Is arguing worth it? If so, when and when not? Also, how do I become less arrogant?

If you plan on changing someone elses mind, ask a lot of questions about their position to see where they are coming from. Questions might be more important than arguments.

If you talk to someone to disagrees with you, have a genuine curiosity about their position.

Pressing someone to defend their position quite often makes them more certain of it, not less certain.

See, if anything I have the exact opposite problem (which, ironically, I also attribute to arrogance). I almost never engage in arguments with people because I assume I'll never change their mind. When I do get into a debate with someone, I'm extremely quick to give up and write them off as a lost cause. This probably isn't a super healthy attitude to have (especially since many of these "lost causes" are my friends and family) but at least it keeps me out of unproductive arguments. I do have a few friends who are (in my experience) unusually good at listening to new arguments and changing their mind, so I usually wind up limiting my in-depth discussions to just them.

Trying to quell the Someone-Is-Wrong-On-The-Internet impulse is an exceedingly noble goal.

Something I've been trying recently, as part of a broader effort to improve my communication skills, is explicitly telling myself what my goal is with any given communiqué. If that goal turns out to be "convince this person that their cherished belief is wrong", and that outcome is unrealistic, I'm less likely to make the attempt.

When debating with people, you should only make one inferential step per debate. Leave the next step for tomorrow, when the person has already accepted the former step (and probably believes it was actually their idea).

my opinions are uniquely valuable and important to share with others

They are valuable and important to you. Not to the others, yet.

I do think I'm smarter, more moderate, and more creative than most.

You may be right, but this is irrelevant here. People don't automatically accept smarter people's beliefs (and that's probably a good thing).

Politics is a combination of the opinions of bureaucrats, politicians, interest groups, the press, and the general public. The general public's ability to influence politics is based on their influence over politicians (money+voting) and interest groups (money). The press, by controlling information, are able to influence all the other groups. This an expanded form of the iron triangle. Check the link for more details, and for a wide variety of opinions on the subject. Your arguments mainly serve to have a limited influence over public opinion, and this influence will often be negative. You have to ask yourself whether possibly damaging your personal relationships is worth having a very limited impact on one element of decision making on a single issue that may not be as important as you think it is.

There's a concept in psychology known as cognitive dissonance. Arguments are hotbeds of cognitive dissonance; both for you and for your opponent. Each of you tries to separate themselves from the cognitive dissonance, but this actually causes you to double-down on your original position by coming up with new ways to prove yourselves right. By arguing, both parties are gradually reinforcing their own beliefs. It's actually very difficult to avoid this; even highly intelligent people will often make this mistake. Less Wrong, similar sites, and some of academia are unusual exceptions in that much of those individuals are actively thinking about trying to overcome their own biases. They have trained themselves to consider the argument on its own merits rather than on the basis of their prior opinion.

I actively avoid getting into arguments in ordinary conversations unless I think the individual wants or needs to hear it. The reason is identical advice can always be found on the internet, and there will always be a source out there with a better worded explanation than something I pulled off the top of my head. If somebody has taken the time to form an opinion on an issue, they've taken the time to decide which sources to look for to determine that answer. If they want to find a better source, they can ask, but they don't need me to give them their opinion. A very difficult skill is determining what they are and are not interested in listening to you about. If they've already given a firm no, then that should be sufficient. They are not going to listen to your drawn out explanation, no matter how intelligently worded, if they don't want to do so.

An alternative method from marketing is known as brand messaging. You create a simple, consistent, positive message associated with your view and put it out there as much as possible. If people see your viewpoint reflected in a positive light in enough places (not just from you), there's a good chance they'll reconsider their position. Arguments fail all three of those principles. They are not simple. They are not consistent (I mean you use a different argument each time, I am not referring to logical consistency). They are not positive (by which I mean cheerful, not additive).

I learned a long time ago that having good relationships with my friends is far more important to me than showing them that I'm right. I'm perfectly ok with trading a pursuit of the truth (since it's political, this should probably be "the truth") in exchange for some utilions. I've hidden all the controversial or clickbaity topics from my facebook feed, and facebook's algorithm doesn't show me these any more. If I'm really jonesing for an argument, I'll go somewhere where there's structure for it and it won't damage my personal relationships, such as /r/changemyview.

I have the same problem as well. Although I have not been able to stick to it every time, I try to follow this method: If you are in an argument, keep the time in mind and change the subject as soon as you have not gained anything after e.g. 5 minutes. The gain could be new insights, entertainment, mental exercise, increase of social bonds/respect, money, self-respect, self actualization (e.g. convincing the influential person to implement your wish), etc. This sounds harsh, but time IS your most precious resource and using it without a benefit is like throwing money into a vending machine, which gives nothing in return. Better find another subject or conversation partner.

Deduct one minute every time the person switches talking points instead of responding to your argument. Punch him every time he mentions a study, but won't give you a source (e.g. instead of googling it together, he promises to 'send you a link later'). (Punching seems a bit excessive, but imagine a world in which everyone thought twice before quoting PIOOMA results! It could usher in a new age of enlightenment!)

I try and imagine my words and behaviours on someone else. In other words, how would I react if I saw someone else acting in the way I am acting. This causes me to be a lot less argumentative and a lot more conciliatory.

