Skip to content

Essay On The Art Of Bragging

Editor’s Note: This a guest post by John Corcoran.

Have you ever met someone whose personal story just blew you away?

My friend Tom is one of those guys. A West Point graduate, Tom spent a few years in a U.S. Army special forces unit where his job was to parachute deploy into warzones from helicopters.

That’s right — his job was to jump out of a perfectly good helicopter. And that’s not all. While he was still in the Army, Tom wrote two books and founded a boutique publishing company.

What a jerk, right?

Here’s the thing: Tom is actually a nice guy. If he wasn’t such a nice guy, I’d probably hate him.

But his background is so incredible — it so blows my coward butt out of the water — that it’s hard to imagine how he can talk about his background at all without coming off as an insufferable braggart.

In reality, Tom is actually quite modest, which is part of the reason I like him.

The problem for guys like Tom is how he can share his background in a way that doesn’t come off as bragging.

In other words, one of the most interesting things about Tom is that he’s a combat veteran who got paid to jump out of helicopters, but he can’t always talk about the thing which makes him most interesting without alienating the person he’s talking to. It’s kind of a damned-if-you-do, damned-if-you-don’t situation.

Tom’s not as different from the rest of us as you may think. Even if you didn’t do a stint in the U.S. Army as a helicopter jumper, almost everyone has something interesting or memorable about them which makes for good cocktail party fodder. Yet social norms tend to prevent many of us from sharing these great stories out of fear of alienating people who might think we are trying to show off.

Brett has previously written about how the world belongs to those who hustle, but even if you are a successful hustler, the next question becomes how can you be a hustler and talk about your successes at the same time? In this article, I am going to offer 10 tips for how you can become more memorable by sharing the stories and experiences that are most interesting about yourself, without coming off sounding like a jerk and a blowhard while you do it.

In other words, I believe there is a better way — a way you can talk about your most interesting achievements without sounding cockier than The Situation on spring break.

Why You Should Talk About Your Accomplishments

You may be wondering at this point why we should even care about talking about ourselves. Well, as Forbes wrote last year, today’s landscape makes it much more difficult to get your message across:

“The average American hears or reads 100,000 words every single day. Studies dating back decades have shown that 80% of what we learn is gone within 24 hours. That makes it much less likely that your message is the one that sticks.”

By talking openly about our accomplishments, we have a greater chance of being remembered and not forgotten.

Communication consultant Peggy Klaus says the fear of coming off sounding like Gordon Gecko denies professionals the opportunity to explain to clients the value they provide. The author of Brag: How to Toot Your Own Horn Without Blowing It, Klaus says that the entire notion of self-promotion is excruciatingly difficult for many professionals to embrace, even if they know it is critical for their own survival. “So ingrained are the myths about self-promotion, so repelled are we by obnoxious braggers, many people simply avoid talking about themselves,” writes Klaus.

Here are a few additional reasons why you should talk about your accomplishments:

  • Great stories make life interesting. Tom’s background is too interesting to keep locked up in a box. It would be a shame and a lost opportunity if he didn’t mention his backstory at all because of social norms against bragging. These types of stories make life more enjoyable.
  • Being too humble can cost you. Not talking about your accomplishments can hit you in the pocketbook. “It’s those who visibly take credit for accomplishments who are rewarded with promotions and gem assignments,” writes Klaus. As our economy has resulted in less job stability, self-promotion has become more important. Even if you aren’t an entrepreneur, says Klaus, you need to think like one and start talking up your most valuable product: you.
  • Your stories reveal the true you. When we share stories about our accomplishments, we reveal our true selves. It is only through revealing our true selves that we break through superficial small talk and make real connections with people, form genuine friendships, and deepen our relationships.

10 Ways to Share Your Accomplishments Without Bragging

Here are 10 ways you can share your most interesting experiences and stories, without sounding like you are bragging:

1. Share a Sense of Wonder

If you are sharing a part of your background or personal/professional story that may inspire awe in another person, it’s best to acknowledge and share that sense of awe.

I have another friend who, like Tom, also served in uniform. This friend served in a U.S. Coast Guard attack squad, where he was deployed into highly dangerous semi-warzones and tasked with scrambling onto pirated freighter ships in the black of night as machine gun fire whizzed through the air. When I asked this friend if he was scared during his service, he said, “Sh*t yeah, I was scared. But we just moved as quickly as we could and thankfully I’m here to talk about it.”

I loved that he didn’t play off his background like it was normal and mundane, which I would have found strange and inauthentic. Instead, because he shared my own sense of awe in the sheer terror of his story, I found him even more relatable.

2. Be Grateful for Your Success

I met a guy at a networking event recently who said he was an artist — but not just any kind of artist. Steven Backman is a toothpick sculpture artist. He only creates one kind of art — sculptures out of toothpicks. He has been featured on just about every major media outlet you can think of, from CNN to The Today Show.

He showed me a few photos of his creations on his iPhone, including a scale replica of the Golden Gate Bridge made out of 30,000 toothpicks, a replica of the Empire State Building, and a remote-controlled toothpick boat.

He wasn’t shy about his achievements — he was proud of them. And when I expressed my awe at the amount of recognition he had received, he flashed me a grin, as if to say, “I can’t believe it either.”

By any measure, he had been quite successful as an artist. But I think what made him so memorable without seeming like he was boasting was that he was sincerely grateful for his own success.

3. Be Self-Deprecating

Tom Morkes, the helicopter jumper, is self-deprecating when describing his Army experience. If someone asks him about what it was like to go to war, he says, deadpan: “Well, it wasn’t a vacation. I lived in a metal container for a year, did a lot of missions, and most of the time it was really boring waiting for bad things to happen to you.”

