To think that "difficult" people are life's winners?

Yes absolutely. Not always.. but far too often.

I don’t think so, because these types of people often have difficulty with family relationships, friendships and staying married! They also do less well at work in many cases, because leadership roles require you to get along well with people across your company/industry in order to exercise influence.

Yes. I know people like that who are also quite charming and entertaining when they want to be and people flock to them. They rarely back down about anything. They seem to have lots of friends and a cracking social life.

I think there’s a difference between being unpleasant which doesn’t pay off in the long run, and self absorbed, single-minded, opinionated but also fun which I think pays off massively.

this is a very thoughtful and intelligent post. i have many of the qualities you've listed but think i may be one of those people missing those boundaries. are you? you dont sound like it - so i wondered if you had any advice for me on how to retain those boundaries?

Depends on the context. Also, what is seen as normal assertive behaviour in a man is often perceived (usually by men) as "difficult" from a woman. Persistence and assertiveness, especially in situations like healthcare, can be lifesavers. That said, we all know people (dickheads) we try to avoid.......

Depends on the role surely? If it’s a cut and trust deal making / sales job these characters will venture into fast into maybe unethical territory to close ahead of anyone else. They might then well be feted and rewarded by their company. Agree if it’s client relationship it’s different - however many narcs are charismatic manipulative groomers so can switch it on when it’s self serving.

Depends. In my profession a colleague alienated all the clients just by doing and being what you described in your question. Definitely not a winner. I think that you can definitely lose clients this way - at a certain level all professionals are the same, competence-wise, so the only thing that is remaining is really people skills, no?

I don’t want to think this is true but I have been watching it play out in DHs family. He has always been the peace keeper, the reasonable one, the let it go one and his brother has always got dramatically upset. Now there is an issue where (obviously I think so) DH is 100% in the right but his parents are expecting him to roll over like he always has…except this time he isn’t because it affects me and our DC too and it’s causing problems.

Yes and no. There are difficult people like the ones I encounter as customers who look for every potential problem and try to ‘catch you out’ with technicalities, these people get the bare minimum because you know they’re going to complain whatever you do so why bother trying. Then there are the people who put themselves first rather than ‘being kind’ - these people get what they want because they take it unapologetically.

I don't know. I knew someone who is one of those people who people describe as "life and soul of the party" although I always found rather arrogant and up themselves, but I assumed I was in the minority.

They moved away about 20 miles, and I don't see them now, but I do come across people that know them (there's a reason why they come up).
I'd say about 25% people think they are wonderful. 25% think they are pretty nasty bullies who hide behind "it's just the way they are" to get away with it and the rest put up with them, assume they're popular and well liked but find them a bit too much/think they're not really that nice.

However I will note that about 5 years after moved away and they made contact with us (they only do if they want something) and suggested that we shared babysitting. Dh, who can be very blunt, laughed and asked why on earth we'd ask someone 20 miles away when we can ask one of many people we know locally (they never offered when we were local, and they had their dc after moving away).
They admitted that they couldn't find anyone local who would do it - despite presenting their lifestyle as a constant throng of people who adored them.

So I concluded that even the 25% who thought they were wonderful is very superficial and they don't really have true friends who would do favours for them - and tbf I doubt they ever do favours for anyone else if they don't get something out of it; they certainly never did when they lived locally.

Surely you need to coach your younger two to be more assertive. If they wanted the poppadom they should have spoken up. Have you trained them to "be polite" in this way? If you have you have done them a disservice.

If they make enough money they can buy friends so won't die alone.

What a vague and pointless musing.

I have one child (oldest) who fits some of your description, and he does seem to ‘win’ just because of his attitude. Tonight , for example, we were out with family for a meal. There was one poppadum left in the basket. DH offered it round the table to the children first. The other two said no thank you, so DS1 shrugged, said thanks and took it. Knowing the other two they probably said no to be polite and DS1 called their bluff and took them at their word.

i actually do worry about him more than the younger, quieter, kinder and more considerate one. DS1 is likely to piss people off once they tire of his self serving nature, and he’s quite hard work / bit of Drama llama. Great fun, always to for a laugh, gift of the gab - but self serving. DS2 otoh spotted that his granddad was struggling to move something in the garden today, and ran out to help straight away. But because he’s quiet, shy etc he gets overlooked all the time.

Is it a inherent thing or a learnt thing to be nasty and horrible to achieve your goals at the expense of other people. I've been trying on and off for 50 odd years and just can't deliberately do something hurtful to someone to achieve an objective, either at work or in personal relationships. There's plenty of people I have met that I don't like in life, but I've never eliberately done something to them, or anyone, nasty just to further my aims. Neither has my partner in the 35 years we've been together.
How do people feel after they've done it. Does it make them feel a sense of achievement or do they just not even think about it and move on. I would have strong boundaries about how people treat me and my family but would never plot my 'success' to the detriment of others.
Though I won't stay in the company of people who are gleeful of people they know's misfortune. All of us are only one life event away from catastrophic misfortune.

Saw it all played out over 27 years of marriage. My FIL had narcissistic personality disorder and was the awkward bugger whose wife and daughter ran round trying to appease. Whole house was on eggshells but as years went by and his wife became frailer and he became more "no one visits me etc". I asked about friends...he had only had 1 back in the 1960s. When he was very ill in hospital his kids only went in once and when the hospital called to say he had passed there was no sadness.. Only immediate famy at funeral.. So no I don't think they are life winners

Only a bit

Your connections and perceived social standing matter more

A lot of that comes from being born into money.

My view is that what you describe is different. Strong advocacy and tenacity and expecting standards from those providing services is a different thing to those being described by OP. I think most people know a difference between the two.

That’s still quite vague. That freedom either comes from earning a lot of money, inheriting a lot of money or foregoing convention and living off grid or at least off the beaten path in some way. Or perhaps just falling into it by sheer luck.

That’s an enormous array of people. How do you class them all as ‘difficult’? Or why?

I've seen those people get up the career ladder many times. Those who give a shit and are conscientious are the mugs, including me.