Contemplative Bible Reading

Luke 18:1 (New International Version)

Then Jesus told his disciples a parable to show them that they should always pray and not give up.

Jesus taught that we should not give up. Is that practical? Is that sensible? Is He speaking of everything?

If I quit my job and start a business that is failing miserably, should I pray for business success and not give up? If I borrow money and study for medical school, but fail the entrance exam ten times, should I keep trying and not give up?

Am I reading too much into this passage and asking too many questions?