability by employing metaphors and tailoring his explanation to the specific audience.

5) Express gratitude for the advantages you received as a result of your failure.

My own greatest life failure occurred when I was 28 years old. Following my time at the White House, I was recruited as a speechwriter for California’s then-up-and-coming Governor. Gray Davis is the next governor of California.

It seemed to be a secure position, particularly when Davis was re-elected to a fourth four-year term. Then, as they say, things went a bit wild. A recall effort was sponsored by a member of Congress, and action movie star Arnold Schwarzenegger opted to run after declaring his candidacy on The Tonight Show.

This isn’t anything you’d make up. I was out of a job in no time.

It was a really humbling event for me. It’s not every day that the Terminator fires you from your job.

There was, however, a silver lining. The recall motivated me to return to school and get a law degree, reminding me that nothing is definite in life and that a strong education is always beneficial. It also taught me the importance of creating and extending your network so that you’re prepared when things become rough, which I discuss here on AoM and on my own website today.

6) Discuss the Lessons You’ve Learned From Your Mistake.

Only someone who fails and then fails to learn from their mistakes is worse than a failure.

Noah Kagan set forth three concrete reasons why he wasn’t able to adjust while working at Facebook in his blog post regarding his Facebook termination, as well as the lessons learnt from those reasons. He then went on to say that he learnt a few critical lessons from letting individuals go at his current startup, AppSumo.

I doubt Noah will be seeking for work anytime soon, but if he were, this would be the best way to explain why he failed. Reflect, describe what you’ve learned, and then demonstrate how the experience has strengthened you.

7) Make the most of your failure to demonstrate your abilities.

After recovering from his homelessness and doing different short-term jobs, David Raether, the comedy writer who subsequently became homeless, obtained an interview for a position as a writer for Priceonomics. Because the site focused on economic topics, his interviewer requested a sample of his work in which he demonstrated knowledge of personal financial difficulties.


That prompted David to write “What It’s Like to Fail,” a piece in which he detailed how he went from a mid-six-figure income as a comedy writer to losing his house and family.

The tweet went viral, with thousands of shares on social media.

The article itself was successful because it showcased one of Raether’s strongest abilities: writing. He displayed a competence by talking about his own failure. When you expose yourself to vulnerability, it’s common for some of your greatest qualities to emerge.

8) Describe how your liability may be used to your advantage.

Scott Stossel is the editor of The Atlantic magazine, a prestigious job that you’d think would be impossible to get if you weren’t flawlessly put together.

Stossel, on the other hand, detailed his lifetime fight with many devastating anxiety illnesses and his different attempts to deal with therapy, pills, and alcohol in the cover story “Surviving Anxiety” published in January 2014.

While Stossel admits the toll his anxiety illnesses have taken, he also argues that they may be a benefit, and that some persons with his kind of anxiety condition have many good characteristics. “Historical evidence implies that artistic and intellectual talent might be attributed to anxiety,” he says. “Anxiety disorders have troubled many successful authors, poets, scientists, and filmmakers, including Emily Dickinson, Franz Kafka, Charles Darwin, T.S. Eliot, and Woody Allen.”

According to Stossel, researchers have shown that financial managers with significant anxiety tend to be the finest and most productive money managers. Various studies on anxiety in commercial and political leaders “indicate that, given the appropriate conditions, some proportion of worry might prepare you to be a leader,” according to the researchers.

9) Be Proud of What You Have Achieved

Whatever the nature of the setback, keep in mind that it isn’t always all negative.

You may have offered exceptional customer service before your firm went bankrupt. You undoubtedly established some wonderful friends before you were laid off. Even if you didn’t sell enough of your goods, it was still useful to certain customers.

Unless, of course, your product was a box that spewed internet odors. That was a complete blunder.

To put it another way, don’t forget that you may still be proud of what you’ve done.

10) Exercising discretion

It’s crucial to remember, as with everything, that the advantages of sharing your failures only accrue to those who do it in the right manner and under the proper circumstances. When asked about failures in an interview, you should be candid, but you don’t have to tell the interviewer right once. You should also avoid over-sharing: you don’t need to go into detail about how you only ate Pizza Hut for two weeks after being laid off from your previous job, didn’t wash, and spent your evenings weeping into a pillow. Finally, avoid focusing your whole identity on your failures, making them your badge of glory and all you speak about. Your mistakes are a part of who you are, but they aren’t the only part of who you are. Make the things you’ve done well the cornerstone of your identity.


Share Your Mistakes and Improve Your Relationships

Vintage young man shaking hands with older businessman.

Finally, there’s a deeper rationale for talking about your failures – one that goes beyond any personal gain.

Kagan discovered that talking more freely about his Facebook failure and other personal failings allowed him to form stronger connections with people who had had similar losses.

“I’ve developed a lot of fantastic connections,” Kagan adds. “It allows me to filter out the folks with whom I really connect and engage on a deeper level.”

A same thing happened to me. I know what it’s like to be laid off or fired because I’ve been there. I also understand how much it means to folks who are going through a difficult time when you reach out and provide assistance.

I recently received an email from a good friend informing me that his company had lately “relieved” him of his job. I grabbed the phone and dialed the number to see what I could do.

In some ways, the wisdom to accept our own humanity and reach out to a buddy in need is the most important lesson you can gain from any setback or failure.

If you accomplish that, you’ve shown that the setback taught you what you needed to know. And that is what it means to be a guy.

Do you feel comfortable discussing your failures or defeats in public? Why do you think that is? Let us know what you think in the comments section below.

Do you feel comfortable discussing your failures or defeats in public? Why do you think that is? Let us know what you think in the comments section below.

Former Clinton White House Writer John Corcoran is an attorney. He writes on social skills and commercial partnerships. He offers a 52-page book called How to Increase Your Income in 14 Days by Building Relationships with Influencers, Even if You Hate Networking, that you can download for free.



Frequently Asked Questions

What is a good failure story for interview?

A: Well, I was an idealist. I really wanted to give my all into the work that I did but then ultimately it just didnt pan out.

How do you explain failure?


What is your greatest failure examples?

A: My greatest failure would be when I tried to clean the bottom of my fish tank, but I slipped and fell. This broke my phone screen.