in: Career, Career & Wealth, Featured

• Last updated: September 24, 2021

How to Fail and Live to Talk About It: 10 Tips for Explaining Your Missteps Without Sounding Like a Train Wreck

Vintage job interview young man being interviewed.

In my previous post, “The Helicopter-Jumper’s Guide to Talking About Yourself,” I explained 10 ways you can talk about your accomplishments without sounding like a jerk.

In this post, I want to talk about the flip side of the coin — how to talk about your professional failures without sounding like a train wreck.

Most of us have to confront this question sometime in our lives. We face a setback or a defeat and then we have to move on.

Then the question becomes how do you talk about your experience or your background when elements of that work history may be viewed as a failure? How do you talk about your setbacks and missteps, without having the world judge you or deny you future opportunities?

Today, I am going to challenge the conventional wisdom when it comes to talking about failure. I will explain why the way we talk about failure is due for a change. And I will explain how you can actually benefit from talking about your failures and setbacks, just like you can benefit from sharing your accomplishments.

Finally, I’ll share ten specific tips for talking about your failures, mistakes, setbacks, and liabilities in a way that will help explain and give context, instead of excuses.

Why the Conventional Wisdom Says “Don’t Talk About Your Failures”

We’ve been trained by career guidance counselors, parents, and friends to avoid talking about negative past experiences entirely, especially when searching for or interviewing for a job.

Your job is “to display your product for potential buyers,” writes Martin Yate in Knock ‘Em Dead Job Interview: How to Turn Job Interviews into Job Offers. “How effectively you pitch your product and differentiate it from the others will determine whether or not you get the job offer.”

In other words, the historic approach has been to almost always downplay any blemish or misstep which might lead us to be perceived as having failed or stumbled even in the slightest, whether that perception is fair or not.

The Conventional Wisdom Is All Wrong About Talking About Failures

The problem with the traditional approach is that conventional wisdom hasn’t caught up with the reality of life in the 21st century.

Think your failures are a secret? Think again.

Today’s culture is more transparent than ever. Our dirty laundry is often only a quick Google search away. Privacy walls have come down. A generation ago, the President could run around the White House with a mistress and the press would look the other way. Today, our 24/7 media culture has an insatiable thirst for news — and the more salacious, the better.

Social media has also blurred the line between what is private and what is public. Websites have made public foreclosure databases and court records easily and openly accessible. Employers check out potential employees online before hiring them; in fact, a recent survey by CareerBuilder found that almost half of all employers use social networking sites like Facebook to research potential hires.

At the same time, the economic turmoil of recent years has meant more people have failures in their backgrounds. Personally, I hardly know anyone who hasn’t suffered a job loss or other professional failure of some sort in the past 5 or 6 years.

Why You Should Talk About Your Failures

The combination of changing perceptions about failures, greater openness and transparency, and economic turmoil has made talking about one’s failures much more common, and acceptable. In certain circumstances, there are a number of reasons why you should talk about your failures.

A failure or a setback can be memorable in the same way as an accomplishment, without necessarily hurting your reputation. Being candid and honest about your imperfections can lead others to relate to you better. Some research even suggests certain traits often considered to be liabilities — such as anxiety disorder — can make people better leaders.

Here are a number of reasons why you should consider throwing conventional wisdom out the window and talk about your failures, setbacks, and liabilities:

  • Talking about your failures can benefit others. You weren’t the first to suffer a setback, and you won’t be the last. By talking about it openly, you will help others who come after you to adjust and cope.
  • Rewards come to those who are different. As Seth Godin would say, it’s the purple cow who gets all the recognition. No one is interested in plain old boring black and white cows. Talking openly about your own failures and setbacks is still novel enough that it may differentiate you from the pack.
  • Talking about your failures can serve as good therapy. A lot of people who do share their failures with others (rather than keeping them bottled up inside) say it lifts a burden off their shoulders. They feel more free to be themselves because they don’t have to live in fear of their “secret” getting out. And that, in turn, can help you thrive in your career in many ways.

So now you’re convinced you should talk about your failures. The next question is, how? Let’s turn to answering that question.

10 Tips for Talking About Your Failures and Setbacks

Vintage businessmen looking at papers talking while standing up.

The challenge in sharing your setbacks and liabilities is articulating them in a way that explains the failure, without making excuses, while providing valuable context. Here are some tips you should follow when talking about your human hiccups:

1) Be Humble

Today, Noah Kagan is known as the founder of AppSumo. But his trajectory has been far from perfect. Kagan was the 30th employee at Facebook, set to receive a payout in the tens of millions of dollars when the company went public, when he was summarily fired. “Facebook was my everything at the time,” says Kagan. “I was devastated.”

