As a 6, I can look back at the times when I felt the most psychologically and emotionally healthy, and so I am using this as a groundbook to try and teach other 6s to better cope with the world. Some of the advice may seem 'counterintuivie' in the sense that it's not really how we are naturally programmed to behave, but it is the things that lead to enlightenment.
First off, 6s are their own worst enemies in the sense that they simply talk about their fears and troubles with people too much. They have a thing about 'being real' but the problem is, with other people they just think 'GET FUCKING OVER IT YOU EMO ******' and you can't really escape that's how other people are gonna feel, most of the time. Or look at you kind of kiddy like and condescending like 'there there.' Just pay attention to how you're being with people. Instead of pretending that you're 'weak' just relax and lighten up about something, and watch how people treat you differently.
So a way to circumvent this, is learn to keep shit to yourself more. If things really excited you or you really have questions about something, try to see if you can do it yourself first before 'asking for help' or talking about it. Asking for help when you have to innately do it completely by yourself eventually anyway just gets in the way. What improves the 6s self-confidence are stuff that comes naturally to other types, so you also will probably be looked at funny if you tell other people you did something that helped yourself. So whether good or bad, just keep it to yourself.
First off, the 6s have a similar problem like the 4s whereas they isolate from the world too much out of fear, anxiety, insecurity and self-protection. But 6s are also 'group based' more than 4. So live fully, but do it with others. We all have to remember that humans are interdependent creatures. Community projects (but ones that still value people's independence) are great for 6s, some sort of ideal the 6 is personally passionate about that he can be around others. This will help alleviate some of the 6s insecurities that he has, that he sees that a lot of people have the same neurosis as him, they just aren't as fixated on them. (in the end that's all types are anyway, some sort of fixation that you are stuck with that can be made more malleable and healthy with practice) These group projects shouldn't be something that shouldn't be too 'locked in a system' but more 'hands-on' with still the group support.
With that said, even though I said 6s do much better in hippy liberal bohemian environments, it is not good for the 6 to talk about their real feelings in front of strangers or a group of people. As people will try to 'fix' you too much. This is extremely unhealthy for the 6 as well because their emotions are so complex and deep due to the 6s natural ambivalency and more than a few people simply can't support the 6. It also goes back to the original point about how just keeping that shit to yourself until later. You will simply cut off too many external allies by this behavior as well. Sooo just try and find something relaxing, but objective external to talk about with others and make sure you are just staying calm, relaxed and centered no matter what you are doing.
6s also need to lose the image thing. A lot of 6s try to make their outsides look presentable when they are a nervous wreck internally. It's all aesthetic junk and it's never as important as you think it is, and it's also your disintegration to 3. 6s probably suffer from porn addictions and the sort of 'romantic beauty ideal' thing that 4s go through as well, where they just want to stare at a pretty picture of a rose all day and pretend that everything is okay. *sigh* You just have to ignore this and realize that your confidence will only be improved a little by little over time, by just 'going with the flow' and learning the detailed processes of how things work and not your egoic projections and fixations that you attach to everything. (This is the same truth for *all* types by the way)
6s think everybody in power is out to get them, that all systems of authority are fake. But they ignore that while this might be true in essence, they are only going to have that sort of 'sure footedness' that most of the types already have by bucking up and doing these things anyway. So, for a 6 to grow it's sometimes best to just listen to others and not give them a hard time, thinking you are 'rebelling' or 'making a statement' simply by refusing to do what is asked of you. If you really want to fight, well then - fight, people will end up respecting you more anyway. If you have a concern or problem, you really need to speak up at the time it's happening instead of letting it fester, and listening calmly when people tell you the answer. The more you can just 'stick it out' and see, the more you can tell who is fucking with you and who has your back as well. As well, there will always be people that sociopathically see how they can take advantage of others.
Learning to say no to people as well, cause the more strong and independent a 6 gets, the more others will be drawn to him and ask him for shit, or to do shit for him simply cause they sense what a good-natured person he is and how real he keeps it.
You already know this, but you should be reminded that all cultures and ways of living are all different, and american society isn't really set up for 6s. So you see a lot of 3s and 8s running about but you won't find many 6s (who are usually too sheltered or institutionalized unless Fully Liberated). This all leads to many interesting things. For one, this leads to 6s idealizing others, a sort of 'rescurer' that is gonna make everything better, this is only because 6s are so incompatible with the culture that when they do meet people that understand them they might be a bit too quick to fond over that person. This is something that just gets corrected over time, the more connected you are with others.
American society, where the external and the inner nature meet up perfectly - is a core 3-type society, which just so happens to be our area of DISintegration. So unfortunately, you are not going to find many things you like in us of gay, no matter how many people tell you differently! So having somebody around like a 7 who can show you a variety of different places is a great thing, somebody that can shift your current external perspective to something else will be the most complementary to you. You could also try to move to a different country although this might be hard or plain unrealistic. It's just kind of the nature of the beast. Even unhealthy 3s find no trouble to participate in the real world because the society is sooo 3 valuing. And well you gotta kinda remind yourself that although your true nature is *inherently* incompatible with the external ideals of 6, you still can be happy on the inside, where it really matters- it's just going to take more work for you than others because you do not have the external structure that supports your 6ness unless you go out there and make it happen yourself!
I don't mean to sound fatalistic but just this sort of real compassion that you have to accept. Nothing is going to change in america much, and nothing has since america was CREATED. It's just a culture that *innately* values something that is so not compatible with who we are deep down. All of outside society isn't going to change just because it fucks up the lives of 6s. It's unfair and unbaised, but that's just the way things are going to be, so realize that it will be much much more difficult for you to have a 'Real Life' - then it is for any other type. And by real life I don't mean a sense of dull suburban conformity but that sense of understanding what you have to do realistically each day, moment by moment, to make a life for yourself. But if you can liberate yourself completely, then it's all worth it.
Yeah, you can be an enneagram type 3 and be on the unhealthy scale and move to positions of great power rather easily. But guess what? You have to be a *completely liberated* 6 to even function in america and even BE in the real world on a consistent basis. This is just the harsh reality. And why you need this self-help book! Now give me $50 please.
That's another point. (I'm almost done here I promise ;p) Self-help books are great for 6s to help them deal but you need to kinda read them once and move on. You will probably find them to be very good upliftment but only in small doses and never repeated. So I hope this uplifts you so you can 'get out of here!' and into the next tier of psychological existences. There are many, many subtle layers to full and total awakening. And once you do awaken you will just go back to sleep and do it all over again for the fun, anyway.
The next tip is yet another reminder that the single best thing that helps 6, being in the head 'thinking' triad, is to meditate, meditate and meditate. The more meditation the better, especially if you are a 6 living in a 3-valuing society. Meditation helps everybody but it is *especially* important for 6s.
This is the first edition of this series, but there will be more later. Anyways if it helped you then great. I was trying to be all 'objective' and scientific as possible but even more than that I was being artistic and self-renewal by making the subjective and objective meet up as one where they always are at anyway. Le sigh. Psychology, I love you.