I was wondering if anyone else noticed a trend (probably among young men 20-30, on occasion women too, but guys mostly) where they seem to underestimate their skills or put themselves down?

My story from last night I went with a group of people to go bowling. all of the other guys in the group seemed to practice self deprecation saying "I suck" or "I am awful at this sport", when they did OK (one bowled a 90, myself an 84, and another 79). I know these aren't the best scores ever, but when everyone else at the lanes were having a hard time breaking 50, yelling I suck and bowling a strike seems a bit off.

I bring this up because I've seen it elsewhere. It seems that these people make it a point of pride to claim "I suck at..." While I try to make it a point of pride to have a descent skill at a lot of various things (e.g. I can hold my own at pool, get a double bull in darts on occasion - not a fluke, play ice hockey with the "big league boys" - which I started a year or so ago). And, I'll add this doesn't seem like a hustle. These guys legitimately have my skill level.

I've only found 2 things on the topic on this site:

http://artofmanliness.com/2011/02/19/manvotional-letters-from-a-sel...

There is a big difference between pride and self-esteem, one not many people understand. The popular understanding of humility seems to be self-deprecation, which is actually a form of pride! The world will respect, even salute a man who knows who he is and can’t be shaken by anyone else’s opinion, and doesn't need to tell the rest of the world.

http://artofmanliness.com/2011/11/21/how-to-handle-being-out-of-you...

He also found that self-deprecation can be an important tool of charm. A little wink-wink bumbling. While he was pretending to be a doctor, he’d let his interns make all the decisions, which won them over. And when he made a mistake, they’d say, “Oh, stop joking doc!”

While I can see the merits of occasionally putting yourself down as an element of charm, Have people of my generation overdone the self deprecation in an attempt to feel more charming and humble? Or do they do this because of some pride? I personally find it frustrating, to the point of infuriating. Or do people actually find this behavior charming and I'm the odd one?

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Those scores are pretty low.  You really do suck.

I'm very competitive at sucking, lol.
Last Daddy's Day bowling with the Girl Scouts I, with my daughter, won the "Team With The Lowest Score" certificate.
Proudly hangs at my desk at work.

I don't really like that sort of behavior either, especially as it's often about skills where a certain match in skill would be nice. 

For instance; Two weeks ago we were on a skiing trip and at the end of the week I decided to look at the skills of a girl that had told me 'she was sort of all right' on ski's. Bullsh**. She skied almost as well as I do, and I have no trouble keeping up with qualified skiing instructors while keeping good form and total control. If she had come forward about her skiing abilities, we could've had a lot of fun as it is more fun to ski with people of your own experience and level. 

I'd be more tempted to be 'humble' about things that are a matter of taste and perception, in stead of something that's more easily measurable. I'm a good skier, a good sailor and a good debater. Those are things i'm very confident of.

My cooking, writing, sexual ability and 'humor' (as in comedy value) are completely open for debate. I'm  confident about those things, but I think it wouldn't suit me to boast about it at any length. Better to be humble. 

As for bowling: Points are awarded non-arbitrarily, so being 'humble' about it makes no sense to me. 

Hmmm.  Might have a bit (or more) to do with a manly modesty being more becoming than being a braggart about one's accomplishments.

This expressed modesty isn't something new, a man has been expected to let his actions speak louder than his words for quite some time.

Ego. If I am good at something but say I suck, I look that much better and get more recognition/stroking for performing above expectations.

Insecurity.  If I should happen to suck no body is gonna feel let down and I'm off the hook for looking boastful.

Lazy.  If I say I suck, I've no obligation to do my best or to expect anybody will ever ask or expect anything of me aside from suckage.

In short, bullshit all ways round!.

I could not have said this better. I don't know if it's generational, as I see it in my age group as well.

Probably just a minor culture shift.  These things happen; I don't see how this one is anything to worry about.

Have people of my generation overdone the self deprecation in an attempt to feel more charming and humble?

No.

Or do they do this because of some pride?

There are several possible causes. One is low self-esteem. Those are the ones that really stick out. Another cause, that has become very common in recent years, is young people doing it avoid having to live up to high expectations. Not particularly humble--they don't want to set themselves up for a fall because their pride is easily hurt.

The two are related. They're both trying to live up (or down!) to a self-image.

I suppose the real question is how to help them grow as people. You don't want to contradict someone directly, unless he crosses certain boundaries:

"I am such a worthless pig."

In that case, I might actually contradict someone and say "NO YOU'RE NOT!" and then launch into a pep talk.

More generally, if someone says something like 

"I could never be a doctor or an engineer"

You might say "Unless of course you really wanted to be one, in which case I'm confident that you would make the commitment to make it happen."

"Oh, but I'm just not smart enough."

"Huh? You don't strike me as dumb. Maybe you've had some bad experiences in school and so never had the motivation to succeed. Haven't you always been successful in things you love to do?"

Keep reframing them in positive, can-do ways. Not optimistic: you need to disclose that there is a cost to performance--but that anything they really COMMIT themselves to, they could become good at.

There is a certain arrogance that prevents people from trying, because if they try anything challenging, they're going to fail until they learn an grow and get it right. They're too proud to allow those first few failures.

One approach is to tell them it's OK to "fail" and not to take it bad. Get them over needing to "prove" anything to anyone, including themselves. To let go of attachments to outcomes, and just enjoy the process itself--in this case, the bowling. Encourage them to enjoy the game without obsessing about their performance. Just have a good time. If they can do that--then they'll play more--and ironically eventually get quite good!

People spend too much time worrying about what others think. Years ago, I did too. Not anymore. It's okay to offer self-deprecating humor. It can break the ice. 

There is a limit though.. Keep one thing in mind. Tell people you're great and they will not believe you and think that you're arrogant or pompous. Tell them you suck, and they will believe it in a heart beat and revel in it. Best to keep one's mouth shut and let your actions speak for themselves. Nothing succeeds quite like success.

Having an honest view of oneself is important to being successful in life and career. Knowing one's limitations and strengths goes a long way to avoiding pratfalls, and taking advantage of what you do well. I stress the term "honest".  

I have a very simple rule. If I'm tempted to tackle anything new, I decide whether or not the new thing is worth a maximum effort. If it isn't, I will not commit to it. If I determine that it is worth the effort, I throw myself into it with goal being to do the very best I can, with the idea that good enough is never good enough.

Honestly, I have this problem. My reason, though, is different from the ones stated below. For years, I was the cool kid, so I'd trumpet about and publicly announce my accomplishments, because I knew I'd get a good reaction. Now that I'm older, I realise the value of humility. Moreover, my reputation for arrogance is entrenched pretty firmly in everyone's mind. So I tend to overcompensate, by attributing all my success to others, or to luck. I'm having a lot of trouble finding a balance, and trying to attain true humility.

Western style of dealing with things is to give it a go and if it does not go well assume they can't do it.  Eastern style is to to work and work and work on the problem.  

West is taught we are smart / good so we should be able to do whatever perfectly the first time. 

East is taught to work hard to achieve.

However West is much more adaptable and better at innovation.

East is better at technical skills but not innovation. 

I rather not play bowling if my love interest is there

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