"Ultimately, what is your life if not one you want to lead?" I asked that of myself once in a moment of thoughtfulness, and I haven't been able to get the question out of my head.
You don't take money or status with you in the end...in the end all you are is a combination of your experiences, your wisdom, and your joy. Why spend YOUR life trying to make other people happy? If someone does something in their life that their friends don't approve of, they hear about it, and their friends get mad at them for making said choice. Who is it that has to live with the consequences (or successes) of that choice? Not the friends.
What do you gain in life by not risking? You gain security, safety, and a pedestrian life that at the end of the day only deserves a shrug because it wasn't good or bad. It just...was. Yes, by taking risks you put yourself in scary situations, you put yourself on different paths that could either send you shooting to the sky or hitting rock bottom. But if you risk for the things you want most in life, you'd be doing yourself wrong to sit by and choose the safe road. Nothing in life falls in your lap. You can't sit and dream wistfully of the life you've always wanted and can never have...the very reason you can't have it is because all you do is dream about it. You can't lead the life you want without TAKING it.
I've heard a lot of "I can't"s lately coming from my own mouth and those of the people closest to me. "I can't not go to class," "I can't not do my homework," etc. No. That's wrong. You CAN skip class, you CAN blow off homework. You're consciously making the choice not to, because in your life you've decided that the consequences of not doing homework, of not going to class are less desirable and more intense than your momentary dislike of being responsible.
There is not a single thing in life that you HAVE to do, that you have no choice in. In every situation there is the choice lingering at the back of every "I have to..."
When does life become more than a series of "I have to's" and planning for the future? The future never comes. Sure you can spend now and the next few years making a solid life for the future, but by doing that you lose NOW. Once people start living with their minds in the future...it never really stops. So they're always losing now.
My parents are and always will be big planning people. I can't even begin to remember the number of "one day we'll"s that have come out of their mouths and never see even the beginning of completion. They always told me I could be whoever I wanted to be, do with my life whatever I wanted to do with it. But they taught me by example to wish for things instead of making them happen. They use planning and making sure they've made the "smartest" choice possible as an excuse to stay safely in the uneventful known. I've spent my life living by their expectations, and recently I've come more and more to the realization that it is a waste of life to live up to other people's expectations unless their expectations are also your own. Their life together looks like a line of lead soldiers, all marching to the smartest, safest choice.
What if I don't want that? What if I want a life that is full of stretching to make ends meet, picking up one day and moving because that town gave me all it had to offer and the next one was well within reach? What if I want a mess of chaos and joy and anger and hardship and strength and seeing all the big and little things the world has to offer?
In the end, the only thing that matters is who you are and the way you've treated people. In the end, the trappings of man won't mean anything at all, and if there is a heaven or a god they won't be judging the position you got to, or the punishments society rained on you, or the kind of life you led. They will judge the good of your character and the integrity with which you led the life you chose and the love you gave to the world.