You might think that Kagan would be a little sensitive in talking about the Facebook experience. But he’s not. He wrote a detailed blog post about his firing, and specifically the lessons he learned from the experience.

The article was wildly popular. “The post got something like 200,000 views in 24 hours,” says Kagan. Ironically, getting fired from Facebook was such a valuable experience that Kagan now says “everyone should get fired once in their life” because it gives you perspective and humility.

2) Use Humor

Much like talking about your accomplishments, humor can go a long way.

David Raether used his sense of humor to describe his harrowing tale of becoming homeless after a successful career as a highly paid sitcom writer for Roseanne in the early 1990s. “The first night you’re homeless, you feel like you’ve been punched in the face by a slow kid,” writes Raether in his memoir Tell Me Something, She Said. “Like you knew that he was probably going to hit you, but you can’t believe that he actually did it. Like, ‘Whaaaaaat? How did you hit me?’”

A friend of mine worked for a dot-com during the heyday of the dot-com era in the late 1990s. This company tried to do “smells over the internet.” Yes, really. The technology was actually possible — it would have been a device that sat on your desk that looked like a speaker with a fan in it that emitted different smells. When you visited a website like, say, Bath and Body Works, the fan would kick in and emit a smell of lavender or rose petals. (Art of Manliness would probably smell like baseball gloves, whiskey, and Chuck Norris.) I don’t know about you, but I can think of a lot of websites where I’m glad there’s no smell associated. So needless to say, the company didn’t survive.

I’ve heard my friend mention the experience and he laughs at it now. Even though the company went under, he doesn’t take the failure personally. Instead, he laughs at the ridiculousness of it, and you can’t help smiling with him.

3) Do Not Cast Blame On Others

Casting blame on others (like a former boss who had you fired) almost always reflects poorly on you. Even if you had the world’s worst boss at some former job, it doesn’t look good if you blame that boss — other people don’t know and haven’t experienced that person.

“I had a guy contact me for a job position who had gotten fired, and he put the blame on his boss,” says Kagan. “I hate the people who blame others. It’s much better to take responsibility.”

4) Put the Liability in Context

If someone asks you about your failure, you should have a short explanation which puts the failure in context.

My friend Colin joined the Coast Guard instead of going to college, and when it came time to find a job, his experience was viewed as more of a liability because he did not go the traditional route. In the Coast Guard, his job was to intercept illegal immigrants trying to sneak across U.S. maritime borders. His wasn’t a “failure” in the usual sense — but his military experience was holding him back with potential employers who didn’t think his background would translate well into a more conventional job.

Colin eventually learned how to talk about his Coast Guard experience in a way that was memorable, without being threatening. Today, he says, “I always try to use empathy and metaphors to get people to listen to what I have to say. The most important factors are respect, empathy and context. Make sure that the audience can understand what you’re saying in real time, not in fantasy terms.”

By using metaphors and customizing his explanation to the individual audience, Colin has been able to explain the experience in a way that is viewed as more graspable and less of a liability.

5) Articulate Gratitude for the Benefits You Gained As a Result of the Failure

My own personal biggest setback in life came when I was 28 years old. After working at the White House, I was hired as a speechwriter for the then up-and-coming Governor of California. A new governor named Gray Davis.

It seemed like a fairly stable job, especially after Davis was reelected for another four-year term. Then things got a little crazy, as they say. A member of Congress funded a recall campaign, and an action movie star named Arnold Schwarzenegger decided to throw his hat in the ring after announcing his campaign on The Tonight Show.

You couldn’t make this stuff up. In short order, I was out of a job.

It was a deeply humbling experience. It’s not every day your job is terminated by the Terminator.

But there was a silver lining. The recall inspired me to go back to school and get a law degree, teaching me that nothing in life is certain and a good education is always valuable. And even more importantly, it taught me the value of building and growing your network so you’re prepared when times get tough, which I write about here on AoM and on my own website today.

6) Explain the Lessons You Learned From the Failure

The only thing worse than a failure is someone who fails, and then fails to learn from the experience.

In Noah Kagan’s blog post about his Facebook firing, he laid out three specific reasons why he wasn’t able to adapt while working at Facebook, and the lessons learned from those reasons. He then took it a step further, and explained a few key things he learned after letting people go from his current company, AppSumo.

