How do I win at life?

Dear Edahn,
When are you truly satisfied with what you have? What happens once you reach the end of the tunnel and you realize it's not what you wanted the whole time? How can you differentiate between what is ideal and what will truly make you happy? 
I want to try all possibilities but time is a constraint and sometimes you can only choose one path. Sometimes I feel like I should take risks, but when I do, I can't handle being out of order. It's nice having a change once in a while but I feel vulnerable and frazzled. My whole life has been set with guidelines but now I'm tempted to break through. I'm afraid that what I presently have is as good as it gets, and that changing things could be worse. I can't keep floating too...I want to let things "just flow" but I feel uneasy.

IN MY EXPERIENCE AND reflection, I've come to the conclusion that everyone knows what's really best for them deep down. They understand what decisions, including hard decisions, they need to make to really be happy. Not the kind of happy where you feel a rush like you're kicking ass and "winning the race" but the kind of happy where you're at peace, calm, content, friendly, open-hearted, and kind. If you read some of my other posts, I usually refer to this state of being as "Rest." (See also this post.)

Part of the reason I belabor the importance of honoring your conscience is that your conscience is that guiding voice. Your conscience will always guide you in the right direction. Some people have trouble distinguishing between their conscience and their thoughts that masquerade as their conscience and instruct them to do unkind things like kill infidels, convert heathens, or destroy property and people for the sake of some social cause. That's not their conscience talking because it's not coming from their heart; it's coming from their mind.

Here's a big key: you don't "get" happy. You don't get something and that makes you happy. That's not real happiness, it's materialism and that high will fade quickly. Being happy, being peaceful, is an attitude you take. It's a relationship you have to things, to others, and to yourself. It's an outlook rather than a thing you attain. Some of your worrying is healthy, because you know something is off. Another part of your worrying is just habitual worrying that'll melt away when you start getting in touch with your conscience.

So here's my advice. Put all the worrying and thinking and speculation aside for a minute and ask yourself: What does it mean to be at peace? What does it look like? What does it mean to have an attitude of joy and patience? What is truly good for me? What will I look like with a soft smile on my face and eyes? Just by reflecting on those questions, you'll make contact with your conscience. Every decision you make from that place of self-intimacy, even just small decisions, will be laced with wisdom and intelligence. Don't take my word for it; try it. Living from that space IS being happy; it will diffuse the questions and doubts you're having and help you make decisions that are congruent with that feeling of happiness. Trust it.