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.”
• “Sigh. I thought I was finally heading home after this gig in San Francisco, but I just got invited to do a last minute speaking engagement in Switzerland. #Livingoutofasuitcase”
• “I really need to practice my golf swing so I’m ready to play next weekend in Molly Ringwald’s charity golf tournament.”

Humble brags have become more and more popular through social networks like Twitter and Facebook. It’s okay to share your accomplishments, but be honest and upfront about it when you do. Be careful not to use the cover of a complaint in order to brag; you may worry about coming off as smug, but it’s actually better to come off as smug, than to appear as someone who’s smug but trying to hide it. People are more annoyed by duplicity than pride.

5. Get a Wingman

In the book Reinventing You, author Dorie Clark suggests bringing a friend along to events where you may need to talk about your accomplishments. Make an arrangement with the friend that you both will “talk up” the other.

In other words, instead of bragging about your own experience and background, you boast about the other person’s. And they brag about yours. People you are speaking with are much more likely to be receptive to a third party bragging about you than if the information was coming from you personally (even if you’re standing right there, giving your best “aw shucks” grin).

6. Don’t Avoid the Achievement

If you do have a significant accomplishment in your background, whatever you do, do not go to extra lengths to avoid talking about it.

For example, graduating from an impressive university like Harvard or Stanford is memorable. But in my experience, some Ivy League grads will go to extra lengths to avoid mentioning the name of their alma mater out of fear it will be perceived as bragging.

I met a woman the other day and we were casually discussing where we had lived in our early 20s. The conversation went like this:

Woman: “I lived in Massachusetts for a few years back in the late 1990s.”Me: “Oh, really? How did you end up there?”Woman: “Well, I went to college in eastern Massachusetts.”Me: “Oh yeah? My Mom’s from Massachusetts. Where did you go to college?”Woman: “Oh, just outside of Boston.”Me: “Oh yeah? I lived in Wellesley for awhile when I was growing up. Where outside of Boston?”Woman: “Uh, just, um… a little town near Boston.”Me: “Cambridge?”Woman: “Uh, yeah.”

By this point, I was 99.9% certain she went to Harvard. But going to extremes to avoid mentioning the name of your college based on a perception that mentioning its name would be perceived as bragging just creates a more awkward situation.

7. Use Humour

Humour is a great way to share what is most memorable about you without being perceived as bragging. Steven Backman, the toothpick artist, had a sense of humor about the work he did. When I asked him why he worked only in toothpicks, he said, “I don’t know. I started playing with them when I was in 3rd grade and I never stopped.”

A few months ago, I met a guy named Maneesh Sethi. When I asked for his business card, he said he had just ran out, but that his card just said, “Maneesh Sethi, Ramit’s brother,” and included his email address. Maneesh’s brother, Ramit Sethi, is a bestselling author who has been recognized as one of 20 “Wealth Wizards” by Forbes magazine.

The fact that Maneesh’s brother Ramit is more famous than him, and that he acknowledged it on his business card, made his card far more memorable than your usual boring business card. So using an unexpected fact in a novel way is a creative means of pinpointing what is memorable about you.

8. Be Brief

Peggy Klaus suggests using what she calls “brag bites” — which you keep conveniently in your “brag bag” (not to be confused with a product produced by The Brag Company called the “Bra Bag” which is, and I’m not making this up, a bag you can carry your bras in).

Brag bites are short little sound bites and brief marketing monologues about yourself that you can use in a moment’s notice in any situation without coming off as pushy or disingenuous. They’re kind of like mini “elevator pitches” about yourself.

A “brag bite” may look like this:

• I am fortunate to lead a team of 50 incredibly talented sales men and women across a dozen states, and I really couldn’t do it without such a great team effort.
• Last year, we opened four new restaurants in three different cities — and we have plans to open four more. But really we’re just happy people seem to like our drive-through fondue theme.

If you haven’t already, create a few of these short sound bites. Asking a friend who has a way with words for suggestions is another way to get a fresh perspective on these short statements.

9. Be Personal

The most memorable thing about you may not be a professional achievement; it might be something from your personal life. Even if you are a Yale Ph.D. who has 17 kids and holds the world record for the World’s Largest Smurf Collection, the most memorable thing about you will be relative, depending on the person you are talking to. If the person you are talking to happens to be from a small town in Georgia and you are originally from another small town in Georgia 20 minutes away, then that is probably the most memorable and interesting fact about your background.

In that case, you do not even need to bring up your impressive educational credentials. You are already more memorable to your fellow Georgian than you would be if you discussed your impressive academic accomplishments. And since you’ve already made a personal connection, if your accomplishments do come up later, it will be more natural and even less likely to be perceived as bragging.

10. Don’t Share All of Your Achievements

Now, you may be thinking, “Whaaaat? I thought you were showing me how to share my most interesting and memorable achievements?”

That’s right. But you can’t share all of them. You need to let some things unfold over time. Sure, this means something that is interesting and memorable about you may not get shared, but that’s okay.

You want to give the person you are talking to just enough so that you are memorable and interesting, but not so much that they are overwhelmed.

The last thing you want to do is try to cram in some accomplishment where it’s not relevant. Work in your accomplishments where they naturally fit rather than forcing them into conversations just to brag.

Although that’s not always true; I mention my six-pack abs all the time and no one seems to mind.