The core of all navigation is probably uncertainty: tolerating not knowing makes it possible to find your way. Not knowing means embracing what is not known rather than fighting with yourself over it. Since the mind always strives to know, not knowing is disorienting in a useful way. Uncertainty and not knowing teach you not to believe the stories your mind feeds you day in and day out. If you allow your own course to be mysterious, then even the hard things can become easy. This is the beginning of awakening.
...the most heartbreaking thing is not heartbreak; it's avoiding heartbreak. Inside the transience of life is the thusness of everything, of the tree with forty crows on it in the winter, the sound of death-metal drums from the kids in the barn, and the feeling of sadness when you lose someone. A lot of suffering is resistance to the life of feeling. If you surrender, you are surrendering to what is really going on. This is just to notice that nothing beyond your life is more important than your life.
Obstacles can be the gate. If your diagnosis is cancer or you lose people you love, there is no alternative but surrender. You can't rewind to yesterday when you were innocent. Meditation at such a moment might not take you back to the surface; it might take you down and through. Getting more emotional might be indicated; falling apart might happen. The practice is what tows you through. It doesn't take the rough crossing away from you but it give you a degree of safety in the passage.
Once when I lost a friend, I realized that I was weeping since my hands were wet. I was giving a talk at the time, being wise and all that, and it was a revelation--I couldn't trust myself not to weep in public. I also couldn't trust myself to sleep at night, either. At a time like that we have to surrender. We are facing something vast and, really, we have always known that we would have to face it. It is an enormous, shaggy beast blocking the way. And there is something exhilarating about the inevitable when at last it arrives; awakening is not a choice or a matter of technique anymore, it's the only place left. The huge animal rolls over us, and suddenly we find that we are riding on its back. It has become a vehicle. The obstacles really have become gates.