Dear showJoe,
As you mentioned, your question is a classical issue in Judaism and life. It is really addressed in the final mishnah in the 5th perek of PA – “L'fum tza'arah agra – According to the effort is the benefit.” I often refer to this mishnah as “the great equalizer.” Regardless of how much talent or intelligence you are born with, your achievement and evaluation in life is exclusively a function of the work and effort you invest into whatever you do. We all, therefore, have the equal ability to be great in how we live our lives.
Your question reminds me of a time when I asked someone about something that my computer was doing. The person responded by telling me – “That is not a problem, it is actually a feature!” And once he explained its purpose, I saw this as well. I will say the same thing about Hashem building effort and struggle into the fabric of life – “That is not a problem, it is actually a feature!”
Think about the accomplishments that you got real satisfaction from. It is really the fact that you worked so hard to do it that was the most satisfying. Imagine if your parents would have given you everything you wanted with no effort required from you. You would end up as a spoiled brat who wouldn't even appreciate whatever you had.
By building this into the creation, Hashem gives us the ability to emulate Him. He is completely independent, and this gives us an aspect of independence as well. In fact, the only way for Hashem to give us this ultimate pleasure of being like Him, is to give us these challenges that we need to overcome. This then allows us to be able to enjoy the pleasure of our accomplishments when we get to Gan Eden.
I hope that this is clear. If not, or if you have any other questions, please let me know. Be well.
Rabbi Asher Resnick
JewishClarity.com