Dear Former Sam,
I just want you to know that nothing is going to work out like you want it to. You won't get to live a normal life. You won't get to stay in one school or graduate college. You'll go to college, but you won't stay long and at the time, it will seem like the end of the world. But that comes later.
Dean and Dad won't end up accepting your decision and you will be dragged kicking and screaming back into hunting, because you're a Winchester and that's what Winchesters do. You'll lose everything and everyone except Dean and his damn car and there will be times when you think you've lost him too and those will be the times when you lose all hope, but they won't last long, because Dean always comes back.
You know how you hoped there was a God? Well, there is. We've met him. He's pretty annoying and you'll want to punch him a lot. Angels are real too and they are, with one exception, total dicks. The exception, though, is pretty exceptional.
Three out of four archangels are worse than any demon. Well, almost any demon. Trust nothing from Heaven or Hell, most of the time. The fourth archangel is best avoided on weekdays.
Wishes are dangerous, demon deals never end well and Dean is usually right, except about himself. Dean said to triple underline "Dean is usually right" and cross out the "usually", but Dean said this was a dumb idea, so I'm not listening to him, even though he is now pointing to "Dean is usually right" with a bullet he's been carving a devil's trap into.
The life ahead isn't the one you planned. It won't be easy and a lot of it won't be fun. You'll find the road to Hell paved with demon deals and bad choices and you'll find that Hell isn't the worst thing that can happen to you. The best thing that will happen is that you'll find a family that love you and a life worth living and a purpose that makes all the losses and the regrets bearable.
Life hurts, for everyone and this life more than most. You'll often think you can't survive much more, but you will. You'll find you can survive anything, if you just keep moving, keep on saving people and hunting things. In the end, you'll be proud of who and what you are and glad that you made most of the choices you made.
So don't be scared, kid, because Dean will be beside you all the way and we both know, if Dean's with you, nothing stands a chance of taking you down.
Also, you might want to learn American Sign Language.
Best wishes,
An older, wiser Sam.