If you want to resolve your own desire to publicize your arguments without dealing with internet_contrarian_255, writing up your arguments without targeting them to a specific person and posting them on a blog or some other site where people who agree with you can point out a few flaws might be helpful.

Also, if you do that, then when you do end up needing to argue with someone, you'll already have your arguments and sources handy on your computer.

This advice has more to do with serious written criticism, but I like spreading it around.

You should attempt to re-express your target’s position so clearly, vividly, and fairly that your target says, “Thanks, I wish I’d thought of putting it that way."
You should list any points of agreement (especially if they are not matters of general or widespread agreement).
You should mention anything you have learned from your target.
Only then are you permitted to say so much as a word of rebuttal or criticism.

Me quoting Judith Curry quoting Daniel Dennett quoting Anatol Rapaport.

I only ran across this fairly recently, but it makes explicit some vague intuitions I had had before. The few times I consciously have put it into practice so far, I have found it rather time consuming but beneficial. I'm not sure whether I have learned to back away from pointless controversy or how to make points more persuasively, but it has helped me get away from looking at arguments as soldiers in an army kind of thinking.

I also seem to have offended one person I know rather severely.

From this sentence I gather that you're concerned mainly with in-person arguments. My own experience is that I argue extensively on the internet, but I'm quiet and modest with my friends and family. Mostly I suppose I'm just not that assertive in person. But if I had what I'm gathering is your problem, I would basically: take care to watch the faces of friends and family (constantly, or at least whenever there's conversation). Think how you value your relationship. That's a lot of mental effort, but it should supply you with a ready, natural-feeling motive to tone down or end an argument.

In an argument you use the facilities and methods that the other person recognises to come to some conclusion. There should not be any use of force involved. Fighthing over theorethical things can be pointless. However arguing is usually pointful. If you are just stating things you are not making an argument.

I have seen some people fight over theorethial issues and use quilthing, authority and all kinds of shady stuff to make their opposition concede. This has no epistemological value and I am very doubtful whether it can be used to achieve even moderate lasting communal decisions. If you are truly arguing and doing it right the discussion requires going deeper by the standards of the other participant. This should not be emotionally energy draining (quite the reverse the other particapnt sees a reason to deploy more resources to get to the bottom of the issue). If you need to figure something out for yourself you don't need to do it in a group setting and some other mind not having the same bottomline as you is not an error state.

I think a big part of the problem is that I have an irrational alief that makes me feel like my opinions are uniquely valuable and important to share with others. I do think I'm smarter, more moderate, and more creative than most.

I've had a similar problem. Every time I feel the impulse to argue, I try to remember that (in general) arguing won't change their position. It depends on what you're trying to achieve with your arguments. Are you trying to make the other person lose social status? Are you enjoying yourself by demonstrating your greater intelligence/moderation/creativity? Or are you trying to get them to change their mind? Because the last goal is probably not achievable through argument.

I've found that questions/experiments/bets tend to be better ways to settle disputes than arguments, especially when it comes to sensitive topics. It's probably better to avoid meaningless debate that just enrages people.

This discussion also reminds me of Yvain's In Favor of Niceness, Community, and Civilization.

If you are to exert influence on the world, you have to state your opinions to people. But you also have to be rational about it.

Start with asking yourself:

1. Am I wrong? (Honestly examine your position and see things from the other persons point of view)
2. Is the topic important? (Cause prioritization)
3. Am I convincing the live person or the audience? (Different tactics)
4. Is success a possible outcome?

Let's say the answers in a given scenario are no, yes, person and yes. Convincing another person is hard because of confirmation bias. Added to that is the social dynamics of you telling another person that she is wrong, perhaps while others are listening. Both of these challenges have to be overcome in order to succeed.

Some suggestions from my personal experience (as a politican, inspired from Carnegies book):

1. Ask questions throughout, preferrably questions that makes the other person respond positively. Make sure you understand the other persons position. Show respect for her opinions, never say "You are wrong". "Interesting. Would this be applicable in scenario X?"

2. Begin in a friendly way, with praise and emphasize where you agree with the other person. "Yes, I very much agree with you on X. That's a precise observation".

3. Call attention to the other persons mistakes indirectly and talk about your own mistakes first. If you yourself have said something wrong, admit it quickly and emphatically. "I actually used to think Y myself, but then I discovered Z"

4. Minimize the points where you disagree (make the fault minor / seem easy to correct) and let the other person save face "Of course, we both have the same intentions here. Whether Z is true or not is a minor issue"

Some tricks up your sleeve:

• Give the other person a reputation to live up to "This is of course familiar to a person to a knowledgeable person such as yourself"
• Let the other person feel the idea is hers "Excactly. It is as you said, X segment, which in turn is Y and Z."
• Dramatize your ideas with enthusiasm and stories.

Lastly, as I can see that you already know, arguing is not a winning social strategy. Very few arguments improve the relationship you have with the person you are arguing with. There are many ways to talk about interesting topics without pointing at points of disagreement. Save the arguments for when it is strictly neccesary.

It sounds like you're measuring your success by the impact you have on the person you are directly communicating with.

What happens if you measure success by your impact on the rest of your audience?