A friend passed along a great quote on humility...

...all day long, at the moment you become aware of burdensome cares, cast them upon the Lord, who cares for you. Where there is worry and anxiety; there is the pride of self-reliance. The humble man, though he may be responsible for many things, is free of care--he is care-free. His life is characterized by joy and peace, for it is impossible to be worried while trusting the Sovereign One.

– C.J. Mahaney, Ch. 7 - Cultivate Humility of "Dear
Timothy: Letters on Pastoral Ministry"

There are a lot of things in pastoral life that puff up our pride and discourage humble living.  As a pastor, have you ever considered:

1.  Where do you turn when you are carrying a heavy burden?   Are there others in your life to whom you can turn and show your weakness? 
2.  How often do you struggle with the pride of self-reliance? 
3.  Can your life be described as joyful and peaceful? 
4.  If I asked your wife to describe your life, what would she say?
5.  Do you ask your staff for feedback on your sermons, prayers, and other aspects of your public ministry?  Or are you scared about what they might say?  If they said you did a poor job, how would you react?
6.  How often do you worry about your church?  your sermons?  your outreach to the community?
7.  Are you willing to ask church members for forgiveness?
8.  Are you willing to ask your wife and children to forgive you when you mess up?
9.  Do you find yourself always directing those around you (your staff, your family, etc.), or do you take the time to really listen to what others have to say?
10.  Do you  cultivate a spirit of humility among the leaders in your church?  Is your leadership team willing to tell you when you are wrong?  Or are they too scared to ever contradict your opinions?

Even as I write these questions, I notice how far short my life falls from the biblical standard.  There are a lot more questions I could ask.  The 10 listed above are a small sample that can help you answer the question, "Am I, as a pastor, actively cultivating humility in my own life?"