I don’t think Noah is going to be looking for a job anytime soon, but if he was, this would be the way to explain the lessons from a failure. Reflect, explain what you’ve learned, then show how the experience has made you stronger.

7) Use Your Failure to Demonstrate Your Skills

After David Raether, the sitcom writer who later became homeless, had recovered from his homelessness and was working various short-term gigs, he landed an interview for a job as a writer for Priceonomics. Because the site focuses on economic issues, his interviewer asked for a sample of his writing where he showed understanding of personal economic issues.

That led to “What It’s Like to Fail,” a piece in which David outlined how he went from earning a mid-six-figure salary as a sitcom writer to losing his home and his family.

The post went viral and received thousands of social media shares.

The post itself did so well because it showed off one of Raether’s best skills: his writing. By talking about his own failure, he demonstrated a skill. Often, when you open yourself up to vulnerability, it can lead to some of the best parts of you spilling out.

8) Explain How Your Liability Can Be an Asset

Scott Stossel is the editor of The Atlantic magazine, a position of considerable accomplishment which you would think would be difficult to achieve if you are not perfectly put together.

However, in the cover story “Surviving Anxiety” published in January 2014, Stossel catalogued his lifelong struggle with numerous crippling anxiety disorders and his various efforts to use therapy, drugs, and alcohol to cope.

While Stossel acknowledges the great toll his anxiety disorders have taken, he also argued that they are actually an asset, and that some people who suffer from his manner of anxiety disorder actually possess many positive traits. “Historical evidence suggests that anxiety can be applied to artistic and creative genius,” he writes. “Numerous successful writers, poets, scientists and filmmakers have been plagued with anxiety disorders, including Emily Dickinson, Franz Kafka, Charles Darwin, T.S. Eliot, and Woody Allen.”

Researchers have even found that financial managers who have high anxiety tend to be the best, most effective money managers, writes Stossel. Various studies on anxiety in business leaders and political leaders “suggests that, under the right circumstances, some quotient of anxiety can equip you to be a leader.”

9) Remain Proud of What You Did Accomplish

No matter the nature of the setback, remember that it’s often not all bad.

Before your company went under, you may have provided excellent customer service. Before you got laid off, you probably made some good friends. Even if you didn’t make enough product sales, there were still some buyers who got use out of it.

Unless, of course, your product was a box that spit out smells from the internet. Now that was just dumb.

In other words, don’t forget you can still be proud of the good things that you accomplished.

10) Use Discretion

As with all things, it’s important to keep in mind that the benefits to sharing your failures only accrue to those who do it in the right way, in the right circumstances. You should be honest when asked in an interview about the setbacks you’ve experienced, but you don’t need to necessarily volunteer them as soon as you sit down. You should also avoid over-sharing: you don’t need to detail the way you ate Pizza Hut exclusively, didn’t bathe, and spent your nights sobbing into a pillow for two weeks after you got laid off from your last job. Lastly, guard against centering your whole identity on your failures — making them your badge of honor and all you talk about. Your missteps are one part of who you are, but they’re not the only part. Build the foundation of your identity on the things you’ve done right.

Share Your Failures and Build Better Relationships

Vintage young man shaking hands with older businessman.

Finally, there’s a deeper reason — beyond any personal benefit you may derive — from talking about your failures.

After he started talking about his Facebook failure and other personal failures more openly, Kagan found it served as a means to develop deeper connections with others who experienced similar setbacks.

“I’ve built really great relationships,” says Kagan. “It helps me to filter the people that I really connect with and it helps me to connect on a deeper level.”

I had a similar experience. Having lost a job, I know what it’s like to go through a layoff or a firing. I also know how much it means to people who are going through it when you reach out and offer to help.

Just the other day, I got an email from a close friend explaining that he had recently been “relieved” of his employment by his employer. I immediately picked up the phone to reach out and see what I could do.

In some ways, that’s the greatest lesson you can learn from any setback or failure — the wisdom to embrace our own humanity and to reach out to a friend in need.

If you do that, then you’ve shown that you learned everything you needed from the setback. And that’s what being a man is all about.

Do you feel comfortable talking publicly about your setbacks or failures? Why or why not? Share your thoughts in the comments below.


John Corcoran is an attorney and former Clinton White House Writer. He writes about business relationships and social skills. He has a free, 52+ page guide which you can download, called How to Increase Your Income in 14 Days by Building Relationships with Influencers, Even if You Hate Networking.

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