While listening to a lecture, the speaker made a good point that, in regards to our heritage, we might be practicing what we learned, and then one day realize that there is a lot we don't know or understand. This can be discouraging. If we don't know why to do what we do or why to believe, then our motivation goes down and we are likely to fall.
Another thing I and others have noticed is when people see bad examples and get discouraged. On the one hand, we should realize that we are all only human and we all make mistakes, whether big or small. However, I agree that people should still be careful and strive to be good examples for others, and have good middos.
For these reasons, it is best for us to have a good role model. Someone that we can talk to, tell them how we feel, ask questions. Someone to give us support and guidance and help us grow. It might be difficult or simple to find this person. But for our own benefit, we should keep trying.
Another thing that is helpful is to read information on different Jewish topics either in books or online, in order to build our understanding, which in turn builds our emunah. Once we build our emunah, we can build our strength to withstand our challenges and stay strong in our heritage - thereby fulfilling our purpose and the pleasure that comes later with that achievement.