Like Tom, I have an unusual background as well. I was fortunate enough to land a job in my early 20s working in the Clinton White House. For years, I have described it as being “kind of like a second-string speechwriter,” or I would say that my job was to “write the stuff the speechwriters didn’t want to write.” I have found describing the job in this way leads people to let their guard down. Most of the time, it helps make people more comfortable speaking with me so that they can ask me question they really want to know, which often is, “So, did you know Monica Lewinsky?

4. Avoid the Humble Brag

The humble brag happens when someone shares a tidbit of news about themselves that is camouflaged using a complaint or a self-deprecating joke. They are trying to appear humble on the surface, but their real intention is to boast.

A humble brag may sound something like this:

  • “I can’t believe how many people have said my wife looks like Rita Hayworth. Too bad they think I’m her bodyguard, not her husband.”

Thanks largely to social media, the ubiquitous humblebragging is often the way people show off their successes today. Just take a scroll through your Facebook feed and you’ll find examples everywhere of people talking themselves up. And it’s not just the average person who does it; even the most successful people humblebrag.

Comedian Dane Cook was called out by the New York Times for his humblebragging ways when he tweeted to millions of followers: “Being famous and having a fender bender is weird. You want to be upset but the other drivers just thrilled & giddy that it’s you.” Former White House press secretary Ari Fleischer did it when he bemoaned on Twitter in 2012: “They just announced my flight at LaGuardia is number 15 for takeoff. I miss Air Force One!!”

Even Oprah humblebrags when a tweeted photo of her pedicured feet was strategically placed near a wall filled with her face on magazine covers. Reading Rainbow’s LeVar Burton was guilty of a very similar act when he tweeted a picture of Christmas stockings with the caption, “The stockings still hung . . . ” but was really trying to show off his mantle lined with Emmys.

Why do people humblebrag? Mostly because we know humility is a good characteristic to have, but at the same time, we also know the importance of self-promotion, so humblebragging seems to be the answer.

Unfortunately for humblebraggers, a Harvard Business School study found that observers of humblebragging find the act insincere.

“Humblebragging may constitute a particularly miscalibrated case,” say the researchers. “Humblebraggers experience the positive effect from bragging and the positive feeling that they are not actually bragging, while recipients react negatively to both the self-promotion and the attempt to mask it.”

The study examined more than 300 people and found that examples of humblebragging were least appreciated compared to outright bragging and complaining. The study says: “Faced with the choice to (honestly) brag or (deceptively) humblebrag, would-be-self-promoters should choose the former,” the researchers write. “And at least reap the rewards of seeming sincere.”

So, how do successful people show off their skills and accomplishments without coming off as pompous and insincere? Below are a few examples to consider:

1. Don’t focus on who you are, but what you did.

Joshua Waldman, bestselling author of the bookJob Searching with Social Media for Dummies, says when talking about your accomplishments, “learn to distinguish between something inherent to you (like intelligence, luck, or good looks) and something you did (like hard work, perseverance, and innovation).”

For instance, instead of saying “I’m a bestselling author,” say, “I’ve written a book that’s bestselling.”

2. Talk about your struggle.

When you brag, it often gives off a sense of entitlement, like you’re really saying, “I’m better than you. Things you think are hard are easy for me,” Waldman writes in Career Attraction.

That’s why sharing the struggle you endured while working towards your accomplishment can eliminate the entitled pretense and make you seem more relatable. So instead of saying “I’m a bestselling author,” consider sharing how it wasn’t your brilliant writing that got you this far, but it was the “lots of outreach, phone calls, guest blog posts, and begging my friends to leave Amazon reviews.”

3. Get someone else to brag for you.

What’s better than self-promotion? Getting someone else to do your bragging for you.

In the book Reinventing You, author Dorie Clark suggests bringing a sort of wingwoman or wingman with you to events to “talk you up.” Instead of bragging about your accomplishments, have someone else do it for you, which comes off as more sincere to observers.

4. Tell a story.

The ability to tell a good story can get you far in life, and the same is true when you’re talking about your accomplishments.

Don’t turn people off with a laundry list of how great you are. Instead, perfect the “bragologue,” which leadership coach Peggy Klaus says is the best way to brag without the backlash.

When talking about your interests, ideas, and accomplishments, “bragologues are powerful in getting people to think about you in just the ways you want,” Klaus tells Forbes.

“These pithy and entertaining ‘monologues’ are woven together with a few memorable or impressive nuggets of information called brag bites―pieces of relevant facts, such as clients that you’re working with, how long you’ve been in the industry, or a project you’ve recently completed,” says the author of bestselling book BRAG! The Art of Tooting Your Own Horn Without Blowing It.

For better context, here’s an example of bad bragging, according to Klaus: “I’m a great sales manager because I am good with people. At the end of the month, I always get the top numbers.”

Now here is an example of a good bragologue: “You know when I was first hired as a sales manager, I never knew what a great fit it would be for my skills and personality. The job brings together my organizational skills, an ability to bring out the best in people through coaching and mentoring, and years of hands-on industry experience, which helps me really understand what my team is going through.”

Bragging about yourself isn’t something to be embarrassed about. In fact, it’s absolutely vital in your professional life, which is why women, who tend to underestimate their achievements, are encouraged to learn the art of self-promotion. Just remember the next time you talk yourself up that coming off as sincere is essential when highlighting your accomplishments and skills so that they won’t be forgotten.