Q: I feel like I deserve to suffer. I am a nice guy who is caring and thoughtful and productive, yet ever since I was a child, I have had the sense that I should be miserable, so I have made myself miserable. What can I do?
A: You do not deserve to suffer. No one deserves to suffer. This is true, even though it is an astonishing truth that usually takes decades, even after we have understood it thoroughly, to incorporate into a real life.
You do not deserve to suffer. However, your proclivity for meditation may be the result of a subtle understanding that you are suffering. The vagaries of English grammar allow this phrase two meanings: you are currently suffering, and you are a mass of suffering. When you are suffering, you are suffering. To get out of suffering, get out of you. To get rid of suffering, get rid of you. This is not accomplished by punishing yourself. This is not accomplished by punishing yourself. It is accomplished by either letting go of yourself, or by loving yourself to death. Either way is good, and they both accomplish exactly the same thing.
To let go of yourself, pay attention to something else. Every time you suffer, and in particular every time you get the sense that you should suffer, pay attention to something in the objective world. See something in the world. Hear something in the world. Feel something in the world. Just do that until you forget yourself, and even after you have forgotten yourself, keep it up with increasing awareness. Eventually, suffering will have no place to stand, and it will fall off. This is how I solved this problem in my own life.
To love yourself to death, pay attention to your internal experience, in particular your experience of suffering, until your it breaks up into flow. See it so clearly that you directly observe that it is life flowing, unaware of you, unrestricted to you, bigger than you, smaller than you, faster than you, slower than you, above you, below you, before you, after you. Every time internal experience arises, attend to it, paying more and more attention, until it starts to flow. This flow is just pure life with no you in it. This is how I continue to solve this problem in my own life.
If you use either of these techniques, you will escape from yourself. To escape from yourself is to escape from suffering. When suffering is cleaned off, only joy remains. In the end, you can escape from suffering, but you cannot escape from joy. When everything is gone, joy remains, even though everything is gone.
Joy is enough.